Quantum chemical calculation of intrinsic reaction coordinates from trans to cis structure of fluvoxamine

Kei Odai*, Tohru Sugimoto, Etsuro Ito

*この研究の対応する著者

研究成果査読

抄録

Fluvoxamine is a selective serotonin reuptake inhibitor. Its trans-isomer [(E)-isomer] is pharmacologically active, whereas its cis-isomer [(Z)-isomer] loses its activity. It is a pharmaceutical interest whether the structural change from the (E)-isomer to the (Z)-isomer spontaneously occurs in aqueous solutions without ultraviolet (UV) irradiation. In the present study, the transition state of fluvoxamine was determined by quantum chemical calculation using density functional theory (DFT), and the intrinsic reaction coordinates (IRCs) from the (E)-isomer to the (Z)-isomer were calculated using UB3LYP/6-311++G(d,p) with the integral equation formalism-polarizable continuum model (IEF-PCM). The activation energy of isomerization from the (E)-isomer to the (Z)-isomer was estimated to be 55 kcal/mol. Further, the absorption spectra, the nuclear magnetic resonance chemical shift values, the Raman spectra and the infrared spectra were calculated for the (E) and (Z)-isomers obtained from the reaction coordinate calculation, and these results were in good agreement with the experimental values. The geometrical structures of the (E) and (Z)-isomers proposed in the present study can be used as theoretical models of fluvoxamine for molecular dynamics calculations in future.

本文言語English
論文番号113051
ジャーナルComputational and Theoretical Chemistry
1192
DOI
出版ステータスPublished - 2020 12 15

ASJC Scopus subject areas

  • 生化学
  • 凝縮系物理学
  • 物理化学および理論化学

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