Cadmium(II) and indium(III) complexes derived from 2-benzoylpyridine N(4)-cyclohexylthiosemicarbazone: Synthesis, crystal structures, spectroscopic characterization and cytotoxicity

Tai, Yanxue; Ji, Yu-Mei; Lu, Yue; Li, Mingxue; Wu, Yuan-Yuan; Han, Qiuxia

doi:10.1016/j.synthmet.2016.05.015

Cited by 38 publications

(12 citation statements)

References 31 publications

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“…Free Cd(II) ion has well-known high toxicity on human health, but several studies have revealed that Cd(II) complexes with organic ligands have interesting bio-activities including DNA binding ability [10], antitumor [11], and antibacterial [12] activities. In addition, the organic ligand itself could be employed as a detoxification agent in the case of complexes with high-stability constants [13]. The DNA interactions of Cd(II) via covalent binding interactions between adenine and guanine in DNA were proved by Hossain and Huq [14].…”

Section: Introductionmentioning

confidence: 99%

X-ray Structure Analyses and Biological Evaluations of a New Cd(II) Complex with S-Triazine Based Ligand

et al. 2022

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The crystal structure of a new penta-coordinated Cd(II) complex of the formula [Cd(BPMT)Br2] was presented. This Cd(II) complex was synthesized by mixing Cd(NO3)2·4H2O and 2,4-bis(3,5-dimethyl-1H-pyrazol-1-yl)-6-methoxy-1,3,5-triazine (BPMT) in the presence of KBr. It crystallized in the monoclinic crystal system and P21/n space group. The crystal parameters are a = 11.3680(8) Å, b = 11.1648(8) Å, c = 15.8593(11) Å, and β = 103.563(2)°, while the unit cell volume is 2190.6(12) Å3 and it comprised four molecules. The supramolecular structure of the [Cd(BPMT)Br2] complex is mainly controlled by the intermolecular Br∙∙∙H interactions. Hirshfeld calculations predicted the H∙∙∙H (38.1%), Br∙∙∙H (24.3%), C∙∙∙H (11.1%), and N∙∙∙H (9.5%) interactions are the most dominant. Biological evaluations for the antimicrobial and anticancer properties of the studied complex are presented. The Cd(II) complex has better anticancer and antibacterial activities than the free BPMT ligand. The anticancer activity against lung carcinoma (A-549) is higher for the former (18.64 ± 1.09 µg/mL) compared to the latter (372.79 ± 13.64 µg/mL). Additionally, the best antibacterial activity for the Cd(II) complex was found against B. subtilis.

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Section: Introductionmentioning

confidence: 99%

X-ray Structure Analyses and Biological Evaluations of a New Cd(II) Complex with S-Triazine Based Ligand

et al. 2022

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“…Indeed, metal thiosemicarbazone compounds have also been extensively studied and have been found to be one of the most promising next-generation metal anticancer agents because they can inhibit tumor growth by multiple mechanisms. − Currently, In compounds are used in antitumor research owing to the following advantages: (1) In 3+ presents affinity for nitrogen and oxygen donor ligands and can form stable compounds with phenol, carboxylate, and amine ligands, as well as with sulfur-containing groups; , (2) In(III) compounds with ligands significantly increased antitumor activity relative to the ligands alone; − and (3) the affinity of In compounds to transferrin might favor targeting of In(III) compounds to tumor cells, improving the selectivity . Excitingly, several In thiosemicarbazone compounds have also been synthesized and have shown remarkable antitumor activity. − However, there still remain mysteries about their antitumor function and mechanism, including the ability and mechanism of In compounds to overcome cisplatin resistance. Furthermore, the anticancer activity of the In(III) 2,6-diacetylpyridine bis(thiosemicarbazone) complex was lower than that of the In(III) 2-acetylpyridine thiosemicarbazone complexes. − Thus, we proposed to design and synthesize an In(III) 2-pyridinecarboxaldehyde thiosemicarbazone compound to reverse the resistance to cisplatin.…”

Section: Introductionmentioning

confidence: 99%

Developing a Novel Indium(III) Agent Based on Liposomes to Overcome Cisplatin-Induced Resistance in Breast Cancer by Multitargeting the Tumor Microenvironment Components

et al. 2021

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To overcome the resistance of cancer cells to platinumbased drugs and effectively suppress tumor growth, we developed a novel indium (In) agent based on liposomes (Lips). Thus, we not only obtained an In(III) thiosemicarbazone agent (5b) with remarkable cytotoxicity by optimizing a series of In(III) thiosemicarbazone agents (1b−5b) but also successfully constructed a novel 5b-loaded Lip (5b-Lip) delivery system. Importantly, in vitro and in vivo results revealed that 5b/5b-Lip overcame the tumor cell resistance and effectively inhibited MCF-7/DDP tumor growth. In addition, Lips improved the intracellular accumulation of 5b. We also confirmed the mechanism by which 5b/5b-Lip overcomes breast cancer cell resistance. 5b/5b-Lip cannot act against DNA in cancer cells but attacks the two cell components in the tumor microenvironment, namely, by inducing apoptosis and lethal autophagy of cancer cells and resetting tumor-promoting M2 macrophages to the tumor-killing M1 phenotype.

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“…A scarcely explored part of medicinal inorganic chemistry is that related to the potential anticancer activity of Cd complexes, since it has been classified by the International Agency for Research on Cancer as a human carcinogen [15]. Cadmium toxicity derives from the fact that it is rapidly localized intracellularly, mainly in the liver, and then is bound to metallothionein forming a complex that is slowly transferred to the bloodstream to be deposited in the kidneys [16]. Some studies indicate that Cd may exert a paradoxical effect in cancer perhaps dependent on the form it exists in: free Cd, protein-bound Cd, and Cd complexes.…”

Section: Introductionmentioning

confidence: 99%

“…It seems that ligand type used for preparation of Cd complexes may cause their very favorable anti-tumor effects [17]. Ligands used for preparation of Cd complexes can be classified as: thiosemicarbazones [16,[18][19][20][21][22][23][24], selenosemicarbazones [25][26][27], hydrazones [16,[27][28][29][30][31][32][33][34][35][36], hydrazides [38,39], diimines [40], amides [41,42], aminoacids [43,44], heterocycles [44][45][46][47][48][49][50][51][52][53][54][55][56], macrocycles [58][59][60], drugs [61][62][63]…”

Section: Introductionmentioning

confidence: 99%

A novel binuclear hydrazone-based Cd(II) complex is a strong pro-apoptotic inducer with significant activity against 2D and 3D pancreatic cancer stem cells

Bjelogrlić

Todorović

Cvijetić

et al. 2019

Journal of Inorganic Biochemistry

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A novel binuclear Cd complex (1) with hydrazone-based ligand was prepared and characterized by spectroscopy and single crystal X-ray diffraction techniques. Complex 1 reveals a strong pro-apoptotic activity in both human, mammary adenocarcinoma cells (MCF-7) and pancreatic AsPC-1 cancer stem cells (CSCs). While apoptosis undergoes mostly caspase-independent, 1 stimulates the activation of intrinsic pathway with noteworthy down regulation of caspase-8 activity in respect to non-treated controls. Distribution of cells over mitotic division indicates that 1 caused DNA damage in both cell lines, which is confirmed in DNA interaction studies. Compared to 1, cisplatin (CDDP) does not achieve cell death in 2D cultured AsPC-1 cells, while induces different pattern of cell cycle changes and caspase activation in 2D cultured MCF-7 cells, implying that these two compounds do not share similar mechanism of action. Additionally, 1 acts as a powerful inducer of mitochondrial superoxide production with dissipated trans-membrane potential in the majority of the treated cells already after 6 h of incubation. On 3D tumors, 1 displays a superior activity against CSC model, and at 100 μM induces disintegration of spheroids within 2 days of incubation. Fluorescence spectroscopy, along with molecular docking show that compound 1 binds to the minor groove of DNA. Compound 1 binds to the human serum albumin (HSA) showing that the HSA can effectively transport and store 1 in the human body. Thus, our current study strongly supports further investigations on antitumor activity of 1 as a drug candidate for the treatment of highly resistant pancreatic cancer.

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Cadmium(II) and indium(III) complexes derived from 2-benzoylpyridine N(4)-cyclohexylthiosemicarbazone: Synthesis, crystal structures, spectroscopic characterization and cytotoxicity

Cited by 38 publications

References 31 publications

X-ray Structure Analyses and Biological Evaluations of a New Cd(II) Complex with S-Triazine Based Ligand

X-ray Structure Analyses and Biological Evaluations of a New Cd(II) Complex with S-Triazine Based Ligand

Developing a Novel Indium(III) Agent Based on Liposomes to Overcome Cisplatin-Induced Resistance in Breast Cancer by Multitargeting the Tumor Microenvironment Components

A novel binuclear hydrazone-based Cd(II) complex is a strong pro-apoptotic inducer with significant activity against 2D and 3D pancreatic cancer stem cells

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