Synthesis, crystal structures and DNA-binding properties of dinuclear complexes with macrocyclic ligands

Cheng, Qingrong; Zhou, Hong; Pan, Zhiquan; Chen, Jinzhong

doi:10.1007/s11243-012-9602-7

Cited by 10 publications

(5 citation statements)

References 32 publications

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“…They are applied as antitumor, 2 antiviral (including HIV activity), 3,4 antibacterial, antifungal or antimalarial agents. [14][15][16] In particular, many studies were focused on binuclear copper complexes due to their presence in metalloproteinase as well as their affinity for DNA. Copper is a physiologically important metal that plays a significant role in endogenous oxidative DNA damage associated with aging and cancer.…”

Section: Introductionmentioning

confidence: 99%

Correlations between the in vitro antiproliferative activity, structure and thermal stability of some macrocyclic dinuclear Cu(II) complexes

Tanasković¹,

Antonijević-Nikolić²,

Holló

et al. 2014

JSCS

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Seven macrocyclic dinuclear Cu(II) complexes with tpmc = = N, N',N",N'"-tetrakis(2-pyridylmethyl)-1,4,8,11-tetraazacyclotetradecane of coordination formulae [Cu 2 tpmc](ClO 4 ) 4 (1), [Cu 2 (X)tpmc](ClO 4 ) 3 ·nH 2 O, X= F -, n = 0 (2), X = Cl -, n = 1 (3), X = Br -, n = 0 (4), X= I -, n = 1 (5), X = = NO 2 -, n = 0 (6), [Cu 2 (NCS) 2 tpmc](ClO 4 ) 2 (7) were evaluated for their cytotoxic activity against human cervix adenocarcinoma (HeLa), human melanoma (Fem-x) and human colon carcinoma (LS174) cell lines. The results were compared with the corresponding data for the cis-diamminedichloridoplatinum(II) (CDDP) as referent cytostatic, as well as with the free ligands and the solvent dimethyl sulfoxide (DMSO) as controls. The complexes showed considerable antiproliferative effect, although significantly less than CDDP. The thermal decomposition pattern of the complexes was determined by simultaneous TG/DSC measurements. The thermal stability of the compounds 2-7 followed the trend of their antiproliferative activity against the HeLa cell line, as well as their corresponding stability constants. The highest thermal stability and cytotoxicity belonged to complex [Cu 2 tpmc](ClO 4 ) 4 , with no anionic coligand. Complex [Cu 2 (NO 2 )tpmc](ClO 4 ) 3 exhibited a selective cytotoxicity against LS174 cells, at the level of the most active [Cu 2 tpmc](ClO 4 ) 4 .

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Section: Introductionmentioning

confidence: 99%

Correlations between the in vitro antiproliferative activity, structure and thermal stability of some macrocyclic dinuclear Cu(II) complexes

Tanasković¹,

Antonijević-Nikolić²,

Holló

et al. 2014

JSCS

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“…The molecular structure of 1 is analogous to the one in literature by a single‐step [2+2] condensation reaction of 4‐methyl‐2,6‐diformylphenol and 1,3‐ diaminopropane in the presence of Cu(ClO 4 ) 2 ⋅ 6H 2 O [17] . The Cu(II) centers are penta‐coordinated, and the apical positions are occupied by the perchlorate oxygens in the opposite direction.…”

Section: Resultsmentioning

confidence: 68%

Macrocyclic Complexes Derived from 2,6‐Diformyl‐4‐X‐phenol: Substituent Effects and Phosphate Hydrolysis Activity

Wang

Mao

Wu³

et al. 2021

ChemistrySelect

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Two 20‐membered macrocyclic complexes, [Cu2L1(ClO4)2] (1) and [Ni2L2(ClO4)2(H2O)2][Cu2L2(H2O)2](ClO4)2 (2) (where H2L1 and H2L2 are the condensation products of ɑ, ω‐amine with 3,3′‐((propane‐1,3‐diylbis(azanylylidene)) bis(methanylylidene))bis(5‐X‐2‐hydroxybenzaldehyde)), have been synthesized and characterized by X‐ray diffractions single crystal structure analysis. The results indicated that the structures of two complexes are symmetrical. In complex 1, the geometry around each copper(II) center is a slightly distorted square pyramidal with structural index parameter τ=0.062 for Cu1 and 0.067 for Cu2, the distance between Cu1 and Cu2 is 3.1075 Å. Complex 2 contains two similar macrocyclic units (A and B), the metal‐metal distances in A and B are 3.0760 and 3.0922 Å, respectively. The interaction between the complexes and calf thymus (CT‐DNA) were investigated by spectroscopic method. The phosphate hydrolysis activities of the complexes were examined using 4‐nitrophenyl phosphate disodium salt hexahydrate (pNPP) as the substrate. The corresponding catalytic rate constant (kcat) at pH 7.2 are 2.14×10−5 and 2.85×10−5 s−1, respectively, 104 times faster than the spontaneous hydrolysis of phosphate monoester.

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“…The absorption band v(C=S) was observed at 1490 cm −1 , and the above band appears nearly at the same position as found in the free ligand, meaning non coordination of thioimide sulfur (Singh et al , 2006). Also, the IR of the complex (L-Zn) divulged absorption bands at 3446 cm −1 assigned for v(NH) groups, and the characteristic band for v(C=N) shifted from 1593 cm −1 in the uncoordinated ligand to 1614 cm −1 in the complex (L-Zn), indicating that the nitrogen atoms in the macroligand are coordinated with zinc ions (Lodeiro et al , 2003; Zeng et al , 1998). In addition, the absorption peaks for v(C=S), which appear at 1482 cm −1 , indicate that sulfur is not coordinating with the zinc ion (Singh et al , 2006), as shown in Figure 2.…”

Section: Resultsmentioning

confidence: 99%

Anti-corrosive agents based benzil-thiocarbohydrazone macrocyclic ligand-derived Cu (II) and Zn (II) chelates: template synthesis and physically admixing with epoxy coating

Elgammal

Eliwa

Goomaa

et al. 2023

PRT

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Purpose This paper aims to focus on the synthesis of the macrocyclic complexes (Cu and Zn) and their applications as anticorrosive materials in epoxy paint formulation for surface coating application. Design/methodology/approach A selected macrocyclic Cu(II) and Zn(II) complexes were prepared via template synthesis and characterized using Fourier transform infrared, thermal gravimetric analysis, scanning electron microscope, flexibility, hardness and adhesion of coating films prepared using epoxy paint. Findings The corrosion resistance of the epoxy-painted films was improved due to the incorporation of the Zn and Cu complexes into the formulation. Originality/value It was found that the metal complex-based formulation with Cu(II) and Zn(II) had outperformed the sample blank.

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Synthesis, crystal structures and DNA-binding properties of dinuclear complexes with macrocyclic ligands

Cited by 10 publications

References 32 publications

Correlations between the in vitro antiproliferative activity, structure and thermal stability of some macrocyclic dinuclear Cu(II) complexes

Correlations between the in vitro antiproliferative activity, structure and thermal stability of some macrocyclic dinuclear Cu(II) complexes

Macrocyclic Complexes Derived from 2,6‐Diformyl‐4‐X‐phenol: Substituent Effects and Phosphate Hydrolysis Activity

Anti-corrosive agents based benzil-thiocarbohydrazone macrocyclic ligand-derived Cu (II) and Zn (II) chelates: template synthesis and physically admixing with epoxy coating

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