Synthesis, characterization and anticancer activity of new palladacycles derived from chiral α‐diimines

Cruz, S. Cruz; Bernès, Syl­vain; Sharma, Pankaj; Vázquez, Rosa A.; Hernández, Guadalupe; Portillo, Roberto; Tolentino, Rey Gutiérrez

doi:10.1002/aoc.1570

Cited by 16 publications

(7 citation statements)

References 45 publications

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“…This refers to higher biological activity of primary amine metallacycles than secondary amines due to the possibility of being involved in hydrogen bonds through the NH 2 group . Although the IC 50 values of complexes against MCF‐7 cells are close to or higher than cisplatin, they are comparable with other similar palladium complexes …”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization and molecular docking of new C,N‐palladacycles containing pyridinium‐derived ligands: DNA and BSA interaction studies and evaluation as anti‐tumor agents

Karami

Jamshidian

Zakariazadeh

2019

Applied Organom Chemis

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Four new monomeric Pd (II) complexes with formulas [Pd(C,N)‐(2′‐NH2C6H4)C6H4 (N3)(L)] (A), (B) and [Pd(C,N)‐C6H4CH2NH(C4H9)(N3)(L)] (C), (D), [L = isonicotinamide for (A) and (C), L = 4‐N,N‐dimethylaminopyridine for (B) and (D)] have been synthesized using four initial dimers [Pd2{(C,N)‐(2′‐NH2C6H4)C6H4}2(μ‐OAc)2] (1), [Pd2{(C,N)‐ (2′‐NH2C6H4)C6H4}2(μ‐N3)2] (3) for A and C, and [Pd2{(C,N)‐C6H4CH2NH(C4H9)}2(μ‐OAc)2] (2) and [Pd2{(C,N)‐C6H4CH2NH(C4H9)}2(μ‐N3)2] (4) for B and D. Then synthesized complexes have been characterized by Fourier transform‐infrared, NMR spectroscopy and thermal gravimetric‐differential thermal analysis. Furthermore, UV–Vis spectroscopy, fluorescence spectroscopy, circular dichroism (CD) and helix melting temperature measurements have been employed to study the binding interaction of them with calf thymus‐deoxyribonucleic acid (DNA). The results reveal that all synthesized complexes can interact with DNA via groove‐binding mode. Bovine serum albumin (BSA)‐binding studies have been carried out using UV–Vis spectroscopy, emission titration and CD. However, competitive binding studies using warfarin, ibuprofen and digoxin on site markers demonstrated that the complexes bind to different sites on BSA. The results also indicated that the binding site was mainly located within site‐III for complex A, and site‐I for complexes B, C and D of BSA. In addition, molecular docking studies have been executed to determine the binding site of the DNA and BSA with complexes. Eventually, in vitro cytotoxicity of synthesized palladium complexes and cisplatin were carried out against human promyelocytic leukemia cancer (Hela) and breast cancer (MCF‐7) cell lines. Pursuant to the IC50 values, the cytotoxicity of complexes against MCF‐7 was more than Hela.

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Section: Resultsmentioning

confidence: 99%

Synthesis, characterization and molecular docking of new C,N‐palladacycles containing pyridinium‐derived ligands: DNA and BSA interaction studies and evaluation as anti‐tumor agents

Karami

Jamshidian

Zakariazadeh

2019

Applied Organom Chemis

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“…28). 148 The complexes were tested in vitro against a series of human cancer cell lines U251 (CNS), PC-3 (prostate), K562 (leukaemia), HCT-15 (colon) and MCF-7 (breast). Relative to cisplatin, the palladium complexes were less effective although in certain cases appreciable cytotoxicity was observed (mainly against U251 and K562 cancer cell lines).…”

Section: Nitrogen Based Multidentate Ligandsmentioning

confidence: 99%

Anti-cancer palladium complexes: a focus on PdX₂L₂, palladacycles and related complexes

2014

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Much success has been achieved with platinum-based chemotherapeutic agents, i.e. through interactions with DNA. The long-term application of Pt complexes is thwarted by issues, leading scientists to examine other metals such as palladium which could exhibit complementary modes of action (given emphasis wherever known). Over the last 10 years several research groups have focused on the application of an eclectic array of palladium complexes (of the type PdX2L2, palladacycles and related structures) as potential anti-cancer agents. This review therefore provides readers with an up to date account of the advances that have taken place over the past several decades.

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“…Although these advantages of palladocycles based on multidentate ligands has been successfully used in catalysis and organic synthesis for several decades, in the field of palladium(II)-based anticancer drug design this is a relatively new and unexplored strategy. However, already known cyclopalladated complexes featuring functionalized thiosemicarbazone, diimine, terpyridine, and bis(2-pyridylmethyl)amine , ligands and single examples of related derivatives with other skeletons, − including 6-phenyl-2,2′-bipyridine complexes with auxiliary NHC ligands possessing high in vivo anticancer activity, show a lot of promise (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Highly Cytotoxic Palladium(II) Pincer Complexes Based on Picolinylamides Functionalized with Amino Acids Bearing Ancillary S-Donor Groups

et al. 2017

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The reactions of picolinyl and 4-chloropicolinyl chlorides with methyl esters of S-methyl-l-cysteine, l- and d-methionine, and l-histidine afforded a series of functionalized carboxamides, which readily formed pincer-type complexes upon interaction with PdCl(NCPh) in solution under mild conditions. The direct cyclopalladation of the ligands derived was also accomplished in the solid phase, in particular, mechanochemically, although it was complicated by the partial deactivation of the starting amides. The resulting complexes with 5,5- and 5,6-membered fused metallocycles were fully characterized by IR and NMR spectroscopy, including variable-temperature and 2D-NMR studies. In the case of some cysteine- and methionine-based derivatives, the realization of κ-N,N,S-coordination was supported by X-ray diffraction. The cytotoxic effects of these complexes were examined on HCT116, MCF7, and PC3 human cancer cell lines as well as HEK293 as a representative of normal cells. The comparative studies allowed us to determine that the presence of the sulfide ancillary donor group is crucial for cytotoxic activity of this type of Pd(II) complexes. The main structure-activity relationships and the most promising palladocycles were outlined. The additional studies by gel electrophoresis revealed that 4-chloropicolinyl derivatives, despite the nature of an amino acid, can bind with DNA and inhibit topoisomerase I activity.

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Synthesis, characterization and anticancer activity of new palladacycles derived from chiral α‐diimines

Cited by 16 publications

References 45 publications

Synthesis, characterization and molecular docking of new C,N‐palladacycles containing pyridinium‐derived ligands: DNA and BSA interaction studies and evaluation as anti‐tumor agents

Synthesis, characterization and molecular docking of new C,N‐palladacycles containing pyridinium‐derived ligands: DNA and BSA interaction studies and evaluation as anti‐tumor agents

Anti-cancer palladium complexes: a focus on PdX₂L₂, palladacycles and related complexes

Highly Cytotoxic Palladium(II) Pincer Complexes Based on Picolinylamides Functionalized with Amino Acids Bearing Ancillary S-Donor Groups

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Synthesis, characterization and anticancer activity of new palladacycles derived from chiral α‐diimines

Cited by 16 publications

References 45 publications

Synthesis, characterization and molecular docking of new C,N‐palladacycles containing pyridinium‐derived ligands: DNA and BSA interaction studies and evaluation as anti‐tumor agents

Synthesis, characterization and molecular docking of new C,N‐palladacycles containing pyridinium‐derived ligands: DNA and BSA interaction studies and evaluation as anti‐tumor agents

Anti-cancer palladium complexes: a focus on PdX2L2, palladacycles and related complexes

Highly Cytotoxic Palladium(II) Pincer Complexes Based on Picolinylamides Functionalized with Amino Acids Bearing Ancillary S-Donor Groups

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Anti-cancer palladium complexes: a focus on PdX₂L₂, palladacycles and related complexes