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The adsorption of the drug gemcitabine on nucleobases was investigated using a dispersioncorrected density functional theory (DFT) study. The planar structure of complexes is more stable than those with stacked and buckle-angled configurations. The complexes were found to possess at least two intermolecular hydrogen bonds. The binding energy and interaction energy are both negative, with the highest values observed for the gemcitabine–guanine and the lowest in the gemcitabine–thymine complex. The complex formation was found to be an enthalpy-driven process. Pyrimidine nucleobases have a lower enthalpy of formation than purine nucleobases. The computed HOMA and NICS values on the gemcitabine–nucleobase complexes show a substantial increase compared to the pristine nucleobases.
An MESP analysis of the complexes shows a directional interaction and electron density shift between the gemcitabine and the nucleobases. A QTAIM analysis indicates that the intermolecular hydrogen bonds have a partial covalent character. The computed bond energy demonstrates that intermolecular NH···N bonds are more potent than other bonds. An energy decomposition analysis using the DLPNO−CCSD(T) method indicates that the complexes exhibit a substantial electrostatic attraction, and dispersion contributes the least towards the system stability. The intermolecular bonds are stronger than the intramolecular bonds in the drug–nucleobase complexes. The strength of intramolecular bonds is determined by the deformation of the gemcitabine ring during the complex formation.

権利情報:

• Creative Commons BY Attribution 4.0 International
  

キーワード: drug, nucleobases, non-covalent interactions, DFT calculations, energy decomposition analysis

刊行年月日: 2025-06-25

出版者: MDPI AG

掲載誌:

• Molecules (ISSN: 14203049) vol. 30 issue. 13 2732

研究助成金:

原稿種別: 出版者版 (Version of record)

MDR DOI:

公開URL: https://doi.org/10.3390/molecules30132732

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更新時刻: 2025-11-27 08:30:18 +0900

MDRでの公開時刻: 2025-11-27 08:24:02 +0900