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Ab initio DFT study of bisphosphonate derivatives as a drug for inhibition of cancer: NMR and NQR parameters

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Abstract

DFT computations were carried out to characterize the 17Oand 2H electric field gradient, EFG, in various bisphosphonate derivatives. The computations were performed at the B3LYP level with 6-311++G (d,P) standard basis set. Calculated EFG tensors were used to determine the 17O and 2H nuclear quadrupole coupling constant, χ and asymmetry parameter, η. For better understanding of the bonding and electronic structure of bisphosphonates, isotropic and anisotropic NMR chemical shieldings were calculated for the 13C, 17O and 31P nuclei using GIAO method for the optimized structure of intermediate bisphosphonates at B3LYP level of theory using 6-311++G (d, p) basis set. The results showed that various substituents have a strong effect on the nuclear quadrupole resonance (NQR) parameters (χ, η) of 17O in contrast with 2H NQR parameters. The NMR and NQR parameters were studied in order to find the correlation between electronic structure and the activity of the desired bisphosphonates. In addition, the effect of substitutions on the bisphosphonates polarity was investigated. Molecular polarity was determined via the DFT calculated dipole moment vectors and the results showed that substitution of bromine atom on the ring would increase the activity of bisphosphonates.

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Authors and Affiliations

  1. Faculty of chemistry, North Tehran branch, Islamic Azad University, Tehran, Iran

    Hussein Aghabozorg

  2. Department of chemistry, Surface Chemistry Research Laboratory, Iran University of Science and Technology, P.O. Box 16765–163, Tehran, Iran

    Beheshteh Sohrabi & Sara Mashkouri

  3. Research Institute of Petroleum Industry (RIPI), Tehran, Iran

    Hamid Reza Aghabozorg

Authors
  1. Hussein Aghabozorg
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  2. Beheshteh Sohrabi
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  3. Sara Mashkouri
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  4. Hamid Reza Aghabozorg
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Correspondence to Beheshteh Sohrabi.

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Aghabozorg, H., Sohrabi, B., Mashkouri, S. et al. Ab initio DFT study of bisphosphonate derivatives as a drug for inhibition of cancer: NMR and NQR parameters. J Mol Model 18, 929–936 (2012). https://doi.org/10.1007/s00894-011-1114-4

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  • DOI: https://doi.org/10.1007/s00894-011-1114-4

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