Influence of 6-ketocholestanol on skin permeation of 5-aminolevulinic acid and evaluation of chemical stability

Journal of Pharmaceutical Sciences

Volumn 93, Issue 11, 2004, Pages 2780-2787

  Auner, Barbara Gabriele ^a   Petzenhauser, Elke ^a   Valenta, Claudia ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

5 aminolevulinic acid; 6 ketocholestanol; Diffusion experiments; Liposomes; Porcine skin; Stability

Indexed keywords

6 OXOCHOLESTANOL; AMINOLEVULINIC ACID; CHOLESTANOL; FLUORESCENT DYE; LIPOSOME; PHOSPHOLIPID; PRODRUG; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CHEMICAL REACTION; CREAM; DIFFUSION; DRUG DIFFUSION; DRUG FORMULATION; DRUG PENETRATION; DRUG STABILITY; FLUORESCENCE; GELATION; MICROBIAL CONTAMINATION; NONHUMAN; SKIN; SUSPENSION; SWINE;

EID: 8644290733     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1002/jps.20130     Document Type: Article

References (34)

1. Kennedy J, Pottier R, Pross D. 1990. Photodynamic therapy with endogenous protoporphyrin IX. Basic principles and present clinical experience. J Photochem Photobiol B 6:143-148.
2. Szeimies RM, Sassy T, Landthaler N. 1994. Penetration potency of topical applied 5-aminolevulinic acid for photodynamic therapy of basal cell carcinoma. Photochem Photobiol 59:73-76.
3. Peng Q, Warloe T, Moan J, Heyerdahl H, Steen HB, Nesland JM, Giercksky KE. 1995. Distribution of 5-aminolevulinic acid-induced porphyrins in noduloulcerative basal cell carcinoma. J Photochem Photobiol B 62:906-913.
4. Juzenas P, Sharfaei S, Moan J, Bissonnette R. 2002. Protoporphyrin IX fluorescence kinetics in UV-induced tumours and normal skin of hairless mice after topical application of 5-aminolevulinic acid methyl ester. J Photochem Photobiol B: Biol 67:11-17.
5. Barry BW. 2001. Novel mechanisms and devices to enable successful transdermal drug delivery. Eur J Pharm Sci 14:101-114.
6. Lopez RF, Bentley MV, Delgado-Charro MB, Guy RH. 2001. Iontophoretic delivery of 5-aminolevulinic acid (ALA): Effect of pH. Pharm Res 18:311-315.
7. De Rosa FS, Marchetti JM, Thomazini JA, Tedesco AC, Bentley MV. 2000. A vehicle for photodynamic therapy of skin cancer: Influence of dimethylsulphoxide on 5-aminolevulinic acid in vitro cutaneous permeation and in vivo protoporphyrin IX accumulation determined by confocal microscopy. J Controlled Release 65:359-366.
8. Casas A, Perotti C, Fukuda H, Rogers L, Butler AR, Batlle A. 2001. ALA and ALA hexyl ester-induced porphyrin synthesis in chemically induced skin tumours: The role of different vehicles on improving photosensitization. Br J Cancer 85:1794-1800.
9. Moan J, Ma LW, Iani V. 2001. On the pharmacokinetics of topically applied 5-aminolevulinic acid and two of its esters. Int J Cancer 92:139-143.
10. De Rosa FS, Tedesco AC, Lopez RF, Riemma Pierre MB, Lange N, Marchetti JM, Gomes Rotta JC, Lopes Badra Bentley MV. 2003. In vitro skin permeation and retention of 5-aminolevulinic acid ester derivatives for photodynamic therapy. J Controlled Release 89:261-269.
11. Svaasand LO, Wyss P, Wyss-Desserich MT, Tadir Y, Tromberg BJ, Berns MW. 1996. Dosimetry model for photodynamic therapy with topically administered photosensitizers. Lasers Surg Med 18:139-149.
12. Lopez RF, Lange N, Guy R, Bentley MV. 2004. Photodynamic therapy of skin cancer: Controlled drug delivery of 5-ALA and its esters. Adv Drug Deliv Rev 56:77-94.
13. Hadgraft J. 2001. Skin, the final frontier. Int J Pharm 224:1-18.
14. Franklin JC, Cafiso DS. 1993. Internal electrostatic potentials in bilayers: Measuring and controlling dipole potentials in lipid vesicles. Biophys J 65:289-299.
15. Cladera J, O'Shea P, Hadgraft J, Valenta C. 2003. Influence of molecular dipoles on human skin permeability: Use of 6-ketocholestanol to enhance the transdermal delivery of bacitracin. J Pharm Sci 92:1018-1027.
16. Auner BG, Valenta C, Hadgraft J. 2003. Influence of phloretin and 6-ketocholestanol on the skin permeation of sodium-fluorescein. J Controlled Release 89:321-328.
17. Auner BG, Valenta C, Hadgraft J. 2003. Influence of lipophilic counter-ions in combination with phloretin and 6-ketocholestanol on the skin permeation of 5-aminolevulinic acid. Int J Pharm 255:109-116.
18. Valenta C, Janout H. 1994. Corticosteroid analysis by HPLC with increased sensitivity by use of precolumn concentration. J Liquid Chromatogr 17:1141-1146.
19. Cladera J, O'Shea P. 1998. Intramembrane molecular dipoles affect the membrane insertion and folding of a model amphiphilic peptide. Biophys J 74:2434-2442.
20. Oishi H, Nomiyama H, Nomiyama K, Tomokuni K. 1996. Fluorometric HPLC determination of delta-aminolevulinic acid (ALA) in the plasma and urine of lead workers: Biological indicators of lead exposure. J Anal Toxicol 20:106-110.
21. Wester RC, Maibach HI. 1987. Animal models for transdermal delivery. In: Kydonieus AF, Berner B, editors. Transdermal delivery of drugs. Boca Raton, FL: CRC Press, p 61-70.
22. Valenta C, Janisch M. 2003. Permeation of cyproterone acetate through pig skin from different vehicles with phospholipids. Int J Pharm 258:133-139.
23. Lautenschläger H. 2001. Liposomes. In: Barel AO, Paye M, Maibach HI, editors. Handbook of cosmetic science and technology. New York: Marcel Dekker. p 201-209.
24. Fabbrocine G, Di Constanzo MP, Riccardo AM, Quarto M, Colasanti A, Roberti G, Monfrecola G. 2001. Photodynamic therapy with topical 5-aminolevulinic acid for the treatment of plantar warts. J Photochem Photobiol B: Biol 61:30-34.
25. Peng Q, Soler AM, Warloe T, Nesland JM, Giercksky KE. 2001. Selective distribution of porphyrins in skin thick basal cell carcinoma after topical application of methyl 5-aminolevulinate. J Photochem Photobiol B 62:140-145.
26. Calzavara-Pinton PG. 1995. Repetitive photodynamic therapy with topical 5-aminolevulinic acid as an appropriate approach to the routine treatment of superficial non-melanoma skin tumours. J Photochem Photobiol B: Biol 29:53-57.
27. Casas A, Fukuda H, Di Venosa G, Battle AM. 2000. The influence of the vehicle on the synthesis of porphyrins after topical application of 5-aminolaevulinic acid. Implications in cutaneous photodynamic sensitization. Br J Dermatol 143:564-572.
28. Pierre MB, Tedesco AC, Marchetti JM, Bentley MV. 2001. Stratum corneum lipids liposomes for the topical delivery of 5-aminolevulinic acid in photodynamic therapy of skin cancer: Preparation and in vitro permeation study. BMC Dermatol. http:// www.biomedcentral.com/1471-5945/1471/1475/.
29. Rougier A, Lotte C. 1986. Correlations between horny layer concentration and percutaneous absorption. In: Shroot BS, editor. Pharmacology and skin: 1 Skin pharmacokinetics. Basel: Karger.
30. Valenta C, Nowak M, Hadgraft J. 2001. Influence of phloretin and 6-ketocholestanol on the permeation of progesterone through porcine skin. Int J Pharm 217:79-86.
31. Ando HY, Schultz TW, Schnaare RL, Sugita ET. 1984. Percutaneous absorption: A new physicochemical predictive model for maximum human in vivo penetration rates. J Pharm Sci 73:461-467.
32. Lim CW, Fujiwara S, Yamashita F, Hashida M. 2002. Prediction of human skin permeability using a combination of molecular orbital calculations and artificial neural network. Biol Pharm Bull 25:361-366.
33. Brockman H. 1994. Dipole potential of lipid membranes. Chem Phys Lipids 73:57-59.
34. Turchiello RF, Vena FCB, Maillard P, Souza CS, Bentley MVBL, Tedesco AC. 2003. Cubic phase gel as a drug delivery system for topical application of 5-ALA, its ester derivatives and m-THPC in photodynamic therapy (PDT). J Photochem Photobiol B: Biol 70:1-6.