Synthesis, spectral characterization and X-ray crystallographic study of new copper(I) complexes. Antitumor activity in colon cancer

González-Ballesteros, Noelia; Pérez-Álvarez, David; Rodrı́guez-Argüelles, Marı́a C.; Henriques, Marta S. C.; Paixão, J. A.; Prado‐Lopez, Sonia

doi:10.1016/j.poly.2016.08.023

Cited by 10 publications

(10 citation statements)

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“…13,14 Notably, three coordinate copper(I) complexes have been investigated for DNA interaction, antibacterial and anticancer activity on human colon and breast cancer cells. [15][16][17][18] The copper(I) chelator MT-3 (metallothionein-3) was signicantly protecting cells from Cu-Ab toxicity compared to copper(II) chelator HSA (Human Serum Albumin). For this reason, +I state of Cu is as much biologically relevant as the +II state.…”

Section: Introductionmentioning

confidence: 99%

“…25 To the best of our knowledge, DFT calculations, DNA/BSA interaction, in vitro and in vivo anti-proliferative, cell cycle arrest, generation of ROS, Western blot and molecular modeling studies of bis(thiosemicarbazones)-based copper(I) complexes and their derivatives are scare in literature. 17 Based on the above information, we are prompted to target selected cancer cells by both in vitro and in vivo, and study their mechanism of action. To achieve this, we have synthesized new thiosemicarbazone based-copper(I) complexes.…”

Section: Introductionmentioning

confidence: 99%

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Copper complexes as prospective anticancer agents: in vitro and in vivo evaluation, selective targeting of cancer cells by DNA damage and S phase arrest

et al. 2018

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Copper complexes as prospective anticancer agents: in vitro and in vivo evaluation, selective targeting of cancer cells by DNA damage and S phase arrest

et al. 2018

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“…[14][15][16] To the best of our knowledge, in vitro antiproliferative, cell cycle arrest, generation of reactive oxygen species (ROS) and induction of apoptosis studies of copper(I)-phosphine complexes are scarce in literature. [17] Based on the above information, we are prompted to target A549 cancer cells by in vitro and study their biological mechanism of action for anticancer drug screening. To achieve this, we have synthesized new 3-substituted 1-pyridin-2-ylimidazo [1,5-a]…”

Section: Introductionmentioning

confidence: 99%

“…[ 14–16 ] To the best of our knowledge, in vitro antiproliferative, cell cycle arrest, generation of reactive oxygen species (ROS) and induction of apoptosis studies of copper(I)–phosphine complexes are scarce in literature. [ 17 ]…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structure, characterization and biological evaluation of 3‐substituted 1‐pyridin‐2‐ylimidazo[1,5‐a]pyridine‐based copper(I)–phosphine complexes for anticancer drug screening

Pathaw

Khamrang

Selvakumaran

et al. 2020

Applied Organom Chemis

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Copper(I) complexes of the types [Cu(N-N)(PPh 3) 2 ]NO 3 (LC41-LC44) and [Cu(N-N)(PPh 3)(NO 3)] (LC45) carrying 3-substituted 1-pyridine-2-ylimidazo[1,5-a]pyridine (N-N) derivatives and triphenylphosphine (PPh 3) ligands have been prepared. The synthesized copper(I)-phosphine complexes were fully characterized by NMR, IR, ESI-MS and UV-visible spectroscopy as well as by cyclic voltammetry. Selected structures such as LC42, LC43 and LC45 were additionally analysed by single-crystal X-ray method, which show that copper(I) centre adopts a highly distorted tetrahedral geometry. The 1 H and 13 C NMR spectral data of the complexes throw light on the nature of metal-ligand bonding. They display dπ-π* metal-to-ligand charge transfer (MLCT) transition and show quasireversible Cu I /Cu II metal oxidation. Among the copper(I)-phosphine complexes, LC41-LC44 exhibit moderate cytotoxicity (IC 50 : 24 h, 67-74 μM; 48 h, 58-70 μM) against human lung epithelial adenocarcinoma A549 cells, whereas LC45 displays the best activity (IC 50 : 24 h, 42 μM; 48 h, 34 μM) for A549 cancer cell line, which is better than that of the commercial antitumor drug cisplatin. All the complexes also displayed excellent selectivity by being relatively inactive against the human lung epithelial L132 normal cell line with selectivity index (SI) values ranging from 3.4 to 7.4. The complexes block cell cycle progression of A549 cells in G 0 /G 1 phase. FACSVerse analyses are suggestive of reactive oxygen species (ROS) generation and apoptotic cell death induced by the LC41, LC43 and LC45. The induction of apoptosis in A549 cells was shown by Annexin V with propidium iodide (PI) and 4 0 ,6-diamidino-2-phenylindole (DAPI) staining methods and established the ability of LC41, LC43 and LC45 to accumulate in the cell nuclei. Larica Pathaw and Themmila Khamrang contributed equally to this work.

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“…The complexes C 48 and C 49 strongly induced the apoptosis of Caco-2 cell model. The order of anticancer activity of the complexes was found to be C 49 > C 48 > C 50(Gonzalez-Ballesteros et al, 2016).Copper(I) complexes of N-aryl triaza phosphaadamantane and imidazolyl benzene derivativeThe study of in vitro cytotoxic activity of copper(I) complexes), [Cu(L)(PTA-PhR)](PF 6 ) (C 51 -C 53 ) (Fig.7) having NCN pincer (L) and N-aryl-1,3,5-triaza-7phosphaadamantane (PTA-PhR) ligand[L = 5-methoxy- 1,3-bis (1-methyl-1H-benzo[d]imidazol-2-yl)benzene)] against A549 (human lung), A375 (melanoma), MCF-7 (breast), LoVo (colon adenocarcinoma), HeLa cervical cancer cell lines, and HEK293 (non-malignant fibroblasts) showed higher antitumor activity (IC 50 0.98-21.57 μM)…”

mentioning

confidence: 96%

Anticancer Potency of Copper(I) Complexes Against a Range Cancer Cell Lines: A Review

Singh

Yadav

2021

J. Inst. Sci. Tech.

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The copper(I) complexes of N,N-diimine, N,O- and/or N, S-bidentate systems perform significant dose-dependent anticancer activity toward various cell lines viz. MCF-7, LNCap, PSN-1, A431, BxPC3, H157, A2780, HeLa, MDA-MB231, MGC-803 etc. The copper(I) complexes can cross the cellular plasmalemma that results in the accumulation of copper ion in the cancer cells, exhibit significant anticancer effect and overcome the multidrug resistance because these can slightly induce the DNA cleavage as a result of limited generation of reactive oxygen species (ROS). Copper(I) complexes exhibit significantly higher broad-spectrum antiproliferation and cell apoptosis via mitochondrial pathway than that of their corresponding Cu(II), Co(II), Pd(II), and Ni(II) complexes. The copper(I) complexes inhibit the cancer cells not only via ROS generation but also via DNA interactions possibly by attacking the sugar-phosphate backbone of DNA due to their oxidative and partial dissociation behavior. Copper(II/I) complexes are also able to cleave DNA by hydrolytic pathway and induce caspase-dependent-mitochondrial-mediated cell apoptosis by ROS production or blocking the progression of cell cycles. In many cases, the modification in organic moiety and the placement of electronegative substituent near the metallic center of complexes have been found to enhance their anticancer potency in a significant manner. Thus copper(I) complexes may be used as the better anticancer drugs with multiple modes of action compared to the copper(II) complexes due to having oxidative behavior and generation of empty site on copper(I) ion during partial dissociation.

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Synthesis, spectral characterization and X-ray crystallographic study of new copper(I) complexes. Antitumor activity in colon cancer

Cited by 10 publications

References 33 publications

Copper complexes as prospective anticancer agents: in vitro and in vivo evaluation, selective targeting of cancer cells by DNA damage and S phase arrest

Copper complexes as prospective anticancer agents: in vitro and in vivo evaluation, selective targeting of cancer cells by DNA damage and S phase arrest

Synthesis, structure, characterization and biological evaluation of 3‐substituted 1‐pyridin‐2‐ylimidazo[1,5‐a]pyridine‐based copper(I)–phosphine complexes for anticancer drug screening

Anticancer Potency of Copper(I) Complexes Against a Range Cancer Cell Lines: A Review

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