Inactivation and inhibition of γ-aminobutyric acid aminotransferase by conformationally restricted vigabatrin analogues

Journal of Medicinal Chemistry

Volumn 45, Issue 20, 2002, Pages 4531-4539

  Choi, Sun ^b   Silverman, Richard B ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

^b TRIPOS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOCYCLOHEX 3 ENE 1 CARBOXYLIC ACID; 3 AMINOCYCLOHEX 4 ENE 1 CARBOXYLIC ACID; 3 AMINOCYCLOHEX 4 ENE CARBOXYLIC ACID; 4 AMINOBUTYRATE AMINOTRANSFERASE; 4 AMINOBUTYRIC ACID; BETA ALANINE; CYCLOPENTENE DERIVATIVE; UNCLASSIFIED DRUG; VIGABATRIN; VIGABATRIN DERIVATIVE;

ARTICLE; DRUG CONFORMATION; DRUG DEPENDENCE; DRUG INACTIVATION; ENZYME INACTIVATION; ENZYME INHIBITION; EPILEPSY; MOLECULAR MODEL;

4-AMINOBUTYRATE TRANSAMINASE; BINDING SITES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLOHEXANES; ENZYME ACTIVATION; ENZYME INHIBITORS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STRUCTURE-ACTIVITY RELATIONSHIP; VIGABATRIN;

EID: 0037179616     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020134i     Document Type: Article

References (41)

1. (a) Krnjevic, K. Chemical nature of synaptic transmission in vertebrates. Physiol. Rev. 1974, 54, 418-540.
2. (b) Faingold, C. L.; Gehlbach, G.; Caspary, D. M. On the role of GABA as an inhibitory neurotransmitter in inferior colliculus neurons: iontophoretic studies. Brain Res. 1989, 500, 302-312.
3. (c) Bohme, I.; Luddens, H. The inhibitory neural circuitry as target of antiepileptic drugs. Curr. Med. Chem. 2001, 8, 1257-1274.
4. Cooper, A. J. L. Glutamate-γ-aminobutyrate transaminase. Methods Enzymol. 1985, 113, 80-82.
5. Gale, K. GABA in epilepsy: the pharmacologic basis. Epilepsia 1989, 30 (Suppl. 3), S1-S11.
6. (a) Hornykiewicz, O.; Lloyd, K. G.; Davidson, L. The GABA system, function of the basal ganglia and Parkinson's disease. In GABA in Nervous System Function; Roberts, E., Chase, T. N., Tower, D. B., Eds.; Raven Press: New York, 1976; pp 479-485.
7. (b) Kleppner, S. R.; Tobin, A. J. GABA signaling: Therapeutic targets for epilepsy, Parkinson's disease and Huntington's disease. Emerging Ther. Targets 2001, 5, 219-239.
8. Perry, T. L.; Hansen, S.; Kloster, M. Huntington's chorea: deficiency of α-aminobutyric acid in brain. N. Engl. J. Med. 1973, 288, 337-342.
9. (a) Aoyagi, T.; Wada, T.; Nagai, M.; Kojima, F.; Harada, S.; Takeuchi, T.; Takahashi, H.; Hirokawa, K.; Tsumita, T. Increased γ-aminobutyrate aminotransferase activity in brain of patients with Alzheimer's disease. Chem. Pharm. Bull. 1990, 38, 1748-1749.
10. (b) Weiner, M. F. Treatment of behavioral/psychological symptoms in Alzheimer's disease. Exp. Rev. Neurother. 2001, 1, 70-80.
11. (a) Kushner, S. A.; Dewey, S. L.; Kornetsky, C. The irreversible γ-aminobutyric acid (GABA) transaminase inhibitor γ-vinyl-GABA blocks cocaine self-administration in rats. J. Pharmacol. Exp. Ther. 1999, 290, 797-802.
12. (b) Dewey, S. L.; Morgan, A. E.; Ashby, C. R., Jr.; Horan, B.; Kushner, S. A.; Logan, J.; Volkow, N. D.; Fowler, J. S.; Gardner, E. L.; Brodie, J. D. A novel strategy for the treatment of cocaine addiction. Synapse 1998, 30, 119-129.
13. Lippert, B.; Metcalf, B. W.; Jung, M. J.; Casara, P. 4-Aminohex-5-enoic Acid, a Selective Catalytic Inhibitor of 4-Aminobutyric-Acid Aminotransferase in Mammalian Brain. Eur. J. Biochem. 1977, 74, 441-445.
14. Nanavati, S. M.; Silverman, R. B. Design of Potential Anticonvulsant Agents: Mechanistic Classification of GABA Aminotransferase Inactivators. J. Med. Chem. 1989, 32, 2413-2421.
15. (a) Silverman, R. B. Mechanism-Based Enzyme Inactivation: Chemistry and Enzymology; CRC Press: Boca Raton, 1988; Vols. I and II.
16. (b) Silverman, R. B. Mechanism-Based Enzyme Inactivators. Methods Enzymol. 1995, 249, 240-283.
17. Davies, J. A. Mechanism of action of antiepileptic drugs. Seizure 1995, 4, 267-271.
18. Brennan, M. Treating substance abuse. Chem. Eng. News 1999, August 23, 8.
19. Nanavati, S. M.; Silverman, R. B. Mechanism of Inactivation of γ-Aminobutyric Acid Aminotransferase by the Antiepilepsy Drug γ-Vinyl GABA (Vigabatrin). J. Am. Chem. Soc. 1991, 113, 9341-9349.
20. Choi, S.; Storici, P.; Schirmer, T.; Silverman, R. B. Design of a Conformationally Restricted Analogue of the Antiepilepsy Drug Vigabatrin that Directs Its Mechanism of Inactivation of γ-Aminobutyric Acid Aminotransferase. J. Am. Chem. Soc. 2002, 124, 1620-1624.
21. Qiu, J.; Pingsterhaus, J. M.; Silverman, R. B. Inhibition and Substrate Activity of Conformationally Rigid Vigabatrin Analogues with γ-Aminobutyric Acid Aminotransferase. J. Med. Chem. 1999, 42, 4725-4728.
22. Murahashi, S.-I.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. Palladium(0)-Catalyzed Azidation of Allyl Esters. Selective Synthesis of Allyl Azides, Primary Allylamines, and Related Compounds. J. Org. Chem. 1989, 54, 3292-3303.
23. Marshall, J. A.; Xie, S. Synthesis of a C22-34 Subunit of the Immunosuppressant FK-506. J. Org. Chem. 1995, 60, 7230-7237.
24. Nagarajan, S.; Ganem, B. Chemistry of Naturally Occurring Polyamines. 11. Unsaturated Spermidine and Spermine Derivatives. J. Org. Chem. 1987, 52, 5044-5046.
25. Overman, L. E.; Taylor, G. F.; Houk, K. N.; Domelsmith, L. N. Diels-Alder Reactions between trans-1-N-Acylamino-1,3-dienes and Methyl Acrylate. A Correlation between Diene Photoelectron Ionization Potentials and Reactivity, Stereoselectivity, and Regioselectivity. J. Am. Chem. Soc. 1978, 100, 3182-3189.
26. (a) Jung, M. E.; Lyster, M. A. Conversion of Alkyl Carbamates into Amines via Treatment with Trimethylsilyl Iodide. J. Chem. Soc. Chem. Commun. 1978, 315-316.
27. (b) Jung, M. E.; Lyster, M. A. Quantitative Dealkylation of Alkyl Esters via Treatment with Trimethylsilyl Iodide. A New Method for Ester Hydrolysis. J. Am. Chem. Soc. 1977, 99, 968-969.
28. Kitz, R.; Wilson, I. B. Esters of Methanesulfonic Acid as Irreversible Inhibitors of Acetylcholinesterase. J. Biol. Chem. 1962, 237, 3245-3249.
29. Storici, P.; Capitani, G.; De Biase, D.; Moser, M.; John, R. A.; Jansonius, J. N.; Schirmer, T. Crystal Structure of GABA-aminotransferase, a Target for Antiepileptic Drug Therapy. Biochemistry 1999, 38, 8628-8634.
30. (a) De Biase, D.; Barra, D.; Bossa, F.; Pucci, P.; John, R. A. Chemistry of the Inactivation of 4-Aminobutyrate Aminotransferase by the Antiepileptic Drug Vigabatrin. J. Biol. Chem. 1991, 266, 20056-20061.
31. (b) De Biase, D.; Bolton, J. B.; Barra, D.; Bossa, F.; John, R. A. Stoichiometry and stability of the adduct formed between human 4-aminobutyrate aminotransferase and 4-aminohex-5-enoate: sequence of a labelled peptide. Biochimie 1989, 71, 491-495.
32. Toney, M. D.; Pascarella, S.; De Biase, D. Active Site Model for γ-Aminobutyrate Aminotransferase Explains Substrate Specificity and Inhibitor Reactivities. Protein Sci. 1995, 4, 2366-2374.
33. Dunathan, H. C. Conformation and Reaction Specificity in Pyridoxal Phosphate Enzymes. Proc. Natl. Acad. Sci. U.S.A. 1966, 55, 712-716.
34. Ross, J. H. 2,6-Dichloroquinone 4-Chloroimide as a Reagent for Amines and Aromatic Hydrocarbons on Thin-layer Chromatograms. Anal. Chem. 1968, 40, 2138-2143.
35. Rarey, M.; Kramer, B.; Lengauer, T.; Klebe, G. A Fast Flexible Docking Method Using an Incremental Construction Algorithm. J. Mol. Biol. 1996, 261, 470-489.
36. Johnson, T. R.; Silverman, R. B. Syntheses of (Z)- and (E)-4-Amino-2-(trifluoromethyl)-2-butenoic Acid and Their Inactivation of γ-Aminobutyric Acid Aminotransferase. Bioorg. Med. Chem. 1999, 7, 1625-1636.
37. Silverman, R. B.; Bichler, K. A.; Leon, A. J. Mechanisms of inactivation of γ-aminobutyric acid aminotransferase by 4-amino-5-fluoro-5-hexenoic acid. J. Am. Chem. Soc. 1996, 118, 1241-1252.
38. Penefsky, H. S. A centrifuged-column procedure for the measurement of ligand binding by beef heart F1. Methods Enzymol. 1979, 56, 527.
39. Fu, M.; Silverman, R. B. Isolation and characterization of the product of inactivation of γ-aminobutyric acid aminotransferase by gabaculine. Bioorg. Med. Chem. 1999, 7, 1581-1590.
40. Dixon, M. The Determination of Enzyme Inhibitor Constants. Biochem. J. 1953, 55, 170-171.
41. Cornish-Bowden, A. Fundamentals of Enzyme Kinetics; Portland Press: London, 1995; pp 102-108.