A semiempirical study on inhibition of catechol O-methyltransferase by substituted catechols

Journal of Computer-Aided Molecular Design

Volumn 12, Issue 3, 1998, Pages 301-307

  Ovaska, Martti ^a   Yliniemelä, Ari ^b  

^a ORION CORPORATION   (Finland)

^b UNIVERSITY OF HELSINKI   (Finland)

Author keywords

COMT; Drug design; Inhibition mechanism; PM3; Semiempirical calculation

Indexed keywords

AMINO ACIDS; INDIUM COMPOUNDS; METHYLATION; PHENOLS;

CATECHOL DERIVATIVES; CATECHOL-O-METHYLTRANSFERASE; DRUG DESIGN; ELECTRONEGATIVE SUBSTITUENTS; HYDROXYL GROUPS; INHIBITION MECHANISMS; PM3; SEMI-EMPIRICAL; SEMI-EMPIRICAL CALCULATION; X-RAY STRUCTURE;

ALKYLATION;

CATECHOL DERIVATIVE; CATECHOL METHYLTRANSFERASE; ENZYME INHIBITOR;

ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; METABOLISM; THERMODYNAMICS;

BINDING SITES; CATECHOL O-METHYLTRANSFERASE; CATECHOLS; ENZYME INHIBITORS; MODELS, MOLECULAR; THERMODYNAMICS;

EID: 0032060840     PISSN: 0920654X     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1007965026738     Document Type: Article

References (30)

1. Männistö, P.T., Ulmanen, I., Lundström, K., Taskinen, J., Tenhunen, J., Tilgmann, C. and Kaakkola, S., In Juner, E. (Ed.) Progress in Drag Research, Birkhäuser Verlag, Basel, 1992, pp. 291-350.
2. Flohe, L. and Schwabe, K., Biochim. Biophys. Acta, 220 (1970) 469.
3. Coward, J.K., Slisz, E.P. and Wu, F.Y.-H., Biochemistry, 12 (1973) 2291.
4. Borchardt, R.T., J. Med. Chem., 16 (1973) 377.
5. Woodard, R.W., Tsai, M.-D., Floss, H.G., Crooks, RA. and Coward, J.K., J. Biol. Chem., 255 (1980) 9124.
6. Malherbe, P., Bertocci, B., Caspers, P., Zürcher, G. and Da Prada, M., J. Neurochem., 58 (1992) 1782.
7. Lotta, T., Vidgren, J., Tilgmann, C., Ulmanen, L, Melén, K., Julkunen, I. and Taskinen, J., Biochemistry, 34 (1995) 4202.
8. Borchardt, R.T., In Usdin, E. (Ed.) Structure and Function of Monoamine Enzymes, Marcel Dekker, New York, NY, 1977, pp. 707-726.
9. Knipe, J.O., Vasquez, P.J. and Coward, J.K., J. Am. Chem. Soc., 104 (1982) 3202.
10. Thakker, D.R., Boehlert, C., Kirk, K.L., Antkowiak, R. and Creveling, C.R., J. Biol. Chem., 261 (1986) 178.
11. Creveling, C.R., Dalgard, N., Shimizu, H. and Daly, J.W., Mol. Pharmacol., 6 (1970) 691.
12. Borchardt, R.T. and Huber, J.A., J. Med. Chem., 25 (1982) 321.
13. Vidgren, J., Svensson, L.A. and Liljas, A., Nature, 368 (1994) 354.
14. Bäckström, R., Honkanen, E., Pippuri, A., Kairisalo, P., Pystynen, J., Heinola, K., Nissinen, E., Lindén, I.-B., Männistö, P., Kaakkola, S. and Pohto, P., J. Med. Chem., 32 (1989) 841.
15. Borgulya, J., Bruderer, H., Bernauer, K., Zurcher, G. and Da Prada, M., Helv. Chim. Acta, 72 (1989) 952.
16. Kaakkola, S., Gordin, A. and Männistö, P.T., Gen. Pharmacol., 25 (1994) 813.
17. Taskinen, J., Vidgren, J., Ovaska, M., Bäckström, R., Pippuri, A. and Nissinen, E., Quant. Struct.-Act. Relatsh., 8 (1989) 210.
18. Lotta, T., Taskinen, J., Bäckström, R. and Nissinen, E., J. Comput.-Aided Mol. Design, 6 (1992) 253.
19. Vidgren, J. and Ovaska, M., In Veerapandian, P. (Ed.) Structure-Based Drug Design, Marcel Dekker, New York, NY, 1997, pp. 343-363.
20. Mulholland, A.J., Grant, G.H. and Richards, W.G., Protein Eng., 6 (1993) 133.
21. Peräkylä, M. and Pakkanen, T.A., J. Am. Chem. Soc., 115 (1993) 10958.
22. Bernstein, F.C., Koetzle, T.F., Williams, G.J.B., Meyer Jr., E.F., Brice, M.D., Rodgers, J.R., Kennard, O., Shimanouchi, T. and Tasumi, M., J. Mol. Biol., 112 (1977) 535.
23. Stewart, J.J.P., J. Comput. Chem., 10 (1989) 209.
24. Schröder, S., Daggett, V. and Kollman, P.A., J. Am. Chem. Soc., 113 (1991) 8922.
25. Rzepa, H.S. and Yi, M.Y., J. Chem. Soc. Perkin Trans., 2 (1991) 531.
26. Furuki, F., Sakurai, M. and Inoue, Y., J. Comput. Chem., 16 (1995) 378.
27. Wikberg, T., Biotransformation and Bioanalytics of Nitecapone and Entacapone, Ph.D. Thesis, University of Helsinki, Helsinki, Finland, 1993, p. 29.
28. Toney, M.D. and Kirsch, J.F., Science, 243 (1989) 1485.
29. Zheng, Y.-J. and Bruice, T.C., J. Am. Chem. Soc., 119 (1997) 8137.
30. Kraulis, P.J., J. Appl. Crystallogr., 24 (1991) 946.