Novel bioactive azo-azomethine based Cu (II), Co (II) and Ni(II) complexes, structural determination and biological activity

Venugopal, N.; Krishnamurthy, G.; Bhojyanaik, Halehatti S.; Giridhar, M.

doi:10.1016/j.molstruc.2019.04.022

Cited by 26 publications

(6 citation statements)

References 39 publications

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“…The azo derivatives of ruthenium were found to be more cytotoxic as compared to the oxadiazole derivatives, on human glioblastoma cell lines, inspiring further study of azo-coordinated complexes . The redox reactions of the metal-coordinated azo ligands have been known to increase the cytotoxicity of half-sandwich organometallic (arene)-ruthenium(II) complexes. , As compared to the free arylazo ligand, the transition-metal chelated azo complexes target cancer cells better than normal cells due to increased lipophilicity on chelation; this prompts the design and exploration of more metal-coordinated azo compounds . Significant in vitro cytotoxic results of azo-vanadium complexes have also been reported in our earlier works, which further stimulates us to design and study azo-functionalized complexes .…”

Section: Introductionmentioning

confidence: 79%

Probing CO Generation through Metal-Assisted Alcohol Dehydrogenation in Metal-2-(arylazo)phenol Complexes Using Isotopic Labeling (Metal = Ru, Ir): Synthesis, Characterization, and Cytotoxicity Studies

et al. 2020

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The reaction of 2-{2-(benzo [1,3]dioxol-5-yl)-diazo}-4-methylphenol (HL) with [Ru(PPh 3 ) 3 Cl 2 ] in ethanol resulted in the carbonylated ruthenium complex [RuL(PPh 3 ) 2 (CO)] (1), wherein metal-assisted decarbonylation via in situ ethanol dehydrogenation is observed. When the reaction was performed in acetonitrile, however, the complex [RuL(PPh 3 ) 2 (CH 3 CN)] (2) was obtained as the main product, probably by trapping of a common intermediate through coordination of CH 3 CN to the Ru(II) center. The analogous reaction of HL with [Ir(PPh 3 ) 3 Cl] in ethanol did not result in ethanol decarbonylation and instead gave the organoiridium hydride complex [IrL(PPh 3 ) 2 (H)] (3). Unambiguous evidence for the generation of CO via rutheniumassisted ethanol oxidation is provided by the synthesis of the 13 C-labeled complex, [Ru(PPh 3 ) 2 L( 13 CO)] (1A) using isotopically labeled ethanol, CH 3 13 CH 2 OH. To summarize all the evidence, a ruthenium-assisted mechanistic pathway for the decarbonylation and generation of alkane via alcohol dehydrogenation is proposed. In addition, the in vitro antiproliferative activity of complexes 1−3 was tested against human cervical (HeLa) and human colorectal adenocarcinoma (HT-29) cell lines. Complexes 1−3 showed impressive cytotoxicity against both HeLa (half-maximal inhibitory concentration (IC 50 ) value of 3.84−4.22 μM) and HT-29 cancer cells (IC 50 values between 3.3 and 4.5 μM). Moreover, the complexes were comparatively less toxic to noncancerous NIH-3T3 cells.

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Section: Introductionmentioning

confidence: 79%

Probing CO Generation through Metal-Assisted Alcohol Dehydrogenation in Metal-2-(arylazo)phenol Complexes Using Isotopic Labeling (Metal = Ru, Ir): Synthesis, Characterization, and Cytotoxicity Studies

et al. 2020

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“…The ESR parameters observed for the complex are analogous to already reported systems and confirm the presence of distorted octahedral geometry. [ 62 ]…”

Section: Resultsmentioning

confidence: 99%

Exploration of structural, electrostatic and photophysical behaviour of novel Ni(II), Cu(II) and Zn(II) complexes and their utility as potent antimicrobial agents

Bala

Singh

Kataria

et al. 2022

Applied Organom Chemis

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In the present manuscript, a series of Ni(II), Cu(II) and Zn(II) based metal complexes were synthesized, and their molecular geometry was established using single‐crystal X‐ray diffraction studies. The surface characteristic along with the presence of various intermolecular interactions was quantified using crystal explorer. The atom‐based contribution of various molecular interactions in the overall interactions was evaluated by the decomposition of Hirshfeld surfaces into a 2D fingerprint region. DFT‐based global reactivity descriptors were calculated to gain an idea about the chemical reactivity and stability. A reduction in the energy gap on complexation along with a red shift in the absorption spectra confirms the formation of metal complexes. The presence of a small energy gap in case of Cu(II) complex reflects the presence of an efficient electronic charge transfer mechanism in this case. The photophysical properties of L2 and its metal complexes were also evaluated in different solvents. A maximum stoke shift of 6234.51 cm−1 was exhibited by M2D when its spectra were recorded in MeOH. The bio‐efficacy of L2 and its metal complexes (M2A, M2C and M2D) were evaluated using in vitro anti‐microbial assays. Maximum inhibition of both bacterial and fungal growth was exhibited by M2A with an MIC value of 32 μg mL−1 against B. cereus, X. campestris, and C. albicans. The fluorescence‐based approach was used to conduct BSA binding studies with all three metal complexes. The presence of a positive entropy change (S) value implies that protein‐ligand binding is entropy‐driven by hydrophobic interactions. Finally, in silico molecular docking and dynamics investigations were carried out to explore the most probable mode of C. albicans inhibition.

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“…The bands for M À O and M À N seemed to a novel peaks in the scales 779:514 cm À1 as well as 403-553 cm À1 , separately. 45 Finally, the Ft-IR spectra of Ag(I) and Cu (II) and Pd (II) chelates revealed a further absorption peak at 1385:1300 as well as 1,525: 1212 cm À1 associated with the extending vibrations of (NO 3 À ) and…”

Section: Infrared (Ft-ir) Spectroscopymentioning

confidence: 93%

Design, preparation, physicochemical characterization, structural conformational, biological evaluation, and DNA interaction for some new benzimidazole complexes

Abu‐Dief,

El‐Khatib,

El‐Dabea

et al. 2024

Applied Organom Chemis

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New Cu (II), VO (II), Ag(I), and Pd (II)‐[BIP = 4,6‐dimethyl‐N‐(octahydro‐2H‐benzimidazol‐2‐ylidene)pyrimidin‐2‐amine] chelates have been synthesized by the reaction of BIP ligand resulting from the condensation of benzimidazole guanidine as well as acetylacetone with tested metal salts. The suggested structures of prepared compounds have been investigated spectroscopically through (FT‐IR, NMR, Mass spectra, and UV–Vis spectra), CHN analyses, conductivity, pH stability as well asmagnetic moment measurements. TGA studies have been also studied to govern the thermal behavior, stability, and decomposition of the metal chelates. Structural study of the tested chelates exposed their chemical transformation of ligand by chelation with the studied metals. The studies predicted a hexa‐coordinated geometry for the Cu and VO chelates, whereas tetra‐coordinated for the Ag and Pd chelates. DFT/B3LYP theoretical method was applied to obtain optimized geometry, molecular electrostatic potential (MEP) surface, and HOMO‐LUMO analysis for tested compounds. For estimation in the in vitro study, all the tested compounds have been screened for their biochemical features, including antioxidant, antimicrobial performances, and cytotoxicity. The antioxidant performance of prepared molecules has been studied by DPPH study and all the tested chelates displayed close antioxidant performance against the standard drugs. The cytotoxic analysis of tested compounds has been estimated against various cancer cell lines: (Hep‐G2, HCT‐116, and MCF‐7) using MTT analysis as well as calculated the cell viability for the corresponding human cell. The DNA binding capability for the tested compounds has been evaluated through absorption spectroscopic, viscosity estimation, as well as gel electrophoresis. The outcomes displayed a good binding tendency through the binding constant from 1.01 × 104 to 1.99 × 104 M−1 in the order BIPCu> BIPVO > BIPPd > BIPAg, respectively. Finally, docking simulation results indicated that the complexes were located in the intercalation site of DNA and confirmed experimental findings.

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Novel bioactive azo-azomethine based Cu (II), Co (II) and Ni(II) complexes, structural determination and biological activity

Cited by 26 publications

References 39 publications

Probing CO Generation through Metal-Assisted Alcohol Dehydrogenation in Metal-2-(arylazo)phenol Complexes Using Isotopic Labeling (Metal = Ru, Ir): Synthesis, Characterization, and Cytotoxicity Studies

Probing CO Generation through Metal-Assisted Alcohol Dehydrogenation in Metal-2-(arylazo)phenol Complexes Using Isotopic Labeling (Metal = Ru, Ir): Synthesis, Characterization, and Cytotoxicity Studies

Exploration of structural, electrostatic and photophysical behaviour of novel Ni(II), Cu(II) and Zn(II) complexes and their utility as potent antimicrobial agents

Design, preparation, physicochemical characterization, structural conformational, biological evaluation, and DNA interaction for some new benzimidazole complexes

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