Synthesis and evaluation of nuciferine and roemerine enantiomers as 5-HT2 and α1 receptor antagonists

Heng, Hui Li and Chee, Chin Fei and Chin, Sek Peng and Ouyang, Yifan and Wang, Hao and Buckle, Michael James Christopher and Herr, Deron R. and Paterson, Ian Charles and Doughty, Stephen W. and Abd Rahman, Noorsaadah and Chung, Lip Yong (2018) Synthesis and evaluation of nuciferine and roemerine enantiomers as 5-HT2 and α1 receptor antagonists. MedChemComm, 9 (3). pp. 576-582. ISSN 2040-2503, DOI

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In this study, the (S)-enantiomers of the aporphine alkaloids, nuciferine and roemerine, were prepared via a synthetic route involving catalytic asymmetric hydrogenation and both stereoisomers were evaluated in vitro for functional activity at human 5-HT2 and adrenergic α1 receptor subtypes using a transforming growth factor-α shedding assay. Both enantiomers of each of the compounds were found to act as antagonists at 5-HT2 and α1 receptors. (R)-roemerine was the most potent compound at 5-HT2A and 5-HT2C receptors (pKb = 7.8-7.9) with good selectivity compared to (S)-roemerine at these two receptors and compared to its activity at 5-HT2B, α1A, α1B and α1D receptors.

Item Type: Article
Funders: Ministry of Science, Technology and Innovation, Malaysia (02-01-03-SF0937), Ministry of Higher Education, Malaysia, High Impact Research Grant (HIR-MoHE: UM.C/625/1/HIR/MOHE/MED/17 & UM.C/625/1/HIR/MOHE/MED/33)
Uncontrolled Keywords: biosynthesis; catalysis; enantiomer; human; hydrogenation; in vitro study; isomer; priority journal; protein function; stereoselectivity
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
R Medicine
Divisions: Faculty of Dentistry
Faculty of Medicine
Faculty of Science > Department of Chemistry
Depositing User: Ms. Juhaida Abd Rahim
Date Deposited: 08 Aug 2019 04:26
Last Modified: 08 Aug 2019 04:26

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