Interactions of nitrogen-containing xenobiotics with monoamine oxidase (MAO) isozymes A and B: SAR studies on MAO substrates and inhibitors

Chemical Research in Toxicology

Volumn 14, Issue 9, 2001, Pages 1139-1162

  Kalgutkar, A S ^a   Dalvie, D K ^a   Castagnoli Jr , N ^b   Taylor, T J ^a  

^a PFIZER INC   (United States)

^b VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,6 TETRAHYDRO 1 METHYL 4 PHENYLPYRIDINE; 5H INDENO[1,2 C]PYRIDAZINE DERIVATIVE; AMINE OXIDASE (FLAVIN CONTAINING); ANTIMIGRAINE AGENT; CITALOPRAM; CLORGYLINE; COUMARIN DERIVATIVE; DILTIAZEM; ELETRIPTAN; HALOPERIDOL; HETEROCYCLIC AMINE; HYDROQUINONE DERIVATIVE; INDOLE DERIVATIVE; ISOENZYME; ISOQUINOLINE DERIVATIVE; MILACEMIDE; MOCLOBEMIDE; MONOAMINE DERIVATIVE; MONOAMINE OXIDASE INHIBITOR; OXAZOLIDINONE DERIVATIVE; PRIMAQUINE; PYRIDAZINE DERIVATIVE; RIZATRIPTAN; SUMATRIPTAN; TRICYCLIC ANTIDEPRESSANT AGENT; TRYPTOLINE; UNCLASSIFIED DRUG; XENOBIOTIC AGENT; ZOLMITRIPTAN;

CATALYSIS; CIGARETTE SMOKING; DRUG METABOLISM; DRUG STRUCTURE; ENZYME INHIBITION; FIRST PASS EFFECT; HUMAN; LIVER MICROSOME; MOLECULAR INTERACTION; OXIDATION; REACTION ANALYSIS; REVIEW; SITE DIRECTED MUTAGENESIS; STRUCTURE ACTIVITY RELATION; TISSUE DISTRIBUTION;

ANIMALS; HUMANS; ISOENZYMES; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; MUTAGENESIS, SITE-DIRECTED; NITROGEN; STRUCTURE-ACTIVITY RELATIONSHIP; TISSUE DISTRIBUTION; XENOBIOTICS;

EID: 0034814085     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx010073b     Document Type: Review

References (302)

1. Monoamine oxidases
2. The discovery of monoamine oxidases A and B
3. Perspectives in MAO: Past present and future
4. Biochemistry and mechanism of action of monoamine oxidases A and B
5. Metabolism of the neurotoxic tertiary amine, MPTP, by brain monoamine oxidase
6. The role of amine oxidases in xenobiotic metabolism
7. Monoamine oxidases and related amine oxidases as phase I enzymes in the metabolism of xenobiotics
8. Biotransformation of xenobiotics
9. Contribution of amine oxidase to the metabolism of xenobiotics
10. Interactions of monoamine oxidase with substrates and inhibitors
11. Monoamine oxidase: Physiology and pathophysiology to the design and clinical applications of reversible inhibitors
12. Some observations upon a new inhibitor of monoamine oxidase in brain tissue
13. Some puzzling pharmacological effects of monoamine oxidase inhibitors
14. Mitochondrial monoamine oxidase: II. Action of various inhibitors for the bovine kidney enzyme. Catalytic mechanism
15. Monoamine oxidase inhibiton
16. Amine oxidases and their endogenous substrates (with special reference to monoamine oxidase and the brain)
17. cDNA cloning of human liver monoamine oxidase A and B: Molecular basis of differences in enzymatic properties
18. Structural features of human monoamine oxidase A elucidated from cDNA and peptide sequences
19. The primary structure of bovine monoamine oxidase A: Comparison with peptide sequences of bovine monoamine oxidase B and other flavoenzymes
20. Biochemistry and genetics of monoamine oxidase
21. Molecular biology of monoamine oxidase A and B: Their role in the degradation of serotonin
22. Molecular and functional properties of the monoamine oxidases
23. Multiple forms of monoamine oxidase in intact mitochondria as characterized by selective inhibitors and thermal stability: A comparison of eight mammalian species
24. Additional evidence for the existence of several forms of mitochondrial monoamine oxidase in the mouse
25. Species differences in the deamination of dopamine and other substrates for monoamine oxidase in brain
26. Dramatic species differences in the susceptibility of monoamine oxidase B to a group of powerful inhibitors
27. Species differences in the interactions of anticonvulsants milacemide and some analogs with monoamine oxidase B
28. Species-dependent differences in monoamine oxidase A and B-catalyzed oxidation of various C4 substituted 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridinyl derivatives
29. Determination of the absolute concentrations of monoamine oxidase A and B in human tissues
30. Localization of monoamine oxidases in human peripheral tissues
31. The expression of human MAO-A and B genes
32. Tissue distribution of human monoamine oxidase A and B mRNA
33. Localization of monoamine oxidase A and B in human pancreas, thyroid, and adrenal glands
34. Immunocytochemical localization of monoamine oxidases A and B in human peripheral tissues and brain
35. Properties of monoamine oxidase (MAO) in human blood platelets, plasma, lymphocytes and granulocytes
36. The distribution of monoamine oxidases A and B in normal human brain
37. The functional role of monoamine oxidases A and B in the mammalian central nervous system
38. Structural aspects of monoamine oxidase and its reversible inhibition
39. Primary structure of rat monoamine oxidase A deduced from cDNA and its expression in rat tissues
40. Molecular cloning of cDNA for rat liver monoamine oxidase B
41. The deduced amino acid sequences of human platelet and frontal cortex monoamine oxidase B are identical
42. Secondary structure of monoamine oxidase by FTIR spectroscopy
43. Cloning of a novel monoamine oxidase cDNA from trout liver
44. Investigation on the structure of the active site of monoamine oxidase B by affinity labeling with the selective inhibitor lazabemide and by site directed mutagenesis
45. Structure-function relationships of mitochondrial monoamine oxidase A and B, chimeric enzymes and site directed mutagenesis studies
46. Is one amino acid responsible for substrate specificity of monoamine oxidase A and B
47. A key amino acid responsible for substrate selectivity of monoamine oxidase A and B
48. Site-directed mutagenesis of monoamine oxidase A and B: Role of cysteines
49. Identification of the active site cysteine in bovine liver monoamine oxidase B
50. Monoamine oxidase contains a redox-active disulfide
51. Structure-function relationships of mitochondrial monoamine oxidase A and B chimeric forms
52. Identification of a region important for human monoamine oxidase B substrate and inhibitor selectivity
53. Regions of the molecule responsible for substrate specificity of monoamine oxidase A and B: A chimeric enzyme analysis
54. Imidazoline binding domains on MAO-B: Localization and accessibility
55. Imidazoline/gaunidinium binding domains on monoamine oxidases: Relationship to subtypes of imidazoline-binding proteins and tissue specific interaction of imidazoline ligands with MAO B
56. Identification of imidazoline-receptor binding sites in cortex and medulla of the bovine adrenal gland: Colocalization with MAO-A and MAO-B
57. The elusive family of imidazoline binding sites
58. 2-imidazoline receptors in rat liver
59. Modulation of MAO activity by imidazoline and guanidine derivatives
60. 2-imidazoline binding sites on monoamiine oxidases
61. Localization of IBD on monoamine oxidase B
62. 2 specific ligands in vitro
63. +1
64. Phe(208) and Ile(199) in human monoamine oxidase A and B do not determine substrate and inhibitor specificities in rat
65. Susbtrate and inhibitor specificities for human monoamine oxidase A and B are influenced by a single amino acid
66. Imidazoline-binding domains on monoamine oxidase B and sub-populations of enzymes
67. 2-imidazoline-binding proteins using monoamine oxidasedeficient mouse models
68. The covalently bound flavin of hepatic monoamine oxidase: Isolation and sequence of a flavin peptide and evidence for binding at the 8α-position
69. Sequence and structure of a cysteinyl flavine peptide from monoamine oxidase
70. Characterization of rat monoamine oxidase A with noncovalently bound FAD expressed in yeast cells
71. Influence of FAD structure on its binding and activity with the C406A mutant of recombinant human liver monoamine oxidase A
72. Influence of flavin analogue structure on the catalytic activities and flavinylation reactions of recombinant human liver monoamine oxidases A and B
73. Characterization of a highly conserved FAD-binding site in human monoamine oxidase B
74. Mutagenesis at a highly conserved tyrosine in monoamine oxidase B affects FAD incorporation and catalytic activity
75. Arginine-42 and Threonine-45 are required for FAD incorporation and catalytic activity in human monoamine oxidase B
76. Substrate regulation of monoamine oxidases
77. Stereospecific deamination of benzylamine catalyzed by different amine oxidases
78. Radical ideas about monoamine oxidase
79. A mechanism for mitochondrial monoamine oxidase catalyzed amine oxidation
80. Structure activity relationships in the oxidation of benzylamine analogs by bovine liver mitochondrial monoamine oxidase B
81. Flavin chemical models for monoamine oxidase in activation by cyclopropylamine, α-silylamines and hydrazines
82. 3-Methyllumiflavin promoted oxidative deamination of amines. A model for catalysis by monoamine oxidases
83. Evidence for a hydrogen atom transfer mechanism or a proton/fast electron-transfer mechanism for monoamine oxidase
84. The use of mechanism based inhibitors to probe the mechanism of monoamine oxidase
85. Stereoselective ring opening of 1-phenylcyclopropylamine catalyzed by monoamine oxidase B
86. Inactivation of monoamine oxidase by (aminomethyl)cubane. First evidence for an α-radical during enzyme catalysis
87. Mechanistic probes of monoamine oxidase B catalysis: Rapid scan stopped flow and magnetic field independence of the reductive half reaction
88. Mechanistic studies on the monoamine oxidase B catalyzed oxidation of 1,4-disubstituted tetrahydropyridines
89. Probing the mechanism of bioactivation of MPTP type analogs by monoamine oxidase B: Structure activity studies on substituted 4-phenyl-4-phenoxy- and 4-thiophenoxy-1-cyclopropyl-1,2,3,6-tetrahydropyridines
90. Deuterium isotope effect studies on the MAO B catalyzed oxidation of 4-benzyl-1-cyclopropyl-1,2,3,6-tetrahydropyridines
91. Aminium cation radical mechanism proposed for monoamine oxidase B catalysis: Are there alternatives?
92. Observation of a flavin semiquinone in the resting state of monoamine oxidase B by electron paramagnetic resonance and electron nuclear double resonance spectroscopy
93. High-level expression of human liver monoamine oxidase B in pichia pastoris
94. Putrescine catabolism in mammalian brain
95. Novel substrates and products of amine oxidase-catalyzed reactions
96. Oxidation of tertiary amines by monoamine oxidase
97. Evaluation of N,N-dimethylphenethylamine and N,N-dimethyltyramine as substrates for monoamine oxidase B
98. Characterization of eight biogenic indoleamines as substrates for type A and type B monoamine oxidase
99. Deamination of aliphatic amines of different chain lengths by rat liver monoamine oxidase A and B
100. N-[2-(oiodophenoxy)ethyl]cyclopropylamine hydrochloride (LY121768), a potent and selective irreversible inhibitor of type A monoamine oxidase
101. β-Phenylethanolamine as a substrate for monoamine oxidase
102. Stereoselective biotransformation of the selective serotonin reuptake inhibitor Citalopram, and its demethylated metabolites by monoamine oxidases in human liver
103. Sumitriptan. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in the acute treatment of migraine and cluster headache
104. Zolmitriptan. A review of its use in migraine
105. Crossover comparison of rizatriptan 5 and 10 mg versus Sumatriptan 25 mg and 50 mg in migraine
106. Elitriptan
107. Naratriptan: A review
108. Characterization of the enzyme responsible for the metabolism of Sumatriptan in human liver
109. Determination of the human cytochrome P450 isoforms involved in the metabolism of zolmitriptan
110. Potential drug interactions with the novel antimigraine compound, zolmitriptan (Zomig 311C90)
111. Disposition and pharmacokinetics of the anti-migraine drug, rizatriptan, in humans
112. Conversion of the orally administered 2-n-pentylaminoacetamide into glycinamide and glycine in rat brain
113. Anti-convulsant drug action and neuronal neurotransmitter amino acid changes
114. Formation of the neurotransmitter glycine from the anti-convulsant milacemide is mediated by brain monoamine oxidase B
115. Mechanism of inactivation of monoamine oxidase-B by the anti-convulsant agent milacemide (2-(n-pentylamino)acetamide)
116. A primate model of Parkinsonism: Selective destruction of dopaminergic neurons in the pars compacta of the substantia nigra by N-methyl-4phenyl-1,2,3,6-tetrahydropyridine
117. +): Identification of a metabolite of MPTP, a toxin selective to the substantia nigra
118. Parkinsonism-inducing neurotoxin. N-methyl-4phenyl-1,2,3,6-tetrahydropyridine: Uptake of the metabolite N-methyl-4-phenylpyridine by dopamine neurons explains selective toxicity
119. Metabolism of the neurotoxic tertiary amine. MPTP, by brain monoamine oxidase
120. Studies on the molecular mechanism of bioactivation of the selective nigrostriatal neurotoxin 1-methyl -4-phenyl-1,2,3,6-tetrahydropyridine
121. Identification of the major transport pathway for the parkinsonism inducing neurotoxin 1-methyl-4-phenylpyridinium
122. Inhibition of NADH-linked oxidation in brain mitochondria by 1-methyl-4phenylpyridinium, a metabolite of the neurotoxin 1-methyl-4phenyl-1,2,3,6-tetrahydropyridine
123. Inhibition of mitochondrial NADPH dehydrogenase by pyridine derivatives and possible relation to experimental and idiopathic parkinsonism
124. Studies on the characterization of the inhibitory mechanism of 4′-alkylated 1-methyl-4-phenylpyridinium and phenylpyridine analogues in mitochondria and electron transport particles
125. + in both electron transport particles and intact mitochondria
126. Interaction of flexible MAO-B of analogs N-methyl4-phenyl-1,2,3,6-tetrahydropyridine and of N-methyl-4-phenylpyridinium with highly purified monoamine oxidase A and B
127. Structure-activity study of the mechanism of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced neurotoxicity. I. Evaluation of the biological activity of MPTP analogs
128. Pargyline prevents MPTP-induced parkinsonism in primates
129. Protection against the dopaminergic neurotoxicity of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine by monoamine oxidase inhibitors
130. Studies with the neurotoxicant 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and several of its analogs
131. +, the monoamine oxidase catalyzed oxidation product of the nigrostriatal toxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
132. The formation of reactive intermediates in the MAO-catalyzed oxidation of the nigrostriatal toxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)
133. Metabolism of the nigrostriatal toxin 1-methyl-4phenyl-1,2,3,6-tetrahydropyridine by liver homogenate fractions
134. Cytochrome P4502D and -2C enzymes catalyze the oxidative N-demethylation of the parkinsonism-inducing substance 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in rat liver microsomes
135. 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) is N-demethylated by cytochromes P450 2D6, 1A2, and 3A4 - Implications for susceptibility to Parkinson's disease
136. Studies on the cytochrome P-450 catalyzed ring α-carbon oxidation of the nigrostriatal toxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)
137. +
138. Immunohistochemical localization of aldehyde and xanthine oxidase in rat tissues using polyclonal antibodies
139. The importance of the 4′-5′ double bond for neurotoxicity in primates of the pyridine derivative MPTP
140. + are not mimicked by analogues of MPTP lacking an N-methyl moiety
141. Structure-activity Study of the mechanism of 1-methyl-4-phenyl- 1,2,3,6-tetrahydropyridine (MPTP)-induced neurotoxicity. I. Evaluation of the biological activity of MPTP analogs
142. Effects of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and several of its analogues on the dopaminergic nigrostriatal pathway in mice
143. Synthesis of novel MPTP analogs as potential monoamine oxidase B (MAO-B) inhibitors
144. Oxidation of 1-amino-4-phenyl-1,2,3,6-tetrahydropyridine, a 1-amino analog of MPTP, by type A and B monoamine oxidase
145. Further explorations of unnatural alkaloids
146. Inactivation of monoamine oxiclase by 3,3-dimethyl analogues of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine and 1-methyl4-phenyl-2,3-dihydropyridinium ion. Dramatic effect of betamercaptoethanol on substrate turnover and enzyme inactivation
147. Oxidation of analogs of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine by monoamine oxidases A and B and the inhibition of monoamine oxidases by the oxidation products
148. Potent neurotoxic fluorinated 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine analogs as potential probes in models of Parkinson's disease
149. Importance of the monoamine oxidase A in the bioactivation of neurotoxic analogs of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
150. Persistent depletion of striatal dopamine in mice by m-hydroxy-MPTP
151. The development of amine substituted analogues of MPTP as unique tools for the study of MPTP toxicity and Parkinson's disease
152. The MPTP story: MAO activates tetrahydropyridine derivatives to toxins causing Parkinsonism
153. Studies on 4-benzyl-1-methyl-1,2,3,6-tetrahydropyridine, a non-neurotoxic analogs of the Parkinsonian inducing agent, 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
154. Molecular size and flexibility as determinants of selectivity in the oxidation of N-methyl-4phenyl-1,2,3,6-tetrahydropyridine analogs by monoamine oxidase A and B
155. Oxidation products arising from the action of monoamine oxidase B on 1-methyl-4-benzyl-1,2,3,6-tetrahydropyridine, a nonneurotoxic analog of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
156. Interaction of tetrahydrostilbazoles with monoamine oxidase A and B
157. Studies of the in vitro oxidation of 1-methyl-4-(1-methylpyrrol-2-yl)-4-piperidinol and its dehydration product 1,2,3,6-tetrahydro-1-methyl-4-(methylpyrrol-2-yl)pyridine by human monoamine oxidases A and B
158. Studies on the monoamine oxidase B-catalyzed biotransformation of 4-azaaryl-1-methyl-1,2,3,6-tetrahydropyridine derivatives
159. Synthesis and monoamine oxidase B substrate properties of 1-methyl-4-heteroaryl-1,2,3,6-tetrahydropyridines
160. Design, synthesis, and biological evaluation of novel 4-substituted 1-methyl-1,2,3,6-tetrahydropyridine analogs of MPTP
161. Synthesis and selective monoamine oxidase-B-inhibiting properties of 1-methyl-1,2,3,6-tetrahydropyrid-4-yl carbamate derivatives: Potential prodrugs of (R)- and (S)-nordeprenyl
162. Potential latent nitrogen mustard derivatives designed to target monoamine oxidase rich cells
163. Characterization of an unexpected product from a monoamine oxidase B generated 2,3-dihydropyridinium species
164. Oxidation of N-methyl1,2,3,4-tetrahydroisoquinoline into the N-methylisoquinolinium ion by monoamine oxidase
165. Studies on semirigid tricyclic analogues of the nigrostriatal toxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
166. Presence of tetrahydroisoquinoline and 2-methyltetrahydroisoquinoline in Parkinsonian and normal human brains
167. 1-Methyl3-pyrroline and 2-methylisoindolines: New classes of cyclic tertiary amine monoamine oxidase B substrates
168. Motor and mental aspects of extrapyrimidal syndromes
169. Tardive dyskinesia
170. Dehydration is the first step in the bioactivation of haloperidol to its pyridinium metabolite
171. Studies on the in vitro conversion of haloperidol to a potentially neurotoxic pyridinium metabolite
172. Identification of a potentially neurotoxic pyridinium metabolite of haloperidol in rats
173. +-like neurotoxicity of a pyridinium metabolite derived from haloperidol: In vivo microdialysis and in vitro mitochondrial studies
174. Toxication of MPTP (1-methyl-4-phenyl1,2,3,6-tetrahydropyridine) and analogs by monoamine oxidase, a structure-activity relationship study
175. Quantitative structure-metabolism relationship analyses of MAO-mediated toxication by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine and analogues
176. Molecular determinants in the bioactivation of the dopaminergic neurotoxin, N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)
177. Assessment of structural requirements for the monoamine oxidase-B-catalyzed oxidation of 1,4-disubstituted-1,2,3,6-tetrahydropyridine derivatives related to the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
178. Structure-activity relationships in the oxidation of para-substituted benzylamine analogues by recombinant human liver monoamine oxidase A
179. Structure-activity relations in the oxidation ofphenethylamine analogues by recombinant human liver monoamine oxidase A
180. Carbon radicals in the metabolism of alkyl hydrazines
181. Pargyline-induced hepatotoxicity: Possible mediation by the reactive metabolite, propiolaldehyde
182. Metabolism of deprenyl, a selective monoamine oxidase (MAO) B inhibitor in rat: Relationship of metabolism to MAO-B inhibitor potency
183. Pressor amines and monoamine-oxidase inhibitors for treatment of postural hypotension in autonomic failure. Limitations and hazards
184. Preclinical profiles of the novel reversible MAO-A inhibitors, moclobemide and brofaromine, in comparison with irreversible MAO inhibitors
185. Stereoselectivity and isozyme selectivity of monoamine oxidase inhibitors
186. Selective inhibitors of monoamine oxidase A and B: Biochemical, pharmacological, and clinical properties
187. Inhibition of rat liver monoamine oxidase by alphamethyl- and N-propargyl-amine derivatives
188. Studies on 5-fluoro-α-methyltryptamine and p-chloroβ-methylphenylethylamine. Determination of the MAO-A or MAO-B selective inhibition in vitro
189. Characterization of phentermine and related compounds as monoamine oxidase (MAO) inhibitors
190. New monoamine oxidase inhibitors
191. Model studies for the mechanism of inactivation of monoamine oxidase by 5-(aminomethyl)-3-aryl-2-oxazolidinones
192. 5-(Aminomethyl)-3-aryl2-oxazolidinones. A novel class of mechanism-based inactivators of monoamine oxidase B
193. Mono-amine oxidase inhibitory properties of 5-hydroxymethyl-3-mtolyloxazolidin-2-one (toloxatone)
194. Cimoxatone is a reversible tight-binding inhibitor of the A form of rat brain monoamine oxidase
195. Activity of toloxatone, antidepressants, and various reserpine antagonists in 3 behavioral experiments in mice treated with nialamide
196. Befloxatone
197. E2011, a novel, selective and reversible inhibitor of monoamine oxidase type A
198. In vivo characterization of T-794, a novel reversible inhibitor of monoamine oxidase-A, as an anti-depressant with a wide safety margin
199. Monoamine oxidase A and B inhibitors
200. Linezolid
201. 5-Aryl-1,3,4-oxadiazol-2(3H)-one derivatives and sulfur analog as new selective and competitive monoamine oxidase type B inhibitors
202. 5-[4-(Benzyloxy)phenyl]-1,3,4-oxadiazol-2(3H)-one derivatives and related analogues: New, reversible, highly potent, and selective monoamine oxidase type B inhibitors
203. Selective and potent monoamine oxidase type B inhibitors: 2-substituted-5-aryltetrazole derivatives
204. Selective and potent monoamine oxidase type B inhibitors: Substituted semicarbazones and acylhydrazones of aromatic aldehydes and ketones
205. Alkyl benzyl ethers of hydroquinones as monoamine oxidase B inhibitors
206. Synthesis and monoamine oxidase inhibitory activity of 3-substituted 5H-indeno[1,2-c]pyridazines
207. Inhibition of monoamine oxidase-B by 5H-Indeno[1,2-c]pyridazines. Biological activities, quantitative structure-activity relationships (QSARs) and 3D-QSAR
208. Inhibition of monoamine oxidase-B by condensed pyridazines and pyrimidines: Effects of lipohilicity and structure-activity relationships
209. Synthesis of coumarins as subtype-selective inhibitors of monoamine oxidase
210. Experimental animal studies of the psychotropic activity of a Hypericum extract
211. An antifungal γ-pyrone and xanthones with monoamine oxidase inhibitory activity from Hypericum brasiliense
212. A selective, reversible, competitive inhibitor of monoamine oxidase A containing no nitrogen with negligible potentiation of tyramineinduced blood pressure rise
213. Selective inhibitors of monoamine oxidase (MAO). 5. 1-Substituted phenoxathiin inhibitors containing no nitrogen that inhibit MAO-A by binding it to a hydrophobic site
214. Mechanism of monoamine oxidase-A inhibition by BW 137OU87
215. Selective inhibitors of monoamine oxidase. 2 Arylamide SAR
216. Selective inhibitors of monoamine oxidase. 3 Structure-activity relationship of tricyclics bearing imidazoline, oxadiazole, or tetrazole groups
217. Biochemical and pharmacologic properties of 2614W94, a reversible, competitive inhibitor of monoamine oxidase-A
218. Selective inhibitors of monoamine oxidase. 4 SAR of tricyclic N-methylcarboxamides and congeners binding at the tricydics hydrophobic binding site
219. Inhibition of monoamine oxidase B in the brains of smokers
220. Brain monoamine oxidase A inhibition in cigarette smokers
221. Attenuation of 1-methyl4-phenyl-1,2,3,6-tetrahydropyridine-induced neurotoxicity by tobacco smoke
222. Irreversible inhibition of monoamine oxidase by some components of cigarette smoke
223. Effects of tobacco smoke constituents on MPTP-induced toxicity and monoamine oxidase activity in the mouse brain
224. Smoking Cessation: Recent developments in behavioral and pharmacologic interventions
225. Antidepressants for smoking cessation: A promising new approach?
226. Smoking and Parkinson's disease
227. Epidemiologie approaches to the study of Parkinson's disease etiology
228. A reversible monoamine oxidase A inhibitor (moclobemide) facilitates smoking cessation and abstinence in heavy, dependent smokers
229. Isolation and characterization of a monoamine oxidase inhibitor from tobacco leaves
230. Neuroprotection in the MPTP parkinsonian C57BL/6 mouse model by a compound isolated from tobacco
231. Reversible inhibition and mechanism-based irreversible inactivation of monoamine oxidases by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)
232. A new class of powerful inhibitors of monamine oxidase A
233. Inhibitory potency of some isatin analogues on human monoamine oxidase A and B
234. Studies on the mechanism of action of caroxazone, a new antidepressant drug
235. [3H]Harmaline as a specific ligand of MAO-A.-I. Properties of the active site of MAO-A from rat and bovine brain
236. Characteristics of the inhibition of rat brain monoamine oxidase in vitro by MD780515
237. Inhibition of monoamine oxidase-A by β-carboline derivatives
238. Imino-1,2,3,4-tetrahydrocyclopent[blindole carbamates as dual inhibitors of acetylcholinesterase and monoamine oxidase
239. Pharmacological properties of 2,3,3a,4,5,6-hexahydro-8-methyl-1H-pyrazino [3,2,1jk]carbazole hydrochloride, (pirindole), a new antidepressant
240. Inhibition of monoamine oxidases A and B by simple isoquinoline alkaloids: Racemic and optically active 1,2,3,4-tetrahydro-, 3,4-dihydro-, and fully aromatic isoquinolines
241. Inhibition of type A and B monoamine oxidase by 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolines and their N-methyluted derivatives
242. Inhibition of monoamine oxidase by isoquinoline derivatives. Qualitative and 3D-quantitative structure-activity relationships
243. Moclobemide. A review of its pharmacological properties and therapeutic use in depressive illness
244. From moclobemide to Ro and Ro 41-1049, the development of a new class of reversible, selective MAO-A and MAO-B inhibitors
245. Biochemistry and pharmacology of moclobemide, a prototype RIMA
246. Pharmacology of moclobemide
247. Interactions of the novel inhibitors of MAO-B Ro 19-6327 and Ro 16-6491 with the active site of the enzyme
248. A new reversible and highly selective MAO-B inhibitor protects mice from the dopaminergic toxicity of MPTP
249. Selective inactivation of monoamine oxidase B by aminoethyl-3-chlorobenzyl ether
250. A new time-dependent reversible inhibitor of monoamine oxidase
251. N-Alkylcarbonyl derivatives of ethylenediamine as monoamine oxidase inhibitors
252. The monoamine oxidase inhibiting properties of CGP 11305 A
253. CGP 4718A, a new potential antidepressant with a dual mode of action
254. Effects of brofaremine (CGP 11 305A), a short-acting, reversible, and selective inhibitor of MAO-A on sleep, nocturnal penile tumescence and nocturnal hormonal secretion in three healthy volunteers
255. Results of an open clinical trial of brofaromine (CGP 11 305A), a competitive, selective, and short-acting inhibitor of MAO-A in major endogenous depression
256. Effects of RS-2232, a potential antidepressant, on the levels of monoamines, precursor amino acids and their related metabolites in mouse brain
257. Comparative studies of the effects of RS-8359 and safrazine on monoamine oxidase in-vitro and in-vivo in mouse brain
258. A study of the biological pharmacology of IFO, a new selective and reversible monoamine oxidase-B inhibitor
259. The neuronal nitric oxide synthase inhibitor 7-nitroindazole also inhibits the monoamine oxidase-B-catalyzed oxidation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
260. The nature of the inhibition of rat liver monoamine oxidase types A and B by the acetylenic inhibitors clorgyline, 1-deprenyl, and pargyline
261. Phenylisopropyl-methylpropynylamine (E-250), a monoamino oxidase inhibitor antagonising the effects of tyramine
262. Novel (-)-deprenyl-derived selective inhibitors of B-type monoamine oxidase. The relation of structure to their action
263. Inhibition of clorgyline and deprenyl of the different forms of monoamine oxidase in rat liver mitochondria
264. Amine oxidases: XIX. Inhibition of monoamine oxidase by phenylcyclopropylamines and iproniazid
265. Mitochondiral monoamine oxidase. Mechanism of inhibition of phenyl hydrazine and by aralkylhydrazines. Role of enzymic oxidations
266. The pseudoirreversible inhibition of monoamine oxidase by allylamine
267. Inactivation of monoamine oxidase by allylamine does not results in flavin attachment
268. (E)-2-(3,4-dimethoxyphenyl)-3fluoroallylamine: A selective, enzyme-activated inhibitor of type B monoamine oxidase
269. 4a,5-Cycloaddition reaction of acetylenic compounds at the flavoquinone nucleus as mechanism of flavoprotein inhibitions
270. The structure of the covalent adduct formed by the interaction of 3-dimethyalmino-1-propyne and the flavine of mitochondrial amine oxidase
271. Flavin suicide inhibitor adducts
272. The development of N-Cyclopropyl-arylalkylamines as monoamine oxidase inhibitors
273. Mechanism of inactivation of mitochondrial monoamine oxidase by N-cyclopropyl-N-arylalkylamines
274. N-(1-methyl)cyclopropyl benzylamine: A novel inactivator of mitochondrial monoamine oxidase
275. Mechanism-based inactivation of mitochondrial monoamine oxidase by N-(1methylcyclopropyl)benzylamine
276. Mechanism of cytochrome P-450 inhibition by cyclopropylamines
277. Suicidal inactivation of cytochrome P-450 by cyclopropylamines. Evidence for cation-radical intermediates
278. Revised mechanism for inactivation of mitochondrial monoamine oxidase by N-cyclopropylbenzylamine
279. Model studies for the mechanism of inactivation of monoamine oxidase by 5-(aminomethyl)-3-aryl-2-oxazolidinones
280. 5-(Aminomethyl)-3-aryl-2-oxazolidinones. A novel class of mechanism-based inactivators of monoamine oxidase B
281. 5-(Aminomethyl)-3aryldihydrofuran-2(3H)-ones, a new class of monoamine oxidase-B inactivators
282. 4-(Aminomethyl)-1-aryl2-pyrrolidinones, a new class of monoamine oxidase-B inactivators
283. Mechanism-based inactivation of monoamine oxidases A and B by tetrahydropyridines and dihydropyridines
284. Reversible inhibition and mechanism-based irreversible inactivation of monoamine oxidases by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)
285. The kinetics of monoamine oxidase inhibition by three 2-indolyl-methylamine derivatives
286. Selective acetylenic suicide and reversible inhibitors of monoamine oxidase types A and B
287. New 2-[(5-methoxy-1-methylindolyl)]-alkylamine derivatives: The effect of branching and elongation of the side chain on MAO inhibition
288. FA-70: A novel selective and irreversible monoamine oxidase-A inhibitor: Effect on monoamine metabolism in mouse cerebral cortex
289. Relevance of benzyloxy group in 2-indolylmethylamines in the selective MAO-B inhibition
290. Inhibition of monoamine oxidase by the R and S enantiomers of N-[3-(2,4-dichlorophenoxy)propyl]-N-methyl-3-butyn-2-amine
291. Inversion of selectivity of N-substituted propargylamine monoamine oxidase inhibitors following structural modifications to quaternary salts
292. Aliphatic propargylamines: Potent, selective, irreversible monoamine oxidase B inhibitors
293. Effect of structural modification of alkyl-N-propargylamines on the selective inhibition of monoamine oxidase B activity
294. Aliphatic N-methyl propargylamines: Monoamine oxidase-B inhibitors and antiapoptotic drugs
295. Immunohistochemical evidence of neuroprotection by (R)-deprenyl and N-(2-hexyl)-N-methylpropargylamine on DSP4-induced degeneration of rat brain noradrenergic axons and terminals
296. Neurochemical and neuroprotective effects of some aliphatic propargylamines: New selective non-amphetamine-like MAO-B inhibitors