A new micro/nanoencapsulated porphyrin formulation for PDT treatment

International Journal of Pharmaceutics

Volumn 376, Issue 1-2, 2009, Pages 76-83

  Deda, Daiana K ^a   Uchoa, Adjaci F ^a   Caritá, Eduardo ^a   Baptista, Maurício S ^a   Toma, Henrique E ^a   Araki, Koiti ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Cationic porphyrin; HeLa cells; PDT; Polymeric encapsulation

Indexed keywords

5,10,15 TRIPHENYL 20 (3 N METHYLPYRIDINIUM YL)PORPHYRIN; ATELOCOLLAGEN; CATION; PHOSPHATIDYLCHOLINE; POLYMER; POLYSORBATE 20; PORPHYRIN DERIVATIVE; SURFACTANT; UNCLASSIFIED DRUG;

ARTICLE; COACERVATION; CONTROLLED STUDY; CREAM; CYTOTOXICITY; DRUG FORMULATION; DRUG STRUCTURE; EMULSION; HELA CELL; HUMAN; HUMAN CELL; HYDROPHOBICITY; MICROCAPSULE; MICROENCAPSULATION; NANOENCAPSULATION; PARTICLE SIZE; PHOTODYNAMIC THERAPY; PHOTODYNAMICS; PHOTOTOXICITY; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; SYNTHESIS; ULTRASOUND;

CAPSULES; CELL SURVIVAL; DRUG CARRIERS; DRUG DELIVERY SYSTEMS; HELA CELLS; HUMANS; NANOCAPSULES; PHOTOCHEMOTHERAPY; PORPHYRINS;

EID: 67349276974     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2009.04.024     Document Type: Article

References (44)

1. Allison R.R., Mota H.C., Bagnato V.S., and Sibata C.H. Bio-nanotechnology and photodynamic therapy state of the art review. Photodiagn. Photodyn. Ther. 5 (2008) 19-28
2. Araki K., Engelmann F.M., Mayer I., Toma H.E., Baptista M.S., Maeda H., Osuka A., and Furuta H. Doubly N-confused porphyrins as efficient sensitizers for singlet oxygen generation. Chem. Lett. 32 (2003) 244-245
3. Araki K., Silva C.A., Toma H.E., Catalani L.H., Medeiros M.H.G., and Mascio P.D. Zinc tetraruthenated porphyrin binding and photoinduced oxidation of calf-thymus DNA. J. Inorg. Biochem. 78 (2000) 269-273
4. Araki K., Winnischofer H., Toma H.E., Maeda H., Osuka A., and Furuta H. Acid-base and spectroelectrochemical properties of doubly N-confused porphyrins. Inorg. Chem. 40 (2001) 2020-2025
5. Bamford C.H., and Tompa H. The theory of coacervation. Trans., Faraday Soc. 46 (1950) 310-316
6. Bechet D., Couleaud P., Frochot C., Viriot M.L., Guillemin F., and Barberi-Heyob M. Nanoparticles as vehicles for delivery of photodynamic therapy agents. Trends Biotechnol. 26 (2008) 612-621
7. Cevc G. Lipid vesicles and other colloids as drug carriers on the skin. Adv. Drug Deliv. Rev. 56 (2004) 675-711
8. Coffin M.D., and Mcginity J.W. Biodegradable pseudolatexes-the chemical-stability of poly(d,l-lactide) and poly (epsilon-caprolactone) nanoparticles in aqueous-media. Pharm. Res. 9 (1992) 200-205
9. Dong Z.J., Toure A., Jia C.S., Zhang X.M., and Xu S.Y. Effect of processing parameters on the formation of spherical multinuclear microcapsules encapsulating peppermint oil by coacervation. J. Microencapsul. 24 (2007) 634-646
10. Dougherty T.J. Photodynamic therapy. Photochem. Photobiol. 58 (1993) 895-900
11. Engelmann F.M., Mayer I., Araki K., Toma H.E., Baptista M.S., Maeda H., Osuka A., and Furuta H. Photochemistry of doubly N-confused porphyrin bonded to non-conventional high oxidation state Ag(III) and Cu(III) ions. J. Photochem. Photobiol. A 163 (2004) 403-411
12. Engelmann F.M., Mayer I., Gabrielli D.S., Toma H.E., Kowaltowski A.J., Araki K., and Baptista M.S. Interaction of cationic meso-porphyrins with liposomes, mitochondria and erythrocytes. J. Bioenerg. Biomembr. 39 (2007) 175-185
13. Engelmann F.M., Rocha S.V.O., Toma H.E., Araki K., and Baptista M.S. Determination of n-octanol/water partition and membrane binding of cationic porphyrins. Int. J. Pharm. 329 (2007) 12-18
14. Engelmann F.M., Winnischofer H., Araki K., and Toma H.E. Synthesis, electrochemistry, spectroscopy and photophysical properties of a series of meso-phenylpyridylporphyrins with one to four pyridyl rings coordinated to [Ru(bipy)2Cl]+ groups. J. Porphyrins Phthalocyanines 6 (2002) 33-42
15. Furuta H., Asano T., and Ogawa T. N-confused porphyrin-a new isomer of tetraphenylporphyrin. J. Am. Chem. Soc. 116 (1994) 767-768
16. Furuta H., Ishizuka T., Osuka A., and Ogawa T. N-fused porphyrin: a new tetrapyrrolic porphyrinoid with a fused tri-pentacyclic ring. J. Am. Chem. Soc. 122 (2000) 5748-5757
17. Furuta H., Morimoto T., and Osuka A. Syntheses, structures, and crystal packing of N-confused 5,20-diphenylporphyrin and Ag(III) complex. Org. Lett. 5 (2003) 1427-1430
18. Furuta H., Ogawa T., Uwatoko Y., and Araki K. N-confused tetraphenylporphyrin-silver(III) complex. Inorg. Chem. 38 (1999) 2676-2682
19. Hopper C. Photodynamic therapy: a clinical reality in the treatment of cancer. Lancet Oncol. 1 (2000) 212-219
20. Hudson R., Savoie H., and Boyle R.W. Lipophilic cationic porphyrins as photodynamic sensitzers. Photodiagn. Photodyn. Ther. 2 (2005) 193-196
21. Ikeda A., Doi Y., Nishiguchi K., Kitamura K., Hashizume M., Kikuchi J.I., Yogo K., Ogawa T., and TakeyaA T. Induction of cell death by photodynamic therapy with water-soluble lipid-membrane-incorporated [60]fullerene. Org. Biomol. Chem. 5 (2007) 1158-1160
22. 2+, Cu(Ii), and Zn(Ii). J. Phys. Chem. 95 (1991) 427-431
23. Konan Y.N., Gurny R., and Allemann E. State of the art in the delivery of photosensitizers for photodynamic therapy. J. Photochem. Photobiol. B 66 (2002) 89-106
24. Machado A.E.D.H. Terapia fotodinâmica: princípios, potencial de aplicação e perspectivas. Quim. Nova 23 (2000) 237-243
25. Mayya K.S., Bhattacharyya A., and Argillier J.F. Micro-encapsulation by complex coacervation: influence of surfactant. Polym. Int. 52 (2003) 644-647
26. Menger F.M., and Sykes B.M. Anatomy of a coacervate. Langmuir 14 (1998) 4131-4137
27. Moreira L.M., Dos Santos F.V., Lyon J.P., Maftoum-Costa M., Pacheco-Soares C., and Da Silva N.S. Photodynamic therapy: porphyrins and phthalocyanines as photosensitizers. Aust. J. Chem. 61 (2008) 741-754
28. Moriwaki S.I., Misawa J., Yoshinari Y., Yamada I., Takigawa M., and Tokura Y. Analysis of photosensitivity in Japanese cancer-bearing patients receiving photodynamic therapy with porfimer sodium (Photofrin (TM)). Photodermatol. Photoimmunol. Photomed. 17 (2001) 241-243
29. Musyanovych A., Schmitz-Wienke J., Mailander V., Walther P., and Landfester K. Preparation of biodegradable polymer nanoparticles by miniemulsion technique and their cell interactions. Macromol. Biosci. 8 (2008) 127-139
30. Needhan D., Mcintosh T.J., and Lasic D.D. Repulsive interactions and mechanical stability of polymer-grafted lipid membranes. Biochim. Biophys. Acta 1108 (1992) 40-48
31. Nihant N., Grandfils C., Jerome R., and Teyssie P. Microencapsulation by coacervation of poly(lactide-co-glycolide): 4. Effect of the processing parameters on coacervation and encapsulation. J. Controlled Release 35 (1995) 117-125
32. Onuki J., Ribas A.V., Medeiros M.H.G., Araki K., Toma H.E., Catalani L.H., and Di Mascio P. Supramolecular cationic tetraruthenated porphyrin induces single-strand breaks and 8-oxo-7,8-dihydro-2′-deoxyguanosine formation in DNA in the presence of light. Photochem. Photobiol. 63 (1996) 272-277
33. Pavani C., Uchoa A.F., Oliveira C.S., Iamamoto Y., and Baptista M.S. Effect of zinc insertion and hydrophobicity on the membrane interactions and PDT activity of porphyrin photosensitizers. Photochem. Photobiol. Sci. 8 (2009) 233-240
34. Pushpan S.K., Venkatraman S., Anand V.G., Sankar J., Parmeswaran D., Ganesan S., and Chandrashekar T.K. Porphyrins in photodynamic therapy-a search for ideal photosensitizers. Curr. Med. Chem. - Anti-Cancer Agents 2 (2002) 187-207
35. Ravanat J.L., Cadet J., Araki K., Toma H.E., Medeiros M.H.G., and Di Mascio P. Supramolecular cationic tetraruthenated porphyrin and light-induced decomposition of 2′-deoxyguanosine predominantly via a singlet oxygen-mediated mechanism. Photochem. Photobiol. 68 (1998) 698-702
36. Reddi E. Role of delivery vehicles for photosensitizers in the photodynamic therapy of tumours. J. Photochem. Photobiol. B 37 (1997) 189-195
37. Reddi E., Ceccon M., Valduga G., Jori G., Bommer J.C., Elisei F., Latterini L., and Mazzucato U. Photophysical properties and antibacterial activity of meso-porphyrin. Photochem. Photobiol. 75 (2002) 462-470
38. Sharman W.M., Allen C.M., and Van Lier J.E. Photodynamic therapeutics: basic principles and clinical applications. D.D.T. 4 (1999) 507-517
39. Simplício F.I., Maionchi F., and Hioka N. Terapia Fotodinâmica: aspectos farmacológicos, aplicações e avanços recentes no desenvolvimento de medicamentos. Quim. Nova 25 (2002) 801-807
40. Tian Y.Y., Wang L.L., and Wang W. Progress in photodynamic therapy on tumors. Laser Phys. 18 (2008) 1119-1123
41. Toma H.E., and Araki K. Supramolecular assemblies of ruthenium complexes and porphyrins. Coord. Chem. Rev. 196 (2000) 307-329
42. Torchilin V.P. Multifunctional nanocarriers. Adv. Drug Deliv. Rev. 58 (2006) 1532-1555
43. Triesscheijn M., Baas P., Schellens J.H.M., and Stewart F.A. Photodynamic therapy in oncology. The Oncologist 11 (2006) 1034-1044
44. Xiang T.X., and Anderson B.D. Liposomal drug transport: a molecular perspective from molecular dynamics simulations in lipid bilayers. Adv. Drug Deliv. Rev. 58 (2006) 1357-1378