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Nitrile functionalized silver(I) N-heterocyclic carbene complexes: DFT calculations and antitumor studies

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Abstract

A series of aliphatic nitrile functionalized benzimidazolium salts and their respective mononuclear N-heterocyclic carbene Ag(I)-NHC complexes are reported. The benzimidazolium salts were synthesized by N-alkylation of 1H-benzimidazole with an appropriate alkyl bromide, followed by reaction with either 5-bromovaleronitrile or 6-bromohexanenitrile. The respective mononuclear Ag(I)-NHC complexes were prepared by the reaction of the benzimidazolium salts with Ag2O. All the synthesized compounds were characterized by physico-chemical and spectroscopic techniques. The molecular structures of the two complexes were elucidated through single-crystal X-ray diffraction analyses. Density functional theory was used to model the structures of the other complexes. The benzimidazolium salts and their complexes were screened for cytotoxicity against a breast cancer cell line (MCF-7), using the MTT assay. All the Ag(I)-NHC complexes gave IC50 values ranging from 7.0 ± 1.06 to 12.9 ± 1.55 µM which are comparable to the standard drug, tamoxifen (IC50 = 11.2 ± 1.84 µM), while all of the benzimidazolium salts proved to be inactive.

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Acknowledgements

R. A. Haque and M. R. Razali thank Universiti Sains Malaysia for RUI Grant (1001/PKIMIA/811346). Sunusi Y. Hussaini thanks Kano University of Science and Technology, Wudil, Nigeria.

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Authors and Affiliations

  1. School of Chemical Sciences, Universiti Sains Malaysia, Penang, Malaysia

    Sunusi Y. Hussaini, Rosenani A. Haque, Tabinda Fatima & Mohd. R. Razali

  2. Department of Chemistry, Kano University of Science and Technology Wudil, Kano, Nigeria

    Sunusi Y. Hussaini

  3. EMAN Research and Testing Laboratory, School of Pharmacy, Universiti Sains Malaysia, Penang, Malaysia

    Taleb M. Agha & A. M. S. Abdul Majid

  4. School of Pharmacy, Universiti Sains Malaysia, Penang, Malaysia

    Hassan H. Abdallah

  5. Chemistry Department, College of Education, Salahaddin University, Erbīl, Iraq

    Hassan H. Abdallah

Authors
  1. Sunusi Y. Hussaini
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  2. Rosenani A. Haque
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  3. Tabinda Fatima
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  4. Taleb M. Agha
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  5. A. M. S. Abdul Majid
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  6. Hassan H. Abdallah
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  7. Mohd. R. Razali
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Corresponding author

Correspondence to Mohd. R. Razali.

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Hussaini, S.Y., Haque, R.A., Fatima, T. et al. Nitrile functionalized silver(I) N-heterocyclic carbene complexes: DFT calculations and antitumor studies. Transit Met Chem 43, 301–312 (2018). https://doi.org/10.1007/s11243-018-0216-6

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  • DOI: https://doi.org/10.1007/s11243-018-0216-6

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