Influence of the substituent on the phosphine ligand in novel rhenium(i) aldehydes. Synthesis, computational studies and first insights into the antiproliferative activity

Abstract

Cyrhetrenyl aldehyde derivatives [(η5-C5H4CHO)Re(CO)2PR3] with R = methyl (Me, 2a), phenyl (Ph, 2b), and cyclohexyl (Cy, 2c) were synthesized by a photochemical reaction from the starting material [(η5-C5H4CHO)Re(CO)3] (1) and the corresponding phosphines. The complexes were fully characterized by FT-IR, 1H, 13C and 31P NMR spectroscopy, elemental analysis and mass spectrometry. The molecular structures of 2a-c have also been determined. Electronic structure calculations by TD-DFT and electrochemical studies are in sound agreement with the effect of the substitution of one carbonyl group by a phosphine ligand. Additionally, the antiproliferative activity of complexes 1 and 2a-c was studied on the human cancer cell lines HT-29 and PT-45 using an MTT assay. Out of all new compounds, only the triphenylphosphine derivative 2b exhibited pronounced cytotoxic effects on both cell lines, being ca. 1.5 times more potent than cisplatin.

Target-specific mononuclear and binuclear rhenium(i) tricarbonyl complexes as upcoming anticancer drugs

“…36 They induce anticancer activity through various mechanisms, which are focused mainly on targeting cancer cell organelles, interaction with DNA, inhibition of enzymes and protein kinases, disruption of the activity of mitochondria, inducing cytoplasmic vacuolization and apoptosis. 55,56 In the subsequent sections of this study, we discuss the cytotoxicity of rhenium organometallic complexes, focusing mainly on rhenium tricarbonyl complexes and highlighting their potential as cancer theranostics.…”

Design of Rhenium Compounds in Targeted Anticancer Therapeutics

“…The  5cyclopentadienyl group has emerged as an alternative versatile organometallic fragment to build Reanticancer agents. For example, complex 2b was found highly active on pancreatic adenocarcinoma PT-45 cell line reaching an IC50 value of 11.5 μM while 2a is devoid of activity [23]. Beside Re(I)(CO) 3 compounds, new derivatives emerged based on the N-heterocyclic carbene complexes scaffold such as 3.…”

Highly Potent Rhenium(I) Tricarbonyl Complexes with Dual Anticancer and Anti-Angiogenic Activity Against Colorectal Carcinoma

“…0.1 (HeLa), 30 1 (MCF-7), 15 0.75 (A549), 67 4 (NB69 and H4 cells) μM. 12 To our knowledge, only a few rhenium(I) carbonyl complexes have been tested against colon cancer cell lines 16,20,[69][70][71][72][73][74][75] (some of which are shown in (Table 3). As evident from…”