Structures, antimicrobial activity, DNA interaction and molecular docking studies of sulfamethoxazolyl-azo-acetylacetone and its nickel(II) complex

Das, Dipankar; Sahu, Nilima; Mondal, Sudipa; Roy, Suman; Dutta, Paramita; Gupta, Suvroma; Mondal, Tapan Kumar; Sinha, Chittaranjan

doi:10.1016/j.poly.2015.06.027

Cited by 17 publications

(13 citation statements)

References 52 publications

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“…Therefore, a significant challenge of interest is to design metal-based compounds that can interact with DNA. Thus, in recent years, [8][9][10] the interaction between transition metal complexes and DNA has been investigated. Schiff base ligands and their metal chelates are included in a number of biological reactions, such as the inhibition of DNA and RNA; protein synthesis; nitrogen fixation; and carcinogenes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, DNA binding/cleavage, and anticancer and antimicrobial activities: Nano‐sized Co(II) and Cd(II) complexes and their use as a precursor for CoO and CdO nanoparticles

Alothman

Ammar

2020

Applied Organom Chemis

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In the search of effective bioactive compounds, Co(II) (C1) and Cd(II) (C2) complexes of the type [M(FMAPIMP)(H2O)Cl].nH2O (where M = Co(II); n = 2, Cd(II); n = 3, and FMAPIMP = ligand[2‐((E)‐((2‐(((E)‐furan‐2‐ylmethylene)amino)phenyl)imino)methyl)phenol]) were synthesized and characterized using elemental analysis, UV–Vis., cyclic voltammetry, Fourier‐transform infrared (FT‐IR), nuclear magnetic resonance, and mass spectral studies. The thermal stability of nano‐sized Co(II) and Cd(II) complexes was studied using thermogravimetric analysis (TGA). Cobalt and cadmium oxides were synthesized using cobalt and cadmium nanoparticle (NP) structure Schiff base complexes as the raw material after calcination for 5 h at 600 °C. According to the results, Co(II) and Cd(II) complexes with mole ratio 1:1 of metal: H‐FMAPIMP which octahedral are the most probable geometry for it. On the contrary, synthesized C1 and C2 NPs were used as suitable precursors for the preparation of CoO and CdO NPs. The obtained NPs were characterized using FT‐IR, UV–Vis., TGA, powder X‐ray diffraction (PXRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), and atomic force microscopy techniques. PXRD analysis revealed that the obtained oxides were crystalline and corresponded to CoO and CdO phases. Crystal size, shape, and morphology were determined using SEM and TEM. H‐FMAPIMP and its two complexes (C1 and C2) were tested against human ovarian cancer cell line (PA‐1). The synthesized Co(II) and Cd(II) complexes exhibited enhanced activity against the tested bacterial (Staphylococcus aureus and Escherichia Coli) and fungal strains (Candida albicans and Aspergillus fumigatus) as compared to H‐FMAPIMP. The results of the DNA‐cleavage activity indicated that the ligand and its two complexes can cleave calf thymus‐DNA at different degrees. Further, antituberculosis activity was performed using microplate alamarBlue assay. Among all these synthesized compounds, C1 exhibited good cleaving ability compared to the newly synthesized C2. Finally, the geometry of H‐FMAPIMP and its Co(II) and Cd(II) complexes was optimized using molecular modeling.

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Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, DNA binding/cleavage, and anticancer and antimicrobial activities: Nano‐sized Co(II) and Cd(II) complexes and their use as a precursor for CoO and CdO nanoparticles

Alothman

Ammar

2020

Applied Organom Chemis

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“…They are usually prepared by the reaction between primary amines and azo aldehyde derivatives. These compounds show a variety of biological activities such as antibacterial, antifungal, herbicidal and clinical . In additional, optical properties of azo dyes make them suitable for potential application in chemosensors.…”

Section: Introductionmentioning

confidence: 99%

New Chloro‐Based Azo‐Azomethine Dyes: Synthesis, Biological and Optical Spectroscopic Studies for Detection of some Transition Metal Ions

Shaghaghi

Rezanezhad

2018

ChemistrySelect

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Two new chromogenic receptors 1,2-[1-(3-imino-4-hydroxophenylazobenzene)]-4-chlorobenzene (1 a) and 1,2-[1-(3-imino-4hydroxophenylazo-4-nitrobenzene)]-4-chlorobenzene (1 b) have been designed and chearcterized for detection of some transition metal ions in DMSO solution by UV/Vis spectroscopy. Upon addition of Cd 2 + , Zn 2 + and Cu 2 + ions to 1 a in DMSO, the peak at 460 nm increases in intensity, while the band at 352 nm decreases in intensity and approximately disappears. n!p* transition of azo groups of 1 a decreases in intensity after adding Hg 2 + ions and does not change after adding Ni 2 + ions. This indicates high tendency of 1 a towards Cd 2 + , Zn 2 + and Cu 2 + against Ni 2 + and Hg 2 + ions. Compound 1 b shows some color changes after addition of metal ions. Upon addition of all metal ions to 1 b in DMSO, the band at 560 nm increases in intensity with the hypsochromic shift for Cu 2 + , Zn 2 + , Co 2 + and Ni 2 + . But the largest blue shift (-67 nm) is seen after adding Cu 2 + ion with remarkable color change from violet-green to orange. Benesi-Hildebrand plot and Job's method are used for determination of binding constant (K a ) and stoichiometry of formed complexes with 1 b. Then, complex Cu(II) with 1 b is synthezied for recognition of binding sites of ligand. The results indicate that 1 b behaves as one tetradentate ligand with N and O donor atoms when bound to Cu(II). Moreover, the study of antioxidant properties of 1 a and 1 b with DPPH method reveals good and significant activity.[a] Dr.

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“…DNA is the first antitumor or therapy intracellular objective. The interaction between metal complexes and DNA (deoxyribonucleic acid) was thus pursued in latest years 9, 23–27 . Therefore, the design of metal‐based complexes that can communicate with DNA and cleave it effectively is an important interest.…”

Section: Introductionmentioning

confidence: 99%

New Zn (II) and Cd (II) complexes of 2,4‐dihydroxy‐5‐[(5‐mercapto‐1H‐1,2,4‐triazole‐3‐yl)diazenyl]benzaldehyde: Synthesis, structural characterization, molecular modeling and docking studies, DNA binding and biological activity

Atlam

Awad

Gaber

et al. 2020

Applied Organom Chemis

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The molecular structures of the so‐called azo dye and its Zn (II) and Cd (II) complexes were predicted in the present manuscript: 2,4‐dihydroxy‐5‐[(5‐mercapto‐1H‐1,2,4‐triazole‐3‐yl) diazenyl] benzaldehyde(H2L). The analyses elemental and thermal, spectra (FT‐IR, MS, UV–Vis), DFT/B3LYP/GENECP at which 6‐31G** basis set is used for C, H, N, O and S and LANL2DZ for Cd and Zncalculations and conductivity, the structures of these newly synthesized complexes were allocated. The small conductivity values exposed the non‐electrolytic nature. TGA curves used Coats‐Redfern to calculate the activation parameters for the thermal decomposition phases. The interaction between calf thymus DNA and investigated compounds was explored through UV–visible measurements of absorption and viscosity. The findings stated that through intercalative binding mode, the complexes communicate with DNA by calculating the constants of binding. In addition, the antimicrobial activity for the ligand and complexes in vitro were tested. The calculations demonstrate that the investigated complexes have octahedral geometry which agrees with the experimental observations. Molecular docking simulation was conducted using molecular operator environment (MOE) for ligand (H2L), Zn (II) and Cd (II) complexes. The docking calculations verified that the Zn (II)‐complex has greater potency and affinity to the (GLUT1) protein than those of the ligand and Cd (II)‐complex, which is inconsistent with the experimental activity. Finally, quantum mechanical and molecular docking are effective methods to better describe the studied molecules ‘biological activity.

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Structures, antimicrobial activity, DNA interaction and molecular docking studies of sulfamethoxazolyl-azo-acetylacetone and its nickel(II) complex

Cited by 17 publications

References 52 publications

Synthesis, characterization, DNA binding/cleavage, and anticancer and antimicrobial activities: Nano‐sized Co(II) and Cd(II) complexes and their use as a precursor for CoO and CdO nanoparticles

Synthesis, characterization, DNA binding/cleavage, and anticancer and antimicrobial activities: Nano‐sized Co(II) and Cd(II) complexes and their use as a precursor for CoO and CdO nanoparticles

New Chloro‐Based Azo‐Azomethine Dyes: Synthesis, Biological and Optical Spectroscopic Studies for Detection of some Transition Metal Ions

New Zn (II) and Cd (II) complexes of 2,4‐dihydroxy‐5‐[(5‐mercapto‐1H‐1,2,4‐triazole‐3‐yl)diazenyl]benzaldehyde: Synthesis, structural characterization, molecular modeling and docking studies, DNA binding and biological activity

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