17β-carboxamide steroids - In vitro prediction of human skin permeability and retention using PAMPA technique

European Journal of Pharmaceutical Sciences

Volumn 52, Issue 1, 2014, Pages 95-108

  Dobričić, Vladimir ^a   Marković, Bojan ^a   Nikolic, Katarina ^a   Savić, Vladimir ^a   Vladimirov, Sote ^a   Čudina, Olivera ^a  

^a UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

Human skin permeability and retention; PAMPA; Quantitative structure property relationship; Soft corticosteroids

Indexed keywords

BETAMETHASONE; DEXAMETHASONE; ETHYL 2 (11BETA,17ALPHA DIHYDROXY 3 OXO ANDROST 1,4 DIEN 17BETA CARBOXAMIDO) 3 PHENYL PROPIONATE; ETHYL 2 (11BETA,17ALPHA DIHYDROXY 3 OXO ANDROST 1,4 DIEN 17BETA CARBOXAMIDO)ACETATE; ETHYL 2 (11BETA,17ALPHA DIHYDROXY 3 OXO ANDROST 4 EN 17BETA CARBOXAMIDO)ACETATE; ETHYL 2 (11BETA,17ALPHA DIHYDROXY 6ALPHA METHYL 3 OXO ANDROST 1,4 DIEN 17BETA CARBOXAMIDO)ACETATE; ETHYL 2 (11BETA,17ALPHA DIHYDROXY 9ALPHA FLUORO 16ALPHA METHYL 3 OXO ANDROST 1,4 DIEN 17BETA CARBOXAMIDO)ACETATE; ETHYL 2 (11BETA,17ALPHA DIHYDROXY 9ALPHA FLUORO 16BETA METHYL 3 OXO ANDROST 1,4 DIEN 17BETA CARBOXAMIDO ACETATE; ETHYL 3 (11BETA,17ALPHA DIHYDROXY 3 OXO ANDROST 1,4 DIEN 17BETA CARBOXAMIDO)PROPIONATE; ETHYL 3 (11BETA,17ALPHA DIHYDROXY 3 OXO ANDROST 4 EN 17BETA CARBOXAMIDO)PROPIONATE; ETHYL 3 (11BETA,17ALPHA DIHYDROXY 6ALPHA METHYL 3 OXO ANDROST 1,4 DIEN 17BETA CARBOXAMIDO)PROPIONATE; ETHYL 3 (11BETA,17ALPHA DIHYDROXY 9ALPHA FLUORO 16ALPHA METHYL 3 OXO ANDROST 1,4 DIEN 17BETA CARBOXAMIDO)PROPRIONATE; HYDROCORTISONE; METHYL 2 (11BETA,17A DIHYDROXY 9ALPHA FLUORO 16BETA METHYL 3 OXO ANDROST 1,4 DIEN 17BETA CARBOXAMIDO ACETATE; METHYL 2 (11BETA,17ALPHA DIHYDROXY 3 OXO ANDROST 1,4 DIEN 17BETA CARBOXAMIDO)ACETATE; METHYL 2 (11BETA,17ALPHA DIHYDROXY 3 OXO ANDROST 1,4 DIEN 17BETA CARBOXAMIDO)PROPIONATE; METHYL 2 (11BETA,17ALPHA DIHYDROXY 3 OXO ANDROST 4 EN 17BETA CARBOXAMIDO) 3 PHENYL PROPIONATE; METHYL 2 (11BETA,17ALPHA DIHYDROXY 3 OXO ANDROST 4 EN 17BETA CARBOXAMIDO)ACETATE; METHYL 2 (11BETA,17ALPHA DIHYDROXY 3 OXO ANDROST 4 EN 17BETA CARBOXAMIDO)PROPIONATE; METHYL 2 (11BETA,17ALPHA DIHYDROXY 6ALPHA METHYL 3 OXO ANDROST 1,4 DIEN 17BETA CARBOXAMIDO) 3 PHENYL PROPIONATE; METHYL 2 (11BETA,17ALPHA DIHYDROXY 6ALPHA METHYL 3 OXO ANDROST 1,4 DIEN 17BETA CARBOXAMIDO)ACETATE; METHYL 2 (11BETA,17ALPHA DIHYDROXY 6ALPHA METHYL 3 OXO ANDROST 1,4 DIEN 17BETA CARBOXAMIDO)PROPIONATE; METHYL 2 (11BETA,17ALPHA DIHYDROXY 9ALPHA FLUORO 16ALPHA METHYL 3 OXO ANDROST 1,4 DIEN 17BETA CARBOXAMIDO) 3 PHENYL PROPIONATE; METHYL 2 (11BETA,17ALPHA DIHYDROXY 9ALPHA FLUORO 16ALPHA METHYL 3 OXO ANDROST 1,4 DIEN 17BETA CARBOXAMIDO)ACETATE; METHYL 2 (11BETA,17ALPHA DIHYDROXY 9ALPHA FLUORO 16ALPHA METHYL 3 OXO ANDROST 1,4 DIEN 17BETA CARBOXAMIDO)PROPIONATE; METHYLPREDNISOLONE; PREDNISOLONE; UNCLASSIFIED DRUG;

AMIDATION; ANALYTIC METHOD; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; DRUG SYNTHESIS; GEOMETRY; HUMAN; IN VITRO STUDY; KERNEL METHOD; OXIDATION; PARALLEL ARTIFICIAL MEMBRANE PERMEABILITY ASSAY; PHYSICAL CHEMISTRY; PREDICTION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE PROPERTY RELATION; SKIN PERMEABILITY; THERMODYNAMICS;

HUMAN SKIN PERMEABILITY AND RETENTION; PAMPA; QUANTITATIVE STRUCTURE-PROPERTY RELATIONSHIP; SOFT CORTICOSTEROIDS;

ADRENAL CORTEX HORMONES; AMIDES; ANDROSTENEDIOLS; HUMANS; MEMBRANES, ARTIFICIAL; PERMEABILITY; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; SKIN; SKIN ABSORPTION;

EID: 84888236652     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2013.10.017     Document Type: Article

References (45)

1. Anthes, J.C., McCormick, K.D., Hey, J.A., Aslanian, R.G., Biju, P.J., Berlin, M.Y., Solomon, D.M., Wang, H., Lim, Y.-H., Lee, Y.J., Bitar, R.D., 2009. C20-C21 Substituted Glucocorticoid Receptor Agonists. WO 2009/085879 A2.
2. A. Avdeef Absorption and Drug Development 2003 John Wiley & Sons Hoboken, New Jersey
3. A. Avdeef, M. Strafford, E. Block, M. Balogh, W. Chambliss, and I. Khan Drug absorption in vitro model: filter-immobilized artificial membranes. Studies of the permeability properties of lactones in Piper methysticum Forst Eur. J. Pharm. Sci. 14 2001 271 280
4. Bladh, H., Burkamp, F., Gabos, B., Hansen, P., 2010. Novel Derivatives of Steroidal[3,2-c]pyrazole Compounds with Glucocorticoid Activity. WO 2010/114476 A1.
5. N. Bodor, and P. Buchwald Corticosteroid design for the treatment of asthma: structural insights and the therapeutic potential of soft corticosteroids Curr. Pharm. Des. 12 2006 3241 3260
6. N. Bodor, N. Bodor, and W.M. Wu A comparison of intraocular pressure elevating activity of loteprednol etabonate and dexamethasone in rabbits Curr. Eye. Res. 11 1992 525 530
7. N. Bodor, T. Loftsson, and W.M. Wu Metabolism, distribution, and transdermal permeability of a soft corticosteroid, loteprednol etabonate Pharm. Res. 9 1992 1275 1278
8. CambridgeSoft Corporation. 2005. Chem3D Ultra, Version 9.0.1. Cambridge, MA, USA.
9. ChemAxon. 2008. MarvinSketch 5.1.3. Budapest, Hungary.
10. Dobricic, V., Markovic, B., Savic, V., Milenkovic, N., Vladimirov, S., Cudina. O., 2012. Molecular docking studies, synthesis and structural characterization of two novel soft corticosteroids. In: 11th International Conference on Fundamental and Applied Aspects of Physical Chemistry. Belgrade, Serbia, September 24-28, 2012, pp. 576-578.
11. P. Druzgala, G. Hochhaus, and N. Bodor Soft drugs-10. Blanching activity and receptor binding affinity of a new type of glucocorticoid: loteprednol etabonate J. Steroid. Biochem. Mol. Biol. 38 1991 149 154
12. P. Druzgala, W.M. Wu, and N. Bodor Ocular absorption and distribution of loteprednol etabonate, a soft steroid, in rabbit eyes Curr. Eye. Res. 10 1991 933 937
13. Duax, W.L., Griffin, J.F., Rohrer, D.C., Wecks, C.M., 1982. In: Agarwal, M.K. (Ed.), Hormone Antagonists. Walter de Gruyter, Berlin.
14. P.R. Duchowicz, M. Fernandez, J. Caballero, E.A. Castro, and F.M. Fernandez QSAR for non-nucleoside inhibitors of HIV-1 reverse transcriptase Bioorg. Med. Chem. 14 2006 5876 5889
15. L. Eriksson, E. Johansson, N. Kettaneh-Wold, J. Trygg, C. Wikstrom, and S. Wold Multi-and Megavariate Data Analysis. Basic Principles and Applications I second ed. 2001 Umetrics Academy Umeå
16. S. Filipic, K. Nikolic, I. Vovk, M. Krizman, and D. Agbaba Quantitative structure-mobility relationship analysis of imidazoline receptor ligands in CDs-mediated CE Electrophoresis 34 2013 471 482
17. P. Formstecher, P. Lustenberger, and M. Dautrevaux Synthesis of steroidal 17β-carboxamide derivatives Steroids 35 1980 265 272
18. P.A. Formstecher, Ph. Lefebvre, and T. Burollaud Hormones and antihormones. The steroidal model J. Pharm. Belg. 46 1991 37 48
19. M.P. Gonzalez, M. Puente, Y. Fall, and G. Gomez In silico studies using Radial Distribution Function approach for predicting affinity of 1α,25-dihydroxyvitamin D3 analogues for Vitamin D receptor Steroids 71 2006 510 527
20. D. Gonzalez-Arjona, G. Lopez-Perez, and A. Gustavo-Gonzalez Non-linear QSAR modeling by using multilayer perceptron feedforward neural networks trained by back-propagation Talanta 56 2002 79 90
21. V.K. Gupta, H. Khani, B. Ahmadi-Roudi, S. Mirakhorli, E. Fereyduni, and S. Agarwal Prediction of capillary gas chromatographic retention times of fatty acid methyl esters in human blood using MLR, PLS and back-propagation artificial neural networks Talanta 83 2011 1014 1022
22. T. Hancock, R. Put, D. Coomans, Y.V. Heyden, and Y. Everingham A performance comparison of modern statistical techniques for molecular descriptor selection and retention prediction in chromatographic QSRR studies Chemometr. Intell. Lab. 76 2005 185 196
23. R.P. Iczkowski, and J.L. Margrave Electronegativity J. Am. Chem. Soc. 83 1961 3547 3551
24. M. Jalali-Heravi, and Z. Garkani-Nejad Prediction of electrophoretic mobilities of alkyl- and alkenylpyridines in capillary electrophoresis using artificial neural networks J. Chromatogr. A 971 2002 207 215
25. M. Kansy, F. Senner, and K. Gubernator Physicochemical high-throughput screening: Parallel artificial membrane permeation assay in the description of passive absorption processes J. Med. Chem. 41 1998 1007 1010
26. P. Maes, P. Formstecher, P. Lustenberger, and M. Dautrevaux High-performance liquid chromatography in the evaluation of the lipophilicity of 17β-carboxamide steroid derivatives J. Chromatogr. 445 1988 409 416
27. B. Manz, J. Grill, R. Kreienberg, and K. Pollow Methyl 17β-carboxyester derivatives of natural and synthetic glucocorticoids: correlation between receptor binding and inhibition of in vitro phytohaemagglutinin-induced lymphocyte blastogenesis J. Clin. Chem. Clin. Biochem. 21 1983 69 75
28. B. Manz, M. Rehder, A. Heubner, R. Kreienberg, H.J. Grill, and K. Pollow 17β-carboxamide steroids: highly effective inhibitors of the phytohaemagglutinin mediated blastogenesis of normal human peripheral lymphocytes J. Clin. Chem. Clin. Biochem. 22 1984 209 214
29. B. Markovic, S. Vladimirov, O. Cudina, J. Odovic, and K. Karljikovic-Rajic A PAMPA assay as fast predictive model of passive human skin permeability of new synthesized corticosteroid C-21 esters Molecules 17 2012 480 491
30. G.R. Marshall Binding-site modeling of unknown receptors H. Kubinyi, 3D QSAR in Drug Design - Theory, Methods and Applications 1994 ESCOM Leiden 80 116
31. Microsoft Corporation. 2010. Microsoft Office Excel 2010. Redmond, WA, USA.
32. P.K. Ojha, and K. Roy Comparative QSARs for antimalarial endochins: Importance of descriptor-thinning and noise reduction prior to feature selection Chemometr. Intell. Lab. 109 2011 146 161
33. G. Ottaviani, S. Martel, and P.-A. Carrupt Parallel artificial membrane permeability assay: a new membrane for the fast prediction of passive human skin permeability J. Med. Chem. 49 2006 3948 3954
34. R.G. Parr, and W. Yang Density-Functional Theory of Atoms and Molecules 1989 Oxford University Press New York
35. G. Rousseau, J. Kirchhoff, P. Formstecher, and P. Lustenberger 17β-carboxamide steroids are a new class of glucocorticoid antagonists Nature 279 1979 158 160
36. B. Sinkó, J. Kökösi, A. Avdeef, and K. Takács-Novák A PAMPA study of the permeability-enhancing effect of a new ceramide analogues Chem. Biodivers. 6 2009 1867 1874
37. B. Sinkó, T.M. Garrigues, G.T. Balogh, K.N. Zsombor, O. Tsinman, A. Avdeef, and K. Takács-Novák Skin-PAMPA: a new method for fast prediction of skin penetration Eur. J. Pharm. Sci. 45 2012 698 707
38. G.W. Snedecor, and W.G. Cochran Statistical Methods 1967 Oxford & IBH New Delhi
39. StatSoft Inc., 1998. STATISTICA Neural Networks 4.0. Tulsa, OK, USA.
40. TALETE srl. 2010. Dragon 6.0. Milano, Italy.
41. TALETE srl. 2013. Molecular Descriptors, QSAR, Chemometrics and Chemoinformatics-Dragon Molecular Descriptor List. .
42. R. Todeschini, and V. Consonni Handbook of Molecular Descriptors 2000 Wiley-VCH Weinheim
43. Tropsha. 2010. Best practices for QSAR model development, validation and exploration. Mol. Inf. 29, 476-488.
44. Umetrics AB. 2008. SIMCA P+ Program, Version 12.0.0.0. Umea, Sweden.
45. Y.X. Zhang Artificial neural networks based on principal component analysis input selection for clinical pattern recognition analysis Talanta 73 2007 68 75