Studies on the interaction of mononuclear metal(II) complexes of amino‑naphthoquinone with bio-macromolecules

Kosiha, A.; Lo, Kong Mun; Parthiban, C.; Elango, Kuppanagounder P.

doi:10.1016/j.msec.2018.10.021

Cited by 19 publications

(4 citation statements)

References 41 publications

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“…The major reason for this is that the contact of compound ( 3–5 ) is very large; as the contact surface of the molecules increases, the biological activity value may increase. [ 55,56 ] Increased contact surface of molecules increases the interaction between molecules and proteins. These interactions are hydrogen bonds, polar and hydrophobic interactions, and π–π and halogen bonds.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of (4R)‐2‐(3‐hydroxyphenyl)thiazolidine‐4‐carboxylic acid substituted phthalocyanines: Anticancer activity on different cancer cell lines and molecular docking studies

Bilgiçli

Hepokur

et al. 2021

Applied Organom Chemis

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In this study, firstly, (4R)‐2‐(3‐hydroxyphenyl)thiazolidine‐4‐carboxylic acid (1) and (4R)‐2‐(3‐(3,4‐dicyanophenoxy)phenyl)thiazolidine‐4‐carboxylic acid (2) were prepared. Then, the novel type metallophthalocyanines (ZnPc (3), CuPc (4), and CoPc (5)) bearing thiazolidine groups in peripheral positions were synthesized using by compound (2). The synthesized new compounds (1–5) were characterized by the combination of standard spectroscopic methods such as FT‐IR, 1H NMR, 13C NMR, UV–Vis spectral data, and MALDI‐TOF. Aggregation behaviors of peripheral tetra‐substituted metallophthalocyanines were investigated in dimethyl sulfoxide (DMSO) media. Fluorescence properties and fluorescence quantum yield of the new type zinc phthalocyanine (3) were performed in DMSO at room temperature. The anticancer activity of novel type metallophthalocyanines bearing thiazolidine groups in peripheral positions were investigated on rat glioma cancer (C6), human prostate carcinoma (DU‐145), and normal human lung fibroblast (WI‐38) cell lines. Finally, the biological and chemical activities of (4R)‐2‐(3‐(3,4‐dicyanophenoxy)phenyl)thiazolidine‐4‐carboxylic acid (2) and its novel type metallophthalocyanines (ZnPc (3), CuPc (4), and CoPc (5)) have been compared with many parameters obtained using theoretical methods that are the Gaussian software and molecular docking.

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Section: Resultsmentioning

confidence: 99%

Synthesis of (4R)‐2‐(3‐hydroxyphenyl)thiazolidine‐4‐carboxylic acid substituted phthalocyanines: Anticancer activity on different cancer cell lines and molecular docking studies

Bilgiçli

Hepokur

et al. 2021

Applied Organom Chemis

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“…The crystal structure of the B-DNA dodecamer d(CGCAAATTTCGC) 2 (PDB ID: 1BNA) was downloaded from the protein data bank. [18,19] Outputs of the docked poses were exported to Discovery Studio for visual inspection of the binding modes and for the probable polar and hydrophobic interactions of the complexes with DNA. The results were visualized using VMD software.…”

Section: Molecular Docking Studymentioning

confidence: 99%

In vitro biomolecular interaction studies and cytotoxic activities of copper(II) and zinc(II) complexes bearing ONS donor thiosemicarbazones

Mathews

Kurup

2020

Applied Organom Chemis

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Among all the bio-metals, zinc and copper derivatives of ONS donor thiosemicarbazone have aroused great interest because of their potential biological applications. Multisubstituted thiosemicarbazone ligand H 2 dspt (3,5-dichlorosalicylaldehyde-N 4-phenylthiosemicarbazone) derived new ternary complexes like [Zn(dspt)(phen)]‧DMF (1) and [Cu(dspt)(phen)]‧DMF (2), and another thiosemicarbazone, H 2 dsct (3,5-dichlorosalicylaldehyde-N 4cyclohexylthiosemicarbazone), derived [Cu(dsct)(bipy)]‧DMF (3). These complexes have been characterized by elemental analysis (CHNS), Fourier transform infrared (FT-IR), ultraviolet-visible (UV-Vis) and proton nuclear magnetic resonance (1 H-NMR) spectra. The structures of the complexes were obtained by single-crystal X-ray diffraction analysis. Compounds 1 and 2 got crystallized in the monoclinic P2 1 /c space group. The complexes showed interesting supramolecular interaction, which in turn stabilizes the complexes. The ground state electronic configurations of the complexes were studied using the B3LYP/LANL2DZ basis set, and ESP plots of complexes were investigated. The interaction of the complexes with calf thymus DNA (CT-DNA) was studied using absorption and fluorescence spectroscopic methods. A UV study of the interaction of the complexes with calf thymus DNA (CT-DNA) has shown that the complexes can effectively bind to CT-DNA, and [Cu(dspt)(phen)]Á DMF (2) exhibited the highest binding constant to CT-DNA (K b = 3.7 × 10 4). Fluorescence spectral studies also indicated that Complex 2 binds relatively stronger with CT DNA through intercalative mode, exhibiting higher binding constant (K q = 4.7 × 10 5). The DNA cleavage result showed that the complexes are capable of cleaving the DNA without the help of any external agent. Molecular docking studies were carried out to understand the binding of complexes with the molecular target DNA. Complex 2 exhibited the highest cytotoxicity against human breast cancer cell line MD-MBA-231 (IC 50 = 23.93 μg/mL) as compared to Complex 1 (IC 50 = 44.40 μg/mL).

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“…18 It is worth noting that some 1,4-quinones have also found use as functional ligands for transition metals. [19][20][21][22] What's more, the Coenzyme Qn (CoQn) family, also named as the ubiquinones, has occupied a unique position in the design and synthesis of novel biologically active lead molecules that exert remarkable medicinal activity. 23 Besides of versatile properties, not surprisingly, ubiquinone participating in the cellular aerobic respiration process, 24 plastoquinone and phylloquinone serving as electron acceptors in electron transport chains in photosynthesis, and vitamin K participating coagulation process and preventing bleeding have also a 1,4-quinone motif.…”

Section: Introductionmentioning

confidence: 99%

“…18 It is worth noting that some 1,4-quinones have also found use as functional ligands for transition metals. 19–22…”

Section: Introductionmentioning

confidence: 99%

Natural-product-inspired design and synthesis of thiolated coenzyme Q analogs as promising agents against Gram-positive bacterial strains: insights into structure–activity relationship, activity profile, mode of action, and molecular docking

et al. 2022

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Studies on the interaction of mononuclear metal(II) complexes of amino‑naphthoquinone with bio-macromolecules

Cited by 19 publications

References 41 publications

Synthesis of (4R)‐2‐(3‐hydroxyphenyl)thiazolidine‐4‐carboxylic acid substituted phthalocyanines: Anticancer activity on different cancer cell lines and molecular docking studies

Synthesis of (4R)‐2‐(3‐hydroxyphenyl)thiazolidine‐4‐carboxylic acid substituted phthalocyanines: Anticancer activity on different cancer cell lines and molecular docking studies

In vitro biomolecular interaction studies and cytotoxic activities of copper(II) and zinc(II) complexes bearing ONS donor thiosemicarbazones

Natural-product-inspired design and synthesis of thiolated coenzyme Q analogs as promising agents against Gram-positive bacterial strains: insights into structure–activity relationship, activity profile, mode of action, and molecular docking

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