Quantitative estimation of hydrogen bond contribution to permeability and absorption processes of some chemicals and drugs

European Journal of Medicinal Chemistry

Volumn 33, Issue 10, 1998, Pages 799-807

  Raevsky, Oleg A ^a   Schaper, Klaus Jürgen ^b  

^a INSTITUTE OF PHYSIOLOGICALLY ACTIVE COMPOUNDS   (Russian Federation)

^b RESEARCH CENTER BORSTEL   (Germany)

Author keywords

Absorption; Descriptors; H bond acceptor; H bond donor; Membrane; Permeability; QSAR

Indexed keywords

ALCOHOL; CYANAMIDE; ENDOTHELIN RECEPTOR ANTAGONIST; ERYTHRITOL; ETHYLENE GLYCOL; GLYCEROL; HEXANOL; METHANOL; PROPANOL; THIOUREA; UREA;

ARTICLE; DRUG ABSORPTION; DRUG PENETRATION; HYDROGEN BOND; MEMBRANE PERMEABILITY; MOLECULAR RECOGNITION; PARTITION COEFFICIENT; REGRESSION ANALYSIS; SKIN PERMEABILITY; SOLVATION; THERMODYNAMICS;

EID: 0032321367     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0223-5234(99)80031-2     Document Type: Article

References (30)

1. [1] Hansch C., Leo A., Exploring QSAR, Vol. 1: Fundamentals and Applications in Chemistry and Biology, ACS, Washington, 1995.
2. [2] Seiler P., Eur. J. Med.Chem. 9 (1974) 473-479.
3. [3] Young R.C., Mitchell R.C., Brown T.H., Ganellin C.R., Griffiths R., Jones M., Rana K.K., Saunders D., Smith I.R., Sore N.E., Wilks T.J., J. Med. Chem. 31 (1988) 656-371.
4. [4] Scott R.C., Leahy D.E., Evans J.R., Bole E., J. Pharm. Pharmacol. 38 (1986) 66P.
5. [5] El Tayar N., Tsai R.S., Testa B., Carrupt P.A., Hansch C., Leo A., J. Pharm. Sci. 80 (1991) 744-749.
6. [6] Abraham M.H., Chadha M.S., Mitchell R.C., J. Pharm. Sci. 83 (1994) 1257-1268.
7. [7] Abraham M.H., Chadha M.S., In: Pliska V., Testa B., van de Waterbeemd H. (Eds.), Lipophilicity in Drug Action and Toxicology, VCH, Weinheim, 1996, pp. 311-337.
8. [8] Abraham M.H., In: Politzer P., Murray J.S. (Eds.), Quantitative Treatments of Solute/Solvent Interactions. Theoretical and Computational Chemistry, Vol. 1, Elsevier, Amsterdam, 1994, pp. 83-134.
9. [9] Raevsky O.A., Grigor'ev V.J., Kireev D.B., Zefirov N.S., Quant. Struct. Act. Relat. 11 (1992) 49-63.
10. [10] Raevsky O.A., Schaper K.J., Seydel J.K., Quant. Struct. Act. Relat. 14 (1995) 433-436.
11. [11] Raevsky O.A., In: van de Waterbeemd H., Testa B., Folkers G. (Eds.), Computer-Assisted Lead Finding and Optimization; Current Tools for Medicinal Chemistry, Wiley-VCH, Weinheim, 1997, pp. 367-378.
12. [12] Ruevsky O.A., J. Phys. Org. Chem. 10 (1997) 405-413.
13. [13] van de Waterbeemd H., Camenish G., Folkers G., Raevsky O., Quant. Struct. Act. Relat. 15 (1996) 480-490.
14. [14] Stein W.D., Lieb W.R., Transport and Diffusion Across Cell Membranes, Academic Press, Orlando, 1986, pp. 69-112.
15. [15] Anderson B.D., Raykar P.V., J. Invest. Dermatol. 93 (1989) 280-286.
16. [16] Lien E.J., Lien L.L., Gao H., In: Sanz F., Giraldo J., Manaut F. (Eds.), QSAR and Molecular Modelling: Concepts, Computational Tools and Biological Applications, Prous Science, Barcelona, 1995, pp. 94-100.
17. [17] von Geldern T.W., Hoffman D.J., Kester J.A., Nellans H.N., Dayton B.D., Calzadilla S.V., Marsh K.C., Hernandez L., Chiou W., Dixon D.B., Wu-Wong J.R., Opgenoth T.J., J. Med. Chem. 39 (1996) 982-991.
18. [18] Abraham M.H., Chadha H.S., Whiting G.S., Mitchell R.C., J. Pharm. Sci. 83 (1994) 1085-1100.
19. [19] Roberts M.S., Anderson R.A., Swarbrick J., J. Pharm. Pharmacol. 29 (1977) 677-683.
20. [20] Scheuplein R.J., J. Invest. Dermatol. 45 (1964) 334-346.
21. [21] Scheuplein R.J., Blank I.H., Brauner G.J., MacFarlane D.J., J. Invest. Dermatol. 52 (1969) 63-70.
22. [22] Xiang T.X., Anderson B.D., J. Membrane Biol. 140 (1994) 111-122.
23. [23] Potts R.O., Guy R.H., Pharm. Res. 12 (1995) 1628-1634.
24. [24] Ho N.F.H., Higuchi W.I., J. Pharm. Sci. 60 (1972) 537-541.
25. [25] Schaper K.-J., Quant. Struct. Act. Relat. 1 (1982) 13-27.
26. [26] Commercially available software HYBOT (Raevsky O., Grigor'ev V., Institute of Physiologically Active Compounds of the Russian Academy of Sciences, 142432, Chernogolovka, Moscow region, Russia, Fax+ 7-095-302-9159, E-mail raevsky@ipac3.sherna.msksu, Internet E-mail raevsky@ipac.ac.ru).
27. [27] Schaper K.-J., Kaliszan R., In: Mutschler E., Winterfeldt E. (Eds.), Trends in Medicinal Chemistry, VCH, Weinheim, 1987, pp. 125-139.
28. [28] Cooley W.W., Lohnes P.R., Multivariate Data Analysis, Wiley, New York, 1971.
29. [29] Trepalin S., Yarkov A., Dolmatova L., Zefirov N.S., J. Chem. Inform Comput. Sci. 35 (1995) 405-411.
30. [30] Miller K.J., J. Am. Chem. Soc. 112 (1990) 8533-8538.