Enzymology of monoamine oxidase

Tipton, Keith F.

doi:10.1002/cbf.290040202

Cited by 96 publications

(67 citation statements)

References 101 publications

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“…For all models training set (2,3,4,5,6,7,8,9,10,11,12,13,14,15,19,22,23,24,25,26,27,28) of compounds and test set (1,16,17,18,20,21) of compounds were taken randomly by VALSTAT software computer program and intercorrelation limit was used at 0.5. Out of all 5 models, model 5 was selected based on high value of stastical data Q2, r2 and r2 prediction.…”

Section: Resultsmentioning

confidence: 99%

A QSAR study of some Phenoxyacetamide derivatives as a MAO-A inhibitor

Bais¹,

Yadav²,

Mafidar³

et al. 2018

IJRDPL

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Available online on:15.01.2018@http://ijrdpl.com http://dx.doi.org/10.21276/IJRDPL. 2278-0238.2018.7(1).2931-2940 ABSTRACT: Antidepressants are the most prescribed therapy for depression. The prevailing theory is that antidepressants increase the concentration of one or more brain chemicals (neurotransmitters) that nerves in the brain use to communicate with one another.The neurotransmitters affected by antidepressants are norepinephrine, serotonin, and dopamine. In order to address the need for new MAO inhibitors with less side effects, we can aim compounds previously discovered for their potential as MAOIs. Among them, safinamide was reported to be a potent anti-MAO B agent, and milacemide, which was found to be a potent MAO inhibitor and a prodrug for glycine. The present work deals with the aim because Currentely available MAO inhibitors {Isocarboxazid (Marplan), Phenelzine (Nardil), Selegiline (Emsam), Tranylcypromine (Parnate) etc} develop side effects because they do not selectively for MAO-A and MAO-B. So, the present study is focused to develop potent selective MAO-A inhibitors, to treat depression, that may be of better pharmacological activity with less adverse effect.

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Section: Resultsmentioning

confidence: 99%

A QSAR study of some Phenoxyacetamide derivatives as a MAO-A inhibitor

Bais¹,

Yadav²,

Mafidar³

et al. 2018

IJRDPL

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“…The inhibitory compound of monoamine oxidase (MAO) activity was isolated from the CH 2 amitriptyline for 30 min at 37°C, and then the reaction mixture was dialyzed against 10 mM potassium phosphate buffer pH 7.4 at 4°C overnight. MAO-B activity in the dialysate was examined using 100 mM kynuramine.…”

Section: Resultsmentioning

confidence: 99%

“…[1][2][3] MAO exists in two isoforms, namely type A and type B (MAO-A and MAO-B), which are characterized by their sensitivity towards specific substrates and inhibitors. MAO-A preferentially deaminates serotonin and norepinephrine, and is selectively inhibited by clorgyline.…”

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confidence: 99%

1-Methyl-2-undecyl-4(1<i>H</i>)-quinolone as an Irreversible and Selective Inhibitor of Type B Monoamine Oxidase

et al. 2003

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Monoamine oxidase (MAO; EC 1.4.3.4) is a flavin-containing enzyme that catalyzes the oxidation of a variety of amine-containing neurotransmitters such as catecholamines and serotonin to yield the corresponding aldehyde. [1][2][3] MAO exists in two isoforms, namely type A and type B (MAO-A and MAO-B), which are characterized by their sensitivity towards specific substrates and inhibitors. MAO-A preferentially deaminates serotonin and norepinephrine, and is selectively inhibited by clorgyline. However, MAO-B preferentially deaminates b-phenylethylamine and benzylamine, and is selectively inhibited by l-deprenyl and pargyline. 4,5) The inhibitors of MAO-A are expected to be clinically useful to treat depression and anxiety, while those of MAO-B appear to be helpful in the prevention and adjunct treatment of Parkinson's disease.6,7) A number of inhibitors of MAO activity such as quinolines, 8,9) isoquinolines, 10-12) coumarins, 13,14) and xanthones 15,16) have been reported. As a part of our ongoing research for MAO inhibitors from natural resources, we found that a MeOH extract from the fruits of Evodia rutaecarpa BENTHAM (Rutaceae) strongly inhibited the MAO activity in mouse brain. The MeOH extract was, therefore, subjected to the bioactivity-guided fractionations to isolate the active compound. The finally purified bioactive substance, compound 1 (Fig. 1), was identified by comparison of its spectral data as 1-methyl-2-undecyl-4(1H)-quinolone and was shown to be a selective inhibitor on MAO-B. Results and DiscussionIn the search for MAO inhibitors from the medicinal plants, we found that CH 2 Cl 2 fraction of the dried unripe fruits of E. rutaecarpa showed the potent inhibitory effects on MAO in mouse brain. A CH 2 Cl 2 fraction of E. rutaecarpa at a concentration of 200 mg/ml (89.1% inhibition) showed a potent inhibitory activity against MAO in mouse brain. Activity-guided separation and purification of the extract yielded a known quinolone alkaloid, 1-methyl-2-undecyl-4(1H)-quinolone (1) as an active compound (Fig. 1). The structure was identified by comparison with the physical properties and spectral data (UV, IR, MS, 1 H-and 13 C-NMR) with literature values. 17,18) Compound 1 inhibited MAO activity in a concentrationdependent manner and the IC 50 value was 35.2 mM: compound 1 exhibited a less inhibitory effect than iproniazid (IC 50 value: 12.5 mM) which was used as a positive control (data not shown).The inhibitory activity of compound 1 against MAO-A and MAO-B activities in mouse brain were investigated. lDeprenyl-treated MAO preparation was used for the measurement of MAO-A activity, and a clorgyline-treated one was for MAO-B. MAO-A activity in our preparations was about 32% of the total MAO activity and MAO-B activity was about 61% (Table 1).Compound 1 preferentially inhibited the MAO-B activity than MAO-A activity in a concentration-dependent manner with the IC 50 values of 15.3 and 338.2 mM, respectively (Table 1). These data indicate that compound 1 is a potent inhibitor for MAO-B activity.According ...

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“…1 There are two isoforms are found namely MAO-A and MAO-B. 2 MAO plays an essential role in the regulation of significant role in central nervous system activity and contributes to the pathogenesis of human neurodegenerative and depressive disorders.…”

Section: Introductionmentioning

confidence: 99%

QSAR Studies of 2-Phenoxyacetamide Analogues, a Novel Class of Potent and Selective Monoamine Oxidase Inhibitors

Singh¹,

Patel²,

Jain³

et al. 2018

Curr. Res. Pharm. Sci.

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The primary objective of this investigation was to develop a QSAR model for novel series of phenoxy acetamide derivatives as Monoamine Oxidase Inhibitors. The data series were taken from the reported work of Wei Shen et al., 2014. The selected series consists of total 20 compounds, divided into two sets training set having 18 compounds and test set with 2 compounds. All the structures of phenoxy acetamide derivatives were sketched using Chem Office 2001. QSAR models were obtained by using VALSTAT software. The best-developed model showed a good correlative and predictive ability having regression coefficient (r2) of 0.9033 and q2 is 0.8376. For MAO B inhibitor activity, MW has positively correlated. The positive correlation of MW indicates that bulky group or higher molecular weight compounds are important for better MAO enzymes inhibition activity. The negative correlation of HOMO indicated that electrophilic group may increase the activity. The BetaPol also negatively correlated indicated less polar group give more activity. Based on the developed QSAR model, it may be concluded that highest occupied molecular orbital (HOMO) energy, molecular weight and Beta Polarizability are to be considered while designing newer compounds, for their potential MAO inhibitory activity.

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Enzymology of monoamine oxidase

Cited by 96 publications

References 101 publications

A QSAR study of some Phenoxyacetamide derivatives as a MAO-A inhibitor

A QSAR study of some Phenoxyacetamide derivatives as a MAO-A inhibitor

1-Methyl-2-undecyl-4(1<i>H</i>)-quinolone as an Irreversible and Selective Inhibitor of Type B Monoamine Oxidase

QSAR Studies of 2-Phenoxyacetamide Analogues, a Novel Class of Potent and Selective Monoamine Oxidase Inhibitors

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