Stereospecific binding of chemically modified salen-type Schiff base complexes of copper(II) with DNA [salen = bis(salicyclidene)ethylenediamine]

Sato, Kousuke; Chikira, Makoto; Fujii, Yuki; Komatsu, Atsushi

doi:10.1039/c39940000625

Cited by 40 publications

(20 citation statements)

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“…1) were synthesized [21] by the reaction of 5-(triethylammoniummethyl)salicylaldehyde chloride, 1,2 phenylendiamine and copper(II) or zinc(II) acetate in a 2:1.1:1 molar ratio, in doubly distilled water, and isolated as perchlorate salts. The 5-(triethylammoniummethyl) salicylaldeide chloride ligand was prepared from 5-chloromethyl salicylaldeide [28] and triethylamine in THF.…”

Section: Methodsmentioning

confidence: 99%

“…ESR measurements on DNA-fibres [21] have revealed that the orientation of water-soluble cationic Salen-type Schiff base complexes of copper(II), relative to the DNA axis, changes by modification of the chain length bridging the two imino nitrogens in the complex. Such measurements allowed to conclude that the 1,2-phenylenediamine bridge enables the metal complex to intercalate DNA.…”

Section: Introductionmentioning

confidence: 99%

“…To further investigate the role of the metal ion in the interaction with DNA, in the present paper, we have synthesized the Cu(II) and Zn(II) complexes of 5-triethyl ammonium methyl salicylidene orto-phenylendiimine [21] and studied their interaction with native calf thymus DNA in aqueous solution.…”

Section: Introductionmentioning

confidence: 99%

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The interaction of native DNA with Zn(II) and Cu(II) complexes of 5-triethyl ammonium methyl salicylidene orto-phenylendiimine

Silvestri

Barone

Ruisi

et al. 2007

Journal of Inorganic Biochemistry

106

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The interaction of native calf thymus DNA with the Zn(II) and Cu(II) complexes of 5-triethyl ammonium methyl salicylidene ortophenylendiimine (ZnL 2+ and CuL 2+ ), in 1 mM Tris-HCl aqueous solutions at neutral pH, has been monitored as a function of the metal complex-DNA molar ratio by UV absorption spectrophotometry, circular dichroism (CD) and fluorescence spectroscopy. The results support for an intercalative interaction of both ZnL 2+ and CuL 2+ with DNA, showing CuL 2+ an affinity of approximately 10 times higher than ZnL 2+ . In particular, the values of the binding constant, determined by UV spectrophotometric titration, equal to 7.3 · 10 4 and 1.3 · 10 6 M À1 , for ZnL 2+ and CuL 2+ , respectively, indicate the occurrence of a marked interaction with a binding size of about 0.7 in base pairs. The temperature dependence of the absorbance at 258 nm suggests that both complexes strongly increase the DNA melting temperature (Tm) already at metal complex-DNA molar ratios equal to 0.1. As evidenced by the quenching of the fluorescence of ethidium bromide-DNA solutions in the presence of increasing amounts of metal complex, ZnL 2+ and CuL 2+ are able to displace the ethidium cation intercalated into DNA. A tight ZnL 2+ -DNA and CuL 2+ -DNA binding has been also proven by the appearance, in both metal complex-DNA solutions, of a broad induced CD band in the range 350-450 nm. In the case of the CuL 2+ -DNA system, the shape of the CD spectrum, at high CuL 2+ content, is similar to that observed for w-DNA solutions. Such result allowed us to hypothesize that CuL 2+ induces the formation of supramolecular aggregates of DNA in aqueous solutions.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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The interaction of native DNA with Zn(II) and Cu(II) complexes of 5-triethyl ammonium methyl salicylidene orto-phenylendiimine

Silvestri

Barone

Ruisi

et al. 2007

Journal of Inorganic Biochemistry

106

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“…The mode of interaction of Cu(II) Schiff bases with DNA has been extensively investigated. It has been shown that the mode of binding of the metal complex to DNA depends on the substituent in the phenyl ring as well as on the nature of diamine used for forming the Schiff base [16]. Griffin and coworkers have investigated DNA binding/cleaving properties of 26 salen complexes of Mn(III) in the presence of terminal oxidants using DNA affinity cleaving techniques and found that DNA cleaving efficiency varies with both the structure and stereochemistry of the bridging substituent [17].…”

Section: Introductionmentioning

confidence: 99%

DNA damage induced by a chromium(III) Schiff base complex is reversible under physiological condition

Vaidyanathan

Weyhermüller

Nair

et al. 2005

Journal of Inorganic Biochemistry

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“…19 Sato et al reported stereospecific binding of chemically modified Salen-type Schiff-base complexes of copper(II) with DNA by ESR technique, and found the substitution of the phenylene or naphthalene bridging group for the ethylene group transforming the complexes from groove binders to intercalators. 20 Bhattacharya et al reported a new water-soluble Co-salen complex that can cleave DNA spontaneously under ambient aerobic conditions. The cleavage is further enhanced by including dithiothreitol in the reaction buffer.…”

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confidence: 99%

Fluorescence Spectral Study of Interaction of Water-soluble Metal Complexes of Schiff-base and DNA

et al. 2001

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Recent years have seen growing interest in the employment of small molecules for deoxyribonucleic acid (DNA) studies. [1][2][3][4][5][6] DNA might interact with small molecules according to three possible patterns: (1) The electrostatic interaction, which extends the external wall of DNA double helix and lacks selectivity; (2) Interaction with grooves of DNA; and (3) intercalation model. Some metal complexes such as Cuphenanthroline, Fe-EDTA, Mn-porphyrin and Ru-polypyridyl, can cleave or bind DNA in the presence of co-oxidants such as peroxides. 7-11 Schiff-bases are potential anticancer drugs, so they are currently studied extensively. [12][13][14][15][16] The anticancer activity of these complexes tends to increase when they complex with metal ions. 17,18 21 Gravert and his co-workers investigated DNA binding/cleaving properties of twenty-six salen complexes of Mn(III) in the presence of terminal oxidants using DNA affinity cleaving techniques, and found DNA cleaving efficiency varying with both the structure and stereochemistry of the bridge. 23 We reported metal complexes of salen interaction of DNA and found that Co-salen showed the strongest interaction of DNA and that the interactive model between Co-salen is an intercalative one. 24 This paper reports on the fluorescence spectra characteristics of water-soluble metal complexes of Schiff-base and their interactive effects on calf thymus DNA under physiological condition. The interactive pattern between metal complexes of Schiff-base and DNA was investigated by UV spectroscopy, KI quenching and competitive binding of ethidium bromide (EB) and Mn-Schiff-base with DNA.The effects of salt concentration and pH of medium on interaction of DNA and metal complexes of Schiff-base have also been investigated. Mn-Schiff-bases as a novel fluorescence probe have potential analytical applications for the determination of traces of DNA. Experimental ReagentsWater-soluble Metal-Schiff-base complexes ( The fluorescence spectral characteristics and the interaction of several water-soluble metal complexes of Schiff-base with DNA are described. Among the complexes tested, Mn-Schiff-base bound to DNA showed a marked decrease in the fluorescence intensity with a blue shift of the excitation and emission peaks. Some hypochromism in the UV absorption spectra was also observed. KI quenching and competitive binding to DNA between Mn-Schiff-base and ethidium bromide (EB) were studied in connection with other experimental observations to show that the interactive model between Mn-Schiff-base and DNA is an intercalative one. The pH and salt effect on the fluorescence properties was also investigated. The linear relationship between F/F0 and the concentration of calf thymus DNA covers 3.0 × 10 -6 -2 × 10 -4 mol L -1 , which can be utilized for determining traces of calf thymus DNA with a detection limit of 8.0 × 10 -7 mol L -1 in base pairs.

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Stereospecific binding of chemically modified salen-type Schiff base complexes of copper(II) with DNA [salen = bis(salicyclidene)ethylenediamine]

Cited by 40 publications

References 5 publications

The interaction of native DNA with Zn(II) and Cu(II) complexes of 5-triethyl ammonium methyl salicylidene orto-phenylendiimine

The interaction of native DNA with Zn(II) and Cu(II) complexes of 5-triethyl ammonium methyl salicylidene orto-phenylendiimine

DNA damage induced by a chromium(III) Schiff base complex is reversible under physiological condition

Fluorescence Spectral Study of Interaction of Water-soluble Metal Complexes of Schiff-base and DNA

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