Evaluation of hydrophobic/hydrophilic balance of bile acids by comparative molecular field analysis (CoMFA)

Steroids

Volumn 65, Issue 9, 2000, Pages 483-489

  Costantino, Gabriele ^a   Wolf, Christian ^a   Natalini, Benedetto ^a   Pellicciari, Roberto ^a  

^a Dipartimento di Chimica e Tecnologia del Farmaco   (Italy)

Author keywords

3D QSAR; CoMFA; Hydrophobicity; Steroids

Indexed keywords

BILE ACID;

ANALYTIC METHOD; ARTICLE; HYDROPHILICITY; HYDROPHOBICITY; MOLECULAR INTERACTION; MOLECULAR MODEL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; VALIDATION PROCESS;

BILE ACIDS AND SALTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ELECTROSTATICS; HUMANS; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0033818059     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(00)00108-2     Document Type: Article

References (25)

1. Small D.M. The physical chemistry of the cholenoic acids. Nair P.P., Kritchivsky D. The bile acids chemistry, physiology and metabolism. 1971;249-346 Plenum Publishing, New York.
2. Hofmann A.F., Roda A. Pysico-chemical properties of bile acids and their relationship to biological properties an overview of the problem. J Lipid Res. 25:1984;1477-1489.
3. Makishima M., Okamoto A.Y., Repa J.J., et al. Identification of a nuclear receptor for bile acids. Science. 284:1999;1362-1365.
4. Parks D.J., Blanchard S.G., Bledsoe R.K., et al. Bile acids natural ligands for an orphan nuclear receptor. Science. 284:1999;1365-1368.
5. Makino J., Shinizaki K., Nakagawa K., Yoshino K. Dissolution of cholesterol by long term administration of ursodeoxycholic acid. Jpn J Gastroenterol. 72:1975;690-702.
6. Bacharach W.H., Hofmann A.F. Urosodeoxycholic acid in the treatment of cholesterol chololithiasis. Dig Dis Sci. 27:1982;737-761.
7. Rodrigues C.M., Kren B.T., Steer C.J., Setchell K.D. The site-specific delivery of ursodeoxycholic acid to the rat colon by sulfate conjugation. Gastreoenterology. 109:1995;1835-1844.
8. Parquet M., Metman H.H., Raizman A., Rambaud J.C., Berthaux N., Infante N. Bioavailability, gastrointestinal transit, solubilization and feacal excretion of ursodeoxycholic acid in man. Eur Clin Invest. 15:1985;171-178.
9. Schreiber A.J., Simon F.R. Overview of clinical aspects of bile salt physiology. J Pediatr Gastroenterol Nutr. 2:1983;337-345.
10. Roda A., Grigiolo B., Minutello A., Pellicciari R., Natalini B. Physicochemical and biological properties of natural and synthetic C-22 and C-23 hydroxilated bile acids. J Lipid Res. 31:1989;289-298.
11. Roda A., Aldini R., Grigiolo B., et al. 23-Methyl-3α,7β-dihydroxy-5βcholan-24-oic-acid dose response study of biliary secretion in rat. Hepatology. 8:1988;1571-1576.
12. Pellicciari R., Cecchetti S., Natalini B., Roda A., Grigiolo B., Fini A. Bile acids with cyclopropane containing side chain 1. Preparation and properties of 3α-7β-dihydroxy 22-23-methylene-5β-cholan-24-oic-acid. J Med Chem. 27:1984;746-749.
13. Pellicciari R., Natalini B., Cecchetti S., et al. Bile acids with a cyclopropyl-containing side chain 3. Separation, identification and properties of all the four stereoisomers of 3α-7β-dihydroxy 22-23 methylene-5β-cholan-24-oic-acid (CUDCA). J Med Chem. 31:1988;730-736.
14. Roda A., Pellicciari R., Cerr C., et al. New 6-substituted bile acids. Physicochemical and biological properties of 6α-methyl ursodeoxycholic acid and 6α-methyl-7-epicholic acid. J Lipid Res. 35:1994;2268-2279.
15. Roda A., Pellicciari R., Polimeni C., et al. Metabolism, pharmacokinetics and activity of new 6-fluoro analogs of ursodeoxycholic acid in rats and hamsters. Gastroeneterology. 108:1995;1204-1214.
16. Costantino G, Marinozzi M, Mattoli L, et al. "A Chemometric Model for the Prediction of Physicochemical Properties of Bile Acids." Abstract of the First Italian-Swiss Meeting on Medicinal Chemistry, Torino, 1997. p. 250.
17. Rekker RF. The hydrophobic fragmental constant. Its derivation and application. A means of characterizing membrane system. Pharmacochem. Lib. 1, Elsevier, Amsterdam, 1977.
18. Hansch C., Leo A. The FRAGMENT method of calculating partition coefficients. In Substituent constants for correlation analysis in chemistry and biology. 1979;18-43 Wiley-Interscience, New York.
19. Dunn W.J. III, Koehler M.G., Grigoras S. The role of solvent accessible surface area in determining partition coefficient. J Med Chem. 30:1987;1121-1122.
20. Bodor N., Gabanyi Z., Wong C.K. A new method for the estimation of partition coefficient. J Am Chem Soc. 111:1989;3783-3786.
21. Bodor N., Huang M.J. An extended version of a novel method for the estimation of partition coefficient. J Pharm Sci. 81:1992;272-281.
22. Wireko F.C., Kellog G.E., Abraham D.J. Allosteric modifiers of hemoglobin. 2. Crystallographically determined binding sites and hydrophobic binding/interactions analysis of novel hemoglobin oxygen effectors. J Med Chem. 34:1991;758-767.
23. Kellog G.E., Semus S.F., Abraham D.J. HINT-A new method of empirical field calculation for CoMFA. J Comput Aided Mol Des. 5:1991;545-552.
24. Gaillard P., Carrupt P.A., Testa B., Boudon A. Molecular lipophilicity potential, a tool in 3D-QSAR. Method and applications. J Comput Aided Mol Des. 1994;83-96.
25. Cramer R.D., Patterson D.E., Bunce J.D. Comparative molecular fields analysis (CoMFA). 1. Effect of shape and binding of steroids to carrier proteins. J Am Chem Soc. 110:1988;5959-5967.