A PAMPA assay as fast predictive model of passive human skin permeability of new synthesized corticosteroid C-21 esters

Molecules

Volumn 17, Issue 1, 2012, Pages 480-491

  Markovic, Bojan D ^a   Vladimirov, Sote M ^a   Cudina, Olivera A ^a   Odovic, Jadranka V ^a   Karljikovic Rajic, Katarina D ^a  

^a UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

Corticosteroid C 21 esters; Membrane retention; PAMPA; Permeation parameter; Prodrug

Indexed keywords

ESTER; MYRISTIC ACID DERIVATIVE; MYRISTIC ACID ISOPROPYL ESTER; PREGNANE DERIVATIVE; PRODRUG; SILICONE OIL;

ARTICLE; ARTIFICIAL MEMBRANE; BIOLOGICAL MODEL; CHEMISTRY; HUMAN; PERMEABILITY; SKIN ABSORPTION; STANDARD; SYNTHESIS;

ESTERS; HUMANS; MEMBRANES, ARTIFICIAL; MODELS, BIOLOGICAL; MYRISTATES; PERMEABILITY; PREGNANES; PRODRUGS; REFERENCE STANDARDS; SILICONE OILS; SKIN ABSORPTION;

EID: 84856199554     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17010480     Document Type: Article

References (33)

1. Sweetman, S.C. Martindale: The Complete Drug Reference, 36th ed.; Pharmaceutical Press: London, UK, 2009.
2. Carrascosa, J.M.; Vanaclocha, F.; Borrego, L.; Fernandez-Lopez, E.; Fuertes, A.; Rodriguez-Fernandez-Freire, L.; Zulaica, A.; Tuneu, A.; Caballe, G.; Colome, E.; et al. Update of the topical treatment of psoriasis. Actas Dermosifiliogr. 2009, 100, 190-200.
3. Wiedersberg, S.; Leopold, C.S.; Gay, R.H. Bioavailability and bioequivalence of topical glucocorticoids. Eur. J. Pharm. Biopharm. 2008, 68, 453-466. (Pubitemid 351318206)
4. Pershing, L.K.; Corlett, J.L.; Lambert, L.D.; Poncelet, C.E. Circadian activity of topical 0.05% betamethasone dipropionate in human skin in vivo. J. Invest. Dermatol. 1994, 102, 734-739. (Pubitemid 24144253)
5. Topical Steroids Potency Chart; National Psoriasis Foundation: Portland, OR, USA, 1998. Available online: http://www.psoriasis.org/page.aspx?pid=469 (accessed on 9 December 2011).
6. British National Formulary; British Medical Association and the Royal Pharmaceutical Society of Great Britain: London, UK, 2004.
7. Brazzini, B.; Pimpinelli, N. New and established topical corticosteroids in dermatology. Am. J. Clin. Dermatol. 2002, 3, 47-58.
8. Escuder-Gilabert, L.; Martínez-Pla, J.J.; Sagrado, S.; Villanueva-Camañas, R.M.; Medina-Hernández, M.J. Biopartitioning micellar separation methods: Modelling drug absorption. J. Chromatogr. B 2003, 797, 21-35. (Pubitemid 37424027)
9. Henchoz, Y.; Bard, B.; Guillarme, D.; Carrupt, P.A.; Veuthey, J.L.; Martel, S. Analytical tools for the physicochemical profiling of drug candidates to predict absorption/distribution. Anal. Bioanal. Chem. 2009, 394, 707-729.
10. Yourick, J.J.; Jung, C.T.; Bronaugh, R.L. In vitro and in vivo percutaneous absorption of retinol from cosmetic formulations: Significance of the skin reservoir and prediction of systemic absorption. Toxicol. Appl. Pharmacol. 2008, 231, 117-121.
11. Godin, B.; Touitou, E. Transdermal skin delivery: Predictions for humans from in vivo, ex vivo and animal models. Adv. Drug Deliv. Rev. 2007, 59, 1152-1161. (Pubitemid 47615204)
12. Friend, D.R. In vitro skin permeation techniques. J. Control. Release 1992, 18, 235-248.
13. Hadgraft, J. Skin deep. Eur. J. Pharm. Biopharm. 2004, 58, 291-299. (Pubitemid 39037236)
14. Fasano, W.J.; Berge, W.F.; Banton, M.I.; Heneweer, M.; Moore, N.P. Dermal penetration of propylene glycols: Measured absorption across human abdominal skin in vitro and comparison with a QSAR model. Toxicol. In Vitro 2011, 25, 1664-1670.
15. Moss, G.P.; Dearden, J.C.; Patel, H.; Cronin, M.T.D. Quantitative structure-permeability relationships (QSPRs) for percutaneous absorption. Toxicol. In Vitro 2002, 16, 299-317. (Pubitemid 34521704)
16. Barbato, F.; Cappello, B.; Miro, A.; La Rotonda, M.I.; Quaglia, F. Chromatographic indexes on immobilized artificial membranes for the prediction of transdermal transport of drugs. Il Farmaco 1998, 53, 655-661. (Pubitemid 29139835)
17. Kansy, M.; Senner, F.; Gubernator, K. Physicochemical high-throughput screening: Parallel artificial membrane permeation assay in the description of passive absorption processes. J. Med. Chem. 1998, 41, 1007-1010. (Pubitemid 28207375)
18. Mensch, J.; Melis, A.; Mackie, C.; Verreck, G.; Brewster, E. Evaluation of various PAMPA models to identify the most discriminating method for the prediction of BBB permeability. Eur. J. Pharm. Biopharm. 2010, 74, 495-502.
19. Di, L.; Kerns, E.H.; Fan, K.; McConnell, O.J.; Carter, G.T. High throughput artificial membrane permeability assay for blood-brain barrier. Eur. J. Med. Chem. 2003, 38, 223-232. (Pubitemid 36349665)
20. Hiremath, P.S.; Soppimath, K.S.; Betageri, G.V. Proliposomes of exemestane for improved oral delivery: Formulation and in vitro evaluation using PAMPA, Caco-2 and rat intestine. Int. J. Pharm. 2009, 380, 96-104.
21. Ottaviani, G.; Martel, S.; Carrupt, P.-A. Parallel artificial membrane permeability assay: A new membrane for the fast prediction of passive human skin permeability. J. Med. Chem. 2006, 49, 3948-3954. (Pubitemid 43967892)
22. Ottaviani, G.; Martel, S.; Carrupt, P.-A. In silico and in vitro filters for the fast estimation of skin permeation and distribution of new chemical entities. J. Med. Chem. 2007, 50, 742-748. (Pubitemid 46332986)
23. Sinkó, B.; Kökösi, J.; Avdeef, A.; Takács- Novák, K. A PAMPA study of the permeability-enhancing effect of a new ceramide analogues. Chem. Biodivers. 2009, 6, 1867-1874.
24. Ruell, J. Membrane-based drug assays. Mod. Drug Discov. 2003, 6, 28-30.
25. Kerns, E.H. High throughput physicochemical profiling for drug discovery. J. Pharm. Sci. 2001, 90, 1838-1858. (Pubitemid 33062605)
26. Liu, H.; Sabus, C.; Carter, G.T.; Du, C.; Avdeef, A.; Tischler, M. In Vitro permeability of poorly aqueous soluble compounds using different solubilizers in the PAMPA assay with liquid chromatography/mass spectrometry detection. Pharm. Res. 2003, 20, 1820-1826. (Pubitemid 37449456)
27. Carrara, S.; Reali, V.; Misiano, P.; Dondio, G.; Bigogno, C. Evaluation of in vitro brain penetration: Optimized PAMPA and MDCKII-MDR1 assay comparison. Int. J. Pharm. 2007, 345, 125-133. (Pubitemid 350103647)
28. Mensch, J.; Noppe, M.; Adriaensen, J.; Melis, A.; Mackie, C.; Augustijns, P.; Brewster, M.E. Novel generic UPLC/MS/MS method for high throughput analysis applied to permeability assessment in early Drug Discovery. J. Chromatogr. B 2007, 847, 182-187. (Pubitemid 46331026)
29. Markovic, B.D.; Dobricic, V.D.; Vladimirov, S.M.; Cudina, O.A.; Savic, V.M.; Karljikovic-Rajic, K.D. An investigation of solvolysis kinetics of new synthesized fluocinolone acetonide C-21 esters-In vitro model for prodrug activation. Molecules 2011, 16, 2658-2671.
30. Markovic, B.; Vladimirov, S.; Pitic, D.; Savic, V.; Jacevic, V.; Dobric, S. Synthesis and anti-inflammatory activity of new a-oxyalcanoyl esters of fluocinolone acetonide. Proceedings of Hungarian-Austrian-Czech-German-Greek- Italian-Polish-Slovak Joint Meeting on Medicinal Chemistry, Budapest, Hungary, 24-27 June 2009; Medimond S.r.l.-Monduzzi Editore International Proceedings Division: Bologna, Italy, 2009; pp. 41-44.
31. Benninger, M.S.; Ahmad, N.; Marple, B.F. The safety of intranasal steroids. Otolaryngol. Head Neck Surg. 2003, 129, 739-750. (Pubitemid 37509776)
32. Katz, M.; Gans, E.H. Topical Corticosteroids, Structure-activity and the glucocorticoid receptor: Discovery and development-A process of "planned serendipity". J. Pharm. Sci. 2008, 97, 2936-2947.
33. Phillipps, G.H.; Bailey, E.J.; Bain, B.M.; Borella, R.A.; Buckton, J.B.; Clark, J.C.; Doherty, A.E.; English, A.F.; Fazakerley, H.; Laing, S.B.; et al. Synthesis and structure-activity relationships in a series of anti-inflammatory corticosteroid analogues, halomethyl androstane-17β-carbothioates and -17β-carboselenoates. J. Med. Chem. 1994, 37, 3717-3729. (Pubitemid 24346756)