Like a bolt from the blue: Phthalocyanines in biomedical optics

Molecules

Volumn 17, Issue 1, 2012, Pages 98-144

  Sekkat, Nawal ^a   Van Den Bergh, Hubert ^b   Nyokong, Tebello ^c   Lange, Norbert ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

^b EPFL   (Switzerland)

^c RHODES UNIVERSITY   (South Africa)

Author keywords

Biomedical optics; Fluorescence diagnosis; NIR dyes; Photodynamic therapy; Phthalocyanines

Indexed keywords

INDOLE DERIVATIVE; PHOTOSENSITIZING AGENT; PHTHALOCYANINE;

ANIMAL; CHEMISTRY; HUMAN; MOLECULAR IMAGING; NEOPLASM; PHOTOCHEMOTHERAPY; REVIEW;

ANIMALS; CHEMISTRY, PHARMACEUTICAL; HUMANS; INDOLES; MOLECULAR IMAGING; NEOPLASMS; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS;

EID: 84856156941     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17010098     Document Type: Review

References (249)

1. McKeown, N.B. The synthesis of symmetrical phthalocyanines. In The Porphyrin Handbook; Kadish, K.M., Smith, K.M., Guilard, R., Eds.; Academic Press: San Diego, CA, USA, 2003; pp. 61-124.
2. Thomas, A.L. Phthalocyanine Research and Applications; CRC Press: Baton Rouge, FL, USA, 1990; p. 2.
3. McKeown, N.B. An introduction to the phthalocyanines. In Phthalocyanine Materials: Synthesis, Structure and Function; McKeown, N.B., Ed.; Cambridge University Press: Cambridge, UK, 1998; pp. 1-10.
4. Geng,Y.Y.; Gu, D.H.; Wu, Y.Q.; Gan, F.X. High speed recording property of phthalocyanine thin film for compact disc recordable. Proc. SPIE Int. Soc. Opt. Eng. 2003, 63, 63-66.
5. Petritsch, K.; Friend, R.H.; Lux, A.; Rozenberg, G.; Moratti, S.C.; Holmes, A.B. Liquid crystalline phthalocyanines in organic solar cells. Synth. Met. 1999, 102, 1776-1777.
6. Nyokong, T.; Vilakazi, S. Phthalocyanines and related complexes as electrocatalysts for the detection of nitric oxide. Talanta 2003, 61, 27-35.
7. Ali, H.; van Lier, J.E. Porphyrins and phthalocyanines as photosensitizers and radiosensitizers. In Handbook of Porphyrin Science with Applications to Chemistry, Physics, Materials Science, Engineering, Biology and Medecine; Kadish, K.M., Smith, K.M., Guilard, R., Eds.; World Scientific: Singapore, 2010; pp. 1-119.
8. Alonso, C.; Boyle, R.W. Bioconjugates of porphyrins and related molecules for photodynamic Therapy. In Handbook of Porphyrin Science with Applications to Chemistry, Physics, Materials Science, Engineering, Biology and Medecine; Kadish, K.M., Smith, K.M., Guilard, R., Eds.; World Scientific: Singapore, 2010; pp. 121-190.
9. Ethirajan, M.; Patel, N.J.; Pandey, R.K. Porphyrin-based multifunctional agents for tumorimaging and photodynamic therapy (PDT). In Handbook of Porphyrin Science with Applications to Chemistry, Physics, Materials Science, Engineering, Biology and Medecine; Kadish, K.M., Smith, K.M., Guilard, R., Eds.; World Scientific: Singapore, 2010; pp. 249-323.
10. Jux, N.; Röder, B. Targeting strategies for tetrapyrrole-based photodynamic therapy. In Handbook of Porphyrin Science with Applications to Chemistry, Physics, Materials Science, Engineering, Biology and Medecine; Kadish, K.M., Smith, K.M., Guilard, R., Eds.; World Scientific: Singapore, 2010; pp. 325-401.
11. Nyokong, T.; Antunes, E. Photochemical and photophysical properties of metallophthalocyanines. In Handbook of Porphyrin Science with Applications to Chemistry, Physics, Materials Science, Engineering, Biology and Medecine; Kadish, K.M., Smith, K.M., Guilard, R., Eds; World Scientific: Singapore, 2010; pp. 247-349.
12. Fukuda, T.; Kobayashi, N. UV-visible absorption spectroscopic properties of phthalocyanines and related macrocycles. In Handbook of Porphyrin Science with Applications to Chemistry, Physics, Materials Science, Engineering, Biology and Medecine; Kadish, K.M., Smith, K.M., Guilard, R., Eds.; World Scientific: Singapore, 2010; pp. 1-645.
13. Dietze, A.; Peng, Q.; Selbo, P.K.; Kaalhus, O.; Muller, C.; Bown, S.; Berg, K. Enhanced photodynamic destruction of a transplantable fibrosarcoma using photochemical internalisation of gelonin. Br. J. Cancer 2005, 92, 2004-2009. (Pubitemid 40897422)
14. Selbo, P.K.; Sivam, G.; Fodstad, O.; Sandvig, K.; Berg, K. In vivo documentation of photochemical internalization, a novel approach to site specific cancer therapy. Int. J. Cancer 2001, 92, 761-766. (Pubitemid 32385722)
15. Adigbli, D.K.; Wilson, D.G.; Farooqui, N.; Sousi, E.; Risley, P.; Taylor, I.; Macrobert, A.J.; Loizidou, M. Photochemical internalisation of chemotherapy potentiates killing of multidrugresistant breast and bladder cancer cells. Br. J. Cancer 2007, 97, 502-512. (Pubitemid 47258452)
16. Norum, O.J.; Selbo, P.K.; Weyergang, A.; Giercksky, K.E.; Berg, K. Photochemical internalization (PCI) in cancer therapy: From bench towards bedside medicine. J. Photochem. Photobiol. B 2009, 96, 83-92.
17. Norum, O.J.; Bruland, O.S.; Gorunova, L.; Berg, K. Photochemical internalization of bleomycin before external-beam radiotherapy improves locoregional control in a human sarcoma model. Int. J. Radiat. Oncol. Biol. Phys. 2009, 75, 878-885.
18. Norum, O.J.; Giercksky, K.E.; Berg, K. Photochemical internalization as an adjunct to marginal surgery in a human sarcoma model. Photochem. Photobiol. Sci. 2009, 8, 758-762.
19. Prasmickaite, L.; Hogset, A.; Selbo, P.K.; Engesaeter, B.O.; Hellum, M.; Berg, K. Photochemical disruption of endocytic vesicles before delivery of drugs: A new strategy for cancer therapy. Br. J. Cancer 2002, 86, 652-657. (Pubitemid 34185106)
20. Hogset, A.; Prasmickaite, L.; Selbo, P.K.; Hellum, M.; Engesaeter, B.O.; Bonsted, A.; Berg, K. Photochemical internalisation in drug and gene delivery. Adv. Drug Deliv. Rev. 2004, 56, 95-115. (Pubitemid 38045426)
21. Ben-Hur, E.; Rosenthal, I. The phthalocyanines: A new class of mammalian cells photosensitizers with a potential for cancer phototherapy. Int. J. Radiat. Biol. Relat. Stud. Phys. Chem. Med. 1985, 47, 145-147. (Pubitemid 15110922)
22. Brasseur, N.; Ali, H.; Autenrieth, D.; Langlois, R.; van Lier, J.E. Biological activities of phthalocyanines-III. Photoinactivation of V-79 Chinese hamster cells by tetrasulfophthalocyanines. Photochem. Photobiol. 1985, 42, 515-521.
23. Ackroyd, R.; Kelty, C.; Brown, N.; Reed, M. The history of photodetection and photodynamic therapy. Photochem. Photobiol. 2001, 74, 656-669.
24. Dolmans, D.E.; Fukumura, D.; Jain, R.K. Photodynamic therapy for cancer. Nat. Rev. Cancer 2003, 3, 380-387. (Pubitemid 37328858)
25. Sharman, W.M.; Allen, C.M.; van Lier, J.E. Photodynamic therapeutics: Basic principles and clinical applications. Drug Discov. Today 1999, 4, 507-517. (Pubitemid 29497854)
26. Allen, C.M.; Langlois, R.; Sharman, W.M.; La, M.C.; van Lier, J.E. Photodynamic properties of amphiphilic derivatives of aluminum tetrasulfophthalocyanine. Photochem. Photobiol. 2002, 76, 208-216.
27. Brown, S.B.; Brown, J.E.; Vernon, D.I. Photosensitising drugs-Their potential in oncology. Expert Opin. Invest. Drugs 1999, 8, 1967-1979.
28. Allison, R.R. Photosenitizers in clinical PDT. Photodiag. Photod. Ther. 2004, 1, 27-42.
29. Lange, N. Controlled drug delivery in photodynamic therapy and fluorescence-based diagnosis of cancer. In Handbook of Biomedical Fluorescence; Mary-Ann, M., Brian, W.P., Eds.; CRC Press: Boca Raton, FL, USA, 2003; pp. 563-635.
30. Josefsen, L.B.; Boyle, R.W. Photodynamic therapy and the development of metal-based photosensitisers. Met. Based Drugs 2008, 2008, 1-24.
31. Ethirajan, M.; Saenz, C.; Gupta, A.; Dobhal, M.P.; Pandey, R.K. Photosensitizers for photodynamic therapy and imaging. In Advances in Photodynamic Therapy: Basic, Translational, and Clinical; Michael, R.H., Pawel, M., Eds.; Artech House: Boston, MA, USA, 2008; pp. 13-39.
32. Stolik, S.; Delgado, J.A.; Perez, A.; Anasagasti, L. Measurement of the penetration depths of red and near infrared light in human "ex vivo" tissues. J. Photochem. Photobiol. B 2000, 57, 90-93.
33. Sevick-Muraca, E.M.; Godavarty, A.; Houston, J.P.; Thompson, A.B.; Roy, R. Near-infrared imaging with fluorescent contrast agents. In Handbook of Biomedical Fluorescence; Mycek, M.-A., Pogue, B.W., Eds.; CRC Press: Boca Raton, FL, USA, 2003; pp. 445-527.
34. MacDonald, I.J.; Dougherty, T.J. Basic principles of photodynamic therapy. J. Porphyr. Phthalocya. 2001, 5, 105-129. (Pubitemid 32125231)
35. Lang, K.; Mosinger, J.; Wagnerova, D.M. Photophysical properties of porphyrinoid sensitizers non-covalently bound to host molecules, models for photodynamic therapy. Coord. Chem. Rev. 2004, 248, 321-350.
36. Jori, G. Far-red-absorbing photosensitizers-Their use in the photodynamic therapy of tumors. J. Photochem. Photobiol. A 1992, 62, 371-378.
37. Haddad, R.; Blumenfeld, A.; Siegal, A.; Kaplan, O.; Cohen, M.; Skornick, Y.; Kashtan, H. In vitro and in vivo effects of photodynamic therapy on murine malignant melanoma. Ann. Surg. Oncol. 1998, 5, 241-247. (Pubitemid 28249315)
38. Boyle, R.W.; Dolphin, D. Structure and biodistribution relationships of photodynamic sensitizers. Photochem. Photobiol. 1996, 64, 469-485. (Pubitemid 27039801)
39. Bonnett, R. Photosensitizers of the porphyrin and phthalocyanine series for photodynamic therapy. Chem. Soc. Rev. 1995, 24, 19-33.
40. Brasseur, N.; Menard, I.; Forget, A.; El Jastimi, R.; Hamel, R.; Molfino, N.A.; van Lier, J.E. Eradication of multiple myeloma and breast cancer cells by TH9402-mediated photodynamic therapy: Implication for clinical ex vivo purging of autologous stem cell transplants. Photochem. Photobiol. 2000, 72, 780-787.
41. Brown, S.B.; Brown, E.A.; Walker, I. The present and future role of photodynamic therapy in cancer treatment. Lancet Oncol. 2004, 5, 497-508. (Pubitemid 39069400)
42. Ferreira, J.; Menezes, P.F.C.; Kurachi, C.; Sibata, C.H.; Allison, R.R.; Bagnato, V.S. Comparative study of photodegradation of three hematoporphyrin derivative: Photofrin (R), Photogem (R) and Photosan. Laser Phys. Lett. 2007, 4, 743-748.
43. Fickweiler, S.; Abels, C.; Karrer, S.; Baumler, W.; Landthaler, M.; Hofstadter, F.; Szeimies, R.M. Photosensitization of human skin cell lines by ATMPn (9-acetoxy-2,7,12,17-tetrakis-(betamethoxyethyl)- porphycene) in vitro: Mechanism of action. J. Photochem. Photobiol. B 1999, 48, 27-35. (Pubitemid 29132261)
44. Jori, G. Tumour photosensitizers: Approaches to enhance the selectivity and efficiency of photodynamic therapy. J. Photochem. Photobiol. B 1996, 36, 87-93. (Pubitemid 27011249)
45. Karrer, S.; Abels, C.; Szeimies, R.M.; Baumler, W.; Dellian, M.; Hohenleutner, U.; Goetz, A.E.; Landthaler, M. Topical application of a first porphycene dye for photodynamic therapy- Penetration studies in human perilesional skin and basal cell carcinoma. Arch. Dermatol. Res. 1997, 289, 132-137. (Pubitemid 27107562)
46. Mathai, S.; Bird, D.K.; Stylli, S.S.; Smith, T.A.; Ghiggino, K.P. Two-photon absorption crosssections and time-resolved fluorescence imaging using porphyrin photosensitisers. Photochem. Photobiol. Sci. 2007, 6, 1019-1026. (Pubitemid 47313192)
47. Mody, T.D. Pharmaceutical development and medical applications of porphyrin-type macrocycles. J. Porphyr. Phthalocya. 2000, 4, 362-367.
48. Nyman, E.S.; Hynninen, P.H. Research advances in the use of tetrapyrrolic photosensitizers for photodynamic therapy. J. Photochem. Photobiol. B 2004, 73, 1-28. (Pubitemid 38145763)
49. Ochsner, M. Light scattering of human skin: A comparison between zinc(II)-phthalocyanine and Photofrin II(R). J. Photochem. Photobiol. B 1996, 32, 3-9.
50. Palumbo, G. Photodynamic therapy and cancer: A brief sightseeing tour. Expert Opin. Drug Del 2007, 4, 131-148.
51. Rosenthal, M.A.; Kavar, B.; Hill, J.S.; Morgan, D.J.; Nation, R.L.; Stylli, S.S.; Basser, R.L.; Uren, S.; Geldard, H.; Green, M.D.; et al. Phase I and pharmacokinetic study of photodynamic therapy for high-grade gliomas using a novel boronated porphyrin. J. Clin. Oncol. 2001, 19, 519-524. (Pubitemid 32112866)
52. Usuda, J.; Kato, H.; Okunaka, T.; Furukawa, K.; Tsutsui, H.; Yamada, K.; Suga, Y.; Honda, H.; Nagatsuka, Y.; Ohira, T.; et al. Photodynamic therapy (PDT) for lung cancers. J. Thorac. Oncol. 2006, 1, 489-493. (Pubitemid 47181428)
53. Ogunsipe, A.; Nyokong, T. Photophysicochemical consequences of bovine serum albumin binding to non-transition metal phthalocyanine sulfonates. Photochem. Photobiol. Sci. 2005, 4, 510-516. (Pubitemid 41044580)
54. Huang, J.D.; Wang, S.; Lo, P.C.; Fong, W.P.; Ko, W.H.; Ng, D.K.P. Halogenated silicon(iv) phthalocyanines with axial poly(ethylene glycol) chains. Synthesis, spectroscopic properties, complexation with bovine serum albumin and in vitro photodynamic activities. New J. Chem. 2004, 28, 348-354. (Pubitemid 38373020)
55. Chen, X.L.; Li, D.H.; Zhu, Q.Z.; Yang, H.H.; Zheng, H.; Wang, Z.H., Xu, J.G. Determination of proteins at nanogram levels by a resonance light-scattering technique with tetra-substituted sulphonated aluminum phthalocyanine. Talanta 2001, 53, 1205-1210. (Pubitemid 32231536)
56. Vrouenraets, M.B.; Visser, G.W.; Stigter, M.; Oppelaar, H.; Snow, G.B.; van Dongen, G.A. Targeting of aluminum (III) phthalocyanine tetrasulfonate by use of internalizing monoclonal antibodies: Improved efficacy in photodynamic therapy. Cancer Res. 2001, 61, 1970-1975. (Pubitemid 32692015)
57. Peng, X.; Draney, D.R.; Volcheck, W.M.; Bashford, G.R.; Lamb, D.T.; Zhang, Y.; Johnson, C.M. Phthalocyanine dye as an extremely photostable and highly fluorescent near-infrared labeling reagent. Proc. SPIE Int. Soc. Opt. Eng. 2006, 6097, 60970E.
58. Mitsunaga, M.; Ogawa, M.; Kosaka, N.; Rosenblum, L.T.; Choyke, P.L.; Kobayashi, H. Cancer cell-selective in vivo near infrared photoimmunotherapy targeting specific membrane molecules. Nat. Med. 2011, 17, 1685-1691.
59. Duan, W.; Smith, K.; Savoie, H.; Greenman, J.; Boyle, R.W. Near IR emitting isothiocyanatosubstituted fluorophores: Their synthesis and bioconjugation to monoclonal antibodies. Org. Biomol. Chem. 2005, 3, 2384-2386. (Pubitemid 41028045)
60. Carcenac, M.; Dorvillius, M.; Garambois, V.; Glaussel, F.; Larroque, C.; Langlois, R.; Hynes, N.E.; van Lier, J.E.; Pelegrin, A. Internalisation enhances photo-induced cytotoxicity of monoclonal antibody-phthalocyanine conjugates. Br. J. Cancer 2001, 85, 1787-1793. (Pubitemid 34081528)
61. Devlin, R.; Studholme, R.M.; Dandliker, W.B.; Fahy, E.; Blumeyer, K.; Ghosh, S.S. Homogeneous detection of nucleic acids by transient-state polarized fluorescence. Clin. Chem. 1993, 39, 1939-1943. (Pubitemid 23277036)
62. Hammer, R.P.; Owens, C.V.; Hwang, S.H.; Sayes, C.M.; Soper, S.A. Asymmetrical, watersoluble phthalocyanine dyes for covalent labeling of oligonucleotides. Bioconjug. Chem. 2002, 13, 1244-1252. (Pubitemid 35420016)
63. Koval, V.V.; Chernonosov, A.A.; Abramova, T.V.; Ivanova, T.M.; Fedorova, O.S.; Derkacheva, V.M.; Lukyanets, E.A. Photosensitized and catalytic oxidation of DNA by metallophthalocyanineoligonucleotide conjugates. Nucleos. Nucleot. Nucl. 2001, 20, 1259-1262. (Pubitemid 32821966)
64. Nesterova, I.V.; Verdree, V.T.; Pakhomov, S.; Strickler, K.L.; Allen, M.W.; Hammer, R.P.; Soper, S.A. Metallo-phthalocyanine near-IR fluorophores: Oligonucleotide conjugates and their applications in PCR assays. Bioconjug. Chem. 2007, 18, 2159-2168. (Pubitemid 350220021)
65. Walker, G.T.; Fraiser, M.S.; Schram, J.L.; Little, M.C.; Nadeau, J.G.; Malinowski, D.P. Strand displacement amplification-An isothermal, in vitro DNA amplification technique. Nucleic Acids Res. 1992, 20, 1691-1696.
66. Rio, Y.; Rodriguez-Morgade, M.S.; Torres, T. Modulating the electronic properties of porphyrinoids: A voyage from the violet to the infrared regions of the electromagnetic spectrum. Org. Biomol. Chem. 2008, 6, 1877-1894. (Pubitemid 351693230)
67. Ali, H.; van Lier, J.E. Metal complexes as photo- and radiosensitizers. Chem. Rev. 1999, 99, 2379-2450.
68. Claessens, C.G.; Blau, W.J.; Cook, M.; Hanack, M.; Nolte, R.J.M.; Torres, T.; Whörle, D. Phthalocyanines and phthalocyanine analogues: The quest for applicable optical properties. Monatsh. Chem./Chem. Monthly 2001, 132, 3-11.
69. Nyokong, T.; Isago, H. The renaissance in optical spectroscopy of phthalocyanines and other tetraazaporphyrins. J. Porphyr. Phthalocya. 2004, 8, 1083-1090. (Pubitemid 40164009)
70. Foley, M.S.; Beeby, A.; Parker, A.W.; Bishop, S.M.; Phillips, D. Excited triplet state photophysics of the sulphonated aluminium phthalocyanines bound to human serum albumin. J. Photochem. Photobiol. B 1997, 38, 10-17. (Pubitemid 27183290)
71. Feofanov, A.; Grichine, A.; Karmakova, T.; Kazachkina, N.; Pecherskih, E.; Yakubovskaya, R.; Luk'yanets, E.; Derkacheva, V.; Egret-Charlier, M.; Vigny, P. Chelation with metal is not essential for antitumor photodynamic activity of sulfonated phthalocyanines. Photochem. Photobiol. 2002, 75, 527-533.
72. Karmakova, T.; Feofanov, A.; Nazarova, A.; Grichine, A.; Yakubovskaya, R.; Luk'yanets, E.; Maurizot, J.C.; Vigny, P. Distribution of metal-free sulfonated phthalocyanine in subcutaneously transplanted murine tumors. J. Photochem. Photobiol. B 2004, 75, 81-87. (Pubitemid 38987014)
73. Kolarova, H.; Nevrelova, P.; Bajgar, R.; Jirova, D.; Kejlova, K.; Strnad, M. In vitro photodynamic therapy on melanoma cell lines with phthalocyanine. Toxicol. In vitro 2007, 21, 249-253. (Pubitemid 46205090)
74. Ward, A.J.; Matthews, E.K. Cytotoxic, nuclear, and growth inhibitory effects of photodynamic drugs on pancreatic carcinoma cells. Cancer Lett. 1996, 102, 39-47. (Pubitemid 26097801)
75. Glassberg, E.; Lewandowski, L.; Lask, G.; Uitto, J. Laser-induced photodynamic therapy with aluminum phthalocyanine tetrasulfonate as the photosensitizer: Differential phototoxicity in normal and malignant human cells in vitro. J. Invest. Dermatol. 1990, 94, 604-610. (Pubitemid 20141277)
76. Tralau, C.J.; Macrobert, A.J.; Coleridge-Smith, P.D.; Barr, H.; Bown, S.G. Photodynamic therapy with phthalocyanine sensitisation: Quantitative studies in a transplantable rat fibrosarcoma. Br. J. Cancer 1987, 55, 389-395. (Pubitemid 17080798)
77. Chan, W.S.; Marshall, J.F.; Svensen, R.; Bedwell, J.; Hart, I.R. Effect of sulfonation on the cell and tissue distribution of the photosensitizer aluminum phthalocyanine. Cancer Res. 1990, 50, 4533-4538. (Pubitemid 20230388)
78. Chan, W.S.; West, C.M.; Moore, J.V.; Hart, I.R. Photocytotoxic efficacy of sulphonated species of aluminium phthalocyanine against cell monolayers, multicellular spheroids and in vivo tumours. Br. J. Cancer 1991, 64, 827-832.
79. Chan, W.S.; Brasseur, N.; La, M.C.; Ouellet, R.; van Lier, J.E. Efficacy and mechanism of aluminium phthalocyanine and its sulphonated derivatives mediated photodynamic therapy on murine tumours. Eur. J. Cancer 1997, 33, 1855-1859. (Pubitemid 28129217)
80. Stylli, S.S.; Hill, J.; Sawyer, W.; Kaye, A. Aluminium phthalocyanine mediated photodynamic therapy in experimental malignant glioma. J. Clin. Neurosci. 1995, 2, 146-151.
81. Stylli, S.S.; Hill, J.S.; Sawyer, W.H.; Kaye, A.H. Phthalocyanine photosensitizers for the treatment of brain tumours. J. Clin. Neurosci. 1995, 2, 64-72.
82. Sandeman, D.R.; Bradford, R.; Buxton, P.; Bown, S.G.; Thomas, D.G. Selective necrosis of malignant gliomas in mice using photodynamic therapy. Br. J. Cancer 1987, 55, 647-649. (Pubitemid 17090974)
83. Peng, Q.; Moan, J. Correlation of distribution of sulphonated aluminium phthalocyanines with their photodynamic effect in tumour and skin of mice bearing CaD2 mammary carcinoma. Br. J. Cancer 1995, 72, 565-574.
84. Paquette, B.; Ali, H.; Langlois, R.; van Lier, J.E. Biological activities of phthalocyanines-VIII. Cellular distribution in V-79 Chinese hamster cells and phototoxicity of selectively sulfonated aluminum phthalocyanines. Photochem. Photobiol. 1988, 47, 215-220.
85. Mathews, M.S.; Chighvinadze, D.; Gach, H.M.; Uzal, F.A.; Madsen, S.J.; Hirschberg, H. Cerebral edema following photodynamic therapy using endogenous and exogenous photosensitizers in normal brain. Lasers Surg. Med. 2011, 43, 892-900.
86. Gupta, S.; Dwarakanath, B.S.; Chaudhury, N.K.; Mishra, A.K.; Muralidhar, K.; Jain, V. In vitro and in vivo targeted delivery of photosensitizers to the tumor cells for enhanced photodynamic effects. J. Cancer Res. Ther. 2011, 7, 314-324.
87. Lagoda, T.S.; Kaplan, M.A.; Krivosheev, I.; Zhavoronkov, L.P.; Bokova, M.B. The optimization of a plan for the photodynamic therapy of sarcoma M1 using photosens. Vopr.Onkol. 2000, 46, 327-331.
88. Budzinskaia, M.V.; Likhvantseva, V.G.; Shevxchik, S.A.; Loshchenov, V.B.; Kuz'min, S.G.; Vorozhtsov, G.N. Experimental assessment of the capacities of use of photosense. Communication 2. Photodynamic therapy for epibulbar and choroid tumors. Vestn. Oftalmol. 2005, 121, 17-19.
89. Likhvantseva, V.G.; Osipova, E.A.; Petrenko, M.A.; Merzliakova, O.I.; Kuz'min, S.G.; Vorozhtsov, G.N. Analysis of changes in the accumulation of the photosensitizer Photosens, its elimination kinetics and distribution in the tissues of the eye and eyelids in health and in some tumorous processes. Vestn.Oftalmol. 2008, 124, 38-44.
90. Apolikhin, O.I. Adjuvant photodynamic therapy (PDT) with photosensitizer photosens for superficial bladder cancer. Experimental investigations to treat prostate cancer by PDT with photosens. Soc. Photo-Opt. Instrum. 2007, 8, 45.
91. Trushina, O.I.; Novikova, E.G.; Sokolov, V.V.; Filonenko, E.V.; Chissov, V.I.; Vorozhtsov, G.N. Photodynamic therapy of virus-associated precancer and early stages cancer of cervix uteri. Photodiagn. Photodyn. Ther. 2008, 5, 256-259.
92. Carcenac, M.; Larroque, C.; Langlois, R.; van Lier, J.E.; Artus, J.C.; Pelegrin, A. Preparation, phototoxicity and biodistribution studies of anti-carcinoembryonic antigen monoclonal antibodyphthalocyanine conjugates. Photochem. Photobiol. 1999, 70, 930-936. (Pubitemid 129548339)
93. Vrouenraets, M.B.; Visser, G.W.; Stigter, M.; Oppelaar, H.; Snow, G.B.; van Dongen, G.A. Comparison of aluminium (III) phthalocyanine tetrasulfonate- and meta-tetrahydroxyphenylchlorinmonoclonal antibody conjugates for their efficacy in photodynamic therapy in vitro. Int. J. Cancer 2002, 98, 793-798. (Pubitemid 34225634)
94. Vrouenraets, M.B.; Visser, G.W.; Loup, C.; Meunier, B.; Stigter, M.; Oppelaar, H.; Stewart, F.A.; Snow, G.B.; van Dongen, G.A. Targeting of a hydrophilic photosensitizer by use of internalizing monoclonal antibodies: A new possibility for use in photodynamic therapy. Int. J. Cancer 2000, 88, 108-114.
95. Gueddari, N.; Favre, G.; Hachem, H.; Marek, E., Le, G.F.; Soula, G. Evidence for up-regulated low density lipoprotein receptor in human lung adenocarcinoma cell line A549. Biochimie 1993, 75, 811-819. (Pubitemid 23337721)
96. Urizzi, P.; Allen, C.M.; Langlois, R.; Ouellet, R.; La Madeleine, C.; van Lier, J.E. Low-density lipoprotein-bound aluminum sulfophthalocyanine: Targeting tumor cells for photodynamic therapy. J. Porphyr. Phthalocya. 2001, 5, 154-160. (Pubitemid 32125236)
97. Xiao, D.; Wang, J.; Hampton, L.L.; Weber, H.C. The human gastrin-releasing peptide receptor gene structure, its tissue expression and promoter. Gene 2001, 264, 95-103. (Pubitemid 32195492)
98. Yegen, B.C. Bombesin-like peptides: Candidates as diagnostic and therapeutic tools. Curr. Pharm. Des. 2003, 9, 1013-1022. (Pubitemid 36452289)
99. Dubuc, C.; Langlois, R.; Benard, F.; Cauchon, N.; Klarskov, K.; Tone, P.; van Lier, J.E. Targeting gastrin-releasing peptide receptors of prostate cancer cells for photodynamic therapy with a phthalocyanine-bombesin conjugate. Bioorg. Med. Chem. Lett. 2008, 18, 2424-2427. (Pubitemid 351442889)
100. Gijsens, A.; Derycke, A.; Missiaen, L.; De, V.D.; Huwyler, J.; Eberle, A.; De, W.P. Targeting of the photocytotoxic compound AlPcS4 to Hela cells by transferrin conjugated PEG-liposomes. Int. J. Cancer 2002, 101, 78-85. (Pubitemid 34833001)
101. Derycke, A.S.; Kamuhabwa, A.; Gijsens, A.; Roskams, T.; De, V.D.; Kasran, A.; Huwyler, J.; Missiaen, L.; de Witte, P.A. Transferrin-conjugated liposome targeting of photosensitizer AlPcS4 to rat bladder carcinoma cells. J. Natl. Cancer Inst. 2004, 96, 1620-1630. (Pubitemid 39534886)
102. Bridges, K.R.; Smith, B.R. Discordance between transferrin receptor expression and susceptibility to lysis by natural-killer cells. J. Clin. Invest. 1985, 76, 913-918. (Pubitemid 16225583)
103. Qualls, M.M.; Thompson, D.H. Chloroaluminum phthalocyanine tetrasulfonate delivered via acid-labile diplasmenylcholine-folate liposomes: Intracellular localization and synergistic phototoxicity. Int. J. Cancer 2001, 93, 384-392. (Pubitemid 32592058)
104. Morgan, J.; Gray, A.G.; Huehns, E.R. Specific targeting and toxicity of sulphonated aluminium phthalocyanine photosensitised liposomes directed to cells by monoclonal antibody in vitro. Br. J. Cancer 1989, 59, 366-370. (Pubitemid 19099999)
105. Ben-Hur, E.; Rosenthal, I. Photosensitization of Chinese hamster cells by water-soluble phthalocyanines. Photochem. Photobiol. 1986, 43, 615-619.
106. Decreau, R.; Richard, M.J.; Julliard, M. Photodynamic therapy against achromic M6 melanocytes: Phototoxicity of lipophilic axially substituted aluminum phthalocyanines and hexadecahalogenated zinc phthalocyanines. J. Porphyr. Phthalocya. 2001, 5, 390-396. (Pubitemid 32472455)
107. Brasseur, N.; Ouellet, R.; La, M.C.; van Lier, J.E. Water-soluble aluminium phthalocyaninepolymer conjugates for PDT: Photodynamic activities and pharmacokinetics in tumour-bearing mice. Br. J. Cancer 1999, 80, 1533-1541. (Pubitemid 29308631)
108. Dye, D.; Watkins, J. Suspected anaphylactic reaction to cremophor El. Brit. Med. J. 1980, 280, 1353. (Pubitemid 10124276)
109. Torchilin, V.P. Cell penetrating peptide-modified pharmaceutical nanocarriers for intracellular drug and gene delivery. Biopolymers 2008, 90, 604-610.
110. van Nostrum, C.F. Polymeric micelles to deliver photosensitizers for photodynamic therapy. Adv. Drug Delivery Rev. 2004, 56, 9-16. (Pubitemid 38045421)
111. Iyer, A.K.; Khaled, G.; Fang, J.; Maeda, H. Exploiting the enhanced permeability and retention effect for tumor targeting. Drug Discov. Today 2006, 11, 812-818. (Pubitemid 44280021)
112. Matsumura, Y.; Maeda, H. A new concept for macromolecular therapeutics in cancerchemotherapy- Mechanism of tumoritropic accumulation of proteins and the antitumor agent Smancs. Cancer Res. 1986, 46, 6387-6392. (Pubitemid 17221789)
113. Oerlemans, C.; Bult, W.; Bos, M.; Storm, G.; Nijsen, J.F.W.; Hennink, W.E. Polymeric micelles in anticancer therapy: Targeting, imaging and triggered release. Pharm. Res. 2010, 27, 2569-2589.
114. Taillefer, J.; Jones, M.C.; Brasseur, N.; van Lier, J.E.; Leroux, J.C. Preparation and characterization of pH-responsive polymeric micelles for the delivery of photosensitizing anticancer drugs. J. Pharm. Sci. 2000, 89, 52-62. (Pubitemid 30080154)
115. Taillefer, J.; Brasseur, N.; van Lier, J.E.; Lenaerts, V.; Le, G.D.; Leroux, J.C. In-vitro and in-vivo evaluation of pH-responsive polymeric micelles in a photodynamic cancer therapy model. J. Pharm. Pharmacol. 2001, 53, 155-166. (Pubitemid 32156508)
116. Le, G.D.; Taillefer, J.; van Lier, J.E.; Lenaerts, V.; Leroux, J.C. Optimizing pH-responsive polymeric micelles for drug delivery in a cancer photodynamic therapy model. J. Drug Target 2002, 10, 429-437.
117. Williams, A.C.; Barry, B.W. Penetration enhancers. Adv. Drug Delivery Rev. 2004, 56, 603-618. (Pubitemid 38326936)
118. Kyriazi, M.; Alexandratou, E.; Yova, D.; Rallis, M.; Trebst, T. Topical photodynamic therapy of murine non-melanoma skin carcinomas with aluminum phthalocyanine chloride and a diode laser: Pharmacokinetics, tumor response and cosmetic outcomes. Photodermatol. Photoimmunol. Photomed. 2008, 24, 87-94. (Pubitemid 351436830)
119. Robinson, D.J.; de Bruijn, H.S.; van der Veen, N.; Stringer, M.R.; Brown, S.B.; Star, W.M. Fluorescence photobleaching of ALA-induced protoporphyrin IX during photodynamic therapy of normal hairless mouse skin: The effect of light dose and irradiance and the resulting biological effect. Photochem. Photobiol. 1998, 67, 140-149. (Pubitemid 128471972)
120. Kruijt, B.; van der Ploeg-van den Heuvel; de Bruijn, H.S.; Sterenborg, H.J.; Amelink, A.; Robinson, D.J. Monitoring interstitial m-THPC-PDT in vivo using fluorescence and reflectance spectroscopy. Lasers Surg. Med. 2009, 41, 653-664.
121. Wohrle, D.; Hirth, A.; Bogdahn-Rai, T.; Schnurpfeil, G.; Shopova, M. Photodynamic therapy of cancer: second and third generations of photosensitizers. Russ. Chem. Bull. 1998, 47, 807-816.
122. Kudrevich, S.; Brasseur, N.; La, M.C.; Gilbert, S.; van Lier, J.E. Syntheses and photodynamic activities of novel trisulfonated zinc phthalocyanine derivatives. J. Med. Chem. 1997, 40, 3897-3904. (Pubitemid 27512306)
123. Cauchon, N.; Tian, H.; Langlois, R.; La, M.C.; Martin, S.; Ali, H.; Hunting, D.; van Lier, J.E. Structure-photodynamic activity relationships of substituted zinc trisulfophthalocyanines. Bioconjug. Chem. 2005, 16, 80-89. (Pubitemid 40129680)
124. Potter, W.R.; Henderson, B.W.; Bellnier, D.A.; Pandey, R.K.; Vaughan, L.A.; Weishaupt, K.R.; Dougherty, T.J. Parabolic quantitative structure-activity relationships and photodynamic therapy: Application of a three-compartment model with clearance to the in vivo quantitative structureactivity relationships of a congeneric series of pyropheophorbide derivatives used as photosensitizers for photodynamic therapy. Photochem. Photobiol. 1999, 70, 781-788. (Pubitemid 129555012)
125. Liu, E.S.; Dai, Z.F.; Huang, J.D.; Chen, N.S.; Huang, J.L.; Huang, Z.Q.; Sun, J.C. Syntheses of metal phthalocyanines and their photoinactivations on cancer cells. Acta Biochim. Bioph. Sin. 1998, 30, 31-34.
126. Huang, J.L.; Chen, N.S.; Huang, J.D.; Liu, E.S.; Xue, J.P.; Yang, S.L.; Huang, Z.Q.; Sun, J.C. Metal phthalocyanine as photosensitizer for photodynamic therapy (PDT)-Preparation, characterization and anticancer activities of an amphiphilic phthalocyanine ZnPcS2P2. Sci. China Ser. B 2001, 44, 113-122.
127. Huang, H.F.; Chen, Y.Z.; Wu, Y. Experimental studies of the effects of ZnPcS2P2-basedphotodynamic therapy on bone marrow purging. Chin. Med. J. (Engl.) 2005, 118, 105-110. (Pubitemid 40227801)
128. Zhang, Z.; Jin, H.; Bao, J.; Fang, F.; Wei, J.; Wang, A. Intravenous repeated-dose toxicity study of ZnPcS2P2-based-photodynamic therapy in Wistar rats. Photochem. Photobiol. Sci. 2006, 5, 1006-1017. (Pubitemid 44673143)
129. Boyle, R.W.; Leznoff, C.C.; van Lier, J.E. Biological activities of phthalocyanines-XVI. Tetrahydroxy- and tetraalkylhydroxy zinc phthalocyanines. Effect of alkyl chain length on in vitro and in vivo photodynamic activities. Br. J. Cancer 1993, 67, 1177-1181. (Pubitemid 23172849)
130. Hu, M.; Brasseur, N.; Yildiz, S.Z.; van Lier, J.E.; Leznoff, C.C. Hydroxyphthalocyanines as potential photodynamic agents for cancer therapy. J. Med. Chem. 1998, 41, 1789-1802. (Pubitemid 28248655)
131. Winkelman, J.W.; Arad, D.; Kimel, S. Stereochemical factors in the transport and binding of photosensitizers in biological systems and in photodynamic therapy. J. Photochem. Photobiol. B 1993, 18, 181-189. (Pubitemid 23151450)
132. Fukushima, K.; Tabata, K.; Okura, I. Photochemical properties of water-soluble fluorinated zinc phthalocyanines and their photocytotoxicity against HeLa cells. J. Porphyr. Phthalocya. 1998, 2, 219-222. (Pubitemid 128543123)
133. Gao, L.; Qian, X.; Zhang, L.; Zhang, Y. Tetra-trifluoroethoxyl zinc phthalocyanine: potential photosensitizer for use in the photodynamic therapy of cancer. J. Photochem. Photobiol. B 2001, 65, 35-38. (Pubitemid 34145089)
134. O'Hagan, D.; Rzepa, H.S. Some influences of fluorine in bioorganic chemistry. Chem. Commun. 1997, 645-652. (Pubitemid 127498767)
135. Allemann, E.; Brasseur, N.; Benrezzak, O.; Rousseau, J.; Kudrevich, S.V.; Boyle, R.W.; Leroux, J.C.; Gurny, R.; van Lier, J.E. PEG-coated poly(lactic acid) nanoparticles for the delivery of hexadecafluoro zinc phthalocyanine to EMT-6 mouse mammary tumours. J. Pharm. Pharmacol. 1995, 47, 382-387.
136. Allemann, E.; Rousseau, J.; Brasseur, N.; Kudrevich, S.V.; Lewis, K.; van Lier, J.E. Photodynamic therapy of tumours with hexadecafluoro zinc phthalocynine formulated in PEGcoated poly(lactic acid) nanoparticles. Int. J. Cancer 1996, 66, 821-824. (Pubitemid 26199176)
137. Allemann, E.; Brasseur, N.; Kudrevich, S.V.; La, M.C.; van Lier, J.E. Photodynamic activities and biodistribution of fluorinated zinc phthalocyanine derivatives in the murine EMT-6 tumour model. Int. J. Cancer 1997, 72, 289-294. (Pubitemid 27314887)
138. Boyle, R.W.; Rousseau, J.; Kudrevich, S.V.; Obochi, M.; van Lier, J.E. Hexadecafluorinated zinc phthalocyanine: Photodynamic properties against the EMT-6 tumour in mice and pharmacokinetics using 65Zn as a radiotracer. Br.J. Cancer 1996, 73, 49-53.
139. Liu, J.Y.; Lo, P.C.; Fong, W.P.; Ng, D.K. Effects of the number and position of the substituents on the in vitro photodynamic activities of glucosylated zinc(II) phthalocyanines. Org. Biomol. Chem. 2009, 7, 1583-1591.
140. Choi, C.F.; Huang, J.D.; Lo, P.C.; Fong, W.P.; Ng, D.K. Glycosylated zinc(II) phthalocyanines as efficient photosensitisers for photodynamic therapy.
141. Airley, R.E.; Mobasheri, A. Hypoxic regulation of glucose transport, anaerobic metabolism and angiogenesis in cancer: Novel pathways and targets for anticancer therapeutics. Chemotherapy 2007, 53, 233-256. (Pubitemid 47074647)
142. Medina, R.A.; Owen, G.I. Glucose transporters: Expression, regulation and cancer. Biol. Res. 2002, 35, 9-26. (Pubitemid 34661867)
143. Ometto, C.; Fabris, C.; Milanesi, C.; Jori, G.; Cook, M.J.; Russell, D.A. Tumour-localising and -photosensitizing properties of a novel zinc(II) octadecylphthalocyanine. Br. J. Cancer 1996, 74, 1891-1899. (Pubitemid 27007132)
144. Fabris, C.; Ometto, C.; Milanesi, C.; Jori, G.; Cook, M.J.; Russell, D.A. Tumour-localizing and tumour-photosensitizing properties of zinc(II)-octapentyl-phthalocyanine. J. Photochem. Photobiol. B 1997, 39, 279-284.
145. Jori, G.; Reddi, E. The role of lipoproteins in the delivery of tumour-targeting photosensitizers. Int. J. Biochem. 1993, 25, 1369-1375. (Pubitemid 23285684)
146. Polo, L.; Reddi, E.; Garbo, G.M.; Morgan, A.R.; Jori, G. The distribution of the tumour photosensitizers Zn(II)-phthalocyanine and Sn(IV)-etiopurpurin among rabbit plasma proteins. Cancer Lett. 1992, 66, 217-223.
147. Liu, W.; Jensen, T.J.; Fronczek, F.R.; Hammer, R.P.; Smith, K.M.; Vicente, M.G. Synthesis and cellular studies of nonaggregated water-soluble phthalocyanines. J. Med. Chem. 2005, 48, 1033-1041. (Pubitemid 40270447)
148. Nesterova, I.V.; Erdem, S.S.; Pakhomov, S.; Hammer, R.P.; Soper, S.A. Phthalocyanine dimerization-based molecular beacons using near-IR fluorescence. J. Am. Chem. Soc. 2009, 131, 2432-2433.
149. Tyagi, S.; Kramer, F.R. Molecular beacons: Probes that fluoresce upon hybridization. Nat. Biotechnol. 1996, 14, 303-308.
150. Lo, P.C.; Zhao, B.; Duan, W.; Fong, W.P.; Ko, W.H.; Ng, D.K. Synthesis and in vitro photodynamic activity of mono-substituted amphiphilic zinc(II) phthalocyanines. Bioorg. Med. Chem. Lett. 2007, 17, 1073-1077. (Pubitemid 46177605)
151. Jeremy, M.B.; John, L.T.; Lubert, S. Biochemistry, 5th ed; W. H. Freeman and Company: New York, NY, USA, 2002.
152. Liu, J.Y.; Jiang, X.J.; Fong, W.P.; Ng, D.K. Highly photocytotoxic 1,4-dipegylated zinc(II) phthalocyanines. Effects of the chain length on the in vitro photodynamic activities. Org. Biomol. Chem. 2008, 6, 4560-4566.
153. Tuncel, S.; Dumoulin, F.; Gailer, J.; Sooriyaarachchi, M.; Atilla, D.; Durmus, M.; Bouchu, D.; Savoie, H.; Boyle, R.W.; Ahsen, V. A set of highly water-soluble tetraethyleneglycol-substituted Zn(II) phthalocyanines: Synthesis, photochemical and photophysical properties, interaction with plasma proteins and in vitro phototoxicity. Dalton Trans. 2011, 40, 4067-4079.
154. Bai, M.; Lo, P.C.; Ye, J.; Wu, C.; Fong, W.P.; Ng, D.K. Facile synthesis of pegylated zinc(II) phthalocyanines via transesterification and their in vitro photodynamic activities. Org. Biomol. Chem. 2011, 9, 7028-7032.
155. Banfi, S.; Caruso, E.; Buccafurni, L.; Ravizza, R.; Gariboldi, M.; Monti, E. Zinc phthalocyaninesmediated photodynamic therapy induces cell death in adenocarcinoma cells. J. Organomet. Chem. 2007, 692, 1269-1276. (Pubitemid 46209196)
156. Ball, D.J.; Mayhew, S.; Wood, S.R.; Griffiths, J.; Vernon, D.I.; Brown, S.B. A comparative study of the cellular uptake and photodynamic efficacy of three novel zinc phthalocyanines of differing charge. Photochem. Photobiol. 1999, 69, 390-396. (Pubitemid 129554868)
157. Cruse-Sawyer, J.E.; Griffiths, J.; Dixon, B.; Brown, S.B. The photodynamic response of two rodent tumour models to four zinc (II)-substituted phthalocyanines. Br. J. Cancer 1998, 77, 965-972. (Pubitemid 28101787)
158. Sibrian-Vazquez, M.; Ortiz, J.; Nesterova, I.V.; Fernandez-Lazaro, F.; Sastre-Santos, A.; Soper, S.A.; Vicente, M.G. Synthesis and properties of cell-targeted Zn(II)-phthalocyanine-peptide conjugates. Bioconjug. Chem. 2007, 18, 410-420. (Pubitemid 46493512)
159. Torchilin, V.P. Targeted pharmaceutical nanocarriers for cancer therapy and imaging. AAPS J. 2007, 9, E128-E147.
160. Liu, R.; Cannon, J.B.; Paspal, S.Y.L. Liposomes in solubilization. In Water-Insoluble Drug Formulation; Liu, R., Ed.; CRC Press: Boca Raton, FL, USA, 2008; pp. 375-409.
161. Rodal, G.H.; Rodal, S.K.; Moan, J.; Berg, K. Liposome-bound Zn (II)-phthalocyanine. Mechanisms for cellular uptake and photosensitization. J. Photochem. Photobiol. B 1998, 45, 150-159. (Pubitemid 28550191)
162. Valduga, G.; Reddi, E.; Garbisa, S.; Jori, G. Photosensitization of cells with different metastatic potentials by liposome-delivered Zn(II)- phthalocyanine. Int. J. Cancer 1998, 75, 412-417. (Pubitemid 28100045)
163. Milanesi, C.; Zhou, C.; Biolo, R.; Jori, G. Zn(II)-phthalocyanine as a photodynamic agent for tumours. II. Studies on the mechanism of photosensitised tumour necrosis. Br. J. Cancer 1990, 61, 846-850. (Pubitemid 20196989)
164. Ben-Hur, E.; Chan, W.S. Phthalocyanines in photobiology and their medical applications. In The Porphyrin Handbook; Kadish, K.M., Smith, K.M., Guilard, R., Eds; Academic Press: San Diego, CA, USA, 2003; pp. 1-35.
165. Allison, B.A.; Pritchard, P.H.; Richter, A.M.; Levy, J.G. The plasma distribution of benzoporphyrin derivative and the effects of plasma-lipoproteins on its biodistribution. Photochem. Photobiol. 1990, 52, 501-507.
166. Allison, B.A.; Pritchard, P.H.; Levy, J.G. Evidence for low-density-lipoprotein receptor-mediated uptake of benzoporphyrin derivative. Br. J. Cancer 1994, 69, 833-839. (Pubitemid 24140660)
167. Polo, L.; Bianco, G.; Reddi, E.; Jori, G. The effect of different liposomal formulations on the interaction of Zn(II)-phthalocyanine with isolated low and high density lipoproteins. Int. J. Biochem. Cell Biol. 1995, 27, 1249-1255.
168. Reddi, E.; Zhou, C.; Biolo, R.; Menegaldo, E.; Jori, G. Liposome- or LDL-administered Zn (II)- phthalocyanine as a photodynamic agent for tumours. I. Pharmacokinetic properties and phototherapeutic efficiency. Br. J. Cancer 1990, 61, 407-411. (Pubitemid 20106015)
169. Schmidt-Erfurth, U.; Michels, S.; Indorf, L.; Eggers, R.; Birngruber, R. Mechanism of photodynamic occlusion using liposomal Zn(II)-phtalocyanine. Curr. Eye Res. 2005, 30, 601-612. (Pubitemid 41113563)
170. Gal, D.; Macdonald, P.C.; Porter, J.C.; Simpson, E.R. Cholesterol-metabolism in cancer-cells in monolayer-culture. III. Low-density lipoprotein metabolism. Int. J. Cancer 1981, 28, 315-319. (Pubitemid 11055999)
171. Love, W.G.; Duk, S.; Biolo, R.; Jori, G.; Taylor, P.W. Liposome-mediated delivery of photosensitizers: Localization of zinc (II)-phthalocyanine within implanted tumors after intravenous administration. Photochem. Photobiol. 1996, 63, 656-661. (Pubitemid 126467143)
172. van Leengoed, H.L.; Cuomo, V.; Versteeg, A.A.; van der Veen, N.; Jori, G.; Star, W.M. In vivo fluorescence and photodynamic activity of zinc phthalocyanine administered in liposomes. Br. J. Cancer 1994, 69, 840-845. (Pubitemid 24140661)
173. Schieweck, K.; Capraro, H.G.; Isele, U.; van Hoogevest, P.; Ochsner, M.; Maurer, T.; Batt, E. CGP 55847, liposome-delivered zinc(II) phthalocyanine as phototherapeutic agent for tumours. Proc. SPIE Int.Soc.Opt.Eng. 1994, 2078, 107-118.
174. Gelperina, S.; Kisich, K.; Iseman, M.D.; Heifets, L. The potential advantages of nanoparticle drug delivery systems in chemotherapy of tuberculosis. Am. J. Respir.Crit. Care Med. 2005, 172, 1487-1490. (Pubitemid 43076534)
175. Betancourt, T.; Byrne, J.D.; Sunaryo, N.; Crowder, S.W.; Kadapakkam, M.; Patel, S.; Casciato, S.; Brannon-Peppas, L. PEGylation strategies for active targeting of PLA/PLGA nanoparticles. J. Biomed. Mater. Res. Part A 2009, 91A, 263-276.
176. Fattal, E.; Vauthier, C. Nanoparticles as Drug Delivery Systems. In Encyclopedia of Pharmaceutical Technology; Swarbrick, J., Boylan, J.C., Eds; Marcel Dekker, Inc.: New York, NY, USA, 2011; pp. 1864-1882.
177. Fadel, M.; Kassab, K.; Fadeel, D.A. Zinc phthalocyanine-loaded PLGA biodegradable nanoparticles for photodynamic therapy in tumor-bearing mice. Lasers Med. Sci. 2010, 25, 283-292.
178. Lu, H.L.; Syu, W.J.; Nishiyama, N.; Kataoka, K.; Lai, P.S. Dendrimer phthalocyanine-encapsulated polymeric micelle-mediated photochemical internalization extends the efficacy of photodynamic therapy and overcomes drug-resistance in vivo. J. Control. Release 2011, 155, 458-464.
179. Herlambang, S.; Kumagai, M.; Nomoto, T.; Horie, S.; Fukushima, S.; Oba, M.; Miyazaki, K.; Morimoto, Y.; Nishiyama, N.; Kataoka, K. Disulfide crosslinked polyion complex micelles encapsulating dendrimer phthalocyanine directed to improved efficiency of photodynamic therapy. J. Control. Release 2011, 155, 449-457.
180. Nishiyama, N.; Nakagishi, Y.; Morimoto, Y.; Lai, P.S.; Miyazaki, K.; Urano, K.; Horie, S.; Kumagai, M.; Fukushima, S.; Cheng, Y.; et al. Enhanced photodynamic cancer treatment by supramolecular nanocarriers charged with dendrimer phthalocyanine. J. Control. Release 2009, 133, 245-251.
181. Jang, W.D.; Nakagishi, Y.; Nishiyama, N.; Kawauchi, S.; Morimoto, Y.; Kikuchi, M.; Kataoka, K. Polyion complex micelles for photodynamic therapy: Incorporation of dendritic photosensitizer excitable at long wavelength relevant to improved tissue-penetrating property. J. Control. Release 2006, 113, 73-79. (Pubitemid 43818161)
182. Baugh, S.D.; Yang, Z.; Leung, D.K.; Wilson, D.M.; Breslow, R. Cyclodextrin dimers as cleavable carriers of photodynamic sensitizers. J. Am. Chem. Soc. 2001, 123, 12488-12494. (Pubitemid 33140374)
183. Ruebner, A.; Kirsch, D.; Andrees, S.; Decker, W.; Roeder, B.; Spengler, B.; Kaufmann, R.; Moser, J.G. Dimeric cyclodextrin carriers with high binding affinity to porphyrinoid photosensitizers. J. Inclus. Phenom. Mol. 1997, 27, 69-84.
184. Rossetti, F.C.; Lopes, L.B.; Carollo, A.R.; Thomazini, J.A.; Tedesco, A.C.; Bentley, M.V. A delivery system to avoid self-aggregation and to improve in vitro and in vivo skin delivery of a phthalocyanine derivative used in the photodynamic therapy. J. Control. Release 2011, 155, 400-408.
185. Rodriguez, M.E.; Diz, V.E.; Awruch, J.; Dicelio, L.E. Photophysics of zinc (II) phthalocyanine polymer and gel formulation. Photochem. Photobiol. 2010, 86, 513-519.
186. Souza, J.G.; Gelfuso, G.M.; Simao, P.S.; Borges, A.C.; Lopez, R.F. Iontophoretic transport of zinc phthalocyanine tetrasulfonic acid as a tool to improve drug topical delivery. Anti-Cancer Drugs 2011, 22, 783-793.
187. He, J.; Larkin, H.E.; Li, Y.S.; Rihter, D.; Zaidi, S.I.; Rodgers, M.A.; Mukhtar, H.; Kenney, M.E.; Oleinick, N.L. The synthesis, photophysical and photobiological properties and in vitro structureactivity relationships of a set of silicon phthalocyanine PDT photosensitizers. Photochem. Photobiol. 1997, 65, 581-586. (Pubitemid 27159001)
188. Rodriguez, M.E.; Zhang, P.; Azizuddin, K.; Delos Santos, G.B.; Chiu, S.M.; Xue, L.Y.; Berlin, J.C.; Peng, X.; Wu, H.; Lam, M.; et al. Structural factors and mechanisms underlying the improved photodynamic cell killing with silicon phthalocyanine photosensitizers directed to lysosomes versus mitochondria. Photochem. Photobiol. 2009, 85, 1189-1200.
189. Lo, P.C.; Huang, J.D.; Cheng, D.Y.; Chan, E.Y.; Fong, W.P.; Ko, W.H.; Ng, D.K. New amphiphilic silicon(IV) phthalocyanines as efficient photosensitizers for photodynamic therapy: Synthesis, photophysical properties, and in vitro photodynamic activities. Chemistry 2004, 10, 4831-4838.
190. Lo, P.C.; Chan, C.M.; Liu, J.Y.; Fong, W.P.; Ng, D.K. Highly photocytotoxic glucosylated silicon(IV) phthalocyanines. Effects of peripheral chloro substitution on the photophysical and photodynamic properties. J. Med. Chem. 2007, 50, 2100-2107. (Pubitemid 46683063)
191. Leung, S.C.H.; Lo, P.C.; Ng, D.K.P.; Liu, W.K.; Fung, K.P.; Fong, W.P. Photodynamic activity of BAM-SiPc, an unsymmetrical bisamino silicon(IV) phthalocyanine, in tumour-bearing nude mice. Br. J. Pharmacol. 2008, 154, 4-12. (Pubitemid 351620408)
192. Lai, J.C.; Lo, P.C.; Ng, D.K.; Ko, W.H.; Leung, S.C.; Fung, K.P.; Fong, W.P. BAM-SiPc, a novel agent for photodynamic therapy, induces apoptosis in human hepatocarcinoma HepG2 cells by a direct mitochondrial action. Cancer Biol. Ther. 2006, 5, 413-418.
193. Barge, J.; Decreau, R.; Julliard, M.; Hubaud, J.C.; Sabatier, A.S.; Grob, J.J.; Verrando, P. Killing efficacy of a new silicon phthalocyanine in human melanoma cells treated with photodynamic therapy by early activation of mitochondrion-mediated apoptosis. Exp. Dermatol. 2004, 13, 33-44. (Pubitemid 38165436)
194. Anderson, C.Y.; Freye, K.; Tubesing, K.A.; Li, Y.S.; Kenney, M.E.; Mukhtar, H.; Elmets, C.A. A comparative analysis of silicon phthalocyanine photosensitizers for in vivo photodynamic therapy of RIF-1 tumors in C3H mice. Photochem. Photobiol. 1998, 67, 332-336. (Pubitemid 128472248)
195. Jiang, X.J.; Yeung, S.L.; Lo, P.C.; Fong, W.P.; Ng, D.K. Phthalocyanine-polyamine conjugates as highly efficient photosensitizers for photodynamic therapy. J. Med. Chem. 2011, 54, 320-330.
196. Leng, X.; Choi, C.F.; Lo, P.C.; Ng, D.K. Assembling a mixed phthalocyanine-porphyrin array in aqueous media through host-guest interactions. Org. Lett. 2007, 9, 231-234.
197. Lau, J.T.; Lo, P.C.; Fong, W.P.; Ng, D.K. Preparation and photodynamic activities of silicon(IV) phthalocyanines substituted with permethylated beta-cyclodextrins. Chemistry 2011, 17, 7569-7577.
198. Lau, J.T.; Lo, P.C.; Tsang, Y.M.; Fong, W.P.; Ng, D.K. Unsymmetrical beta-cyclodextrinconjugated silicon(IV) phthalocyanines as highly potent photosensitisers for photodynamic therapy. Chem. Commun. (Camb.) 2011, 47, 9657-9659.
199. Chan, C.M.; Lo, P.C.; Yeung, S.L.; Ng, D.K.; Fong, W.P. Photodynamic activity of a glucoconjugated silicon(IV) phthalocyanine on human colon adenocarcinoma. Cancer Biol. Ther. 2010, 10, 126-134.
200. Agarwal, M.L.; Clay, M.E.; Harvey, E.J.; Evans, H.H.; Antunez, A.R.; Oleinick, N.L. Photodynamic therapy induces rapid cell death by apoptosis in L5178Y mouse lymphoma cells. Cancer Res. 1991, 51, 5993-5996.
201. Ahmad, N.; Feyes, D.K.; Agarwal, R.; Mukhtar, H. Photodynamic therapy results in induction of WAF1/CIP1/P21 leading to cell cycle arrest and apoptosis. Proc. Natl. Acad. Sci. USA 1998, 95, 6977-6982. (Pubitemid 28278092)
202. Colussi, V.C.; Feyes, D.K.; Mulvihill, J.W.; Li, Y.S.; Kenney, M.E.; Elmets, C.A.; Oleinick, N.L.; Mukhtar, H. Phthalocyanine 4 (Pc4) photodynamic therapy of human OVCAR-3 tumor xenografts. Photochem. Photobiol. 1999, 69, 236-241. (Pubitemid 129606912)
203. Whitacre, C.M.; Feyes, D.K.; Satoh, T.; Grossmann, J.; Mulvihill, J.W.; Mukhtar, H.; Oleinick, N.L. Photodynamic therapy with the phthalocyanine photosensitizer Pc 4 of SW480 human colon cancer xenografts in athymic mice. Clin. Cancer Res. 2000, 6, 2021-2027. (Pubitemid 30305101)
204. Whitacre, C.M.; Satoh, T.H.; Xue, L.; Gordon, N.H.; Oleinick, N.L. Photodynamic therapy of human breast cancer xenografts lacking caspase-3. Cancer Lett. 2002, 179, 43-49. (Pubitemid 34195652)
205. Fei, B.; Wang, H.; Meyers, J.D.; Feyes, D.K.; Oleinick, N.L.; Duerk, J.L. High-field magnetic resonance imaging of the response of human prostate cancer to Pc 4-based photodynamic therapy in an animal model. Lasers Surg. Med. 2007, 39, 723-730. (Pubitemid 350086407)
206. Lee, R.G.; Vecchiotti, M.A.; Heaphy, J.; Panneerselvam, A.; Schluchter, M.D.; Oleinick, N.L.; Lavertu, P.; Alagramam, K.N.; Arnold, J.E.; Sprecher, R.C. Photodynamic therapy of cottontail rabbit papillomavirus-induced papillomas in a severe combined immunodeficient mouse xenograft system. Laryngoscope 2010, 120, 618-624.
207. Agarwal, R.; Korman, N.J.; Mohan, R.R.; Feyes, D.K.; Jawed, S.; Zaim, M.T.; Mukhtar, H. Apoptosis is an early event during phthalocyanine photodynamic therapy-induced ablation of chemically induced squamous papillomas in mouse skin. Photochem. Photobiol. 1996, 63, 547-552. (Pubitemid 126468334)
208. George, J.E., Ahmad, Y.; Varghai, D.; Li, X.; Berlin, J.; Jackowe, D.; Jungermann, M.; Wolfe, M.S.; Lilge, L.; Totonchi, A.; et al. Pc 4 photodynamic therapy of U87-derived human glioma in the nude rat. Lasers Surg. Med. 2005, 36, 383-389. (Pubitemid 40942153)
209. Oleinick, N.L.; Morris, R.L.; Belichenko, T. The role of apoptosis in response to photodynamic therapy: What, where, why, and how. Photochem. Photobiol. Sci. 2002, 1, 1-21. (Pubitemid 37069701)
210. Anderson, C.; Hrabovsky, S.; McKinley, Y.; Tubesing, K.; Tang, H.P.; Dunbar, R.; Mukhtar, H.; Elmets, C.A. Phthalocyanine photodynamic therapy: Disparate effects of pharmacologic inhibitors on cutaneous photosensitivity and on tumor regression. Photochem. Photobiol. 1997, 65, 895-901. (Pubitemid 27235805)
211. Lam, M.; Hsia, A.H.; Liu, Y.; Guo, M.; Swick, A.R.; Berlin, J.C.; McCormick, T.S.; Kenney, M.E.; Oleinick, N.L.; Cooper, K.D.; et al. Successful cutaneous delivery of the photosensitizer silicon phthalocyanine 4 for photodynamic therapy. Clin. Exp. Dermatol. 2011, 36, 645-651.
212. Baron, E.D.; Malbasa, C.L.; Santo-Domingo, D.; Fu, P.; Miller, J.D.; Hanneman, K.K.; Hsia, A.H.; Oleinick, N.L.; Colussi, V.C.; Cooper,K.D. Silicon phthalocyanine (Pc 4) photodynamic therapy is a safe modality for cutaneous neoplasms: Results of a phase 1 clinical trial. Lasers Surg. Med. 2010, 42, 728-735.
213. Choi, C.F.; Tsang, P.T.; Huang, J.D.; Chan, E.Y.; Ko, W.H.; Fong, W.P.; Ng, D.K. Synthesis and in vitro photodynamic activity of new hexadeca-carboxy phthalocyanines. Chem. Commun. (Camb.) 2004, 19, 2236-2237. (Pubitemid 39472556)
214. Huang, J.D.; Fong, W.P.; Chan, E.Y.M.; Choi, M.T.M.; Chan, W.K.; Chan, M.C.; Ng, K.P. Photodynamic activities of a dicationic silicon(IV) phthalocyanine and its bovine serum albumin conjugates. Tetrahedron Lett. 2003, 44, 8029-8032. (Pubitemid 37186973)
215. Huang, J.D.; Wang, S.Q.; Lo, P.C.; Fong, W.P.; Ko, W.H.; Ng, D.K.P. Halogenated silicon(IV) phthalocyanines with axial poly(ethylene glycol) chains. Synthesis, spectroscopic properties, complexation with bovine serum albumin and in vitro photodynamic activities. New J. Chem. 2004, 28, 348-354. (Pubitemid 38373020)
216. Lee, P.P.S.; Ngai, T.; Huang, J.D.; Wu, C.; Fong, W.P.; Ng, D.K.P. Synthesis, characterization, biodegradation, and in vitro photodynamic activities of silicon(IV) phthalocyanines conjugated axially with poly(epsilon-caprolactone). Macromolecules 2003, 36, 7527-7533.
217. Lee, P.P.S.; Lo, P.C.; Chan, E.Y.M.; Fong, W.P.; Ko, W.H.; Ng, D.K.P. Synthesis and in vitro photodynamic activity of novel galactose-containing phthalocyanines. Tetrahedron Lett. 2005, 46, 1551-1554. (Pubitemid 40220294)
218. Lo, P.C.; Leung, S.C.H.; Chan, E.Y.M.; Fong, W.P.; Ko, W.H.; Ng, D.K.P. Photodynamic effects of a novel series of silicon(IV) phthalocyanines against human colon adenocarcinoma cells. Photodiagn. Photodyn. Ther. 2007, 4, 117-123. (Pubitemid 46720162)
219. Master, A.M.; Rodriguez, M.E.; Kenney, M.E.; Oleinick, N.L.; Sen Gupta, A. Delivery of the photosensitizer Pc4 in PEG-PCL micelles for in vitro PDT studies. J. Pharm. Sci. 2010, 99, 2386-2398.
220. Roy, I.; Ohulchanskyy, T.Y.; Pudavar, H.E.; Bergey, E.J.; Oseroff, A.R.; Morgan, J.; Dougherty, T.J.; Prasad, P.N. Ceramic-based nanoparticles entrapping water-insoluble photosensitizing anticancer drugs: A novel drug-carrier system for photodynamic therapy. J. Am. Chem. Soc. 2003, 125, 7860-7865. (Pubitemid 36782161)
221. Zhao, B.Z.; Yin, J.J.; Bilski, P.J.; Chignell, C.F.; Roberts, J.E.; He, Y.Y. Enhanced photodynamic efficacy towards melanoma cells by encapsulation of Pc4 in silica nanoparticles. Toxicol. Appl. Pharm. 2009, 241, 163-172.
222. Cheng, Y.; Samia, A.C.; Meyers, J.D.; Panagopoulos, I.; Fei, B.W.; Burda, C. Highly efficient drug delivery with gold nanoparticle vectors for in vivo photodynamic therapy of cancer. J. Am. Chem. Soc. 2008, 130, 10643-10647.
223. Li, H.; Marotta, D.E.; Kim, S.; Busch, T.M.; Wileyto, E.P.; Zheng, G. High payload delivery of optical imaging and photodynamic therapy agents to tumors using phthalocyanine-reconstituted low-density lipoprotein nanoparticles. J. Biomed. Opt. 2005, 10, 41203.
224. Zheng, G.; Chen, J.; Li, H.; Glickson, J.D. Rerouting lipoprotein nanoparticles to selected alternate receptors for the targeted delivery of cancer diagnostic and therapeutic agents. Proc. Natl. Acad. Sci. USA 2005, 102, 17757-17762. (Pubitemid 41803570)
225. Juan, C.; Ian, R.C.; Gang, Z. Novel targeting and activation strategies for photodynamic therapy. In Proceedings of Light-activated Tissue Regeneration and Therapy Conference; Ronald, W., Darrell, B.T., Eds.; Springer: New York, NY, USA, 2008; pp. 127-147.
226. Dutta, S.; Ongarora, B.G.; Li, H.; Vicente, M.G.; Kolli, B.K.; Chang, K.P. Intracellular targeting specificity of novel phthalocyanines assessed in a host-parasite model for developing potential photodynamic medicine. PLoS One 2011, 6, e20786.
227. Giuliani, F.; Martinelli, M.; Cocchi, A.; Arbia, D.; Fantetti, L.; Roncucci, G. In vitro resistance selection studies of RLP068/Cl, a new Zn(II) phthalocyanine suitable for antimicrobial photodynamic therapy. Antimicrob. Agents Chemother. 2010, 54, 637-642.
228. Mantareva, V.; Angelov, I.; Kussovski, V.; Dimitrov, R.; Lapok, L.; Wöhrle, D. Photodynamic efficacy of water-soluble Si(IV) and Ge(IV) phthalocyanines towards Candida albicans planktonic and biofilm cultures. Eur. J. Med. Chem. 2011, 46, 4430-4440.
229. Longo, J.P.; Leal, S.C.; Simioni, A.R.; de Fatima M.A.-S.; Tedesco, A.C.; Azevedo, R.B. Photodynamic therapy disinfection of carious tissue mediated by aluminum-chloridephthalocyanine entrapped in cationic liposomes: An in vitro and clinical study. Lasers Med. Sci. 2011, Epub ahead of print.
230. Montanari, J.; Maidana, C.; Esteva, M.I.; Salomon, C.; Morilla, M.J.; Romero, E.L. Sunlight triggered photodynamic ultradeformable liposomes against Leishmania braziliensis are also leishmanicidal in the dark. J. Control. Release 2010, 147, 368-376.
231. van den, B.H. Photodynamic therapy of age-related macular degeneration: History and principles. Semin. Ophthalmol. 2001, 16, 181-200.
232. Lange, N.; Jichlinski, P.; Zellweger, M.; Forrer, M.; Marti, A.; Guillou, L.; Kucera, P.; Wagnieres, G.; van den, B.H. Photodetection of early human bladder cancer based on the fluorescence of 5-aminolaevulinic acid hexylester-induced protoporphyrin IX: A pilot study. Br. J. Cancer 1999, 80, 185-193. (Pubitemid 29210105)
233. Stepp, H.; Beck, T.; Pongratz, T.; Meinel, T.; Kreth, F.W.; Tonn, J.C.; Stummer, W. ALA and malignant glioma: Fluorescence-guided resection and photodynamic treatment. J. Environ. Pathol. Toxicol.Oncol. 2007, 26, 157-164. (Pubitemid 47295558)
234. Stummer, W.; Novotny, A.; Stepp, H.; Goetz, C.; Bise, K.; Reulen, H.J. Fluorescence-guided resection of glioblastoma multiforme by using 5-aminolevulinic acid-induced porphyrins: A prospective study in 52 consecutive patients. J. Neurosurg. 2000, 93, 1003-1013. (Pubitemid 32800611)
235. Marcus, S.L.; Sobel, R.S.; Golub, A.L.; Carroll, R.L.; Lundahl, S.; Shulman, D.G. Photodynamic therapy (PDT) and photodiagnosis (PD) using endogenous photosensitization induced by 5-aminolevulinic acid (ALA): Current clinical and development status. J. Clin. Laser Med. Surg. 1996, 14, 59-66. (Pubitemid 26141159)
236. Zellweger, M.; Radu, A.; Monnier, P.; van den, B.H.; Wagnieres, G. Fluorescence pharmacokinetics of Lutetium Texaphyrin (PCI-0123, Lu-Tex) in the skin and in healthy and tumoral hamster cheek-pouch mucosa. J. Photochem. Photobiol. B 2000, 55, 56-62. (Pubitemid 30311698)
237. Glanzmann, T.; Forrer, M.; Blant, S.A.; Woodtli, A.; Grosjean, P.; Braichotte, D.; van den, B.H.; Monnier, P.; Wagnieres, G. Pharmacokinetics and pharmacodynamics of tetra(mhydroxyphenyl) chlorin in the hamster cheek pouch tumor model: Comparison with clinical measurements. J. Photochem. Photobiol. B 2000, 57, 22-32.
238. Fotinos, N.; Campo, M.A.; Popowycz, F.; Gurny, R.; Lange, N. 5-Aminolevulinic acid derivatives in photomedicine: Characteristics, application and perspectives. Photochem. Photobiol. 2006, 82, 994-1015. (Pubitemid 44450185)
239. Rao, J.; Dragulescu-Andrasi, A.; Yao, H. Fluorescence imaging in vivo: Recent advances. Curr. Opin. Biotechnol. 2007, 18, 17-25. (Pubitemid 46237739)
240. Dumoulin, F.; Durmus, M.; Ahsen, V.; Nyokong, T. Synthetic pathways to water-soluble phthalocyanines and close analogs. Coordin. Chem. Rev. 2010, 254, 2792-2847.
241. Gabriel, D.; Zuluaga, M.F.; Lange, N. On the cutting edge: protease-sensitive prodrugs for the delivery of photoactive compounds. Photochem. Photobiol. Sci. 2011, 10, 689-703.
242. Weissleder, R.; Tung, C.H.; Mahmood, U.; Bogdanov, A., Jr. In vivo imaging of tumors with protease-activated near-infrared fluorescent probes. Nat. Biotechnol. 1999, 17, 375-378. (Pubitemid 29166041)
243. Campo, M.A.; Gabriel, D.; Kucera, P.; Gurny, R.; Lange, N. Polymeric photosensitizer prodrugs for photodynamic therapy. Photochem. Photobiol. 2007, 83, 958-965. (Pubitemid 47087386)
244. Gabriel, D.; Campo, M.A.; Gurny, R.; Lange, N. Tailoring protease-sensitive photodynamic agents to specific disease-associated enzymes. Bioconjug. Chem. 2007, 18, 1070-1077. (Pubitemid 47122626)
245. Gabriel, D.; Busso, N.; So, A.; van den, B.H.; Gurny, R.; Lange, N. Thrombin-sensitive photodynamic agents: A novel strategy for selective synovectomy in rheumatoid arthritis. J. Control. Release 2009, 138, 225-234.
246. Segalla, A.; Milanesi, C.; Jori, G.; Capraro, H.G.; Isele, U.; Schieweck, K. CGP 55398, a liposomal Ge(IV) phthalocyanine bearing two axially ligated cholesterol moieties: A new potential agent for photodynamic therapy of tumours. Br. J. Cancer 1994, 69, 817-825. (Pubitemid 24140658)
247. de Oliveira, K.T.; de Assis, F.F.; Ribeiro, A.O.; Neri, C.R.; Fernandes, A.U.; Baptista, M.S.; Lopes, N.P.; Serra, O.A.; Iamamoto, Y. Synthesis of phthalocyanines-ALA conjugates: Water-soluble compounds with low aggregation. J. Org. Chem. 2009, 74, 7962-7965.
248. Seotsanyana-Mokhosi, I.; Kresfelder, T.; Abrahamse, H.; Nyokong, T. The effect of Ge, Si and Sn phthalocyanine photo sensitizers on cell proliferation and viability of human oesophageal carcinoma cells. J. Photochem. Photobiol. B 2006, 83, 55-62. (Pubitemid 43372643)
249. Durmus, M.; Ahsen, V. Water-soluble cationic gallium(III) and indium(III) phthalocyanines for photodynamic therapy. J. Inorg. Biochem. 2010, 104, 297-309.