Publication detail

Unexpected solution behaviour of ester-functionalized half-sandwich Ru(II) and Ir(III) complexes

MASARYK, L. NEMEC, I. KAŠPÁRKOVÁ, J. BRABEC, V. ŠTARHA, P.

Original Title

Unexpected solution behaviour of ester-functionalized half-sandwich Ru(II) and Ir(III) complexes

Type

journal article in Web of Science

Language

English

Original Abstract

Complexes [Ru(eta(6)-pcym)(bpy(dca))Cl]PF6 (Ru-dca) and [Ir(eta(5)-Cp*)(bpy(dca))Cl]PF6 (Ir-dca) were developed as model compounds for the investigation of multi-targeted ester-functionalized half-sandwich ruthenium(ii) and iridium(iii) complexes; pcym = 1-methyl-4-(propan-2-yl)benzene (p-cymene), bpy(dca) = 2,2 '-bipyridine-4,4 '-diyldimethanediyl bis(dichloroacetate), Cp* = pentamethylcyclopentadienyl. Aiming to understand the in-solution behaviour of these first-in-class complexes containing the pyruvate dehydrogenase kinase inhibitor dichloroacetate (dca) as the terminal bioactive substituent, several experiments were performed under aqueous conditions for Ru-dca and Ir-dca, as well as for compounds [Ru(eta(6)-pcym)(bpy(OH))Cl]PF6 (Ru-OH) and [Ir(eta(5)-Cp*)(bpy(OH))Cl]PF6 (Ir-OH), and acetyl analogues [Ru(eta(6)-pcym)(bpy(ac))Cl]PF6 (Ru-ac) and [Ir(eta(5)-Cp*)(bpy(ac))Cl]PF6 (Ir-ac) bearing a different (biologically inactive) terminal substituent; bpy(OH) = 2,2 '-bipyridine-4,4 '-diyldimethanol, bpy(ac) = 2,2 '-bipyridine-4,4 '-diyldimethanediyl diacetate. The experiments were also conducted in the presence of porcine liver esterase (PLE). All the six complexes were characterized by relevant techniques (e.g., NMR and mass spectrometry), including a single-crystal X-ray analysis of complexes Ru-dca, Ru-ac, Ru-OH and Ir-OH. Although designed as model compounds, Ru-dca, Ir-dca, Ru-OH and Ir-OH were also screened for their antiproliferative activity in four human cancer cell lines (HCT116 colon carcinoma, MDA-MB-231 and MCF-7 breast adenocarcinomas, DU145 prostate carcinoma), where the tested complexes did not show any effect (IC50 > 100 mu M).

Keywords

FLUORESCENT-PROBE; RUTHENIUM (II); CYTOTOXICITY; CELLS; CARBOXYLESTERASE; INHIBITION; CISPLATIN; IRIDIUM; RHODIUM; DESIGN

Authors

MASARYK, L.; NEMEC, I.; KAŠPÁRKOVÁ, J.; BRABEC, V.; ŠTARHA, P.

Released

21. 6. 2021

Publisher

ROYAL SOC CHEMISTRY

Location

CAMBRIDGE

ISBN

1477-9234

Periodical

Dalton Transactions

Year of study

50

Number

23

State

United Kingdom of Great Britain and Northern Ireland

Pages from

8017

Pages to

8028

Pages count

12

URL

https://pubs.rsc.org/en/content/articlelanding/2021/DT/D1DT00466B

BibTex

@article{BUT173177,
  author="Lukáš {Masaryk} and Ivan {Nemec} and Jana {Kašpárková} and Viktor {Brabec} and Pavel {Štarha}",
  title="Unexpected solution behaviour of ester-functionalized half-sandwich Ru(II) and Ir(III) complexes",
  journal="Dalton Transactions",
  year="2021",
  volume="50",
  number="23",
  pages="8017--8028",
  doi="10.1039/d1dt00466b",
  issn="1477-9234",
  url="https://pubs.rsc.org/en/content/articlelanding/2021/DT/D1DT00466B"
}