DNA-binding studies and antioxidant activities of two-, three- and four-coordinate silver(<scp>i</scp>) complexes containing bis(2-benzimidazolyl)aniline derivatives

Wu, Huilu; Zhang, Yanhui; Chen, Chengyong; Zhang, Jiawen; Bai, Yuchen; Shi, Furong; Wang, Xiaoli

doi:10.1039/c4nj00503a

Cited by 47 publications

(13 citation statements)

References 58 publications

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“…From this case, it is concluded that the ortho‐ nitrogen atom of the pyridine moiety of 2py PyrdC takes part in silver‐ion binding, possibly by forming an additional interaction. This situation is in line with the different coordination numbers of the silver ions (2–4)29 and can explain the changes in silver‐ion binding for the isomeric pyridine residues in silver‐mediated PyrdC–PyrdC base pairs.…”

Section: Resultssupporting

confidence: 66%

Pyrrolo‐dC Metal‐Mediated Base Pairs in the Reverse Watson–Crick Double Helix: Enhanced Stability of Parallel DNA and Impact of 6‐Pyridinyl Residues on Fluorescence and Silver‐Ion Binding

Yang

Mei

Seela

2015

Chemistry A European J

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Reverse Watson-Crick DNA with parallel-strand orientation (ps DNA) has been constructed. Pyrrolo-dC (PyrdC) nucleosides with phenyl and pyridinyl residues linked to the 6 position of the pyrrolo[2,3-d]pyrimidine base have been incorporated in 12- and 25-mer oligonucleotide duplexes and utilized as silver-ion binding sites. Thermal-stability studies on the parallel DNA strands demonstrated extremely strong silver-ion binding and strongly enhanced duplex stability. Stoichiometric UV and fluorescence titration experiments verified that a single (2py) PyrdC-(2py) PyrdC pair captures two silver ions in ps DNA. A structure for the PyrdC silver-ion base pair that aligns 7-deazapurine bases head-to-tail instead of head-to-head, as suggested for canonical DNA, is proposed. The silver DNA double helix represents the first example of a ps DNA structure built up of bidentate and tridentate reverse Watson-Crick base pairs stabilized by a dinuclear silver-mediated PyrdC pair.

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Section: Resultssupporting

confidence: 66%

Pyrrolo‐dC Metal‐Mediated Base Pairs in the Reverse Watson–Crick Double Helix: Enhanced Stability of Parallel DNA and Impact of 6‐Pyridinyl Residues on Fluorescence and Silver‐Ion Binding

Yang

Mei

Seela

2015

Chemistry A European J

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“…On the other hand, hyperchromism can be attributed to external contact (surface binding) with the duplex . Furthermore, the observed hyperchromism and no shift in the location of the peak (258 nm) is indicative of partial or non‐intercalative‐binding modes (Figure ), such as dative bonds, electrostatic forces, hydrogen bonds, van der Waals forces and hydrophobic interactions . These hyperchromic shifts indicate that all the synthesized compounds interact with CT‐DNA with non‐intercalative‐binding modes.…”

Section: Resultsmentioning

confidence: 89%

Spectroscopic studies, structural characterization and electrochemical studies of two cobalt (III) complexes with tridentate hydrazone Schiff base ligands: Evaluation of antibacterial activities, DNA‐binding, BSA interaction and molecular docking

Fekri

Salehi

Asadi

et al. 2017

Applied Organom Chemis

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Co(III) complexes of tridentate Schiff base ligands derived from N‐(2‐hydroxybenzylideneamino)benzamide (H2L1) and 2‐(2‐hydroxybenzylidene)hydrazine‐1‐carboxamide (H2L2) were synthesized and characterized using IR, Raman, 1H–NMR and UV–Vis spectroscopies. X‐ray single crystal structures of complexes 1 and 2 have also been determined, and it was indicated that these Co(III) complexes are in a distorted octahedral geometry. The cyclic voltammetry (CV) of the complexes indicates an irreversible redox behavior for both complexes 1 and 2. The antibacterial effects of the synthesized compounds have been tested by minimum inhibitory concentration and minimum bactericidal concentration methods, which suggested that the metal complexes exhibit better antibacterial effects than the ligands against Gram‐positive bacteria. The effects of the drug (drug = ligands and complexes) on bovine serum albumin (BSA) were examined using circular dichroism (CD) spectropolarimetry, and it was revealed that the BSA (BSA, as a carrier protein) secondary structure changed in the presence of the drug. Interaction of the drug with calf‐thymus DNA (CT‐DNA) was investigated by UV–Vis absorption, fluorescence emission, CV and CD spectroscopy. Binding constants were determined using UV–Vis absorption. The results indicated that the studied Schiff bases bind to DNA, with the hyperchromic effect and non‐intercalative mode in which the metal complexes are more effective than ligands. Furthermore, molecular docking simulation was used to obtain the energetic and binding sites for the interaction of the complexes with Mycobacterium tuberculosis enoyl‐acyl carrier protein reductase (InhA), and results showed that complex 1 has more binding energy.

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“…Some transition metal complexes can show antioxidant activity, as reported in the literature . We compared the abilities of the metal complexes to scavenge hydroxyl radicals with those of the well‐known natural antioxidants mannitol and vitamin C, using the same method as reported previously . The 50% inhibitory concentration (IC 50 ) values of mannitol and vitamin C are about 9.6 × 10 −3 and 8.7 × 10 −3 M, respectively.…”

Section: Resultsmentioning

confidence: 95%

Four‐, five‐ and six‐coordinated transition metal complexes based on naphthalimide Schiff base ligands: Synthesis, crystal structure and properties

Zhang

Shen

et al. 2017

Applied Organom Chemis

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Two bidentate Schiff base ligands (HL 1 = N-n-butyl-4-[(E)-2-(((2-aminoethyl)imino) (3) have been synthesized and characterized. Single-crystal X-ray structure analysis reveals that complex 1 has a four-coordinated square geometry, while complex 2 is a five-coordinated square pyramidal structure and complex 3 is a distorted six-coordinated octahedral structure. Cyclic voltammograms of 1 indicate an irreversible Cu 2+ /Cu + couple. In vitro antioxidant activity assay demonstrates that the ligands and the two complexes 1 and 3 display high scavenging activity against hydroxyl (HO • ) and superoxide (O 2 −• ) radicals. Moreover, the fluorescence properties of the ligands and complexes 1-3 were studied in the solid state. Metal-mediated enhancement is observed in 2, whereas metal-mediated fluorescence quenching occurs with 1 and 3.

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DNA-binding studies and antioxidant activities of two-, three- and four-coordinate silver(i) complexes containing bis(2-benzimidazolyl)aniline derivatives

Abstract: Three novel structure Ag(i) complexes have been synthesized and characterized. The three ligands and Ag(i) complexes bind to DNA in an intercalation mode. The Ag(i) complexes have stronger ability of antioxidation for hydroxyl radical and superoxide radical.

Cited by 47 publications

References 58 publications

Pyrrolo‐dC Metal‐Mediated Base Pairs in the Reverse Watson–Crick Double Helix: Enhanced Stability of Parallel DNA and Impact of 6‐Pyridinyl Residues on Fluorescence and Silver‐Ion Binding

Pyrrolo‐dC Metal‐Mediated Base Pairs in the Reverse Watson–Crick Double Helix: Enhanced Stability of Parallel DNA and Impact of 6‐Pyridinyl Residues on Fluorescence and Silver‐Ion Binding

Spectroscopic studies, structural characterization and electrochemical studies of two cobalt (III) complexes with tridentate hydrazone Schiff base ligands: Evaluation of antibacterial activities, DNA‐binding, BSA interaction and molecular docking

Four‐, five‐ and six‐coordinated transition metal complexes based on naphthalimide Schiff base ligands: Synthesis, crystal structure and properties

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