Iontophoretic transport of zinc phthalocyanine tetrasulfonic acid as a tool to improve drug topical delivery

Anti-Cancer Drugs

Volumn 22, Issue 8, 2011, Pages 783-793

  Souza, Joel G ^a   Gelfuso, Guilherme M ^a   Simão, Patricia S ^a   Borges, Antônio C ^a   Lopez, Renata F V ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

iontophoresis; photodynamic therapy; phthalocyanine; skin; topical delivery

Indexed keywords

PHTHALOCYANINE ZINC; SODIUM CHLORIDE; SULFONIC ACID DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONFOCAL MICROSCOPY; DERMIS; DRUG DELIVERY SYSTEM; DRUG DISTRIBUTION; DRUG TRANSPORT; ELECTROOSMOSIS; EPIDERMIS; FOLLICLE FLUID; HUMAN; HYDROPHILICITY; IN VITRO STUDY; IN VIVO STUDY; ION TRANSPORT; IONTOPHORESIS; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; STRATUM CORNEUM; TOPICAL TREATMENT;

ADMINISTRATION, CUTANEOUS; ANIMALS; DRUG DELIVERY SYSTEMS; ELECTRODES; GELS; HYDROGEN-ION CONCENTRATION; INDOLES; IONTOPHORESIS; MALE; ORGANOMETALLIC COMPOUNDS; RATS; RATS, WISTAR; SKIN ABSORPTION; SOLUBILITY; TIME FACTORS;

EID: 80051552549     PISSN: 09594973     EISSN: 14735741     Source Type: Journal    
DOI: 10.1097/CAD.0b013e3283468979     Document Type: Article

References (38)

1. Gibson SL, Havens JJ, Foster TH, Hilf F. Time-dependent intracellular accumulation of d-aminolevulinic acid, induction of porphyrin synthesis and subsequent phototoxicity. Photochem Photobiol 1997; 65:416-421. (Pubitemid 27158973)
2. Robersts DJH, Cairnduff F. Photodynamic therapy of primary skin cancer: a review. Br Plast Surg 1995; 48:360-370.
3. Araú jo LM, Thomazine JA, Lopez RF. Development of microemulsions to topically deliver 5-aminolevulinic acid in photodynamic therapy. Eur J Pharm Biopharm 2010; 75:48-55.
4. Gelfuso GM, Gratieri T, Souza JG, Thomazini JA, Lopez RFV. The influence of positive or negative charges in the passive and iontophoretic skin penetration of porphyrins used in photodynamic therapy. Eur J Pharm Biopharm 2011; 77:249-256.
5. Tita SPS, Perussi JR. The effect of porphyrins on normal and transformed mouse cell lines in the presence of visible light. Br J Med Biol Res 2001; 34:1331-1336. (Pubitemid 33014502)
6. Sekyia S, Kubota K, Kasai T, Iwasaki H, Yamauchi K, Takamisawa H, Tenjin Y. Cytocidal effects of hematoporphyrin derivate and argon dye laser on human gynecologic tumor cell in vitro. Int J Gynecol Obstet 1998; 26:151-158.
7. Kaestner L, Cesson M, Kassab K, Christensen T, Edminson PD, Cook MJ, et al. Zinc octa-n-alkyl phthalocyanines in photodynamic therapy: photophysical properties, accumulation and apoptosis in cell cultures, studies in erythrocytes and topical application to Balb/c mice skin. Photochem Photobiol Sci 2003; 2:660-667. (Pubitemid 41646662)
8. Van Leengoed HLLM, Cuomo V, Versteeg AAC, Van Der Veen N, Jori G, Star WM. In-vivo fluorescence and photodynamic activity of zinc phthalocyanine administered in liposomes. Br J Cancer 1994; 69:840-845. (Pubitemid 24140661)
9. Beeby A, Fitzgerald S, Stanley CF. Protonation of tetrasulfonated zinc phthalocianine in aqueous acetonitrile solution. Photochem Photobiol 2001; 74:566-569.
10. Vittar NBR, Prucca CG, Strassert C, Awruch J, Rivarola VA. Cellular inactivation and antitumor efficacy of a new zinc phthalocyanine with potential use in photodynamic therapy. Int J Biochem Cell Biol 2008; 40:2192-2205.
11. Allémann E, Brasseur N, Kudrevich SV, Madeleine C, Van Lier JE. 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)
12. Cristó bal J, Stockert JC, Villanueva A, Rello-Varona S, Juarranz A, Cañ ete M. Caspase-2: a possible trigger of apoptosis induced in A-549 tumor cells by ZnPc photodynamic treatment. Int J Oncol 2006; 28:1057-1063.
13. Fadel M, Kassab K, Fadeel DA. Zinc phthalocyanine-loaded PLGA biodegradable nanoparticles for photodynamic therapy in tumor-bearing mice. Lasers Med Sci 2010; 25:283-292.
14. Ricci-Jú nior E, Marchetti JM. Zinc(II) phthalocyanine loaded PLGA nanoparticles for photodynamic therapy use. Int J Pharm 2006; 310:187-195. (Pubitemid 43287983)
15. Fabris C, Soncin M, Miotto G, Fantetti L, Chiti G, Dei D, et al. Zn (II)-phthalocyanines as phototherapeutic agents for cutaneous diseases. Photosensitization of fibroblasts and keratinocytes. J Phtochem Photobiol B: Biol 2006; 83:48-53.
16. Zhao B, Yin JJ, Bilski PJ, Chignell CF, Roberts JE, He YY. Enhanced photodynamic efficacy towards melanoma cells by encapsulation of Pc4 in silica nanoparticles. Toxicol Appl Pharmacol 2009; 241:163-172.
17. Reddi E, Zhou C, Biolo R, Menegaldo E, Jori G. Liposome-and LDLadministered Zn(II)-phtalocyanine as a photodynamic agent for tumours. I. Pharmacokinetic properties and phototherapeutic efficiency. Br J Cancer 1990; 61:407-411. (Pubitemid 20106015)
18. Griffiths J, Cruse-Sawyer J,Wood SR, Schofield J, Brown SB, Dixon B. On the photodynamic therapy action of zinc phthalocyanine tetrasulfonic acid in vivo. J Photochem Photobiol B 1994; 24:195-199. (Pubitemid 24285801)
19. Allen CM, Sharman WM, Van Lier JE. Current status of phthalocyanines in the photodynamic therapy of cancer. J Porphyr Phthalocyanines 2001; 5:161-169. (Pubitemid 32125237)
20. Ben-Hur E. Basic photobiology and mechanisms of action of phthalocyanines. In: Henderson BW, Dougherty TJ, editors. Photodynamic therapy: basic principles and clinical applications. New York: Marcel Dekker; 1992. pp. 63-78.
21. Guy RH, Kalia YN, Delgado-Charro MB, Merino V, Ló pez A, Marro D. Iontophoresis: electrorepulsion and electroosmosis. J Control Release 2000; 64:129-132. (Pubitemid 30035313)
22. Jadoul A, Bouwstra JA, Pré at V. Effects of iontophoresis and electroporation on the stratum corneum: review on the biophysical studies. Adv Drug Deliv Rev 1999; 35:89-105. (Pubitemid 29046388)
23. Kalia YN, Naik A, Garrison J, Guy RH. Iontophoretic drug delivery. Adv Drug Deliv Rev 2004; 56:619-658. (Pubitemid 38326937)
24. Lopez RFV, Bentley MVLB, Delgado-Charro MB, Guy RH. Iontophoretic delivery of 5-aminolevulinic acid (ALA): effect of pH. Pharm Res 2001; 18:311-315. (Pubitemid 32595818)
25. Lopez RFV, Bentley MVLB, Delgado-Charro MB, Guy RH. Optimization of aminolevulinic acid delivery by iontophoresis. J Control Rel 2003; 88:65-70. (Pubitemid 36173952)
26. Lopez RFV, Bentley MVLB, Delgado-charro MB, Salomon D, Van Den Bergh H, Lange N, Guy RH. Enhanced delivery of 5-aminolevulinic acid esters by iontophoresis in vitro. Photochem Photobiol 2003b; 77:304-308.
27. Rhodes LE, Tsoukas MM, Anderson RR, Kollias N. Iontophoretic delivery of ALA provides a quantitative model for ALA pharmacokinetics and PpIX phototoxicity in human skin. J Invest Dermatol 1997; 108:87-91. (Pubitemid 27019851)
28. Gerscher S, Connelly JP, Beijersbergen Van Henegouwen GMJ, Macrobert AJ, Watt P, Rhodes LE. A quantitative assessment of protoporphyrin IX metabolism and phototoxicity in human skin following dose-controlled delivery of the prodrugs 5-aminolaevulinic acid and 5-aminolaevulinic acid-n-pentylester. Br J Dermatol 2001; 144:983-990.
29. Boddé HE, Roemelé PEH, Star WM. Quantification of topically delivered 5-aminolevulinic acid by iontophoresis across ex vivo human SC. Photochem Photobiol 2001; 75:418-423.
30. Gelfuso GM, Figueiredo FV, Gratieri T, Lopez RFV. The effects of pH and ionic strength on topical delivery of a negatively charged porphyrin (TPPS4). J Pharm Sci 2008; 97:4249-4257.
31. Green PG, Hinz RS, Kim A, Szoka FC, Guy RH. Iontophoretic delivery of a series of tripeptides across the skin in vitro. Pharm Res 1997; 8:1121-1127.
32. Boehncke WH. Topical photodynamic therapy for psoriasis. In: Calzavara-Pinton P, Szeimies RM, Ortel B, editors. Photodynamic therapy and fluorescence diagnosis in dermatology. San Francisco: Elsevier Science; 2001. pp. 259-270.
33. Sylvestre JP, Guy R H, Delgado-Charro MB. In vitro optimization of dexamethasone phosphate delivery by iontophoresis. Phys Ther 2008; 88:1177-1185.
34. Barry BW. Novel mechanisms and devices to enable successful transdermal drug delivery. Eur J Pharm Sci 2001; 14:101-114. (Pubitemid 32737532)
35. Kassan DG, Lynch AM, Stiller MJ. Physical enhancement of dermatologic drug iontophoresis and phonophoresis. J Am Acad Dermatol 1996; 34:657-666. (Pubitemid 26098017)
36. Stahl J, Niedorf F, Kietzmann M. Characterisation of epidermal lipid composition and skin morphology of animal skin ex vivo. Eur J Pharm Biopharm 2009; 72:310-316.
37. Welch ML, Grabski WJ, Mccollough ML, Skelton HG, Smith KJ, Menon PA, Anderson LL. 5-Fluorouracil iontophoretic Bowen's disease. J Am Acad Dermatol 1997; 36:956-958.
38. Dougherty TJ, Cooper MT, Mang TS. Cutaneous phototoxic occurrences in patients receiving photofrin. Lasers Surg Med 1990; 10:485-488. (Pubitemid 20366419)