Inhibition of monoamine oxidase by (E)-styrylisatin analogues

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 9, 2009, Pages 2509-2513

  Van der Walt, Elizna M ^a   Milczek, Erika M ^b   Malan, Sarel F ^a   Edmondson, Dale E ^b   Castagnoli Jr , Neal ^c   Bergh, Jacobus J ^a   Petzer, Jacobus P ^a  

^a NORTH WEST UNIVERSITY   (South Africa)

^b EMORY UNIVERSITY   (United States)

^c EDWARD VIA COLLEGE OF OSTEOPATHIC MEDICINE   (United States)

Author keywords

(E) 5 Styrylisatin; (E) 6 Styrylisatin; Isatin; Monoamine oxidase A; Monoamine oxidase B; Reversible inhibitor

Indexed keywords

5 (3 CHLOROSTYRYL)ISATIN; 5 (3 FLUOROSTYRYL)ISATIN; 5 STYRYLISATIN; 6 STYRYLISATIN; AMINE OXIDASE (FLAVIN CONTAINING); AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; ISATIN; MONOAMINE OXIDASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DRUG POTENCY; DRUG SPECIFICITY; ENZYME INHIBITION; ENZYME SUBSTRATE; GEOMETRY; MOLECULAR DOCKING; MUTANT;

BINDING, COMPETITIVE; BRAIN; CHEMISTRY, PHARMACEUTICAL; DRUG DESIGN; HUMANS; INHIBITORY CONCENTRATION 50; ISATIN; KINETICS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; MUTATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 64249159149     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.03.030     Document Type: Article

References (29)

1. Youdim M.B., Collins G.G., Sandler M., Bevan Jones A.B., Pare C.M., and Nicholson W.J. Nature 236 (1972) 225
2. Collins G.G., Sandler M., Williams E.D., and Youdim M.B. Nature 225 (1970) 817
3. Di Monte D.A., DeLanney L.E., Irwin I., Royland J.E., Chan P., Jakowec M.W., and Langston J.W. Brain Res. 738 (1996) 53
4. Finberg J.P., Wang J., Bankiewich K., Harvey-White J., Kopin I.J., and Goldstein D.S. J. Neural Trans. Suppl. 52 (1998) 279
5. Youdim M.B.H., and Bakhle Y.S. Br. J. Pharmacol. 147 (2006) S287
6. Nicotra A., Pierucci F., Parvez H., and Senatori O. Neurotoxicology 25 (2004) 155
7. Fowler J.S., Volkow N.D., Wang G.J., Logan J., Pappas N., Shea C., and MacGregor R. Neurobiol. Aging 18 (1997) 431
8. Karolewicz B., Klimek V., Zhu H., Szebeni K., Nail E., Stockmeier C.A., Johnson L., and Ordway G.A. Brain Res. 1043 (2005) 57
9. Hubálek F., Binda C., Khalil A., Li M., Mattevi A., Castagnoli Jr. N., and Edmondson D.E. J. Biol. Chem. 280 (2005) 15761
10. Binda C., Hubálek F., Restelli N., Edmondson D.E., and Mattevi A. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 9750
11. Vlok N., Malan S.F., Castagnoli Jr. N., Bergh J.J., and Petzer J.P. Bioorg. Med. Chem. 14 (2006) 3512
12. Pretorius J.P., Malan S.F., Castagnoli Jr. N., Bergh J.J., and Petzer J.P. Bioorg. Med. Chem. 16 (2008) 8676
13. Van den Berg D., Zoellner K.R., Ogunrombi M.O., Malan S.F., Terre'Blanche G., Castagnoli Jr. N., Bergh J.J., and Petzer J.P. Bioorg. Med. Chem. 15 (2007) 3692
14. Son S.-Y., Ma J., Kondou Y., Yoshimura M., Yamashita E., and Tsukihara T. Proc. Natl. Acad. Sci. U.S.A. 105 (2008) 5739
15. Binda C., Wang J., Pisani L., Caccia C., Carotti A., Salvati P., Edmondson D.E., and Mattevi A. J. Med. Chem. 50 (2007) 5848
16. Accelrys Discovery Studio 1.7, Accelrys Software Inc., San Diego, CA, USA. 2006, http://www.accelrys.com.
17. Ogunrombi M.O., Malan S.F., Terre'Blanche G., Castagnoli Jr. N., Bergh J.J., and Petzer J.P. Bioorg. Med. Chem. 16 (2008) 2463
18. Yasara Structure, Yasara Biosciences, Graz, Austria. 2008, http://www.yasara.org.
19. Lee Y.-B., Woo H.Y., Yoon C.-B., and Shim H.-K. J. Mater. Chem. 9 (1999) 2345
20. Kuo E.A., Hambleton P.T., Kay D.P., Evans P.L., Matharu S.S., Little E., McDowall N., Jones C.B., Hedgecock C.J., Yea C.M., Chan A.W., Hairsine P.W., Ager I.R., Tully W.R., Williamson R.A., and Westwood R. J. Med. Chem. 39 (1996) 4608
21. Hanna P.E., Gammans R.E., Sehon R.D., and Lee M.K. J. Med. Chem. 23 (1980) 1038
22. Langenbeck V.W., Rühlmann K., Reif H.H., and Stolze F. J. Prakt. Chem. 4 (1957) 136
23. +); HR-EIMS m/z calcd 249.078979, found 249.079214.
24. Salach J.I., and Weyler W. Meth. Enzymol. 142 (1987) 627
25. Newton-Vinson P., Hubálek F., and Edmondson D.E. Protein Exp. Purif. 20 (2000) 334
26. Li M., Hubálek F., Newton-Vinson P., and Edmondson D.E. Protein Exp. Purif. 24 (2002) 152
27. 25,26 The human MAO-B I199A mutant protein was constructed via site-directed mutagenesis. A manuscript is in preparation detailing the construction, expression, and purification protocol for the human MAO-B I199A mutant protein.
28. m value recorded for each inhibitor concentration as a function of inhibitor concentration.
29. Walker M.C., and Edmondson D.E. Biochemistry 33 (1994) 7088