Comparative Molecular Similarity Index Analysis (CoMSIA) to study hydrogen-bonding properties and to score combinatorial libraries

Journal of Computer-Aided Molecular Design

Volumn 13, Issue 1, 1999, Pages 1-10

  Klebe, Gerhard ^a   Abraham, Ute ^b  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b BASF SE   (Germany)

Author keywords

3D QSAR; Comparative molecular field analysis; Contribution map interpretation; Molecular similarity; Thermolysin inhibition

Indexed keywords

COMPUTATIONAL CHEMISTRY; HYDROGEN BONDS; MOLECULAR GRAPHICS;

3D-QSAR; COMBINATORIAL LIBRARY; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE-MOLECULAR-SIMILARITY-INDICES ANALYSIS; CONTRIBUTION MAP INTERPRETATION; MAP INTERPRETATION; MOLECULAR SIMILARITY; PROPERTY; THERMOLYSIN; THERMOLYSIN INHIBITION;

BINDING ENERGY;

ENZYME INHIBITOR; PEPTIDE LIBRARY; THERMOLYSIN;

ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; HYDROGEN BOND; HYDROPHOBICITY; LIGAND BINDING; MOLECULAR MIMICRY; PHYSICAL CHEMISTRY; PREDICTION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STEREOCHEMISTRY;

EID: 0033022163     PISSN: 0920654X     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1008047919606     Document Type: Article

References (25)

1. Müller, K., Perspect. Drug Discov. Design, 3 (1995) 1.
2. Cramer III, R.D., Patterson, D.E. and Bunce, J.D., J. Am. Chem. Soc., 110 (1988) 5959.
3. Thibaut, U., In Kubinyi, H. (Ed.), 3D QSAR in Drug Design, ESCOM, Leiden, 1993, pp. 661-696.
4. Klebe, G., Abraham, U. and Mietzner, T., J. Med. Chem., 37 (1994) 4130.
5. Folkers, G., Merz, A. and Rognan, D., In Kubinyi, H. (Ed.), 3D QSAR in Drug Design, ESCOM, Leiden, 1993, pp. 583-618.
6. Stahle, L. and Wold, S., Prog. Med. Chem., 25 (1988) 292.
7. Cramer III, R.D., De Priest, S.A., Patterson, D.E. and Hecht, P., In Kubinyi, H. (Ed.), 3D QSAR in Drug Design, ESCOM, Leiden, 1993, pp. 443-485.
8. DePriest, S.A., Mayer, D.C.B. and Marshall, G.R., J. Am. Chem. Soc., 115 (1993) 5372.
9. Campbell, D.A., Bermate, J.C., Burkoth, T.S. and Patel, D.V., J. Am. Chem. Soc., 117 (1995) 5381.
10. Martin, Y.C., Bures, M.G., Danaher, E.A., DeLazzer, J., Lico, I. and Pavlik, P., J. Comput.-Aided Mol. Design, 7 (1993) 83.
11. Program DISCO is available from Tripos Ass., St. Louis, MO, USA.
12. Allen, F.H., Kennard, O. and Taylor, R., Acc. Chem. Res., 16 (1983) 146.
13. Klebe, G., J. Mol. Biol., 237 (1994) 212.
14. Dewar, M.J.S., Zoebisch, E.G., Healy, E.F. and Stewart, J.J.P., J. Am. Chem. Soc., 107 (1985) 3902.
15. Viswanadhan, V.N., Ghose, A.K., Revankar, G.R. and Robins, R.K., J. Chem. Inf. Comput. Sci., 29 (1989) 163.
16. Sybyl Molecular Modeling System (Version 6.1), Tripos Ass., St. Louis, MO, USA.
17. Kearsley, S.K. and Smith, G.M., Tetrahed. Comput. Meth., 3 (1990) 615.
18. Klebe, G., Mietzner, T. and Weber, F., J. Comput.-Aided Mol. Design, 8 (1994) 751.
19. Bartlett, P.A. and Marlowe, C.K., Biochemistry, 26 (1987) 8553.
20. Morihara, K. and Tsuzuki, H., Eur. J. Biochem., 15 (1970) 374.
21. We have to admit that is hardly possible to document by black-and-white drawings the graphical advantage of the CoMSIA maps that become obvious using an interactive computer terminal.
22. Morgan, B.P., Scholtz, J.M., Ballinger, M.D., Zipkin, I.D. and Bartlett, P.A., J. Am. Chem. Soc., 113 (1991) 297.
23. Tronrud, D.H., Holden, H.M. and Matthews, B.W., Science, 235 (1987) 571.
24. Bartlett, P.A. and Marlowe, C.K., Science, 235 (1987) 569.
25. Bash, U.C., Singh, P.A., Brown, F.K., Langridge, R. and Kollman, P.A., Science, 235 (1987) 574.