Inactivation of Monoamine Oxidase B by Analogues of the Anticonvulsant Agent Milacemide (2-(n-Pentylamino)acetamide)

Journal of Medicinal Chemistry

Volumn 36, Issue 4, 1993, Pages 446-448

  Nishimura, Kuniko ^a,b   Lu, Xingliang ^a   Silverman, Richard B ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 (PENTYLAMINO)ACETIC ACID; 2 (PENTYLAMINO)ACETONITRILE TOSYLATE; 3 (PENTYLAMINO)PROPIONITRILE; ACETIC ACID DERIVATIVE; ACETONITRILE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; ETHYL 2 (PENTYLAMINO)ACETATE; MILACEMIDE; PROPIONITRILE; UNCLASSIFIED DRUG;

ARTICLE; COMPETITIVE INHIBITION; DRUG EFFICACY; DRUG MECHANISM; DRUG SOLUBILITY; DRUG SYNTHESIS; ELECTRON TRANSPORT; ENZYME INACTIVATION; ENZYME SUBSTRATE; NONHUMAN; PRIORITY JOURNAL;

ACETAMIDES; ACETONITRILES; ANIMAL; ANTICONVULSANTS; CATTLE; COMPARATIVE STUDY; MITOCHONDRIA, LIVER; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS;

EID: 0027404410     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00056a004     Document Type: Article

References (16)

1. Albertson, T. E.; Stark, L. G.; Joy, R. M. The Effect of a Glycine Derivative (CP 1552-S) on Kindled Seizures in Rats. Neuropharmacology 1984, 23, 967–970.
2. van Dorsser, W.; Barris, D.; Cordi, A.; Roba, J. Anticonvulsant Activity of Milacemide. Arch. Int. Pharmacodyn. Ther. 1983, 266, 239–249.
3. Janssensde Varbeke, P.; Cavalier, R.; David-Remade, M.; Youdim, M. B. H. Formation of the Neurotransmitter Glycine from the Anticonvulsant Milacemide Is Mediated by Brain Monoamine Oxidase B. J. Neurochem. 1988, 50, 1011–1016.
4. Janssens de Varebeke, P.; Pauwels, G.; Buyse, G.; David-Remacle, M.; De Mey, J.; Roba, J.; Youdim, M. B. H. The Novel Neuropsychotropic Agent Milacemide Is a Specific Enzyme-Activated Inhibitor of Brain Monoamine Oxidase B. J. Neurochem. 1989, 53, 1109–1116.
5. Silverman, R. B.; Nishimura, K.; Lu, X. Mechanism of Inactivation of Monoamine Oxidase-B by the Anticonvulsant Agent Milacemide (2-(n-Pentylamino)acetamide). J. Am. Chem. Soc., in press.
6. Banik, G. M.; Silverman, R. B. Mechanism of Inactivation of Monoamine Oxidase B by (Aminomethyl)trimethylsilane. J. Am. Chem. Soc. 1990, 112, 4499–4507.
7. Gates, K. S.; Silverman, R. B. 5-(Aminomethyl)-3-aryl-2-oxazolidinones. A Novel Class of Mechanism-Based Inactivators of Monoamine Oxidase B. J. Am. Chem. Soc. 1990, 112, 9364–9372.
8. Lee, Y. B.; Goo, Y. M.; Lee, Y. Y.; Lee, J. K. Conversion of α-Aminonitriles to Amides by a New Pinner Type Reaction. Tetrahedron Lett. 1990, 31, 1169–1170.
9. Kitz, R.; Wilson, I. B. Esters of Methanesulfonic Acid as Irreversible Inhibitors of Acetylcholinesterase. J. Biol. Chem. 1962, 237, 3245–3249.
10. Suelter, C. H. A Practical Guide to Enzymology; Wiley & Sons: New York, 1985; p 241.
11. Silverman, R. B. Mechanism-Based Enzyme Inactivation: Chemistry and Enzymology; CRC Press: Boca Raton, FL, 1988; Vol. 1.
12. Exner, O. In Correlation Analysis in Chemistry; Chapman, N. B., Shorter, J., Eds.; Plenum Press: New York, 1978; pp 439–540.
13. Tarbell, D. S.; Shakespeare, N.; Claus, C. J.; Bunnett, J. F. Synthesis of Some 7-Chloro-4-(3-alkylaminopropylamino)quinolines. J. Am. Chem. Soc. 1946, 68, 1217–1219.
14. Salach, J. I. Monoamine Oxidase from Beef Liver Mitochondria: Simplified Isolation Procedure, Properties, and Determination of Its Cysteinyl Flavin Content. Arch. Biochem. Biophys. 1979, 192, 128–137.
15. Tabor, C. W.; Tabor, H.; Rosenthal, S. M. Purification of Amine Oxidase from Beef Plasma. J. Biol. Chem. 1954, 208, 645–661.
16. Mottola, H. A.; Simpson, B. E.; Gorin, G. Absorptiometry Determination of Hydrogen Peroxide in Submicrogram Amounts with Leuco Crystal Violet and Peroxidase as Catalyst. Anal. Chem. 1970, 42, 410–411.