Theoretical investigation of the molecular structure, vibrational spectra, and molecular docking of tramadol using density functional theory

Umar, Yunusa; Abdalla, Sahar; Haque, S. K. Manirul; Moran, Guillermo Salgado; Ishaq, Abdurrahman; Villada, Wilson Cardona; Leone, Jorge Dagnino; Bunster, Marta

Abstract

The optimized molecular structures, harmonic vibrational wavenumbers, and the corresponding vibrational assignments of (1S,2S)-tramadol and (1R,2R)-tramadol are computationally examined using the B3LYP density functional theory method together with the standard 6-311++G(d,p) and def2-TVZP basis sets. The optimized structures show that phenolic rings of both 1R,2R and 1S,2S tramadol adopt planar geometry, which are slightly distorted due to the substitution at the meta-position; and the six-membered cyclohexane adopts a slightly distorted chair conformation. The 1S,2S enantiomer is energetically more favorable than 1R,2R with the energy differences of 1.32 and 1.03 kcal/mol obtained at B3LYP/6-311++G(d,p) and B3LYP/Def2-TVZP levels, respectively. The analysis of the binding pocket in the silico molecular docking with the m-opioid receptor shows that it originated two clusters with the 1S,2S enantiomer and one cluster with the 1R,2R enantiomer of tramadol. The results point to a more stable complex of the m-opioid receptor with the 1R,2R enantiomer of tramadol.

Más información

Título según WOS: Theoretical investigation of the molecular structure, vibrational spectra, and molecular docking of tramadol using density functional theory
Título según SCOPUS: Theoretical investigation of the molecular structure, vibrational spectra, and molecular docking of tramadol using density functional theory
Título de la Revista: JOURNAL OF THE CHINESE CHEMICAL SOCIETY
Volumen: 67
Número: 1
Editorial: WILEY-V C H VERLAG GMBH
Fecha de publicación: 2020
Página de inicio: 62
Página final: 71
Idioma: English
DOI:

10.1002/jccs.201900051

Notas: ISI, SCOPUS