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

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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.

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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.

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Authors and Affiliations

  1. The School of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia

    Rosenani A. Haque, Muhammad Adnan Iqbal & Patrick Asekunowo

  2. EMAN Research and Testing Laboratory, The School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia

    A. M. S. Abdul Majid, Mohamed B. Khadeer Ahamed, Sawsan S. Al-Rawi & Fouad Saleih R. Al-Suede

  3. The School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia

    Muhammad Ihtisham Umar

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  1. Rosenani A. Haque
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  2. Muhammad Adnan Iqbal
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  3. Patrick Asekunowo
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  4. A. M. S. Abdul Majid
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  5. Mohamed B. Khadeer Ahamed
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  6. Muhammad Ihtisham Umar
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  7. Sawsan S. Al-Rawi
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  8. Fouad Saleih R. Al-Suede
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Correspondence to Rosenani A. Haque or Muhammad Adnan Iqbal.

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Electronic Supplementary information is available: Crystallographic data of the structures have been deposited with the Cambrige Crystallographic Data Center, CCDC 899920 for VII′.2PF6. This data can be obtained free of charge from CCDC via www.ccdc.cam.ac.uk/data_request/cif.

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Haque, R.A., Iqbal, M.A., Asekunowo, P. et al. Synthesis, structure, anticancer, and antioxidant activity of para-xylyl linked bis-benzimidazolium salts and respective dinuclear Ag(I) N-heterocyclic carbene complexes (Part-II). Med Chem Res 22, 4663–4676 (2013). https://doi.org/10.1007/s00044-012-0461-8

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