Rhenium(I)-tricarbonyl complexes with methimazole and its selenium analogue: Syntheses, characterization and cell toxicity

J Inorg Biochem. 2023 Mar:240:112092. doi: 10.1016/j.jinorgbio.2022.112092. Epub 2022 Dec 5.

Abstract

This study explores the effect of a thione/selone ligand on the cell toxicity (in vitro) and light activity of diimine Re(CO)3+ complexes. Six rhenium(I) complexes with general formula fac-[Re(CO)3(N,N')X]+ were prepared, where X = 2-mercapto-1-methylimidazole (methimazole; MMI), and 1-methylimidazole-2-selone (MSeI); N,N' = 2,2'-bipyridine (bpy), 1,10-phenanthroline (phen) and 2,9-dimethyl-1,10-phenanthroline (dmphen). Their triflate salts were characterized using single-crystal X-ray diffraction, 1H, 13C and 2D NMR, UV-vis and vibrational spectroscopy. Their cytotoxic properties were tested, showing significant cytotoxicity (IC50 = 8.0-55 μM) towards the human breast cancer cell line MDA-MB-231. The half-inhibitory concentration (IC50) for fac-[Re(CO)3(dmphen)(MMI)]+, the most toxic complex in this series (8.0 ± 0.2 μM), was comparable to that of the corresponding aqua complex fac-[Re(CO)3(dmphen)(H2O)]+ with IC50 = 6.0 ± 0.1 μM. The fac-[Re(CO)3(bpy)(MMI/MSeI)]+ complexes were somewhat less toxic towards the human embryonic kidney cell line HEK-293 T after 48 h of exposure. The stability of the complexes upon irradiation was monitored using UV-vis spectroscopy, with no CO released when exposed to UV-A light (λ = 365 nm).

Keywords: 1-methylimidazole-2-selone; Cytotoxicity; Methimazole; Rhenium(I) tricarbonyl diimine complexes; Spectroscopy; Structure.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents* / pharmacology
  • HEK293 Cells
  • Humans
  • Methimazole
  • Rhenium* / chemistry
  • Selenium*

Substances

  • Selenium
  • Rhenium
  • Methimazole
  • Antineoplastic Agents