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

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

Resultado de la investigación: Article

1 Cita (Scopus)

Resumen

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.

Idioma originalEnglish
PublicaciónJournal of the Chinese Chemical Society
DOI
EstadoPublished - 1 ene 2019

Huella dactilar

Tramadol
Vibrational spectra
Enantiomers
Molecular structure
Density functional theory
Opioid Receptors
Conformations
Substitution reactions
Geometry

ASJC Scopus subject areas

  • Chemistry(all)

Citar esto

Umar, Yunusa ; Abdalla, Sahar ; Haque, SK Manirul ; Moran, Guillermo Salgado ; Ishaq, Abdurrahman ; Villada, Wilson Cardona ; Leone, Jorge Dagnino ; Bunster, Marta. / Theoretical investigation of the molecular structure, vibrational spectra, and molecular docking of tramadol using density functional theory. En: Journal of the Chinese Chemical Society. 2019.
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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.",
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author = "Yunusa Umar and Sahar Abdalla and Haque, {SK Manirul} and Moran, {Guillermo Salgado} and Abdurrahman Ishaq and Villada, {Wilson Cardona} and Leone, {Jorge Dagnino} and Marta Bunster",
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Theoretical investigation of the molecular structure, vibrational spectra, and molecular docking of tramadol using density functional theory. / Umar, Yunusa; Abdalla, Sahar; Haque, SK Manirul; Moran, Guillermo Salgado; Ishaq, Abdurrahman; Villada, Wilson Cardona; Leone, Jorge Dagnino; Bunster, Marta.

En: Journal of the Chinese Chemical Society, 01.01.2019.

Resultado de la investigación: Article

TY - JOUR

T1 - Theoretical investigation of the molecular structure, vibrational spectra, and molecular docking of tramadol using density functional theory

AU - Umar, Yunusa

AU - Abdalla, Sahar

AU - Haque, SK Manirul

AU - Moran, Guillermo Salgado

AU - Ishaq, Abdurrahman

AU - Villada, Wilson Cardona

AU - Leone, Jorge Dagnino

AU - Bunster, Marta

PY - 2019/1/1

Y1 - 2019/1/1

N2 - 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.

AB - 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.

KW - DFT

KW - frontier molecular orbital

KW - molecular docking

KW - tramadol

KW - vibrational spectra

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