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The first water‐soluble copper(I) complexes bearing sulfonated imidazole‐ and benzimidazole‐derived N‐heterocyclic carbenes: Synthesis and anticancer studies
Author(s) -
Pellei Maura,
Gandin Valentina,
Marzano Cristina,
Marinelli Marika,
Del Bello Fabio,
Santini Carlo
Publication year - 2018
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.4185
Subject(s) - chemistry , benzimidazole , sulfonate , imidazole , cisplatin , hela , electrospray ionization , medicinal chemistry , stereochemistry , sodium , in vitro , nuclear chemistry , mass spectrometry , organic chemistry , biochemistry , medicine , surgery , chemotherapy , chromatography
The first water‐soluble bis(NHC SO3 )CuCl complexes (NHC SO3 = NaIm Bn,PrSO3 , Na 2 (4‐Me)Im PrSO3 and Na 2 BzIm PrSO3 ) derived from the sulfonated N‐heterocyclic carbene precursors HIm Bn,PrSO3 (3‐(1‐benzyl‐1 H ‐imidazol‐3‐ium‐3‐yl)propane‐1‐sulfonate), Na(4‐Me)HIm PrSO3 (sodium 3,3′‐(4‐methyl‐1 H ‐imidazole‐3‐ium‐1,3‐diyl)dipropane‐1‐sulfonate) and NaHBzIm PrSO3 (sodium 3,3′‐(1 H ‐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(NHC SO3 )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 IC 50 values in the micromolar range. Additionally, they were found able to overcome acquired cisplatin resistance.