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Microwave assisted synthesis of rhodium(I) N-heterocyclic carbene complexes and their cytotoxicity against tumor cell lines

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JOURNAL OF ORGANOMETALLIC CHEMISTRY
卷 964, 期 -, 页码 -

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ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2022.122300

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Bioorganometallic chemistry; Carbene; Cytotoxicity; Rhodium

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Organometallic rhodium(I) complexes were synthesized and evaluated for their cytotoxic effects against cancer cells. The complexes exhibited strong cytotoxic effects on various cancer cell lines, with a preference for branched isopropyl side chains on the N-heterocyclic carbene ligands. Further studies suggested that the increased cytotoxicity might be attributed to higher cellular uptake.
Organometallic rhodium(I) complexes of the general type [(COD)(NHC)RhCl] (where COD = 1,5-cyclooctadiene, NHC = N-heterocyclic carbene) were prepared according to a two-step transmetalation method via a silver carbene intermediate. The procedure was supported by microwave irradiation allowing reduced reaction periods. The complexes were evaluated for cytotoxic effects in selected cancer cell lines, namely HT-29 colon adenocarcinoma, MDA-MB-231 breast carcinoma and MCF-7 breast adenocarcinoma, and generally triggered strong cytotoxic effects with IC50 values in the low micromolar range. Evaluation of structure-activity relationships clearly indicated a preference for branched isopropyl side chains at the nitrogen atoms of the NHC ligands versus non-branched ethyl side chains. Further studies on selected examples in HT-29 cells indicated that this could be the result of a higher cellular uptake. (C) 2022 Elsevier B.V. All rights reserved.

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