Oxidative damage to DNA by 1,10-phenanthroline/l-threonine copper (II) complexes with chlorogenic acid

Wang, Yong; Zhang, Xiaoyan; Zhang, Qianru; Yang, Zhousheng

doi:10.1007/s10534-009-9284-6

Cited by 27 publications

(18 citation statements)

References 35 publications

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“…The quenching constants were comparable to the values reported for [Cu-Phen-Thr] complex (K sv = 15.63 9 10 4 M -1 ). The result explained that [Cu-Phen-Tyr] complex has a stronger affinity than [Cu-Phen-Thr] complex (Wang et al 2010), this resulted from L-tyrosine contained aromatic structure. The fluorescence titration data were analyzed to construct the binding curves, and from these curves, binding constants as well as binding site sizes were estimated.…”

Section: Fluorescence Studiesmentioning

confidence: 97%

“…Recent report from our laboratory has shown that 1, 10-phenanthroline/Lthreonine copper (II) complexes with chlorogenic acid as biological reductant can induce DNA oxidative damage (Wang et al 2010). Gallic acid (GA), a naturally occurring plant phenol, was also found to be a strong antioxidant in emulsion or lipid systems (Hirose et al 1993).…”

Section: Introductionmentioning

confidence: 99%

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Copper (II) complex of 1,10-phenanthroline and l-tyrosine with DNA oxidative cleavage activity in the gallic acid

2011

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Copper (II) complex of formulation [Cu-Phen-Tyr](H(2)O)](ClO(4)) (Phen = 1,10-phenanthroline, L: -Tyr = L: -tyrosine), has been prepared, and their induced DNA oxidative cleavage activity studied. The complex binds to DNA by intercalation, as deduced from the absorption and fluorescence spectral data. Scatchard plots constructed from the absorption titration data gave binding constant 2.44 × 10(4) M(-1) of base pairs. Extensive hypochromism, broadening, and red shifts in the absorption spectra were observed. Upon binding to DNA, the fluorescence from the DNA--ethidium bromide system was efficiently quenched by the copper (II) complex. Stern--Volmer quenching constant 0.61 × 10(3) M(-1) obtained from the linear quenching plots. [Cu-Phen-Tyr] complex efficiently cleave the supercoiled DNA to its nicked circular form with gallic acid as biological reductant at appropriate complex concentration. The gallic acid as reductant could observably improve copper (II) complex to DNA damage. The pseudo-Michaelis-Menten kinetic parameters (k(cat), K(M)) were calculated to be 1.32 h(-1) and 5.46 × 10(-5) M for [Cu-Phen-Tyr] complex. Mechanistic studies reveal the involvement of superoxide anions and hydroxyl radical (HO(·)) as the reactive species under an aerobic medium.

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Section: Fluorescence Studiesmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

Copper (II) complex of 1,10-phenanthroline and l-tyrosine with DNA oxidative cleavage activity in the gallic acid

2011

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“…This finding is in accordance with studies that have indicated that higher levels of reactive oxygen species have a destructive effect on DNA and some proteins and that the associated oxidative stress can trigger apoptosis (Simon et al 2000;Sandstrom et al 1994). It is particularly interesting, that the aliphatic 1,4-dithiane complex 14 induced high ROS concentrations similar to those of complex 8, although it does not contain an aromatic diimino donor ligand, whose abilitiy to invoke ROS through either irradiation or through reactions with cellular reductants is well-documented (Levina et al 2009;Wang et al 2010).…”

Section: Measurements Of Reactive Oxygen Species (Ros)mentioning

confidence: 99%

Antileukemic activity and cellular effects of rhodium(III) crown thiaether complexes

et al. 2011

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The cytostatic properties of novel rhodium(III) thiacrown ether complexes [RhCl(LL)([9]aneS(3))](n+) with either aromatic κ(2)N ligands (n = 2) or anionic chelate ligands (n = 1) have been investigated for the human cancer cell lines HT-29 and MCF-7 and for immortalized HEK-293 cells. Taken together with literature IC(50) values for analogous complexes with polypyridyl ligands or 1,4-dithiane, the in vitro assays indicate that dicationic complexes with soft κ(2)N (imino) or κ(2)S (thiaether) ligands exhibit significantly higher antiproliferative effects than those with hard κ(2)N (amino) ligands. Dicationic complexes are more active than monocationic complexes with similar ligands. Pronounced apoptosis-inducing properties towards Jurkat cells were established for complexes with LL = bpm, dpq, and 1,4-dithiane. The order of activity (bpm > 1,4-dithiane > dpq > bpy) contrasts to that observed for adhesive cancer cells (bpm > bpy, 1,4-dithiane > dpq). Necrosis is insignificant in all cases. The percentage of Jurkat cells exhibiting apoptosis after 24 or 48 h incubation periods is directly correlated to the percentage of cells exhibiting high levels of reactive oxygen species. As established by online monitoring with a sensor chip system, treatment of MCF-7 cells with the bpm and 1,4-dithiane complexes leads to a significant and permanent concentration-dependent decrease in oxygen consumption and cellular adhesion.

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“…However, a very few copper carboxylates have been reported so far with alpha glucosidase, acetylcholine and butyrylcholine esterases inhibition activity. [22][23][24][25] Since enzyme targeting is potential therapy in modern era of medicinal research therefore combining an essential metal and two different organic ligands together in a single molecule to develop lifesaving drugs could be attractive solution. Organic ligands in these complexes affect and regulate their activity by neutralizing the charge on copper ion and facilitating the transport across the cell membranes.…”

Section: Introductionmentioning

confidence: 99%

New Bioactive Heteroleptic Copper(II) Carboxylates: Structure, Enzymatic and DNA-Binding Studies

Mushtaq

Ali

Tahir

et al. 2017

ACSi

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Two new binuclear O-bridged copper(II) carboxylates with chemical formulas [Cu 2 (3-ClC 6 H 4 CH 2 COO) 4 (phen) 2 ] (1) and [Cu 2 (3-ClC 6 H 4 CH 2 COO) 4 (bipy) 2 ] (2) where phen = 1,10-phenanthroline and bipy = 2,2'-bipyridine have been synthesized and characterized by FT-IR, UV-Visible spectroscopy, CHN analysis and single crystal XRD. The results revealed distorted square pyramidal geometry around each copper atom of 1 and 2. The DNA interaction studies showed strong binding with K b = 5.07 × 10 3 and 4.62 × 10 3 M -1 for 1 and 2, respectively. Both complexes showed strong enzyme inhibition, i.e., 70% and 90% for α-glucosidase with IC 50 = 34.6 and 30.1 μM for 1 and 2, respectively, where acarbose was employed as control. However, both the complexes were found inactive against α-amylase. Using galantamine hydrobromide as control, 1 showed moderate inhibition activity (47%) with IC 50 = 179.4 μM for acetylcholine esterase whereas 2 showed strong inhibition activity (76%) with IC 50 = 95.8 μM for butyrylcholine esterase. The data reflects active anti-diabetic and anti-Alzheimer's nature of the synthesized complexes.

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Oxidative damage to DNA by 1,10-phenanthroline/l-threonine copper (II) complexes with chlorogenic acid

Cited by 27 publications

References 35 publications

Copper (II) complex of 1,10-phenanthroline and l-tyrosine with DNA oxidative cleavage activity in the gallic acid

Copper (II) complex of 1,10-phenanthroline and l-tyrosine with DNA oxidative cleavage activity in the gallic acid

Antileukemic activity and cellular effects of rhodium(III) crown thiaether complexes

New Bioactive Heteroleptic Copper(II) Carboxylates: Structure, Enzymatic and DNA-Binding Studies

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