Antibacterial, DNA interaction and cytotoxic activities of pendant-armed polyamine macrocyclic dinuclear nickel(II) and copper(II) complexes

Arthi, P.; Haleel, Azees Khan; Srinivasan, Pappu; Prabhu, D.; Chinnasamy, Arulvasu; Rahiman, A. Kalilur

doi:10.1016/j.saa.2014.03.058

Cited by 33 publications

(11 citation statements)

References 43 publications

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“…dNa intercalation study. It was reported that the several anticancer agents and other bioactive compounds can bind DNA and, thus, damage its structure resulting in the impairment of its function leading to cell death [33].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of the novel cage amides and imides and evaluation of their antibacterial and antifungal activity

Palchykov¹,

Gaponov²,

Manko³

et al. 2022

Ukr.Biochem.J.

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Cage amides and imides bearing bicyclo[2.2.1]- and bicyclo[2.2.2]-subunits were synthesized and evaluated both for antimicrobial activity toward five key ESKAPE pathogenic bacteria: one Gram‐positive bacteria methicillin‐resistant Staphylococcus aureus (ATCC 43300), four Gram‐negative bacteria Escherichia coli (ATCC 25922), Klebsiella pneumoniae (ATCC 700603), Acinetobacter baumannii (ATCC 19606) and Pseudomonas aeruginosa (ATCC 27853) and for antifungal activity towards pathogenic fungal strains Candida albicans (ATCC 90028) and Cryptococcus neoformans var. Grubii (H99; ATCC 208821). Compound VP-4539 with bicyclo[2.2.2]octene motif demonstrated the highest cytotoxic activity towards C. neoformans, while human keratinocytes of HaCaT line, murine fibroblasts of Balb/c 3T3 line and mitogen-activated lymphocytes of peripheral human blood were found to be tolerant to its action. VP-4539 compound did not intercalate into salmon sperm DNA indicating that its cytotoxicity is not related to intercalation into nucleic acid. Keywords: antifungal, antimicrobial, bicyclo[2.2.1]heptane, bicyclo[2.2.2]octene, cytotoxicity, DNA intercalation, human keratinocytes, lymphocytes, сage compounds

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Section: Resultsmentioning

confidence: 99%

Synthesis of the novel cage amides and imides and evaluation of their antibacterial and antifungal activity

Palchykov¹,

Gaponov²,

Manko³

et al. 2022

Ukr.Biochem.J.

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“…The ligands 2,2'-(benzoyliminodiethylene)bissalicylidene (L 1 ), 2,2'-(4-nitrobenzoyliminodiethylene)bissalicylidene (L 2 ) and 2,2'-(3,5-dinitrobenzoyliminodiethylene)bissalicylidene (L 3 ) were prepared by following our recently reported procedure [23] .…”

Section: Synthesis Of Ligandsmentioning

confidence: 99%

Synthesis, Antibacterial, Docking and Anticancer Evaluation of N-Substituted Benzoyl Derivatives

Arthi¹,

Shobana²,

Srinivasan³

et al. 2014

Journal of the Chosun Natural Science

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A series of N-benzoylated ligands incorporating three different benzoyl groups 2,2'-(benzoyliminodiethylene)-4substituted phenols (L 1,4,7 ), 2,2'-(4-nitrobenzoyliminodiethylene)-4-substituted phenols (L 2,5,8 ) and 2,2'-(3,5dinitrobenzoyliminodiethylene)-4-substituted phenols (L 3,6,9 ) were synthesized and characterized by IR, 1 H NMR, 13 C NMR and mass spectroscopy. The In vitro antibacterial activity of investigated ligands were tested against human pathogenic bacteria such as four Gram (-) Enterococcus faecalis, Pseudomonas aeruginosa, Staphylococcus aureus, Vibrio cholera, Vibrio harveyi and two Gram (+) Staphylococcus aureus, Streptococcus mutans. Furthermore, docking studies were undertaken to gain insight into the possible binding mode of these compounds with the binding site of the topoisomerase II (PDB: 4FM9) enzyme which is involved in DNA superhelicity and chromosome seggregation. The Nbenzoylated derivatives L 5, 7, 8 have significant anticancer activity as Topoisomerase inhibitors. The ligands L 5 and L 8 were tested for their anticancer activity against human liver adenocarcinoma (HepG2) cell line with the MTT assay.

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“…Nickel was not considered as a metal of biological importance until the discovery of the presence of nickel in metalloproteinase such as 2-mercaptoethanol-inhibited urease and Ni/Fe hydrogenases by Zerner . The interest toward the bioinorganic chemistry of nickel complexes has been rapidly expanded because of their natural biochemical functions and their antiepileptic, anticonvulsant, antimicrobial, and antiproliferative activity …”

Section: Introductionmentioning

confidence: 99%

“…5 The interest toward the bioinorganic chemistry of nickel complexes has been rapidly expanded because of their natural biochemical functions and their antiepileptic, anticonvulsant, antimicrobial, and antiproliferative activity. 6 Thiosemicarbazones (TSCs) and their derivatives have attracted scholarly attention because of different aspects of metal complexing ability leading to splendid fungicidal, antibacterial, anti-inflammatory, antiviral, and antitumor properties. 7 The first discovered thiosemicarbazone-based compound with potent anticancer activity was 2-formylpyridine thiosemicarbazone.…”

Section: ■ Introductionmentioning

confidence: 99%

Biocompatibility, in Vitro Antiproliferative, and in Silico EGFR/VEGFR2 Studies of Heteroleptic Metal(II) Complexes of Thiosemicarbazones and Naproxen

Bharathi

Mahendiran

Raju

et al. 2019

Chem. Res. Toxicol.

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Eight heteroleptic nickel(II) and copper(II) complexes of the type [M(L 1−4 )(nap) 2 ] (1−8), where L 1−4 = 2-(1-(4-substitutedphenyl)ethylidene)hydrazinecarbothioamide, nap = naproxen, and M = Ni(II) or Cu(II), have been synthesized and characterized. UV−vis and EPR spectral studies showed distorted octahedral geometry around metal(II) ions. The cyclic voltammogram of complexes 1−8 displayed an irreversible one-electron transfer process in the cathodic region (E pc = −0.66 to −1.43 V), and nickel(II) complexes 1−4 displayed an irreversible one-electron oxidation process in the anodic region (E pa = 0.75 to 1.10 V). The obtained magnetic moment values (1.82−1.93 μ B ) for copper(II) complexes 5−8 indicate distortion from octahedral geometry, which is further supported by EPR studies. The geometry of the complexes is retained in both solid and solution phases as evidenced from UV−vis and EPR studies. All the complexes showed stability for almost 72 h in biologically relevant solutions. The reducing ability of the copper(II) complexes in the presence of ascorbic acid was analyzed by UV−vis and cyclic voltammetry techniques, which indicates the reduction of the copper(II) to a copper(I) center, and possible interaction within the cells. An in vitro antiproliferative study revealed the nontoxic nature of complexes to normal human dermal fibroblast (NHDF) up to a concentration of 100 ng/mL. The antiproliferative activity of the complexes was tested against three cancerous (human breast adenocarcinoma (MCF-7), hepatoma (HepG2), and lung (A549)) cell lines using MTT reduction assay, which showed enhanced activity for complexes 4 and 8 containing the hydrophobic substituent. Apoptotic and cellular uptake studies showed that complex 8 is readily taken up by HepG2 cell lines and induces ROS-mediated mitochondrial and caspase-dependent apoptosis. In silico studies indicated hydrogen bonding, hydrophobic, and π-pair (π−π, π−σ, and π−cation) interactions between the complexes and EGFR/VEGFR2 kinase receptors.

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Antibacterial, DNA interaction and cytotoxic activities of pendant-armed polyamine macrocyclic dinuclear nickel(II) and copper(II) complexes

Cited by 33 publications

References 43 publications

Synthesis of the novel cage amides and imides and evaluation of their antibacterial and antifungal activity

Synthesis of the novel cage amides and imides and evaluation of their antibacterial and antifungal activity

Synthesis, Antibacterial, Docking and Anticancer Evaluation of N-Substituted Benzoyl Derivatives

Biocompatibility, in Vitro Antiproliferative, and in Silico EGFR/VEGFR2 Studies of Heteroleptic Metal(II) Complexes of Thiosemicarbazones and Naproxen

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