Synthesis, hydrolysis, and skin retention of amino acid esters of α-tocopherol

Journal of Pharmaceutical Sciences

Volumn 98, Issue 7, 2009, Pages 2364-2376

  Marra, Fabio ^a   Ostacolo, Carmine ^b   Laneri, Sonia ^b   Bernardi, Antonietta ^b   Sacchi, Antonia ^b   Padula, Cristina ^a   Nicoli, Sara ^a   Santi, Patrizia ^a  

^a UNIVERSITY OF PARMA   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Amino acids; Esterase; Pro vitamin; Skin metabolism; Tocopherol

Indexed keywords

ALPHA TOCOPHEROL; ALPHA TOCOPHEROL DERIVATIVE; AMINO ACID DERIVATIVE; ASPARAGINE; ASPARAGINE ALPHA TOCOPHERYL ESTER; CITRULLINE; CITRULLINE ALPHA TOCOPHERYL ESTER; ESTER DERIVATIVE; N TERT BUTOXYCARBONYL O BENZYLSERINE ALPHA TOCOPHERYL ESTER; N TERT BUTOXYCARBONYL O TERT BUTYLDIMETHYLSILYLTYROSINE ALPHA TOCOPHERYL ESTER; N TERT BUTOXYCARBONYLASPARAGINE ALPHA TOCOPHERYL ESTER; N TERT BUTOXYCARBONYLCITRULLINE ALPHA TOCOPHERYL ESTER; N TERT BUTOXYCARBONYLPROLINE ALPHA TOCOPHERYL ESTER; N TERT BUTOXYCARBONYLSERINE ALPHA TOCOPHERYL ESTER; N TERT BUTOXYCARBONYLTYROSINE ALPHA TOCOPHERYL ESTER; PROLINE; PROLINE ALPHA TOCOPHERYL ESTER; SERINE; TYROSINE; TYROSINE ALPHA TOCOPHERYL ESTER; UNCLASSIFIED DRUG;

ANIMAL TISSUE; AQUEOUS SOLUTION; ARTICLE; CONTROLLED STUDY; DERMIS; DRUG ACCUMULATION; DRUG HALF LIFE; DRUG METABOLISM; DRUG STABILITY; DRUG SYNTHESIS; EPIDERMIS; HYDROLYSIS; IN VITRO STUDY; LIPOPHILICITY; NONHUMAN; RABBIT; SKIN PERMEABILITY; SYNTHESIS;

EID: 67650178805     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.21608     Document Type: Article

References (24)

1. Yoshida E, Watanabe T, Takata J, Yamazaki A, Karube Y, Kobayashi S. 2006. Topical application of a novel, hydrophilic gamma-tocopherol derivative reduces photo-inflammation in mice skin. J Invest Dermatol 126:1633-1640. (Pubitemid 43910380)
2. Wang X, Quinn PJ. 2000. The location and function of vitamin E in membranes (review). Mol Membr Biol 17:143-156.
3. Thiele JJ, Schroeter C, Hsieh SN, Podda M, Packer L. 2001. The antioxidant network of the stratum corneum. Curr Probl Dermatol 29:26-42.
4. Rumelin A, Humbert T, Fauth U. 2004. Determination of alpha-tocopherol in plasma by high performance liquid chromatography with fluorescence detection and stability of alpha-tocopherol under different conditions. Arzneimittelforschung 54: 376-381. (Pubitemid 38981737)
5. Mahamongkol H, Bellantone RA, Stagni G, Plakogiannis FM. 2005. Permeation study of five formulations of alpha-tocopherol acetate through human cadaver skin. J Cosmet Sci 56:91-103. (Pubitemid 40745674)
6. Norkus EP, Bryce GF, Bhagavan HN. 1993. Uptake and bioconversion of alpha-tocopheryl acetate to alpha-tocopherol in skin of hairless mice. Photochem Photobiol 57:613-615.
7. Beijersbergen van Henegouwen GM, Junginger HE, de Vries H. 1995. Hydrolysis of RRR-alphatocopheryl acetate (vitamin E acetate) in the skin and its UV protecting activity (an in vivo study with the rat). J Photochem Photobiol B 29:45-51.
8. Baschong W, Artmann C, Hueglin D, Roeding J. 2001. Direct evidence for bioconversion of vitamin E acetate into vitamin E: An ex vivo study in viable human skin. J Cosmet Sci 52:155-161. (Pubitemid 33724112)
9. Nabi Z, Tavakkol A, Dobke M, Polefka TG. 2001. Bioconversion of vitamin E acetate in human skin. Curr Probl Dermatol 29:175-186.
10. Ostacolo C, Marra F, Laneri S, Sacchi A, Nicoli S, Padula C, Santi P. 2004. Alpha-tocopherol pro-vitamins: Synthesis, hydrolysis and accumulation in rabbit ear skin. J Control Release 99:403-413. (Pubitemid 39296909)
11. Mavon A, Raufast V, Redoules D. 2004. Skin absorption and metabolism of a new vitamin E prodrug, delta-tocopherol-glucoside: In vitro evaluation in human skin models. J Control Release 100:221-231.
12. Yasuoka S, Takata J, Karube Y, Katoh E, Tsuzuki T, Kizu J, Tsuchiya M, Kobayashi S. 2005. Topical application of a novel, water-soluble gamma-tocopherol derivative prevents UV-induced skin damage in mice. Photochem Photobiol 81:908-913. (Pubitemid 41265057)
13. Marty JP. 2002.NMFand cosmetology of cutaneous hydration. Ann Dermatol Venereol 129:131-136.
14. Perry DK. 2002. Serine palmitoyltransferase: Role in apoptotic de novo ceramide synthesis and other stress responses. Biochim Biophys Acta 1585:146-152. (Pubitemid 36092079)
15. van Nieuwpoort F, Smit NP, Kolb R, van der Meulen H, Koerten H, Pavel S. 2004. Tyrosine-induced melanogenesis shows differences in morphologic and melanogenic preferences of melanosomes from light and dark skin types. J Invest Dermatol 122:1251-1255. (Pubitemid 38651101)
16. Clemmons JJ. 1966. Proline metabolism, collagen formation, and lathyrism. Fed Proc 25:1010-1015.
17. Artusi M, Nicoli S, Colombo P, Bettini R, Sacchi A, Santi P. 2004. Effect of chemical enhancers and iontophoresis on thiocolchicoside permeation across rabbit and human skin in vitro. J Pharm Sci 93: 2431-2438. (Pubitemid 39319427)
18. Nicoli S, Cappellazzi M, Colombo P, Santi P. 2003. Characterization of the permselective properties of rabbit skin during transdermal iontophoresis. J Pharm Sci 92:1482-1488. (Pubitemid 36792760)
19. Mirrlees MS, Moulton SJ, Murphy CT, Taylor PJ. 1976. Direct measurement of Octanol-Water partition coefficient by high-pressure liquid chromatography. J Med Chem 19:615-618.
20. Brent DA, Sabatka JJ, Minick DJ, Henry DW. 1983. A simplified method for determining lipophilicity for structure-activity relationships. J Med Chem 26:1020-1040.
21. Unger SH, Chiang GH. 1981. Octanol-physiological buffer distribution coefficients of lipophilic amines by reversed-phase high-performance liquid chromatography and their correlation with biological activity. J Med Chem 24:262-270. (Pubitemid 11150490)
22. Huang D, Ou B, Hampsch-Woodill M, Flanagan JA, Deemer EK. 2002. Development and validation of oxygen radical absorbance capacity assay for lipophilic antioxidants using randomly methylated beta-cyclodextrin as the solubility enhancer. J Agric Food Chem 50:1815-1821. (Pubitemid 34259972)
23. Laneri S, Sacchi A, di Frassello EA, Luraschi E, Colombo P, Santi P. 1999. Ionized prodrugs of dehydroepiandrosterone for transdermal iontophoretic delivery. Pharm Res 16:1818-1824. (Pubitemid 30040696)
24. Rojas-Garbanzo RE, Mata-Segreda JF. 1998. Assessment of the steric tolerance of the P sector in the catalytic site of porcine liver esterase. Bioorg Med Chem Lett 8:7-10. (Pubitemid 28021684)