Diffusion of E and Z urocanic amphiphiles through skin and their insertion in a membrane model

Skin Pharmacology and Applied Skin Physiology

Volumn 15, Issue 6, 2002, Pages 425-433

  Sirieix Plenet J ^a   Ader, J C ^a   Miquel, C ^b   Mavon, A ^b   Lauth de Viguerie, N ^a  

^a Université Paul Sabatier   (France)

^b INSTITUT DE RECHERCHE PIERRE FABRE   (France)

Author keywords

Amphiphile; Flow through diffusion cells; Membrane model; Monolayer; Urocanic acid isomers

Indexed keywords

AMPHOPHILE; CHOLESTEROL; DIPALMITOYLPHOSPHATIDYLCHOLINE; ESTER; SKIN LIPID; UROCANIC ACID; WATER;

AIR; ANIMAL TISSUE; ARTICLE; COMPARATIVE STUDY; CONTROLLED STUDY; DRUG DIFFUSION; FILM; ISOMER; MEMBRANE; MEMBRANE MODEL; MONOLAYER CULTURE; NONHUMAN; PRIORITY JOURNAL; RAT; SKIN;

ANIMALS; DIFFUSION CHAMBERS, CULTURE; EPIDERMIS; RATS; SKIN ABSORPTION; SURFACE-ACTIVE AGENTS; UROCANIC ACID;

EID: 0036911735     PISSN: 14222868     EISSN: None     Source Type: Journal    
DOI: 10.1159/000066454     Document Type: Article

References (22)

1. Schaefer H, Redelmeier TE: Composition and structure of the stratum corneum; in Schaefer H, Redelmeier TE (eds): Skin Barrier: Principles of Percutaneous Absorption. Basel, Karger, 1996, pp 43-85.
2. Bronaugh RL, Maibach HI (eds): Percutaneous Absorption, Mechanisms, Methodology, Drug Delivery. New York, Dekker, 1989.
3. Zenisck A, Haïs IM, Marklova E: Quelques aspects physiologiques et photobiologiques de l'acide urocanique (imidazolacrylique) et son analogue, l'acide indolocrylique. Parfums Cosmét Arômes 1978;24:79-87.
4. De Fabo EC, Noonan FP: Mechanism of immune suppression by ultraviolet irradiation in vivo. 1. Evidence for the existence of a unique photoreceptor in skin and its role in photoimmunology J Exp Med 1983;158:84-98.
5. Norval M, Simpson TJ, Ross JA: Urocanic acid and immunosuppression. Photochem Photobiol 1989;50:267-275.
6. Norval M, Gibbs NK, Gilmour J: The role of urocanic acid in UV-induced immunosuppression: Recent advances (1992-1994). Photochem Photobiol 1995;62:209-217.
7. Hanson KM, Simon JD: Photochemistry of urocanic acid: Evidence that urocanic acid should be used with caution in cosmetic formulations. J Soc Cosmet Chem 1997;48:151-157.
8. Franceschi S, Andreu V, de Viguerie N, Rivière M, Lattes A: Synthesis and aggregation behaviour of two-headed surfactants containing the urocanic acid moiety. New J Chem 1998;22:225-231.
9. Sirieix J, Lauth-de Viguerie N, Rivière M, Lattes A: Aggregation behaviour of urocanic acid bolaamphiphile. Langmuir 2000;16:9221-9224.
10. Sirieix J, Lauth-de Viguerie N, Rivière M, Lattes A: Biomimetic aggregates formed by heterocyclic amphiphiles. Heterocycles 2000;53:2509-2515.
11. Sirieix J, Lauth-de Viguerie N, Rivière M, Lattes A: From unsymmetrical bolaamphiphiles to supermolecules. New J Chem 2000;24:1043-1048.
12. Monje MC, Lattes A, Rivière M: Urocanates d'alkyle à longue chaîne. Insertion en milieu organisé. Bull Soc Chim Fr 1990;127:292-297.
13. Garrigues JC, Rico-Lattes I, Perez E, Lattes A: Comparative study for the incorporation of a new antifungal family of neoglycolipids and amphotericin B in monolayers containing phospholipids and cholesterol or ergosterol. Langmuir 1998;14:5968-5971.
14. Goyal S, Khuller GK: Phospholipid composition and subcellular distribution in yeast and mycelial forms of Candida albicans. J Med Vet Mycol 1992;30:355-362.
15. Lauth-de Viguerie N, Sergueeva N, Damiot M, Mawlawi H, Rivière M, Lattes A: Selective N-alkylation of (E)-urocanic acid. Heterocycles 1994;37:1561-1578.
16. Bronaugh RL, Stewart RF: Methods for in vitro percutaneous absorption studies. 4. The flow through diffusion cell. J Pharm Sci 1985;74:64-67.
17. De Orsi D, Gagliardi L, Chimenti F, Tonelli D: High-performance liquid chromatographic determination of urocanic acid isomers in cosmetic products. Chromatographia 1995;41:370-372.
18. Viswanadhan VN, Ghose AK, Revankar GR, Robins RK: Atomic physicochemical parameters for three-dimensional structure-directed quantitative structure-activity relationships. 4. Additional parameters for hydrophobic and dispersive interactions and their application for an automated superposition of certain naturally occurring nucleoside antibiotics. J Chem Inf Comput Sci 1989;29:163-172.
19. Kozarak Z, Mobius D: Interaction of ortho- and para-nitrophenol with lipid monolayers studied by monolayer techniques and reflection spectroscopy. Colloids Surf 1994;83:99-108.
20. Mozaffary H: Cholesterol-phospholipid interaction: A monolayer study. Thin Solid Films 1994;244:874-877.
21. Potts RO, Guy RH: Predicting skin permeability. Pharm Res 1992;9:663-669.
22. Heard CM, Fallon RC, Brain KR: Differential in vitro skin permeation of quinine and quinidine demonstrates the importance of discrete interactions during the diffusion process. PPP 1997;5:177-179.