Crystal Structures and Cytotoxicity of Ortho-Xylene Linked Bis-benzimidazolium Salts

Author(s): Muhammad Adnan Iqbal, Rosenani A. Haque, Safaa A. Ahamed, Syedeh Fatemeh Jafari, Mohamed B. Khadeer Ahamed, Amin M.S. Abdul Majid.

Journal Name: Medicinal Chemistry

Volume 11 , Issue 5 , 2015

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Abstract:

Azolium (imidazolium and benzimidazolium) salts are known as stable precursors for the synthesis of Metal-N-Heterocyclic Carbene (M-NHC) complexes. Recently, some reports have been compiled indicating that benzimidazolium salts have anticarcinogenic properties. The current research is the further investigation of this phenomenon. Three ortho-xylene linked bis-benzimidazolium salts (1-3) with octyl, nonyl and decyl terminal chain lengths have been synthesized. Each of the compounds was characterized using FT-IR and NMR spectroscopic techniques. The molecular geometries of two of the salts (1-2) have been established using X-ray crystallographic technique. The compounds were tested for their cytotoxic properties against three cancerous cell lines namely, human colon cancer (HCT 116), human colorectal adenocarcinoma (HT- 29) and human breast adenocarcinoma (MCF-7). Mouse embryonic fibroblast (3T3-L1) was used as the model cell line of normal cells. The compounds showed selective anti-proliferative activities against the colorectal carcinoma cells. For HCT 116 and HT-29 cells, the IC50 values ranged 0.9-2.6 µM and 4.0-10.0 µM, respectively. The salts 1 and 3 displayed moderate cytotoxicity against the breast cancer (MCF-7) cells with IC50 58.2 and 13.3 µM, respectively. However, the salt 2 produced strong cytotoxicity against MCF-7 cells with IC50 4.4 µM. Interestingly, the compounds demonstrated poor cytotoxic effects towards the normal cells (3T3-L1) as the IC50 was found to be as high as 48.0 µM. Salts 2 and 3 demonstrated more pronounced anti-proliferative effect than the standard drugs used (5-Flourouracil and Tamoxifen).

Keywords: Benzimidazole, benzimidazolium salts, HCT116, MCF-7, HT-29.

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Article Details

VOLUME: 11
ISSUE: 5
Year: 2015
Page: [473 - 481]
Pages: 9
DOI: 10.2174/1573406411666150101153115
Price: $58

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