Half-sandwich Ir(III) and Rh(III) 2,2′-dipyridylamine complexes: Synthesis, characterization and in vitro cytotoxicity against the ovarian carcinoma cells

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F18%3A73591063" target="_blank" >RIV/61989592:15310/18:73591063 - isvavai.cz</a>

Výsledek na webu

<a href="https://www.sciencedirect.com/science/article/pii/S0022328X18304935" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0022328X18304935</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.jorganchem.2018.07.035" target="_blank" >10.1016/j.jorganchem.2018.07.035</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Half-sandwich Ir(III) and Rh(III) 2,2′-dipyridylamine complexes: Synthesis, characterization and in vitro cytotoxicity against the ovarian carcinoma cells

Popis výsledku v původním jazyce

A series of the half-sandwich Ir(III) and Rh(III) complexes [M(eta(5)-Cp-x)(dpa)X]PF6 (M = Ir for 1-6 and Rh for 7-12) containing N-(pyridin-2-yl)pyridin-2-amine (2,2&apos;-dipyridylamine, dpa), pentamethylcyclopentadienyl (Cp*; for 1-5 and 7-11) or 1,2,3,4-tetramethyl-5-phenylcyclopentadienyl (Cp-ph; for 6 and 12) ring, and various monodentate ligands (X), specifically Cl- (for 1, 6, 7 and 12), Br- (for 2 and 8), I- (for 3 and 9), valproato (VP; for 4 and 10) or 4-phenylbutyrato (PB; for 5 and 11), was prepared. The complexes were thoroughly characterized by elemental analysis, IR and NMR spectroscopy and mass spectrometry. A single-crystal X-ray analysis was performed for complex [Ir(eta(5)-Cp-ph)(dpa)Cl]PF6 (6), revealing a pseudo-octahedral piano-stool geometry with a bidentate N,N&apos;-coordinated dpa ligand, a penta-hapto coordinated Cp-ph ring and a monodentate chlorido ligand. The crystal structure of complex 6 is stabilized by N-H center dot center dot center dot F, C-H center dot center dot center dot F, C-H center dot center dot center dot Cl, C-H center dot center dot center dot C and C center dot center dot center dot F non-covalent contacts. Complexes 1-12 were screened for their in vitro cytotoxicity against the A2780 human ovarian carcinoma cell line. The best-performing iridium(III) complex 6 showed markedly higher activity (IC50 = 23.5 mu M) than complexes 1-3, 5, 9 and 12, whose IC50 ranged from 68.7 to 87.1 mu M. Iridium(III) complex 4 and rhodium(III) complexes 7, 8, 10 and 11 were inactive against the A2780 cells in the tested concentration range (IC50 &gt; 100.0 mu M). The chlorido complexes 1, 6, 7 and 12 were studied by H-1 NMR spectroscopy for their hydrolytic stability in the 20% DMF-d(7)/80% D2O and 20% MeOD-d(4)/80% D2O mixture of solvents, revealing Ir(III) complexes 1 and 6 as stable, while Rh(III) complexes 7 and 12 partially hydrolysed in the used medium. Moreover, hydrophobicity (lipophilicity) of complexes 1-12 was studied by an octanol/water partition (logP). (C) 2018 Elsevier B.V. All rights reserved.

Název v anglickém jazyce

Half-sandwich Ir(III) and Rh(III) 2,2′-dipyridylamine complexes: Synthesis, characterization and in vitro cytotoxicity against the ovarian carcinoma cells

Popis výsledku anglicky

A series of the half-sandwich Ir(III) and Rh(III) complexes [M(eta(5)-Cp-x)(dpa)X]PF6 (M = Ir for 1-6 and Rh for 7-12) containing N-(pyridin-2-yl)pyridin-2-amine (2,2&apos;-dipyridylamine, dpa), pentamethylcyclopentadienyl (Cp*; for 1-5 and 7-11) or 1,2,3,4-tetramethyl-5-phenylcyclopentadienyl (Cp-ph; for 6 and 12) ring, and various monodentate ligands (X), specifically Cl- (for 1, 6, 7 and 12), Br- (for 2 and 8), I- (for 3 and 9), valproato (VP; for 4 and 10) or 4-phenylbutyrato (PB; for 5 and 11), was prepared. The complexes were thoroughly characterized by elemental analysis, IR and NMR spectroscopy and mass spectrometry. A single-crystal X-ray analysis was performed for complex [Ir(eta(5)-Cp-ph)(dpa)Cl]PF6 (6), revealing a pseudo-octahedral piano-stool geometry with a bidentate N,N&apos;-coordinated dpa ligand, a penta-hapto coordinated Cp-ph ring and a monodentate chlorido ligand. The crystal structure of complex 6 is stabilized by N-H center dot center dot center dot F, C-H center dot center dot center dot F, C-H center dot center dot center dot Cl, C-H center dot center dot center dot C and C center dot center dot center dot F non-covalent contacts. Complexes 1-12 were screened for their in vitro cytotoxicity against the A2780 human ovarian carcinoma cell line. The best-performing iridium(III) complex 6 showed markedly higher activity (IC50 = 23.5 mu M) than complexes 1-3, 5, 9 and 12, whose IC50 ranged from 68.7 to 87.1 mu M. Iridium(III) complex 4 and rhodium(III) complexes 7, 8, 10 and 11 were inactive against the A2780 cells in the tested concentration range (IC50 &gt; 100.0 mu M). The chlorido complexes 1, 6, 7 and 12 were studied by H-1 NMR spectroscopy for their hydrolytic stability in the 20% DMF-d(7)/80% D2O and 20% MeOD-d(4)/80% D2O mixture of solvents, revealing Ir(III) complexes 1 and 6 as stable, while Rh(III) complexes 7 and 12 partially hydrolysed in the used medium. Moreover, hydrophobicity (lipophilicity) of complexes 1-12 was studied by an octanol/water partition (logP). (C) 2018 Elsevier B.V. All rights reserved.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10402 - Inorganic and nuclear chemistry

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2018

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

JOURNAL OF ORGANOMETALLIC CHEMISTRY

ISSN

0022-328X

e-ISSN

—

Svazek periodika

872

Číslo periodika v rámci svazku

OCT

Stát vydavatele periodika

CH - Švýcarská konfederace

Počet stran výsledku

9

Strana od-do

114-122

Kód UT WoS článku

000443285900014

EID výsledku v databázi Scopus

2-s2.0-85050968061