ArticleFrontiers in chemistry2018
Evidence for a Cyanine Link Between Propargylamine Drugs and Monoamine Oxidase Clarifies the Inactivation Mechanism.
Article in Frontiers in chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 30 citations in OpenAlex.
- Structural Principles of Covalent Flavin Modification in Oxidoreductases.Biochemistry · 2026Review
- Covalent Irreversible Inhibitors of Tetracycline Destructases.ACS infectious diseases · 2025Article
- Exploration of the tunability of BRD4 degradation by DCAF16 trans-labelling covalent glues.European journal of medicinal chemistry · 2024Article
- Prominent Neuroprotective Potential of Indole-2-Pharmaceuticals (Basel, Switzerland) · 2024Article
- Are Terminal Alkynes Necessary for MAO-A/MAO-B Inhibition? A New Scaffold Is Revealed.Molecules (Basel, Switzerland) · 2024Article
- Molecular Mechanism and Structure-activity Relationship of the Inhibition Effect between Monoamine Oxidase and Selegiline Analogues.Current computer-aided drug design · 2024Article
- Exploration of the Tunability of BRD4 Degradation by DCAF16bioRxiv : the preprint server for biology · 2023Article
- NMR-Based Metabolomics to Analyze the Effects of a Series of Monoamine Oxidases-B Inhibitors on U251 Cells.Biomolecules · 2023Article
- Parameters for Irreversible Inactivation of Monoamine Oxidase.Molecules (Basel, Switzerland) · 2020Article
- Stereoselective Activity of 1-Propargyl-4-styrylpiperidine-like Analogues That Can Discriminate between Monoamine Oxidase Isoforms A and B.Journal of medicinal chemistry · 2020Article
- Zn-Catalyzed Multicomponent KAACS omega · 2019Article
- Dopamine Autoxidation Is Controlled by Acidic pH.Frontiers in molecular neuroscience · 2018Article
Corrections and comments
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Authors and funding
5 authors at 3 institutions in 3 countries.
Funding
Abstract
Successful propargylamine drugs such as deprenyl inactivate monoamine oxidase (MAO), a target in multi-faceted approaches to prevent neurodegeneration in the aging population, but the chemical structure and mechanism of the irreversible inhibition are still debated. We characterized the covalent cyanine structure linking the multi-target propargylamine inhibitor ASS234 and the flavin adenine dinucleotide in MAO-A using a combination of ultra-high performance liquid chromatography, spectroscopy, mass spectrometry, and computational methods. The partial double bond character of the cyanine chain gives rise to 4 interconverting geometric isomers of the adduct which were chromatographically separated at low temperatures. The configuration of the cyanine linker governs adduct stability with segments of much higher flexibility and rigidity than previously hypothesized. The findings indicate the importance of intramolecular electrostatic interactions in the MAO binding site and provide key information relevant to incorporation of the propargyl moiety into novel multi-target drugs. Based on the structure, we propose a mechanism of MAO inactivation applicable to all propargylamine inhibitors.
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