Vitamin D3-based conjugates for topical treatment of psoriasis: Synthesis, antiproliferative activity, and cutaneous penetration studies

Pharmaceutical Research

Volumn 22, Issue 1, 2005, Pages 50-57

  Ben Shabat, Shimon ^a   Benisty, Rachel ^a   Wormser, Uri ^b   Sintov, Amnon C ^a,b  

^a BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

^b HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

Calcipotriol; Polyunsaturated fatty acids; Psoriasis; Skin penetration; Vitamin D3

Indexed keywords

4 DIMETHYLAMINOPYRIDINE; CALCIPOTRIOL; COLECALCIFEROL; DICYCLOHEXYLCARBODIIMIDE; ESTER; GAMMA LINOLENIC ACID; LINOLENIC ACID; POLYUNSATURATED FATTY ACID; DRUG DERIVATIVE; GROWTH INHIBITOR;

ANIMAL TISSUE; ARTICLE; CELL CULTURE; CHEMICAL BOND; CONCENTRATION (PARAMETERS); CONJUGATE; CONJUGATION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG PENETRATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HYDROLYSIS; IN VITRO STUDY; KERATINOCYTE; NONHUMAN; PRIORITY JOURNAL; PSORIASIS; SKIN PENETRATION; TRANSESTERIFICATION; ANIMAL; CELL PROLIFERATION; CHEMISTRY; COMPARATIVE STUDY; DRUG EFFECT; METABOLISM; PHYSIOLOGY; SKIN ABSORPTION; SWINE; TOPICAL DRUG ADMINISTRATION;

ADMINISTRATION, TOPICAL; ANIMALS; CELL PROLIFERATION; CHOLECALCIFEROL; GROWTH INHIBITORS; PSORIASIS; SKIN ABSORPTION; SWINE;

EID: 17644384003     PISSN: 07248741     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11095-004-9008-0     Document Type: Article

References (32)

1. S. M. Thacher, J. Vasudevan, K. Y. Tsang, S. Nagpal, and R. A. Chandraratna. New dermatological agents for the treatment of psoriasis. J. Med. Chem. 44:281-297 (2001).
2. K. Kragballe, L. Desjarlais, and J. J. Voorhees. Leukotrienes B4, C4 and D4 stimulate DNA synthesis in cultured human epidermal keratinocytes. Br. J. Dermatol. 113:43-52 (1985).
3. T. H. Lee, R. L. Hoover, J. D. Williams, R. I. Sperling, J. Ravalese III, B. W. Spur, D. R. Robinson, E. J. Corey, R. A. Lewis, and K. F. Austen. Effect of dietary enrichment with eicosapentaenoic and docosahexaenoic acids on in vitro neutrophil and monocyte leukotriene generation and neutrophil function. N. Engl. J. Med. 312:1217-1224 (1985).
4. C. R. Darley, W. J. Cunliffe, C. M. Green, P. E. Hutchinson, M. R. Klaber, and N. Downes. Safety and efficacy of calcipotriol ointment (Dovonex) in treating children with psoriasis vulgaris. Br. J. Dermatol. 135:390-393 (1996).
5. L. Dubertret, D. Wallach, P. Souteyrand, M. Perussel, B. Kalis, J. Meynadier, J. Chevrant-Breton, C. Beylot, J. A. Bazex, and H. J. Jurgensen. Efficacy and safety of calcipotriol (MC 903) ointment in psoriasis vulgaris. A randomized, double-blind, right/left comparative, vehicle-controlled study. J. Am. Acad. Dermatol. 27:983-988 (1992).
6. T. Kobayashi, H. Okumura, K. Hashimoto, H. Asada, S. Inui, and K. Yoshikawa. Synchronization of normal human keratinocyte in culture: its application to the analysis of 1,25-dihydroxyvitamin D3 effects on cell cycle. J. Dermatol. Sci. 17:108-114 (1998).
7. K. Kragballe, P. M. Steijlen, H. H. Ibsen, P. C. van de Kerkhof, J. Esmann, L. H. Sorensen, and M. B. Axelsen. Efficacy, tolerability, and safety of calcipotriol ointment in disorders of keratinization. Results of a randomized, double-blind, vehicle-controlled, right/left comparative study. Arch. Dermatol. 131:556-560 (1995).
8. D. Feldman, T. Chen, M. Hirst, K. Colston, M. Karasek, and C. Cone. Demonstration of 1,25-dihydroxyvitamin D3 receptors in human skin biopsies. J. Clin. Endocrinol. Metab. 51:1463-1465 (1980).
9. S. Kienbaum, P. Lehmann, and T. Ruzicka. Topical calcipotriol in the treatment of intertriginous psoriasis. Br. J. Dermatol. 135:647-650 (1996).
10. H. Solvsten, M. L. Svendsen, K. Fogh, and K. Kragballe. Upregulation of vitamin D receptor levels by 1,25(OH)2 vitamin D3 in cultured human keratinocytes. Arch. Dermatol. Res. 289:367-372 (1997).
11. C. Buitrago, R. Boland, and A. R. de Boland. The tyrosine kinase c-Src is required for 1,25(OH)2-vitamin D3 signalling to the nucleus in muscle cells. Biochim. Biophys. Acta 1541:179-187 (2001).
12. C. A. Ramsay, J. Berth-Jones, G. Brundin, W. J. Cunliffe, L. Dubertret, P. C. van de Kerkhof, T. Menne, and E. Wegmann. Long-term use of topical calcipotriol in chronic plaque psoriasis. Dermatology 189:260-264 (1994).
13. S. Kew, S. Wells, F. Thies, G. P. McNeill, P. T. Quinlan, G. T. Clark, H. Dombrowsky, A. D. Postle, and P. C. Calder. The effect of eicosapentaenoic acid on rat lymphocyte proliferation depends upon its position in dietary triacylglycerols. J. Nutr. 133:4230-4238 (2003).
14. S. B. Bittiner, W. F. Tucker, I. Cartwright, and S. S. Bleehen. A double-blind, randomised, placebo-controlled trial of fish oil in psoriasis. Lancet 1:378-380 (1988).
15. P. D. Maurice, B. R. Allen, A. S. Barkley, S. R. Cockbill, J. Stammers, and P. C. Bather. The effects of dietary supplementation with fish oil in patients with psoriasis. Br. J. Dermatol. 117:599-606 (1987).
16. P. Mayser, H. Grimm, and F. Grimminger. n-3 fatty acids in psoriasis. Br. J. Nutr. 87:S77-S82 (2002).
17. S. C. McNeill, R. O. Potts, and M. L. Francoeur. Local enhanced topical delivery (LETD) of drugs: does it truly exist? Pharm. Res. 9:1422-1427 (1992).
18. S. A. Mikulak, C. T. Vangsness, and M. E. Nimni. Transdermal delivery and accumulation of indomethacin in subcutaneous tissues in rats. J. Pharm. Pharmacol. 50:153-158 (1998).
19. J. Austad, J. R. Bjerke, B. T. Gjertsen, S. Helland, J. K. Livden, T. Morken, and N. J. Mork. Clobetasol propionate followed by calcipotriol is superior to calcipotriol alone in topical treatment of psoriasis. J. Eur. Acad. Dermatol. Venereol. 11:19-24 (1998).
20. J. Ring, L. Kowalzick, E. Christophers, W. B. Schill, E. Schopf, M. Stander, H. H. Wolff, and P. Altmeyer. Calcitriol 3 microg g-1 ointment in combination with ultraviolet B phototherapy for the treatment of plaque psoriasis: results of a comparative study. Br. J. Dermatol. 144:495-499 (2001).
21. J. E. Osborne and P. E. Hutchinson. The importance of accurate dosage of topical agents: a method of estimating involved area and application to calcipotriol treatment failures. J. Eur. Acad. Dermatol. Venereol. 16:367-373 (2002).
22. A. C. Sintov, C. Behar-Canetti, Y. Friedman, and D. Tamarkin. Percutaneous penetration and skin metabolism of ethylsalicylate-containing agent, TU-2100: in-vitro and in-vivo evaluation in guinea pigs. J. Control. Rel. 79:113-122 (2002).
23. A. C. Sintov, I. Krymberk, D. Daniel, T. Hannan, Z. Sohn, and G. Levin. Radiofrequency-driven skin microchanneling as a new way for electrically assisted transdermal delivery of hydrophilic drugs. J. Control. Rel. 89:311-320 (2003).
24. P. Liu, W. I. Higuchi, W. Song, T. Kurihara-Bergstrom, and W. R. Good. Quantitative evaluation of ethanol effects on diffusion and metabolism of b-estradiol in hairless mouse skin. Pharm. Res. 8:865-872 (1991).
25. D. Peus, L. Hamacher, and M. R. Pittelkow. EGF-receptor tyrosine kinase inhibition induces keratinocyte growth arrest and terminal differentiation. J. Invest. Dermatol. 109:751-756 (1997).
26. L. Xue, D. R. Gollapalli, P. Maiti, W. J. Jahng, and R. R. Rando. A palmitoylation switch mechanism in the regulation of the visual cycle. Cell 117:761-771 (2004).
27. S. Furuyoshi, Y. Q. Shi, and R. R. Rando. Acyl group transfer from the sn-1 position of phospholipids in the biosynthesis of n-dodecyl palmitate. Biochemistry 32:5425-5430 (1993).
28. L. Demizieux, P. Degrace, J. Gresti, O. Loreau, J. P. Noel, J. M. Chardigny, J. L. Sebedio, and P. Clouet. Conjugated linoleic acid isomers in mitochondria: evidence for an alteration of fatty acid oxidation. J. Lipid Res. 43:2112-2122 (2002).
29. N. Buyuktimkin, S. Buyuktimkin, and J. H. Rytting. Chemical means of transdermal drug permeation enhancement. In T. K. Ghosh, W. R. Pfister, and S. I. Yum (eds.), Transdermal and Topical Drug Delivery Systems, Interpharm Press, Inc., Buffalo Grove, IL, 1997, pp. 382-386.
30. B. Ongpipattanakul, R. R. Burnette, R. O. Potts, and M. I. Francoeur. Evidence that oleic acid exists in a separate phase within stratum corneum lipids. J. Pharm. Sci. 8:350-354 (1991).
31. B. J. Aungst. Structure/effect studies of fatty acid isomers as skin penetration enhancers and skin irritants. Pharm. Res. 6:244-247 (1989).
32. H. Tanojo, J. A. Bouwstra, H. E. Junginger, and H. E. Bodde. In vitro human skin barrier modulation by fatty acids: skin permeation and thermal analysis studies. Pharm. Res. 14:42-49 (1997).