Stereoselectivity and isoenzyme selectivity of monoamine oxidase inhibitors
Abstract
The enantiomers of amphetamine, N-methylamphetamine and deprenyl were studied, using a solubilised rat liver mitochondrial monoamine oxidase (MAO) preparation, as competitive inhibitors of MAO-A and MAO-B (5-hydroxytryptamine and beta-phenylethylamine as substrate respectively). Only in the case of deprenyl enantiomers inhibiting MAO-B was a preference shown towards the [R]-configuration enantiomer justifying the use of [R]-(-)-deprenyl (as compared to the racemate) for the specific inhibition of MAO-B. Recalculation of the observed Ki values in terms of the base form of the inhibitor indicated that the activity of all enantiomers fell within a narrow, approximately 25-fold range when inhibiting MAO-B. The selectivity of inhibition of MAO-B by [R]-(-)-deprenyl cannot therefore be attributed to any specific structural features of the MAO-B isoenzyme form but rather to a lack of affinity of this enantiomer towards MAO-A.
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Amphetamine inhibits monoamine oxidase activity, decreasing cytosolic monoamine breakdown.
“Furthermore, AMP inhibits monoamine oxidase (MAO) activity (79, 90), which decreases cytosolic monoamine breakdown.”
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References 14 · Cited by 96
- Authors
- Robinson, J. B.
- Affiliations
- University of Toronto (CA)
- Corresponding author
- Robinson, J.Barry
- ORCID
- Robinson, J.Barry
- Venue
- Biochemical Pharmacology
- Publisher
- Elsevier BV
- Published
- 1985-12
- Volume
- 34
- Issue
- 23
- Pages
- 4105-4108
- ISSN
- 0006-2952 (ISSN-L)
- OpenAlex
- W2139907216
- Cited by
- 96
- References
- 14
- Citations by year
- 2026: 1 · 2025: 3 · 2023: 1 · 2022: 1 · 2021: 6 · 2020: 5 · 2019: 1 · 2018: 1 · 2017: 3 · 2016: 5 · 2015: 4 · 2014: 6 · 2013: 6 · 2012: 3
- FWCI
- 1.53
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Biochemical Pharmacology (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Amino Acid Enzymes and Metabolism
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Pharmacogenetics and Drug Metabolism
- Health Sciences › Medicine › Pharmacology › Cholinesterase and Neurodegenerative Diseases
- Keywords
- monoamine oxidase inhibitors, stereoselectivity, enantiomers, selegiline, amphetamine, monoamine oxidase A, monoamine oxidase B, competitive inhibition, liver mitochondria, Ki values, serotonin, phenylethylamine
- MeSH terms
- Amphetamine, Animals, Isoenzymes, Kinetics, Liver, Male, Methamphetamine, Monoamine Oxidase Inhibitors, Phenethylamines, Rats, Inbred Strains, Selegiline, Stereoisomerism, Rats
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