Porphycene for cancer photochemotherapy and other biomedical applications;Porficenos para la fotoquimioterapia del cáncer y otras aplicaciones biomédicas

Afinidad

Volumn 59, Issue 500, 2002, Pages 343-356

  Arad, Ofir ^a   Gavaldá, Ana ^a   Rey, Óscar ^a   Rubio, Noemi ^a   Sánchez García, David ^a   Borrell, José I ^a   Teixidó, Jordi ^a   Nonell, Santiago ^a   Cañete, Magdalena ^b   Juarranz, Angeles ^b   Villanueva, Angeles ^b   Stockert, Juan C ^b   Díaz Jiménez, Pablo J ^c  

^a INSTITUT QUÍMIC DE SARRIÀ   (Spain)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^c HOSPITAL UNIVERSITARI DE BELLVITGE   (Spain)

Author keywords

Cancer; Photochemotherapy; Photodetection (PD); Photodynamic therapy (PDT); Photosensitizers; Porphycenes

Indexed keywords

AMINOLEVULINIC ACID; ASPARTYLCHLORIN E6; BENZOPORPHYRIN DERIVATIVE; LUTETIUM TEXAPHYRIN; PHOTOFRIN; PHOTOFRIN II; PHOTOSENSITIZING AGENT; PORPHYCENE; PORPHYRIN DERIVATIVE; PROTOPORPHYRIN; PURLYTIN; PURYLTIN; TEMOPORFIN; UNCLASSIFIED DRUG;

ARTERIOSCLEROSIS; ARTICLE; CANCER; CANCER CHEMOTHERAPY; CANCER DIAGNOSIS; CLINICAL PRACTICE; DRUG EFFECT; DRUG FORMULATION; DRUG INDICATION; DRUG MECHANISM; DRUG STRUCTURE; DRUG TRANSPORT; HUMAN; NONHUMAN; PHOTOCHEMOTHERAPY; PHOTODYNAMIC THERAPY; RETINA MACULA DEGENERATION; SKIN DISEASE; SOLID TUMOR; TUMOR LOCALIZATION; UTERUS DISEASE; VIRUS INACTIVATION;

EID: 0036664932     PISSN: 00019704     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (95)

1. Daniell, M.D.; Hill, J.S.: ←A History of Photodynamic Therapy→. Aust. N. Z. J. Surg. 1991, 61, 340-348.
2. Bonnett, R.: ←Chemical Aspects of Photodynamic Therapy→; Gordon and Breach Science Publishers: Amsterdam, 2000.
3. Spikes, J.D.: ←Historical Review - Photodynamic Action: from Paramecium to Photochemotherapy→. Photochem. Photobiol. 1997, 65, 142-147.
4. Raab, O.: ←Über die Wirkung Fluoreszierender Stoffe auf Infusorien→. Z. Biol. 1900, 39, 524-546.
5. Von Tappeiner, H.: ←Über die Wirkung Fluoreszierender Stoffe auf Infusorien nach Versuchen von O. Raab→. Muench. Med. Wochenschr. 1900, 47, 5-7.
6. Von Tappeiner, H.; Jesionek, A.: ←Therapeutische Versuche mit Fluoreszierenden Stoffen→. Muench Med. Wochenschr. 1903, 1, 2042-2044.
7. Von Tappeiner, H.; Jodlbauer, A.: ←Über die Wirkungen der Photodynamischen (Fluoreszierenden) Stoffe auf Protozoen und Enzyme→. Dtsch. Arch. Klin. Med. 1904, 80, 427-487.
8. Jesionek, A.; Von Tappeiner, H.: ←Die Behandlung der Hautkarzinome mit Fluoreszierenden Stoffen→. Arch. Klin. Med. 1905, 82, 72-76.
9. Hausman, W.: ←Die Sensibilisierende Wirkung des Hematoporphyrins→. Biochern. Z. 1911, 30, 276.
10. Meyer-Betz, Z.: ←Untersuchungen über die Biologische (Photodynamische) Wirkung des Hämatoporphyrins und anderer Derivate des Blut- und Gallenfarbstoffs→. Dtsch. Arch. Klin. Med. 1913, 112, 476-503.
11. Policard, A.: ←Étude sur les Aspects Offerts par des Tumeurs Experimentales Examineés a la Lumiere de Wood→. CR Soc. Biol. 1924, 91, 1423-1425.
12. Auler, H.; Banzer, G.: ←Untersuchungen über die Rolle der Porphyrine bei Geschwulskranker Menschen und Tieren→. Z. Krebsforsch 1942, 53, 65-68.
13. Figge, F.H.J.; Weiland, G.S.; Manganiello, L.O.J.: ←Cancer Detection and Therapy. Affinity of Neoplastic, Embryonic and Traumatised Tissue for Porphyrins and Metalloporphyrins→. Proc. Soc. Exp. Biol. Med. 1948, 68, 640-641.
14. Rassmussen-Taxdal, D.S.; Ward, G.E.; Figge, F.H.J.: ←Fluorescence of Human Lymphatic and Cancer Tissues Following High Doses of Intravenous Haematoporphyrin→. Cancer. 1955, 8, 78-81.
15. Schwartz, S.; Absolon, K.; Vermund, H.: ←Some Relationships of Porphyrins, X-Rays, and Tumors→. Univ. Minn. Med. Bull. 1955, 27, 7-13.
16. Lipson, R.L; Baldes, E.J.: ←The Photodynamic Properties of a Particular Hematoporphyrin Derivative→. Arch. Dermatol. 1960, 82, 508-516.
17. Lipson, R.L.; Baldes, E.J.; Olsen, A.M.: ←Hematoporphyrin derivative: A New Aid for Endoscopic Detection of Malignant Disease→. J. Thorac. Cardiovasc. Surg. 1961, 42, 623-629.
18. Lipson, R.L.; Baldes, E.J.; Olsen, A.M.: ←The Use of a Derivative of Hematoporphyrin in Tumor Detection→. J. Natl. Cancer Inst. 1961, 26, 1-8.
19. Lipson, R.L.; Baldes, E.J.; Olsen, A.M.: ←Further Evaluation of the Use of Hematoporphyrin Derivative as a New Aid for the Endoscopic Detection of Malignant Disease→. Dis. Chest. 1964, 46, 676-679.
20. Lipson, R.L.; Pratt, J.H.; Baldes, E.J.; Dockerty, M.B.: ←Hematoporphyrin Derivative for Detection of Cervical Cancer→. Obstet. Gynecol. 1964, 24, 78-84.
21. Lipson, R.L.; Baldes, E.J.; Gray, M.J.: ←Hematoporphyrin Derivative for Detection and Management of Cancer→. Cancer 1967, 20, 2255-2257.
22. Dougherty, T.J.; Grindey, G.B.; Fiel, R.; Weishaupt, K.R.; Boyle, D.: ←Photoradiation Therapy. II. Cure of Animal Tumors with Hematoporphyrin and Light→. J. Natl. Cancer Inst. 1975, 55, 115-119.
23. Dougherty, T.J.; Kaufman, J.E.; Goldfarb, A.; Weishaupt, K.R.; Boyle, D.; Mittleman, A.: ←Photoradiation Therapy for the Treatment of Malignant Tumors→. Cancer Res. 1978, 38, 2628-2635.
24. Ackroyd, R.; Kelty, C.; Brown, N.; Reed, M.: ←The History of Photodetection and Photodynamic Therapy→. Photochem. Photobiol. 2001, 74(5), 656-669.
25. Konan, N.Y.; Gurny, R.; Alléman, E.: ←State of the Art in the Delivery of Photosensitizers for Photodynamic Therapy→. J. Photochem. Photobiol. B: Biol. 2002, 66, 89-106.
26. Kessel, D.; Woodburn, K.: ←Biodistribution of Photosensitizing Agents→. Int. J. Biochern. 1993, 25, 1377-1383.
27. Reyftmann, J.P.; Morliere, P.; Goldstein, J.L.; Santus, R.; Dubertret, L.; Larange, D.: ←Interaction of Human Serum Low Density Lipoproteins with Porphyrins: A Spectroscopic and Photochemical Study→. Photochem. Photobiol. 1984, 40, 721-729.
28. Kessel, D.; Thompson, P.; Saatio, K.; Nantwi, K.D.: ←Tumor Localization and Photosensitization by Sulphonated Derivatives of Tetraphenylporphine→. Photochem. Photobiol. 1987, 45, 787-790.
29. Kongshaug, M.; Moan, J.; Brown, S.B.: ←The Distribution of Porphyrins with Different Tumour Localising Ability Among Human Plasma Proteins→. Br. J. Cancer 1989, 59, 188
30. Kongshaug, M.; Rimington, C.; Evensen, J.F.; Peng, Q.; Moan, J.: ←Hematoporphyrin Diethers-V. Plasma Protein Binding and Photosensitizing Efficiency→. Int. J. Biochem. 1990, 22, 1127-1131.
31. Mosley, S.T.; Goldstein, J.L.; Brown, M.S.; Falck, J.R.; Anderson, R.G.W.: ←Targeted Killing of Cultured Cells by Receptor-Dependent Photosensitazion→. Proc. Natl. Acad. Sci. 1981, 78, 5717-5721.
32. Jiang, F.N.; Jiang, S.; Liu, D.; Richter, A.M.; Levy, J.G.: ←Development of Technology for Linking Photosensitizers to a Model Monoclonal Antibody→. J. Immunol. Methods 1990, 134, 139-149.
33. Jiang, F.N.; Allison, B.; Liu, D.; Levy, J.G.: ←Enhanced Photodynamic Killing of Target Cells by Either Monoclonal Antibodies or Low Density Lipoprotein Mediated Delivery Systems→. J. Controlled Release 1992, 19, 41-58.
34. Klayshchitsky, B.A.; Nechaeva, I.S.; Ponomaryov, G.V.: ←Approaches to Targetted Photodynamic Tumor Therapy→. J. Controlled Release 1994, 29, 1-16.
35. 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.
36. Norata, G.; Canti, G.; Ricci, L.; Trezzi, E.; Catapano, A.L.: ←In Vivo Assimilation of Low Density Lipoproteins by a Fibrosarcoma Tumour Line in Mice→. Cancer Lett. 1984, 25, 203-208.
37. Netland, P.A.; Zetter, B.R.; Via, D.P.; Voyta, J.C.: In Situ ←Labelling of Vascular Endothelium with Fluorescent Acetylated Low Density Lipoprotein→. Histochem. J. 1985, 17, 1309-1320.
38. Berenbaum, M.C.; Hall, G.W.; Hoyes, A.D.: ←Cerebral Photosensitisation by Haematoporphyrin Derivative. Evidence for an Endothelial Site of Action→. Br. J. Cancer 1986, 53, 81-89.
39. Vitols, S.; Angelin, B.; Ericsson, S.; Gahrton, G.; Juliusson, G.; Masquelier, M.; Paul, C.; Peterson, P.; Rudling, M.; Söderberg-Reid, K.; Tidelfelt, U.: ←Uptake of Low Density Lipoproteins by Human Leukemic Cells In Vivo: Relation to Plasma Lipoprotein Levels and Possible Relevance for Selective Chemotherpy→. Proc. Natl. Acad. Sci. 1990, 87, 2598-2602.
40. Mew, D.; Wat, C.; Neil Towers, G.H.; Levy, J.G.: ←Photoimmunotherapy: Treatment of Animal Tumors with Tumor-Specific Monoclonal Antibody-Hematoporphyrin Conjugates→. J. Immunol. 1983, 130, 1473-1477.
41. Pietersz, G.A.; Cunningham, Z.; McKenzie, I.F.C.: ←Specific in Vitro Anti-Tumour Activity of Methotrexate-Monoclonal Antibody Conjugates Prepared Using Human Serum Albumin as an Intermediary→. Imrnunol. Cell. Biol. 1988, 66, 43-49.
42. Shih, L.B.; Sharkey, R.M.; Primus, F.J.; Goldenberg, D.M.: ←Site-Specific Linkage of Methotrexate to Monoclonal Antibodies Using an Intermediate Carrier→. Int. J. Cancer 1988, 41, 832-839.
43. Rodgers, M.A.J.: ←On The Problems Involved in Detecting Luminescence from Singlet Oxygen in Biological Specimens→. J. Photochem. Photobiol. B: Biol. 1988, 1, 371-378.
44. Patterson, M. S.; Madsen, S. J.; Wilson, B. C.: ←Experimental Tests of the Feasibility of Singlet Oxygen Luminescence Monitoring in Vivo during Photodynamic Therapy→. J. Photochem. Photobiol. B: Biol. 1990, 5, 69-84.
45. Moan, J.: ←On The Diffusion Length of Singlet Oxygen in Cells and Tissues→. J. Photochem. Photobiol. B: Biol. 1990, 6, 343-347.
46. Ochsner, M.: ←Photophysical and Photobiological Processes in the Photodynamic Therapy of Tumors→. J. Photochem. Photobiol. B: Biol. 1997, 39, 1-18.
47. Dubbelman, T.M.A.R.; Van Steveninck, J.: ←Photodynamically Induced Damage to Cellular Functions and its Relations to Cell Death→. J. Photochem. Photobiol. B: Biol. 1990, 6, 345-348.
48. Cañete, M.; Ortiz, A.; Juarranz, A.; Villanueva, A.; Nonell, S.; Borrell, J.I.; Teixidó, J.; Stockert, J.C.: ←Photosensitizing Properties of Palladium-Tetraphenylporphycene on Cultured Tumour Cells→. Anti-Cancer Drug Design 2000, 15, 143-150.
49. Henderson, B.W.; Fingar, V.H.: ←Relationship of Tumor Hypoxia and Response to Photodynamic Treatment in an Experimental Mouse Tumor→. Cancer Res. 1987, 47, 3110-3114.
50. Byrne, C.J.; Marshallsay, L.V.: ←The Composition of Photofrin II→. J. Photochem. Photobiol. B: Biol. 1990, 6, 13-27.
51. Schiwon, K.; Brauer, H.D.; Gerlach, B.; Müller, C.M.; Montforts, F.P.: ←Potential Photosensitizers for Photodynamic Therapy IV. Photophysical and Photochemical Properties of Azaporphyrin and Azachlorin Derivatives→. J. Photochern. Photobiol. B:Biol. 1994, 23, 239-243.
52. Selman, S.H.; Garbo, G.M.; Keck, R.W.; Kreimer-Birnbaum, M.; Morgan, A.R.: ←A Dose Response Analysis of Purpurin Derivatives Used as Photosensitizers for the Photodynamic Treatment of Transplantable FANFT Induced Urothelial Tumors→. J. Urol. 1987, 137, 1255-1257.
53. Morgan, A.R.; Garbo, G.M.; Keck, R.W.; Selman, S.H.: ←New Photosensitizers for Photodynamic Therapy: Combined Effect of Metallopurpurin Derivatives and Light on Transplantable Bladder→. Cancer Res. 1988, 48, 194-198.
54. Ginevra, F.; Biffanti, S.; Pagnan, A.; Biolo, R.; Reddi, E.; Jori, G.: ←Delivery of the Tumour Photosensitizer Zinc(II)-Phtalocyanine to Serum Proteins by Different Liposomes: Studies In Vitro and In Vivo→. Cancer Lett. 1990, 49, 59-65.
55. Sternberg, E.D.; Dolphin, D.; Brückner, C.: ←Porphyrin-based Photosensitizers For Use in Photodynamic Therapy→. Tetrahedron 1998, 54, 4151-4202.
56. Ali, H.; Van Lier, J.E.: ←Metal Complexes as Photo- and Radiosensitizers→. Chem. Rev. 1999, 99, 2379-2450.
57. Jasat, A.; Dolphin, D.: ←Expanded Porphyrins and Their Heterologs→. Chem. Rev. 1997, 97, 2267-2340.
58. Milgrom, L.; MacRobert, S.: ←Light Years Ahead→. Chem. Br. 1998, 45-50.
59. Peng, Q.; Warloe, T.; Berg, K.; Moan, J.; Kongshaug, M.; Giercksky, K.E.; Nesland, J.M.: ←5-Aminolevulinic Acid-Based Photodynamic Therapy→. Cancer 1997, 79, 2282-2308.
60. Fisher, A.M.; Murphree, A.L.; Gomer, C.J.: ←Clinical and Preclinical Photodynamic Therapy→. Lasers Surg. Med. 1995, 17, 2-31.
61. Sharman, W.M.; Allen, C.M.; Van Lier, J.E.: ←Photodynamic Therapeutics: Basic Principles and Clinical Applications→. Drug Discovery Today 1999, 4, 507-517.
62. Dierickx, C.C.; Rox Anderson, R.: ←Why Use PDT in Dermatology?→ Int. Photodyn. 1996, 1, 2-5.
63. Pumarola, A.; Rodríguez-Torres, A.; García-Rodríguez, J.A.; Piédrola-Angulo, G.: ←Microbiología y Parasitología Médica→. 1987; Barcelona.
64. Pumarola, A.; Rodríguez-Torres, A.; García-Rodríguez, J.A.; Piédrola-Angulo, G.: ←Microbiología y Parasitología Médica→. 1987; Barcelona. Nitzan, Y.; Gutterman, M.; Malik, Z.; Ehrenberg, B.: ←Inactivation of Gram-Negative Bacteria by Photosensitized Porphyrins→. Photochem. Photobiol. 1992, 55, 89-96.
65. Merchat, M.; Villanueva, A.; Giacomoni, P.; Bertoloni, G.; Jori, G.: ←Photosensitazion of Bacteria to Visible Light by meso-Substituted Porphyrines→. J. Braz. Chem. Soc. 1995, 6, 123-125.
66. Minnock, A.; Vernon, D.I.; Schofield, J.; Griffiths, J.; Parish, J.H.; Brown, S.B.: ←Photoinactivation of Bacteria. Use of a Cationic Water-Soluble Zinc Phthalocyanine to Photoinactivate both Gram-negative and Gram-positive Bacteria→. J. Photochem. Photobiol. B: Biol. 1996, 32, 159-164.
67. Merchat, M.; Giacomoni, P.; Villanueva, A.; Bertoloni, G.; Jori, G.: ←Meso-substituted Cationic Porphyrins as Efficient Photosensitizers of Gram-positive and Gram-negative Bacteria→. J. Photochern. Photobiol. B: Biol. 1996, 32, 153-157.
68. Jori, G.; Tonlorenzi, D.: ←Photodynamic Therapy for the Treatment of Microbial Infections→. Int. Photodyn. 1999, 2, 2-3.
69. Ben-Hur, E.; Horowitz, B.: ←Advances in Photochemical Approaches for Blood Sterilization→. Photochem. Photobiol. 1995, 62, 383-388.
70. Gaspard, S.; Tempête, C.; Werner, G.H.: ←Studies on Photoinactivation by Various Phthalocyanines of a Free or Replicating non-Enveloped Virus→. J. Photochem. Photobiol. B: Biol. 1995, 31,159-162.
71. Grandadam, M.; Ingrand, D.; Huraux, J.-M.; Aveline, B.; Delgado, O.; Vever-Bizet, C.; Brault, D.: ←Photodynamic Inactivation of Cell-free HIV Strains by a Red-absorbing Chlorin-type Photosensitizer→. J. Photochem. Photobiol. B: Biol. 1995, 31, 171-177.
72. Allen, C.M.; Weber, J.M.; Van Lier, J.E.: ←Sulfophthalocyanines for Photodynamic Inactivation of Viruses in Blood Products: Effect of Structural Modification→. Photochem. Photobiol. 1995, 62, 184-189.
73. Gannon, M.J.; Johnson, N.; Roberts, D.J.H.; Holroyd, J.A.; Vernon, D.I.; Brown, S.B.; Lilford, R.J.: ←Photosensitization of the Endometrium using 5-Aminolevulinic Acid→. Obstet. Gynecol. 1995, 173, 1826-1828.
74. Van Vugt, D.A.; Krzemien, A.; Roy, B.N.; Foster, W.; Lundahl, S.; Marcus, S.L.; Reid, R.L.: ←Photodynamic Endometrial Ablation in the Nonhuman Primate→. J. Soc. Gynecol. Investig. 2000, 7, 125-30.
75. Vogel, E.; Koecher, M.; Schmickler, H.; Lex, J.: ←Porphycene, a New Type of Porphine Isomer→. Angew. Chem. 1986. 98, 262-264.
76. Vogel, E.; Balci, M.; Pramod, K.; Koch, P.; Lex, J.; Ermer, O.: ←2,7,12,17-Tetrapropylporphycene- Counterpart of Octaethylporphyrin in the Porphycene Series→. Angew. Chem. Int. Ed. Engl. 1987, 26, 928-931.
77. Richert, C.; Wessels, J.M.; Müller, M.; Kisters, M.; Benninghaus, T.; Goetz, A.E.: ←Photodynamic Antitumor Agents: β-Methoxyethyl Groups Give Access to Functionalized Porphycenes and Enhance Cellular Uptake and Activity. J. Med. Chem. 1994, 37, 2797-2807.
78. Aramendia, P. F.; Redmond, R. W.; Nonell, S.; Schuster, W.; Braslavsky, S. E.; Schaffner, K.; Vogel, E.: ←The Photophysical Properties of Porphycenes: Potential Photodynamic Therapy Agents→. Photochem. Photobiol. 1986. 44, 555-559.
79. Nonell, S.; Bou, N.; Borrell, J.I.; Teixidó, J.; Villanueva, A.; Juarranz, A.; Cañete, M.: ←Synthesis of 2,7,12,17-Tetraphenylporphycene (TPPo). First Aryl-substituted Porphycene for the Photodynamic Therapy of Tumors→. Tetrahedron Lett. 1995, 36, 3405-3408.
80. Gavaldá, A.; Borrell, J.I.; Teixidó, J.; Nonell, S.; Arad, O.; Grau, R.; Cañete, M.; Juarranz, A.; Villanueva, A.; Stockert, J.C.: ←A non-Tetradecarboxylative Synthesis of 2,7,12,17-Tetraphenylporphycene→. J. Porphyrins Phthalocyanines 2001, 5, 846-852.
81. Vogel, E.; Koch, P. A.; Rahbar, A.; Cross, A. D.: ←Preparation of Porphycenes Useful in Photodynamic Therapy or As Intermediates for Synthesis of Photoactivable Dyes Suitable for Photodynamic Therapy→. Cytopharm, Inc. USA. 92-US364(9212636), 39. 6-8-1992. WO. 1-29-1992. Patente.
82. Vogel, E.; Benninghaus, T.; Richert, C.; Müller, M.; Cross, A. D.: ←Preparation of Porphycene Compounds for Photodynamic Therapy→. (Cytopharm, Inc. USA. 92-US4624(9300087), 76. 7-1-1993. WO. 6-5-1992. Patent.
83. Vogel, E.; Müller, M.; Halpern, O.; Cross, A. D.: ←Preparation of 9-Substituted Porphycenes as Photosensitizers→. (Cytopharm, Inc. USA. 96-US4177(9631452), 30. 10-10-1996. WO. 4-4-1996. Patente.
84. Vogel, E.; Müller, M.; Halpern, O.; Cross, A. D.: ← Preparation of Porphycene Esters and Amides for Use in Photodynamic Therapy→. (Cytopharm, Inc. USA. 96-US4176(9631451), 36. 10-10-1996. WO. 4-4-1996. Patente.
85. Donnerstag, D.: ←Benzoporphycene-Neuartige Tetrapyrrolische Porphyrinoide→. 1993. Universität Köln. Tesis Doctoral.
86. Hoppe, M.: ←9,10-Benzotetrapropylporphycen-Synthese und Eigenschaften→. 1994. Universität Köln. Tesis Doctoral.
87. Nußbaumer, T.; Krieger, C.; Neidlein, R.: ←21,23-Dithia3,13-diazaporphycenes, Novel Aromatic Porphycene Analogues incorporating Thiazole→. Eur. J. Org. Chem. 2000. 13, 2449-2457.
88. Nußbaumer, T.; Neidlein, R.: ←Syntheses of Thiazole-containing Macroheterocycles related to Porphycene→. Helv. Chim. Acta. 2000. 83, 1161-1167.
89. Vogel, E.; Müller, M.; Halpern, O.; Cross, A. D.: ←Synthesis of C-9 Ethers of Porphycenes for Use in the Photodynamic Therapy→. Cytopharm, Inc. USA. 98-US17918(9815271), 62.4-16-1998. WO. 10-9-1997. Patent.
90. Cañete, M.; Lapeña, M.; Juarranz, A.; Vendrell, V.; Borrell, J.I.; Teixidó, J.; Nonell, S.; Villanueva, A.: ←Uptake of Tetraphenylporphycene and its Photoeffects on Actin and Cytokeratin Elements of HeLa Cells→. Anti-Cancer Drug Design 1997, 12, 543-554.
91. Guardiano, M.; Biolo, R.; Jori, G.; Schaffner, K.: ←Tetran-propylporphycene as a Tumor Localizer: Pharmacokinetic and Phototherapeutic Studies in Mice→. Cancer Lett. 1989, 44, 1-6.
92. Villanueva, A.; Cañete, M.; Nonell, S.; Borrell, J.I.; Teixidó, J.; Juarranz, A.: ←Photodamaging Effects of Tetraphenyl-porphycene in a Human Carcinoma Cell Line→. Anti-Cancer Drug Design 1996, 11, 89-99.
93. Karrer, S.; Szeimies, R.-M.; Ebert, A.; Fickweiler, C.; Abels, C.; Bäumler, W.; Landthaler, M.: ←Dose-dependent Photodynamic Effects of 9-Acetoxy-2,7,12,17-tetrakis-(β-methoxyethyl)-porphycene In Vitro→. Lasers Med. Sci. 1997, 12, 307-312.
94. Gavaldá A.: ←Síntesis y Actividad Fotodinámica de Fotosensibilizadores Porficénicos→. 2001. Universidad Ramón Llull. Tesis Doctoral
95. Gavaldá, A.: ←Síntesis y Actividad Fotodinámica de Fotosensibilizadores Porficénicos→. 2001. Universidad Ramón Llull. Tesis Doctoral. Karrer, S.; Abels, C.; Szeimies, R. M.; Baumler, W.; Delilah, 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.