Anticancer activities of manganese-based photoactivatable CO-releasing complexes (PhotoCORMs) with benzimidazole derivative ligands

This paper contains the synthesis and characterization of the seven new benzimidazolium salts and their corresponding new palladium(II)‐NHC complexes with the general formula [PdX2(NHC)2], (NHC = N‐heterocyclic carbene, X = Cl or Br), and also their catalytic activity in direct C‐H bond arylation of 2‐substituted furan derivatives with aryl bromides and aryl chlorides. Under the optimal conditions, these palladium(II)‐NHC complexes showed the good catalytic performance for the direct C‐H bond arylation of 2‐substituted furans with (hetero)aryl bromides, and with readily available and inexpensive aryl chlorides. The C‐H bond arylation regioselectively produced C5‐arylated furans by using 1 mol% of the palladium(II)‐NHC catalysts in moderate to high yields.

show abstract

“…S1–S2). Obtained spectroscopic values are consistent with those found in the literature for other N ‐(alkyl)benzimidazole compounds …”

Section: Resultssupporting

confidence: 89%

Palladium(II)‐N‐Heterocyclic Carbene Complexes: Efficient Catalysts for the Direct C‐H Bond Arylation of Furans with Aryl Halides

Kaloğlu

Özdemır

2018

Applied Organom Chemis

Self Cite

View full text Add to dashboard Cite

show abstract

“…Cell viability is determined at 475‐nm wavelength, depending on the intensity of orange color that occurs after incubation period. [ 23 ]…”

Section: Methodsmentioning

confidence: 99%

Synthesis of (4R)‐2‐(3‐hydroxyphenyl)thiazolidine‐4‐carboxylic acid substituted phthalocyanines: Anticancer activity on different cancer cell lines and molecular docking studies

Bilgiçli

Hepokur

et al. 2021

Applied Organom Chemis

View full text Add to dashboard Cite

In this study, firstly, (4R)‐2‐(3‐hydroxyphenyl)thiazolidine‐4‐carboxylic acid (1) and (4R)‐2‐(3‐(3,4‐dicyanophenoxy)phenyl)thiazolidine‐4‐carboxylic acid (2) were prepared. Then, the novel type metallophthalocyanines (ZnPc (3), CuPc (4), and CoPc (5)) bearing thiazolidine groups in peripheral positions were synthesized using by compound (2). The synthesized new compounds (1–5) were characterized by the combination of standard spectroscopic methods such as FT‐IR, 1H NMR, 13C NMR, UV–Vis spectral data, and MALDI‐TOF. Aggregation behaviors of peripheral tetra‐substituted metallophthalocyanines were investigated in dimethyl sulfoxide (DMSO) media. Fluorescence properties and fluorescence quantum yield of the new type zinc phthalocyanine (3) were performed in DMSO at room temperature. The anticancer activity of novel type metallophthalocyanines bearing thiazolidine groups in peripheral positions were investigated on rat glioma cancer (C6), human prostate carcinoma (DU‐145), and normal human lung fibroblast (WI‐38) cell lines. Finally, the biological and chemical activities of (4R)‐2‐(3‐(3,4‐dicyanophenoxy)phenyl)thiazolidine‐4‐carboxylic acid (2) and its novel type metallophthalocyanines (ZnPc (3), CuPc (4), and CoPc (5)) have been compared with many parameters obtained using theoretical methods that are the Gaussian software and molecular docking.

show abstract

“…[ 32,33 ] The complexes a and b show antiproliferative activity against breast cancer cell lines under UV irradiation whereas c , d , and e show a dose‐dependent toxicity towards breast and colon cancer cells when exposed to low power visible light (Figure 1). [ 34–40 ]…”

Section: Introductionmentioning

confidence: 99%

Synthesis, spectroscopic, CO‐releasing ability, and anticancer activity studies of [Mn(CO)₃(L–L)Br] complexes: Experimental and density functional theory studies

Thomas

Vidhyapriya²,

Sivan

et al. 2022

Applied Organom Chemis

View full text Add to dashboard Cite

Two different series of manganese(I) tricarbonyl complexes containing phosphine‐based (1–5) and 4′‐substituted 2,2′:6′,2″‐terpyridine‐based ligands (6–10) have been synthesized in order to study their CO‐releasing ability and to investigate their anticancer activity. All the synthesized complexes (1–10) have been fully characterized using standard spectroscopic and analytical techniques. Further 5, 7, and 9 have also been characterized by single‐crystal X‐ray diffraction studies. Although both the sets of ligands are π‐acceptors, they tend to change the Mn—CO bond strength upon complexation, thus affecting the CO release. Photoactivation of 1–5 and 6–10 has been achieved using 365 nm UV irradiation and low intensity visible light, respectively. The MnCO bond strength has been examined using the density functional theory (DFT) and time‐dependent DFT (TD‐DFT) calculations. In order to find the therapeutic viability of the visible light activated complexes, their cytotoxicity has been investigated both in the dark and under irradiation. The MTT (3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyl tetrazolium bromide) assay reveals the potential application of some of the synthesized complexes especially towards the lung cancer cells in the dark condition.

show abstract

Anticancer activities of manganese-based photoactivatable CO-releasing complexes (PhotoCORMs) with benzimidazole derivative ligands

Cited by 27 publications

References 33 publications

Palladium(II)‐N‐Heterocyclic Carbene Complexes: Efficient Catalysts for the Direct C‐H Bond Arylation of Furans with Aryl Halides

Palladium(II)‐N‐Heterocyclic Carbene Complexes: Efficient Catalysts for the Direct C‐H Bond Arylation of Furans with Aryl Halides

Synthesis of (4R)‐2‐(3‐hydroxyphenyl)thiazolidine‐4‐carboxylic acid substituted phthalocyanines: Anticancer activity on different cancer cell lines and molecular docking studies

Synthesis, spectroscopic, CO‐releasing ability, and anticancer activity studies of [Mn(CO)₃(L–L)Br] complexes: Experimental and density functional theory studies

Contact Info

Product

Resources

About

Anticancer activities of manganese-based photoactivatable CO-releasing complexes (PhotoCORMs) with benzimidazole derivative ligands

Cited by 27 publications

References 33 publications

Palladium(II)‐N‐Heterocyclic Carbene Complexes: Efficient Catalysts for the Direct C‐H Bond Arylation of Furans with Aryl Halides

Palladium(II)‐N‐Heterocyclic Carbene Complexes: Efficient Catalysts for the Direct C‐H Bond Arylation of Furans with Aryl Halides

Synthesis of (4R)‐2‐(3‐hydroxyphenyl)thiazolidine‐4‐carboxylic acid substituted phthalocyanines: Anticancer activity on different cancer cell lines and molecular docking studies

Synthesis, spectroscopic, CO‐releasing ability, and anticancer activity studies of [Mn(CO)3(L–L)Br] complexes: Experimental and density functional theory studies

Contact Info

Product

Resources

About

Synthesis, spectroscopic, CO‐releasing ability, and anticancer activity studies of [Mn(CO)₃(L–L)Br] complexes: Experimental and density functional theory studies