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Medicinal Chemistry Research

, Volume 22, Issue 10, pp 4663–4676 | Cite as

Synthesis, structure, anticancer, and antioxidant activity of para-xylyl linked bis-benzimidazolium salts and respective dinuclear Ag(I) N-heterocyclic carbene complexes (Part-II)

  • Rosenani A. Haque
  • Muhammad Adnan Iqbal
  • Patrick Asekunowo
  • A. M. S. Abdul Majid
  • Mohamed B. Khadeer Ahamed
  • Muhammad Ihtisham Umar
  • Sawsan S. Al-Rawi
  • Fouad Saleih R. Al-Suede
Original Research

Abstract

The article describes synthesis, characterization (NMR, FT-IR, microanalysis, X-ray crystallography), in vitro anticancer, and antioxidant activity of para-xylyl linked bis-benzimidazolium salts and respective dinuclear Ag–NHC complexes. All the compounds were tested for their cytotoxicity against human colorectal cancer cells (HCT 116) and DPPH antioxidant evaluation. According to cell viability measurements using MTT assay, all the tested compounds showed dose-dependent cytotoxic activity against HCT 116 cells. The tested compounds demonstrated significant activity with IC50 values range 0.29–3.30 μM for HCT 116 and % age inhibition 6.37–21.00 for DPPH antioxidant study. 5-Fluorouracil was used as standard drug (IC50 19.2 μM for HCT 116) whereas for DPPH analysis, Gallic acid was used as positive control (% age inhibition 77.68). All the compounds showed potential anticancer activity against human colorectal cancer whereas antioxidant activity was not significant. We found that as the size of N-alkyl substitution on benzimidazolium salt increases its cytotoxicity against cancer decreases whereas a reverse occurs in case of respective complexes.

Keywords

Benzimidazole Benzimidazolium salts N-Heterocyclic carbenes (NHCs) Ag–NHC complexes Human colon cancer (HCT 116) Antioxidant 

Notes

Acknowledgments

RAH thanks Universiti Sains Malaysia (USM) for the Research University (RU) Grants (1001/PKIMIA/811157) and (1001/PKIMIA/823082). MAI is grateful to (IPS) USM for financial support [fellowship: USM.IPS/JWT/1/19 (JLD 6): P-KD0030/11(R)] and funds [P-KM0018/10(R)-308/AIPS/415401] for a research attachment (Aug. 2011–Nov. 2011) to University of Western Australia (UWA), Perth, Australia.

Supplementary material

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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Rosenani A. Haque
    • 1
  • Muhammad Adnan Iqbal
    • 1
  • Patrick Asekunowo
    • 1
  • A. M. S. Abdul Majid
    • 2
  • Mohamed B. Khadeer Ahamed
    • 2
  • Muhammad Ihtisham Umar
    • 3
  • Sawsan S. Al-Rawi
    • 2
  • Fouad Saleih R. Al-Suede
    • 2
  1. 1.The School of Chemical Sciences, Universiti Sains MalaysiaPenangMalaysia
  2. 2.EMAN Research and Testing LaboratoryThe School of Pharmaceutical Sciences, Universiti Sains MalaysiaPenangMalaysia
  3. 3.The School of Pharmaceutical Sciences, Universiti Sains MalaysiaPenangMalaysia

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