Inactivation of Purified Human Recombinant Monoamine Oxidases A and B by Rasagiline and Its Analogues

Journal of Medicinal Chemistry

Volumn 47, Issue 7, 2004, Pages 1760-1766

  Hubálek, Frantisek ^a   Binda, Claudia ^b   Li, Min ^a   Herzig, Yaacov ^c   Sterling, Jeffrey ^c   Youdim, Moussa B H ^d   Mattevi, Andrea ^b   Edmondson, Dale E ^a  

^a EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b UNIVERSITY OF PAVIA   (Italy)

^c Teva Pharmaceutical Industries   (Israel)

^d TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

6 (N METHYL N ETHYLCARBAMOYLOXY) N PROPARGYL 1 AMINOINDAN; 6 HYDROXY N PROPARGYL 1 AMINOINDAN; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; FLAVINE ADENINE NUCLEOTIDE; HYDROGEN PEROXIDE; N METHYL N (2 PROPYNYL) 1 INDANAMINE; RASAGILINE; UNCLASSIFIED DRUG;

ARTICLE; CIRCULAR DICHROISM; DRUG INHIBITION; DRUG STRUCTURE; ENANTIOMER; ENZYME INACTIVATION; ENZYME PURIFICATION; ENZYME SPECIFICITY; HUMAN; STOICHIOMETRY; ULTRAVIOLET SPECTROPHOTOMETRY;

ALKYNES; CIRCULAR DICHROISM; HUMANS; INDANS; KINETICS; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; RECOMBINANT PROTEINS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 12144287240     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0310885     Document Type: Article

References (25)

1. Shih, J. C.; Chen, K.; Ridd, M. J. Monoamine oxidase: from genes to behavior. Annu. Rev. Neurosci. 1999, 22, 197-217.
2. Pare, C. M. Unwanted effects of long-term medication in schizophrenia and depression. Pharmakopsychiatr./Neuro-Psychopharmakol. 1976, 9, 187-92.
3. The Parkinson Study Group. Effect of deprenyl on the progression of disability in early Parkinson's disease. N. Engl. J. Med. 1989, 321, 1364-1371.
4. Youdim, M. B. The advent of selective monoamine oxidase A inhibitor antidepressants devoid of the cheese reaction. Acta Psychiatr. Scand., Suppl. 1995, 386, 5-7.
5. Kalir, A.; Sabbagh, A.; Youdim, M. B. Selective acetylenic suicide and reversible inhibitors of monoamine oxidase types A and B. Eur. J. Pharmacol. 1981, 73, 55-64.
6. Sterling, J.; Veinberg, A.; Lerner, D.; Goldenberg, W.; Levy, R.; Youdim, M.; Finberg, J. (R)(+)-N-Propargyl-1-aminoindan (rasagiline) and derivatives: highly selective and potent inhibitors of monoamine oxidase B. J. Neural Transm. 1998, 52 (Suppl.), 301-305.
7. Sterling, J.; Herzig, Y.; Goren, T.; Finkelstein, N.; Lerner, D.; Goldenberg, W.; Miskolczi, I.; Molnar, S.; Rantal, F.; Tamas, T.; Toth, G.; Zagyva, A.; Zekany, A.; Lavian, G.; Gross, A.; Friedman, R.; Razin, M.; Huang, W.; Krais, B.; Chorev, M.; Youdim, M. B.; Weinstock, M. Novel dual inhibitors of AChE and MAO derived from hydroxy aminoindan and phenethylamine as potential treatment for Alzheimer's disease. J. Med. Chem. 2002, 45, 5260-5279.
8. Maruyama, W.; Weinstock, M.; Youdim, M. B.; Nagai, M.; Naoi, M. Anti-apoptotic action of anti-Alzheimer drug, TV3326 [(N-propargyl)-(3R)-aminoindan-5-yl]-ethyl methyl carbamate, a novel cholinesterase-monoamine oxidase inhibitor Neurosci. Lett. 2003, 341, 233-236.
9. Weinstock, M.; Gorodetsky, E.; Wang, R. H.; Gross, A.; Weinreb, O.; Youdim, M. B. H. Limited potentiation of blood pressure response to oral tyramine by brain-selective monoamine oxidase A-B inhibitor, TV-3326 in conscious rabbits. Neuropharmacology 2002, 43, 999-1005.
10. Li, M.; Hubálek, F.; Newton-Vinson, P.; Edmondson, D. E. High-Level Expression of Human Liver Monoamine Oxidase A in Pichia pastoris: Comparison with the Enzyme Expressed in Saccharomyces cerevisiae. Protein Expression Purif. 2002, 24, 152-162.
11. Newton-Vinson, P.; Hubálek, F.; Edmondson, D. E. High-level expression of human liver monoamine oxidase B in Pichia pastoris. Protein Expression Purif 2000, 20, 334-345.
12. Binda, C.; Hubálek, F.; Li, M.; Herzig, Y.; Sterling, J.; Edmondson, D. E.; Mattevi, A. Crystal Structures of Monoamine Oxidase B in Complex with Four Inhibitors of the N-Propargylaminoindan Class. J. Med. Chem. 2004, 47, xxxx-xxxx.
13. Maycock, A. L.; Abeles, R. H.; Salach, J. I.; Singer, T. P. The structure of the covalent adduct formed by the interaction of 3-dimethylamino-1-propyne and the flavine of mitochondrial amine oxidase. Biochemistry 1976, 15, 114-25.
14. Binda, C.; Newton-Vinson, P.; Hubálek, F.; Edmondson, D. E.; Mattevi, A. Structure of human monoamine oxidase B, a drug target for the treatment of neurological disorders. Nat. Struct. Biol. 2002, 9, 22-26.
15. Gärtner, B.; Hemmerich, P.; Zeller, E. A. Structure of flavin adducts with acetylenic substrates. Chemistry of monoamine oxidase and lactate oxidase inhibition. Eur. J. Biochem. 1976, 63, 211-221.
16. Youdim, M. B.; Gross, A.; Finberg, J. P. Rasagiline [N-propargyl-1R(+)-aminoindan], a selective and potent inhibitor of mitochondrial monoamine oxidase B. Br. J. Pharmacol. 2001, 132, 500-506.
17. Silverman, R. B. Mechanism-based enzyme inactivators. Methods Enzymol. 1995, 249, 240-283.
18. Chuang, H. Y.; Patek, D. R.; Hellerman, L. Mitochondrial monoamine oxidase. Inactivation by pargyline. Adduct formation. J. Biol. Chem. 1974, 249, 2381-2384.
19. Hellerman, L.; Erwin, V. G. Mitochondrial monoamine oxidase. II. Action of various inhibitors for the bovine kidney enzyme. Catalytic mechanism. J. Biol. Chem. 1968, 243, 5234-5243.
20. Cantor, C. R., Schimmel, P. R., Eds. Biophysical Chemistry; W. H. Freeman and Company: San Francisco, 1980; pp 385-405.
21. Hubálek, F.; Pohl, J.; Edmondson, D. E. Structural comparison of human MAO A and human MAO B. Mass spectrometry monitoring of cysteine reactivities. J. Biol. Chem. 2003, 278, 28612-28618.
22. Nandigama, R. K.; Miller, J. R.; Edmondson, D. E. Loss of serotonin oxidation as a component of the altered substrate specificity in the Y444F mutant of recombinant human liver MAO A. Biochemistry 2001, 40, 14839-14846.
23. Delaire, M.; Labia, R.; Sanama, J. P.; Mason, J. M. Site-directed mutagenesis at the active site of Escherichia coli TEM-1 β-lactamase. Suicide inhibitor-resistant mutants reveal the role of arginine 244 and methionine 69 in catalysis. J. Biol. Chem. 1992, 267, 20600-20606.
24. Holt, A.; Sharman, D. F.; Baker, G. B.; Palcic, M. M. A continuous spectrophotometric assay for monoamine oxidase and related enzymes in tissue homogenates. Anal. Biochem. 1997, 244, 384-392.
25. Hubálek, F.; Edmondson, D. E.; Pohl, J. Synthesis and characterization of a collagen model δ-O-phosphohydroxylysine-containing peptide. Anal. Biochem. 2002, 306, 124-134.