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• W2345648758 endingPage "e0154989" @default.
• W2345648758 startingPage "e0154989" @default.
• W2345648758 abstract "Despite their structural and chemical commonalities, p-chloro-β-methylphenethylamine and p-methoxy-β-methylphenethylamine display distinct inhibitory and substrate activities upon MAO-B binding. Density Functional Theory (DFT) quantum chemical calculations reveal that β-methylation and para-substitution underpin the observed activities sustained by calculated transition state energy barriers, attained conformations and key differences in their interactions in the enzyme's substrate binding site. Although both compounds meet substrate requirements, it is clear that β-methylation along with the physicochemical features of the para-substituents on the aromatic ring determine the activity of these compounds upon binding to the MAO B-isoform. While data for a larger set of compounds might lend generality to our conclusions, our experimental and theoretical results strongly suggest that the contrasting activities displayed depend on the conformations adopted by these compounds when they bind to the enzyme." @default.
• W2345648758 created "2016-06-24" @default.
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• W2345648758 date "2016-05-06" @default.
• W2345648758 modified "2023-10-18" @default.
• W2345648758 title "Why p-OMe- and p-Cl-β-Methylphenethylamines Display Distinct Activities upon MAO-B Binding" @default.
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• W2345648758 doi "https://doi.org/10.1371/journal.pone.0154989" @default.
• W2345648758 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/4859490" @default.
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