Experimental and molecular modeling studies on the DNA-binding of diazacyclam-based acrocyclic copper complex

Shahabadi, Nahid; Hakimi, Mohammad; Morovati, Teimoor; Falsafi, Monireh; Fili, Soraya Moradi

doi:10.1016/j.jphotobiol.2016.12.023

Cited by 33 publications

(17 citation statements)

References 40 publications

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“…Instead, the hyperchromism can be perceived for the groove binding mode between small molecules and DNA, whereas the position of the absorption spectra almost does not change. It can be related with degradation of the DNA double helix structure …”

Section: Resultsmentioning

confidence: 99%

“…The emission intensity data which were obtained from the interaction study of ligand and its complexes with FS‐DNA at four different temperatures (292, 295, 298 and 301 K) were fitted into the Stern–Volmer equation (Equation ):

\frac{F_{0}}{F} = 1 + K_{SV} ([], Q)

Where, F 0 and F are the fluorescence intensities value of compound before and after addition of the quencher, respectively, [Q] is the concentration of FS‐DNA as quencher and K SV is the Stern‐Volmer quenching constant, which can be considered as a measure of fluorescence quenching efficiency of the flurophore. Equation was applied to determine K SV by linear regression of a plot of F 0 /F versus [Q].…”

Section: Resultsmentioning

confidence: 99%

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New transition metal complexes of 9,10‐phenanthrenequinone p‐toluyl hydrazone Schiff base: Synthesis, spectroscopy, DNA and HSA interactions, antimicrobial, DFT and docking studies

Moradinia

Mansournia

Aramesh‐Boroujeni

et al. 2019

Applied Organom Chemis

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The new complexes of Cu (II) and Ni (II) of a tridentate Schiff base ligand derived from 9,10‐phenanthrenequinone and p‐toluic hydrazide have been synthesized and characterized by elemental analysis, electrical conductometry, FT‐IR, Mass, NMR and UV–Vis. The DFT calculations were carried out at B3LYP/6‐31G*(d) level for the determination of the optimized structure of the ligand and its complexes. The as‐synthesized compounds were screened for their antimicrobial activity. Also, their binding behavior with fish salmon‐DNA (FS‐DNA) and human serum albumin (HSA) were studied by different kinds of spectroscopic and molecular modeling techniques. The fluorescence data at different temperatures were applied in order to estimate the thermodynamics parameters of interactions of ligand and its complexes with DNA and HSA. The results showed that the as‐made compounds could bind to FS‐DNA and HSA via the groove binding as the major binding mode. According to molecular docking calculation and competitive binding experiments, these compounds bind to the minor groove of DNA and hydrophobic residues located in the subdomain IB of HSA. In addition, the molecular docking results kept in good consistence with experimental data.

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Section: Resultsmentioning

confidence: 99%

\frac{F_{0}}{F} = 1 + K_{SV} ([], Q)

Section: Resultsmentioning

confidence: 99%

New transition metal complexes of 9,10‐phenanthrenequinone p‐toluyl hydrazone Schiff base: Synthesis, spectroscopy, DNA and HSA interactions, antimicrobial, DFT and docking studies

Moradinia

Mansournia

Aramesh‐Boroujeni

et al. 2019

Applied Organom Chemis

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“…Thermodynamic parameters of the interaction between α‐ESA and DNA are listed in Table . The negative values of Δ G θ revealed that the binding process is spontaneous, a positive value of Δ S θ was frequently regarded as evidence for a hydrophobic interaction driven by means of hydrogen binding interactions . A negative value of ΔH θ showed that the binding process is mainly enthalpy driven and by means of hydrogen binding interactions .…”

Section: Resultsmentioning

confidence: 99%

Spectroscopic studies on the interaction of alpha‐eleostearic acid with calf thymus DNA

Liu

Zhang

Chen

et al. 2019

J Chinese Chemical Soc

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Interaction between alpha‐eleostearic acid (α‐ESA) and calf thymus DNA in Tris‐HCl buffer (pH = 7.4) using neutral red (NR) dye as a spectral probe was investigated using UV–Vis absorption and fluorescence spectroscopy. Spectral data matrix of the complexed reaction between α‐ESA and NR with DNA was processed with an alternative least‐squares (ALS) algorithm, the obtained concentration profiles and the corresponding pure spectra for species (NR, DNA–NR, and DNA–NR–ESA) demonstrated three kinds of reactions might occur in the system. The major groove binding between α‐ESA and DNA was further validated using circular dichroism, viscosity, DNA melting, and ionic strength effect measurements. Moreover, the calculated values of thermodynamic parameters, such as enthalpy (ΔHθ, −22.04 kJ/mol) and entropy change (ΔSθ, 91.52 J K−1 mol−1), suggested binding between α‐ESA and DNA was mainly driven by hydrophobic interactions and hydrogen bonds without electrostatic force.

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“…This reflects the strong interaction between the electronic states of MB and that of adjacent nucleic acid bases. But, if a significant increase occurs in MB emission it means that interaction between synthesized compounds and DNA causes the separation of MB from DNA . There is no remarkable increase in the fluorescence intensity of the probe molecule in the presence of increasing amounts of the synthesized compounds; that suggests non‐weaving interaction of ligands and complexes with DNA.…”

Section: Resultsmentioning

confidence: 99%

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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Experimental and molecular modeling studies on the DNA-binding of diazacyclam-based acrocyclic copper complex

Cited by 33 publications

References 40 publications

New transition metal complexes of 9,10‐phenanthrenequinone p‐toluyl hydrazone Schiff base: Synthesis, spectroscopy, DNA and HSA interactions, antimicrobial, DFT and docking studies

New transition metal complexes of 9,10‐phenanthrenequinone p‐toluyl hydrazone Schiff base: Synthesis, spectroscopy, DNA and HSA interactions, antimicrobial, DFT and docking studies

Spectroscopic studies on the interaction of alpha‐eleostearic acid with calf thymus DNA

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

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