The first water‐soluble copper(I) complexes bearing sulfonated imidazole‐ and benzimidazole‐derived N‐heterocyclic carbenes: Synthesis and anticancer studies |
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| Authors: | Maura Pellei Valentina Gandin Cristina Marzano Marika Marinelli Fabio Del Bello Carlo Santini |
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| Institution: | 1. School of Science and Technology, Chemistry Division, University of Camerino, Camerino, Macerata, Italy;2. Department of Pharmaceutical and Pharmacological Sciences, University of Padova, Padova, Italy;3. School of Pharmacy, Medicinal Chemistry Unit, University of Camerino, Camerino, Macerata, Italy |
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| Abstract: | The first water‐soluble bis(NHCSO3)CuCl complexes (NHCSO3 = NaImBn,PrSO3, Na2(4‐Me)ImPrSO3 and Na2BzImPrSO3) derived from the sulfonated N‐heterocyclic carbene precursors HImBn,PrSO3 (3‐(1‐benzyl‐1H‐imidazol‐3‐ium‐3‐yl)propane‐1‐sulfonate), Na(4‐Me)HImPrSO3 (sodium 3,3′‐(4‐methyl‐1H‐imidazole‐3‐ium‐1,3‐diyl)dipropane‐1‐sulfonate) and NaHBzImPrSO3 (sodium 3,3′‐(1H‐benzoimidazole‐3‐ium‐1,3‐diyl)dipropane‐1‐sulfonate) have been synthesized. These compounds have been characterized using infrared and NMR spectroscopy and electrospray ionization mass spectrometry. The in vitro anti‐tumour effects of the bis(NHCSO3)CuCl complexes and the corresponding free ligands were evaluated for a panel of various human tumour cell lines, including examples of lung, colon, ovarian and cervical carcinoma as well as of melanoma. Their cytotoxic properties were also evaluated against non‐transformed human cells and on a cellular model of cisplatin resistance. NHC–copper complexes induced cell killing effects preferentially against tumour cells, with IC50 values in the micromolar range. Additionally, they were found able to overcome acquired cisplatin resistance. |
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| Keywords: | copper(I) complexes in vitro anti‐tumour activity N‐heterocyclic carbenes water‐soluble complexes |
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