Cyclodextrin-based nanoconstructs for photoactivated therapies

Journal of Drug Delivery Science and Technology

Volumn 22, Issue 3, 2012, Pages 235-242

  Mazzaglia, A ^a   Sciortino, M T ^a   Kandoth, N ^b   Sortino, S ^b  

^a UNIVERSITY OF MESSINA   (Italy)

^b UNIVERSITY OF CATANIA   (Italy)

Author keywords

Cyclodextrins; Multimodal therapy; Nanoparticles; Nitric oxide toxicity; Photodynamic therapy; Photothermal therapy

Indexed keywords

CURCUMIN; CYCLODEXTRIN; NITRIC OXIDE; PORPHYRIN; PURPURIN;

DRUG BIOAVAILABILITY; DRUG DELIVERY SYSTEM; FILM; HUMAN; MATERIAL COATING; NONHUMAN; PHOTODYNAMIC THERAPY; PHOTOSENSITIVITY; PHOTOSTIMULATION; PHOTOTHERAPY; PHOTOTHERMAL THERAPY; PHOTOTOXICITY; REVIEW;

EID: 84862839894     PISSN: 17732247     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1773-2247(12)50034-1     Document Type: Review

References (85)

1. Rai P., Mallidi S., Zheng X., Rahmanzadeh R., Mir Y., Elrington S., Khurshid A., Hasan T. - Development and applications pf photo-triggered theranostic agents. - Adv. Drug. Delivery Rev., 62, 1094-1124, 2010.
2. Alvarez-Lorenzo C., Bromberg L., Concheiro A. - Light-sensitive intelligent drug delivery systems. - Photochem. Photobiol., 85, 848-860, 2009.
3. McCoy C.P., Brady C., Cowley J.F., McGlinchey S.M., McGoldrick N., Kinear D.J., Andrews G.P., Jones D.S. - Triggered drug delivery from biomaterials. - Exp. Opin. Drug. Deliv., 7, 605-616, 2010.
4. Sortino S. - Nanostructured molecular films and nanoparticles with photoactivable functionalities. - Photochem. Photobiol. Sci., 7, 911-924, 2008.
5. Sortino S. - Photoactivated nanomaterials for biomedical release applications. - J. Mater. Chem., 22, 301-318, 2012.
6. Davis M. E., Brewster M. E. - Cyclodextrin-based pharmaceutics: past, present and future. - Nature Rev., 3, 1023-1035, 2004.
7. Loftsson T., Duchêne D. - Cyclodextrins and their pharmaceutical applications. - Int. J. Pharm., 329, 1-11, 2007.
8. McDonald I.J., Doughery T.J. - Basic principles of photodynamic therapy. - J. Porphyrins Phthalocyanines, 5, 105-129, 2001.
9. th ed., BC Decker Inc., Hamilton, 2000.
10. Cai R., Kubota Y., Shuin T., Sakai H., Hashimoto K., Fujishima K. - Induction of cytotoxicity by photoexcited TiO2 particles. - Cancer Res., 52, 2346-2348, 1992.
11. Goldman B. - Multidrug resistance: can new drugs help chemotherapy score against cancer? - J. Natl. Cancer Inst., 95, 255-257, 2003.
12. Ethirajan M., Chen Y., Joshi P., Pandey R.K. - The role of porphyrin chemistry in tumor imaging and photodynamic therapy. - Chem. Soc. Rev., 40, 340-362, 2011.
13. Wang S., Gao R., Zhou F., Selke M. - Nanomaterials and singlet oxygen photosensitizers: potential applications in photodynamic therapy. - J. Mater. Chem., 14, 487-493, 2004.
14. Svaasand L.O., Gomer C.J., Morinelli E. - On the physical rationale of laser induced hyperthermia. - Laser Med. Sci., 5, 121-128, 1990.
15. Jori G., Spikes J.D. - Photothermal sensitizers: possible use in tumor therapy. - J. Photochem. Photobiol. B Biol., 6, 93-101, 1990.
16. Camerin M., Rello S., Villanueva A., Ping X., Kenney M.E., Rodgers M.A.J., Jori G. - Photothermal sensitisation as a novel therapeutic approach for tumours: studies at the cellular and animal level. - Eur. J. Cancer., 41, 1203-1212, 2005.
17. Jori G., Schindl L., Schindl A., Polo L. - Novel approaches towards a detailed control of the mechanism and efficiency of photosensitized processes in vivo. - J. Photochem. Photobiol. A Chem., 102, 101-107, 1996.
18. Jori G., Spikes J.D. - Photothermal sensitizers: possible use in tumor therapy. - J. Photochem. Photobiol. B Biol., 6, 93-101, 1990.
19. Jain P.K., Huang X., El-Sayed I.H., El-Sayed M.A. - Noble metals on the nanoscale: optical and photothermal properties and some applications in imaging, sensing, biology, and medicine. - Acc. Chem. Res., 41, 1578-1586, 2008.
20. Hu M., Chen J., Li Z.-Y., Au L., Hartland G.V., Li X., Marquez M., Xia Y. - Gold nanostructures: engineering their plasmonic properties for biomedical applications. - Chem. Soc. Rev., 35, 1084-1094, 2006.
21. Ignarro L.J. (Ed.) - Nitric Oxide: Biology and Pathobiology. - Elsevier Inc., 2010.
22. Pukumura D., Kashiwagi S., Jain R.K. - The role of nitric oxide in tumour progression. - Nat. Rev. Cancer., 6, 521-534, 2006.
23. Carlsson S., Weitzberg E., Wiklund P., Lundberg J.O. - Intravesical nitric oxide delivery for prevention of catheter-associated urinary tract infections. - Antimicrob. Agents Chemother., 49, 2352-2355, 2005.
24. Radi R. et al. - Peroxynitrite-induced membrane lipid peroxidation: The cytotoxic potential of superoxide and nitric oxide. - Archives of Biochemistry and Biophysics., 288, 481-487, 1991.
25. Noronha-Dutra A. A. et al. - Reaction of nitric oxide with hydrogen peroxide to produce potentially cytotoxic singlet oxygen as a model for nitric oxide-mediated killing. - FEBS Letters., 321, 59-62, 1993.
26. Pryor W.A. et al. - Free radical biology and medicine: it's a gas, man! - American Journal of Physiology, 291, R491, 2006.
27. Wang P.G., Cai T.B., Taniguchi N. (Eds.) - Nitric Oxide Donors for Pharmaceutical and Biological Applications. - Wiley & Co., Weinheim, 2005.
28. Bishop A., Anderson J.E. - NO signaling in the CNS: from the physiological to the pathological. - Toxicology, 208, 193-205, 2005.
29. Sortino S. - Light-controlled nitric oxide delivering molecular assemblies. - Chem. Soc. Rev., 39, 2903-2913, 2010.
30. Pelliccioli A.P., Wirz J. - Photoremovable protecting groups: reaction mechanisms and applications. - Photochem. Photobiol. Sci., 1, 441-458, 2002.
31. Janczuk A., Jia Q., Xian M., Wen Z., Wang P.G., Cai T. - NO donors with anticancer activity. - Expert Opin. Ther. Patents., 12, 819-826, 2002.
32. Ostrowski A.D., Ford P.C. - Metal complexes as photochemical nitric oxide precursors: potential applications in the treatment of tumors. - Dalton Trans., 10660-10669, 2009.
33. Kremsner P.G., Krishna S. - Antimalarial combinations. - Lancet., 364, 285-294, 2004.
34. Sengupta S., Eavarone D., Capila I., Zhao G., Watson N., Kiziltepe T. - Temporal targeting of tumour cells and neovasculature with a nanoscale delivery system. - Nature, 436, 568-572, 2005.
35. Mazzaglia A., Micali N., Monsù Scolaro L., Sciortino M.T., Sortino S., Villari V.J. - Design of photosensitizer/cyclodextrin nanoassemblies: spectroscopy, intracellular delivery and photodamage. - Porphyrins Phthalocyanines, 14, 661-677, 2010.
36. Kano K., Nishiyabu R., Asada T., Kuroda Y. - Static and dynamic behavior of 2:1 inclusion complexes of cyclodextrins and charged porphyrins in aqueous organic media. - J. Am. Chem. Soc., 124, 9937-9944, 2002.
37. Mosinger J., Kliment V., Sejbal J., Kubát P., Lang K.J. - Host-guest complexes of anionic porphyrin sensitizers with cyclodextrins. - Porphyrins Phthalocyanines, 6, 514-526, 2002.
38. El-Hachemi Z., Farrera J.-A., García-Ortega H., Ramírez-Gutíerrez O., Ribó J.M. - Heteroassociation of meso-sulfonatophenylporphyrins with β- and γ-cyclodextrin. - J. Porphyrins Phthalocyanines, 5, 465-473, 2001.
39. 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., 248, 321-350, 2004.
40. Bonchio M., Carofiglio T., Carraro M., Fornasier R., Tonellato U. - Efficient sensitized photooxygenation in water by a porphyrin-cyclodextrin supramolecular complex. - Org. Lett., 4, 4635-4637, 2002.
41. Sekher P., Garbo G.M. - Spectroscopic studies of tin ethyl etiopurpurin in homogeneous and heterogeneous systems. - J. Photochem. Photobiol. B. Biol., 20, 117-125, 1993.
42. Bruzell E.M, Morisbaka E., Tønnesen H.H. - Studies on curcumin and curcuminoids. XXIX. Photoinduced cytotoxicity of curcumin in selected aqueous preparations. - Photochem. Photobiol. Sci., 4, 523-530, 2005.
43. Lay Lay Saw C., Olivo M., Soo K.C., Heng P.W.S. - Delivery of hypericin for photodynamic applications. - Cancer Letters, 241, 23-30, 2006.
44. Bourdon O., Mosqueira V., Legrand P., Blais J. - A comparative study of the cellular uptake, localization and phototoxicity of meta-tetra(hydroxyphenyl) chlorin encapsulated in surface-modified submicronic oil/water carriers in HT29 tumor cells. - J. Photochem. Photobiol. B: Biol., 55, 164-171, 2000.
45. Konishi T., Ikeda A., Asai M., Hatano T., Shinkai S., Fujitsuka M., Ito O., Tsuchiya Y., Kikuchi J.-I. - Improvement of quantum yields for photoinduced energy/electron transfer by isolation of self-aggregative zinc tetraphenyl porphyrin-pendant polymer using cyclodextrin inclusion in aqueous solution. - J. Phys. Chem. B., 107, 11261-11266, 2003.
46. 60] and its aggregated derivatives toward human lens epithelial cell. - Chem. Res. Toxicol., 22, 660-667, 2009.
47. Ikeda A., Matsumoto M., Akiyama M., Kikuchi J.-I., Ogawa T., Takeya T. - Direct and short-time uptake of [70] fullerene into the cell membrane using an exchange reaction from a [70] fullerene-γ-cyclodextrin complex and the resulting photodynamic activity. - Chem. Commun., 1547-1549, 2009.
48. 60 nanoparticles by 2-hydroxypropyl-β- cyclodextrin. - Mol. Pharmaceutics, 8, 1276-1284, 2011.
49. Mazzaglia A., Micali N., Monsù Scolaro L. - Structural characterization of colloidal cyclodextrins: molecular recognition by means of photophysical investigation. - In: Cyclodextrin Materials Photochemistry, Photophysics and Photobiology, Elsevier, 2006, p. 203-222, and ref. therein.
50. Monti S., Sortino S. - Photoprocesses of photosensitizing drugs within cyclodextrin cavities. - Chem. Soc. Rev., 31, 287-300, 2002.
51. Sasaki K., Nakagawa H., Zhang X., Sakurai S., Kano K., Kuroda Y.- Construction of porphyrin-cyclodextrin self-assembly with molecular wedge. - Chem. Commun., 408-409, 2004.
52. Králová J., Synytsya A., Poucková P., Koc M., Dvorak M., Král V. - Novel porphyrin conjugates with a potent photodynamic antitumor effect: differential efficacy of mono- and bis-β-cyclodextrin derivatives in vitro and in vivo. - Photochemistry and Photobiology, 82, 432-438, 2006.
53. Králová J., Kejík Z., Bríza T., Poucková P., Král A., Martásek P., Král V. - Porphyrin-cyclodextrin conjugates as a nanosystem for versatile drug delivery and multimodal cancer therapy. - J. Med. Chem., 53, 128-138, 2010.
54. Puglisi A., Purrello R., Rizzarelli E., Sortino S., Vecchio G. - Spectroscopic and self-association behavior of a porphyrin-β-cyclodextrin conjugate. - New J. Chem., 31, 1499-1506, 2007.
55. Ribeiro A.O., Tomé J.P.C., Neves M.G.P.M.S., Tomé A.C., Cavaleiro J.A.S., Osvaldo A., Serra O.A., Torres T. - First phthalocyanine- β-cyclodextrin dyads. - Tetrahedron Lett., 47, 6129-6132, 2006.
56. Lau J.T.F., Lo P.-C., Tsang Y.-M., Fong W.-P., Ng D.K.P. - Unsymmetrical β-cyclodextrin-conjugated silicon(IV) phthalocyanines as highly potent photosensitisers for photodynamic therapy. - Chem. Commun., 47, 9657-9659, 2011.
57. Lau J.T.F., Lo P.-C., Fong W.-P., Ng D.K.P. - Preparation and photodynamic activities of silicon(IV) phthalocyanines substituted with permethylated β-cyclodextrins. - Chem. Eur. J., 17, 7569-7577, 2011.
58. Leng X., Chi-Fung Choi C.-F., Lo P.-C., Ng D.K.P. - Assembling a mixed phthalocyanine-porphyrin array in aqueous media through host-guest interactions. - Org. Lett., 9, 231-234, 2007.
59. Silva J.N., Silva A.M.G., Tomé J.P.C., Ribeiro A.O., Domingues M.R.M., Cavaleiro J.A.S., Silva A.M.S., Neves G.P.M.S., Tomé A.C., Serra O.A., Bosca F., Pilipe P., Santus R., Morlière P. - Photophysical properties of a photocytotoxic fluorinated chlorin conjugated to four beta-cyclodextrins. - Photochem. Photobiol. Sci., 7, 834-843, 2008.
60. Ou Z.-Z., Chen J.-R., Wang X.-S., Zhang B.-W., Cao Y. - Synthesis of a water-soluble cyclodextrin modified hypocrellin and ESR study of its photodynamic therapy properties. - New J. Chem., 26, 1130-1136, 2002.
61. Kandoth N., Vittorino E., Sortino S. - Gold nanoparticles decorated with a photoactivable nitric oxide donor/cyclodextrin host/guest complex. - New J. Chem., 35, 52-56, 2011.
62. Liu J., Xu R., Kaifer A.E. - In situ modification of the surface of gold colloidal particles, Preparation of cyclodextrin-based rotaxanes supported on gold nanospheres. - Langmuir, 14, 7337-7339, 1998.
63. Callari F., Petralia S., Sortino S. - Highly photoresponsive monolayer-protected gold clusters by self-assembly of a cyclodextrin-azobenzene- derived supramolecular complex. - Chem. Commun., 1009-1011, 2006.
64. Caruso E.B., Petralia S., Conoci S., Giuffrida S., Sortino S. - Photodelivery of nitric oxide from water-soluble platinum nanoparticles. - J. Am. Chem. Soc., 129, 480-481, 2007.
65. Sallas F., Darcy R. - Amphiphilic cyclodextrins, Advances in synthesis and supramolecular chemistry. - Eur. J. Org. Chem., 957-969, 2008, and ref. therein.
66. Ravoo B.J., Darcy R. - Cyclodextrin bilayer vesicles. - Angew. Chem. Int. Ed., 39, 4324-4326, 2000.
67. Lombardo D., Longo A., Darcy R., Mazzaglia A. - Structural properties of non-ionic cyclodextrin colloids in water. - Langmuir, 20, 1057-1064, 2004.
68. Quaglia F., Ostacolo L., Mazzaglia A., Villari V., Zaccaria D., Sciortino M.T. - The intracellular effects of non-ionic amphiphilic cyclodextrin nanoparticles in the delivery of anticancer drugs. - Biomaterials, 30, 374-382, 2009.
69. Mazzaglia A., Donohue R., Ravoo B.J., Darcy R. - Novel amphiphilic cyclodextrins: graft-synthesis of heptakis(6-alkylthio-6-deoxy)-β- cyclodextrin 2-oligo(ethylene glycol) conjugates and their co-halo derivatives. - Eur. J. Org. Chem., 1715-1721, 2001.
70. Mazzaglia A., Angelini N., Darcy R., Donohue R., Lombardo D., Micali N., Sciortino M. T., Villari V., Monsù Scolaro L. - Novel heterotopic colloids of anionic porphyrins entangled in cationic amphiphilic cyclodextrins: spectroscopic investigation and intracellular delivery. - Chem. Eur. J., 9, 5762-5769, 2003.
71. Mazzaglia A., Angelini N., Lombardo D., Micali N., Patanè S., Villari V., Monsù Scolaro L. - Amphiphilic cyclodextrin carriers embedding porphyrins: charge and size modulation of colloidal stability in heterotopic aggregates. - J. Phys. Chem. B., 109, 7258-7265, 2005.
72. Sortino S., Mazzaglia A., Monsù Scolaro L., Marino Merlo F., Valveri V., Sciortino M.T. - Nanoparticles of cationic amphiphilic cyclodextrins entangling anionic porphyrins as carrier-sensitizer system in photodynamic cancer therapy. - Biomaterials, 27, 4256-4265, 2006.
73. Ferro S., Jori, G., Sortino S., Stancanelli R., Nikolov P., Tognon G., Ricchelli F., Mazzaglia A. - Inclusion of 5-[4-(1-dodecanoylpyridinium)]-10,15, 20-triphenylporphine in supramolecular aggregates of cationic amphiphilic cyclodextrins: physicochemical characterization of the complexes and strengthening of the antimicrobial photosensitizing activity. - Biomacromolecules, 10, 2592-2600, 2009.
74. Callari F.L., Mazzaglia A., Monsù Scolaro L., Valli L., Sortino S. - Biocompatible nanoparticles of amphiphilic cyclodextrins entangling porphyrins as suitable vessels for light-induced energy and electron transfer. - J. Mater. Chem., 18, 802-805, 2008.
75. Kandoth N., Vittorino E., Sciortino MT., Colao I., Mazzaglia A., S. Sortino. - Cyclodextrin-based nanoassembly with bimodal photodynamic action. - Chem. Eur. J., 18, 1684-1690, 2012.
76. Ramamurthy V. (Ed.) - Photochemistry in Organized and Constrained Media. - VCH Publisher, New York, 1991.
77. Mazzaglia A., Trapani M., Villari V., Micali N., Marino Merlo F., Zaccaria D., Sciortino M.T., Previti F., Patanè S., Monsù Scolaro L. - Amphiphilic cyclodextrins as capping agents for gold colloids: a spectroscopic investigation with perspectives in photothermal therapy. - J. Phys. Chem. C., 112, 6764-6769, 2008.
78. Mazzaglia A., Forde D., Garozzo D., Malvagna P., Ravoo B.J., Darcy R. - Multivalent binding of galactosylated cyclodextrin vesicles to lectin. - Org. Biomol. Chem., 2, 957-960, 2004.
79. Mazzaglia A., Monsù Scolaro L., Mezzi A., Kaciulis S., De Caro T., Ingo G. M., Padeletti G. - Supramolecular colloidal systems of gold nanoparticles/amphiphilic cyclodextrin: a FE-SEM and XPS investigation of nanostructures assembled onto solid surface. - J. Phys. Chem. C., 113, 12772-12777, 2009.
80. Jin J., Li L.S., Wang X., Li Y., Zhang Y.J., Chen X., Li Y.-Z., Li T.J. - Steady-state spectroscopic and photovoltage studies of hemin and hemin/n-octadecylamine Langmuir-Blodgett films. - Langmuir, 15, 6969-6974, 1999.
81. Azumi R., Matsumoto M., Kuroda S.-I., King L.G., Crossley M.J. - Orientation change of dimer-type porphyrin in langmuir-blodgett films caused by a trigger molecule. - Langmuir, 11, 4056-4060, 1995.
82. Ulman A. (Ed.) - An Introduction to Ultrathin Organic Films: From Langmuir-Blodgett to Self-Assembly. - Academic Press, New York, 1991.
83. Viseu M.I., Goncalves da Silva A.M., Antunes P., Costa. S.M.B. - Organization of cationic porphyrins in mixed Langmuir-Blodgett films, An absorption and steady-state fluorescence study. - Langmuir, 18, 5772-5781, 2002.
84. Valli L., Casilli S., Giotta L., Pignataro B., Conoci S., Borovkov V.V., Inoue Y., Sortino S. - Ethane-bridged zinc porphyrin dimers in Langmuir-Shäfer thin films: structural and spectroscopic properties. - J. Phys. Chem. B., 110, 4691-4698, 2006.
85. Valli L., Giancane G., MazzagliaA., Monsù Scolaro L., Conoci S., Sortino S. - Photoresponsive multilayer films by assembling cationic amphiphilic cyclodextrins and anionic porphyrins at the air/water interface. - J. Mater. Chem., 17, 1660-1663, 2007.