The influence of positive or negative charges in the passive and iontophoretic skin penetration of porphyrins used in photodynamic therapy

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 77, Issue 2, 2011, Pages 249-256

  Gelfuso, Guilherme M ^a   Gratieri, Taís ^a   Souza, Joel G ^a   Thomazine, José A ^a   Lopez, Renata F V ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Electrical charge; Iontophoresis; Photodynamic therapy; Porphyrins; Topical delivery

Indexed keywords

MESO TETRA (4 SULFONATOPHENYL)PORPHYRIN; MESO TETRA (N METHYLPIRIDINIUM 4 YL)PORPHYRIN; PHOTOSENSITIZING AGENT; PORPHYRIN; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; DERMIS; DRUG FORMULATION; DRUG STRUCTURE; ELECTRICITY; EPIDERMIS; FLUORESCENCE ANALYSIS; FLUORESCENCE MICROSCOPY; GEL; HYDROPHILICITY; IONTOPHORESIS; NONHUMAN; PH MEASUREMENT; PHOTODYNAMIC THERAPY; RAT; SKIN CELL; SKIN PENETRATION;

ADMINISTRATION, CUTANEOUS; ADMINISTRATION, TOPICAL; ANIMALS; CELLULOSE; DIFFUSION; EAR; IONTOPHORESIS; MALE; NEOPLASMS; PHOTOCHEMOTHERAPY; PORPHYRINS; RATS; RATS, WISTAR; SKIN; SKIN ABSORPTION; SWINE;

EID: 79551538973     PISSN: 09396411     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejpb.2010.11.018     Document Type: Article

References (37)

1. R.F.V. Lopez, N. Lange, R.H. Guy, and M.V.L.B. Bentley Photodynamic therapy of skin cancer: controlled drug delivery of 5-ALA and its esters Adv. Drug Deliv. Rev. 56 2004 77 94
2. P.G. Calzavara-Pinton, M. Venturini, and R. Sala Photodynamic therapy: update 2006. Part 1: Photochemistry and photobiology J. Eur. Academ. Dermatol. Venereol. 21 2007 293 302
3. P. Mroz, G.P. Tegos, H. Gali, T. Wharton, T. Sarna, and M.R. Hamblin Photodynamic therapy with fullerenes Photochem. Photobiol. Sci. 6 2008 1139 1149
4. 4) J. Pharm. Sci. 97 2008 4249 4257
5. K. Komagoe, K. Tamagake, and T. Katsu The influence of aggregation of porphyrins on the efficiency of photogeneration of hydrogen peroxide in aqueous solution Chem. Pharm. Bull. 54 2006 1004 1009
6. A. Villanueva, L. Caggiari, G. Jori, and C. Milanesi Morphological aspects of an experimental tumour photosensitized with a meso-substituted cationic porphyrin J. Photochem. Photobiol. B. 23 1994 49 56
7. N. Yamakawa, Y. Ishikawa, and T. Uno Solution properties and photonuclease activity of cationic bis-porphyrins linked with a series of aliphatic diamines Chem. Pharm. Bull. 49 2001 1531 1540
8. B. Jin, H.M. Lee, Y.A. Lee, J.H. Ko, C. Kim, and S.K. Kim Simultaneous binding of meso-tetrakis(N-methylpyridinium-4-yl)porphyrin and 4',6-diamidino-2-phenylindole at the minor grooves of poly(dA).poly(dT) and poly[d(A-T)(2)]: fluorescence resonance energy transfer between DNA bound drugs J. Am. Chem. Soc. 127 2005 2417 2424
9. T. Ohyama, H. Mita, and Y. Yamamoto Binding of 5,10,15,20-tetrakis(N- methylpyridinium-4-yl)-21H, 23H-porphyrin to an AT-rich region of a duplex DNA Biophys. Chem. 113 2005 53 59
10. J. Winkelman The distribution of tetraphenylporphinesulfonate in the tumor-bearing rat Cancer Res. 22 1962 589 596
11. T. Zima, M. Jirsa, M. Jirsa Jr, M. Jiráscová, V. Bradová, and B. Stádník Effect of chloroquine wash-out period of photosensitizers in the skin and selected organs in rats Physiol. Res. 53 2004 103 108
12. P.J. Gonalves, L.D.E. Boni, N.M. B Neto, J.J. Rodrigues, S.C. Zílio, and I.E. Borissevitch Effect of protonation on the photophysical properties of meso-tetra(sulfonatophenyl)porphyrin Chem. Phys. Lett. 407 2005 236 241
13. Y. Wanga, R. Thakura, Q. Fanb, and B. Michniakc Transdermal iontophoresis: combination strategies to improve transdermal iontophoretic drug delivery Eur. J. Pharm. Biopharm. 60 2005 79 191
14. V. Merino, Y.N. Kalia, and R.H. Guy Transdermal therapy and diagnosis by iontophoresis Trends Biotechnol. 15 1997 288 290
15. R.F.V. Lopez, M.V.L.B. Bentley, M.B. Delgado-Charro, and R.H. Guy Iontophoretic delivery of 5-aminolevulinic acid (ALA): effect of pH Pharm. Res. 18 2001 311 315
16. R.F.V. Lopez, M.V.L. B Bentley, M.B. Delgado-Charro, D. Salomon, H. Van Den Bergh, N. Lange, and R.H. Guy Enhanced delivery of 5-aminolevulinic acid esters by iontophoresis in vitro Photochem. Photobiol. 77 2003 304 308
17. Y.N. Kalia, A. Naika, J. Garrisonc, and R.H. Guy Iontophoretic drug delivery Adv. Drug Deliv. Rev. 56 2004 619 658
18. C. C Bouissou, J.P. Sylvestre, R.H. Guy, and M.B. Delgado-Charro Reverse iontophoresis of amino acids: identification and separation of stratum corneum and subdermal sources in vitro Pharm. Res. 26 2009 2630 2638
19. J. Cázares-Delgadillo, A. Naik, A. Ganem-Rondero, D. Quintanar-Guerrero, and Y.N. Kalia Transdermal delivery of cytochrome C - A 12.4 kDa protein - across intact skin by constant-current iontophoresis Pharm. Res. 24 2007 1360 1368
20. S. Dubey, and Y.N. Kalia Non-invasive iontophoretic delivery of enzymatically active ribonuclease A (13.6 kDa) across intact porcine and human skins J. Control. Release 145 2010 203 209
21. P. Sebastiani, S. Nicoli, and P. Santi Effect of lactic acid and iontophoresis on drug permeation across rabbit ear skin Int. J. Pharm 292 2005 119 126
22. J.P. Sylvestre, R.H. Guy, and M.B. Delgado-Charro In vitro optimization of dexamethasone phosphate delivery by iontophoresis Phys. Ther. 88 2008 1177 1185
23. R.H. Guy, Y.N. Kalia, M.B. Delgado-Charro, V. Merino, A. Lopez, and D. Marro Iontophoresis: electrorepulsion and electroosmosis J. Control. Release. 64 2000 129 132
24. P.G. Green, R.S. Hinz, C. Cullander, G. Yamane, and R.H. Guy Iontophoretic delivery of amino acids and amino acid derivatives across the skin in vitro Pharm. Res. 8 1991 1113 1120
25. S.P. Tita, and J.R. Perussi The effect of porphyrins on normal and transformed mouse cell lines in the presence of visible light Braz. J. Med. Biol. Res. 34 2001 331 1336
26. 4 aggregation in aqueous solutions Spectrochim. Acta Part A. 63 2006 227 233
27. R.F. Pasternack, P.R. Huber, P. Boyd, G. Engasser, L. Francesconi, E. Gibbs, P. Fasella, G.C. Venturo, and L.C. Hindis On the aggregation of meso-substituted water soluble porphyrins J. Am. Chem. Soc. 94 1972 4511 4517
28. I.E. Borissevitch, and S.C. Gandini Photophysical studies of excited-state characteristics of mesotetrakis (4-N-methyl-pyridiniumyl) porphyrin bound to DNA J. Photochem. Photobiol. B. 43 1998 112 120
29. H.E. Boddé, P.H.E. Roemelé, and W.M. Star Quantification of topically delivered 5-aminolevulinic acid by iontophoresis across ex vivo human stratum corneum Photochem. Photobiol. 75 2002 418 423
30. N. Merclin, T. Bramer, and K. Edsman Iontophoretic delivery of 5-aminolevulinic acid and its methyl ester using a carbopol gel as vehicle J. Control. Release. 98 2004 57 65
31. D. Marro, R.H. Guy, and M.B. Delgado-Charro Characterization of the iontophoretic permselectivity properties of human and pig skin J. Control. Release. 70 2001 213 217
32. V. Nair, and R. Panchagnula Physicochemical considerations in the iontophoretic delivery of a small peptide: in vitro studies using arginine vasopressin as a model peptide Pharmacol. Res. 48 2003 175 182
33. J. Cázares-Delgadillo, I.B. Aziza, C. Balaguer-Fernández, A. Calatayud-Pascual, A. Ganem-Rondero, D. Quintanar-Guerrero A.C. Castellano, V. Merino, and Y.N. Kalia Comparing metoclopramide electrotransport kinetics in vitro and in vivo Eur. J. Pharm. Sci. 41 2010 353 359
34. A.K. Nugroho, L. Li, D. Dijkstra, H. Wikstrom, M. Danhof, and J.A. Bouwstra Transdermal iontophoresis of the dopamine agonist 5-OH-DPAT in human skin in vitro J. Control. Release. 103 2003 393 403
35. A. Jadoul, J. Bouwstra, and V.V. Préat Effects of iontophoresis and electroporation on the stratum corneum: review of the biophysical studies Adv. Drug Deliv. Rev. 35 1999 89 105
36. H. Herai, T. Gratieri, J.A. Thomazine, M.V.L.B. Bentley, and R.F.V. Lopez Doxorubicin skin penetration from monoolein-containing propylene glycol formulations Int. J. Pharm. 329 2007 88 93
37. C. Cullander, and R.H. Guy Sites of iontophoretic current flow into the skin: identification and characterization with the vibrating probe electrode J. Invest. Dermatol. 97 1991 55 64