Spectroscopic, molecular docking and structural activity studies of (E)-N′-(substituted benzylidene/methylene) isonicotinohydrazide derivatives for DNA binding and their biological screening

Arshad, Nasima; Perveen, Fouzia; Saeed, Aamer; Channar, Pervaiz Ali; Farooqi, Shahid Iqbal; Larik, Fayaz Ali; Ismail, Hammad; Mirza, Bushra

doi:10.1016/j.molstruc.2017.03.055

Cited by 23 publications

(19 citation statements)

References 43 publications

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“…No ligand interaction was observed with the Ni 2+ due to the bulky ligand structures. However, the interaction patterns of our docking results were correlated with published results which strengthens the significance of our docking experiments [ 44 , 45 , 46 , 47 , 48 ]. The comparative binding energy and SAR analysis showed the significance of 6a that may be considered as a potent inhibitor targeting jack bean urease.…”

Section: Discussionsupporting

confidence: 90%

Sulfonamide-Linked Ciprofloxacin, Sulfadiazine and Amantadine Derivatives as a Novel Class of Inhibitors of Jack Bean Urease; Synthesis, Kinetic Mechanism and Molecular Docking

et al. 2017

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Sulfonamide derivatives serve as an important building blocks in the drug design discovery and development (4D) process. Ciprofloxacin-, sulfadiazine- and amantadine-based sulfonamides were synthesized as potent inhibitors of jack bean urease and free radical scavengers. Molecular diversity was explored and electronic factors were also examined. All 24 synthesized compounds exhibited excellent potential against urease enzyme. Compound 3e (IC50 = 0.081 ± 0.003 µM), 6a (IC50 = 0.0022 ± 0.0002 µM), 9e (IC50 = 0.0250 ± 0.0007 µM) and 12d (IC50 = 0.0266 ± 0.0021 µM) were found to be the lead compounds compared to standard (thiourea, IC50 = 17.814 ± 0.096 µM). Molecular docking studies were performed to delineate the binding affinity of the molecules and a kinetic mechanism of enzyme inhibition was propounded. Compounds 3e, 6a and 12d exhibited a mixed type of inhibition, while derivative 9e revealed a non-competitive mode of inhibition. Compounds 12a, 12b, 12d, 12e and 12f showed excellent radical scavenging potency in comparison to the reference drug vitamin C.

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Section: Discussionsupporting

confidence: 90%

Sulfonamide-Linked Ciprofloxacin, Sulfadiazine and Amantadine Derivatives as a Novel Class of Inhibitors of Jack Bean Urease; Synthesis, Kinetic Mechanism and Molecular Docking

et al. 2017

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“…The aliquots of DNA and AA used were in the range 2.0–6.0 μM and 1.2–4.4 mM, respectively. The temperature of cell cuvette was maintained at 36.5°C by temperature controller device before running the instrument for the sample analysis [ 39 ].…”

Section: Methodsmentioning

confidence: 99%

“…The best docking conformation having minimum final docking energy or free energy (ΔG) was used for further calculations throughout. Binding propensity of drugs with DNA in terms of binding constants ( K b ) was calculated from the lowest ΔG values [ 38 , 39 , 40 ]. Remaining parameters were set default.…”

Section: Methodsmentioning

confidence: 99%

Electrochemical, spectroscopic and theoretical monitoring of anthracyclines’ interactions with DNA and ascorbic acid by adopting two routes: Cancer cell line studies

et al. 2018

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Pharmacodynamic interactions of three anthracycline antibiotics namely doxorubicin (DXH), epirubicin (EpiDXH) and daunorubicin (DNR) with DNA in the absence and presence of ascorbic acid (AA) as natural additive were monitored under physiological conditions (pH = 7.4, 4.7 and T = 309.5K). Route–1 (Anthracycline–AA–DNA) and Route–2 (Anthracycline–DNA–AA) were adopted to see the interactional behavior by cyclic voltammetry (CV) and UV-visible spectroscopy. In comparison to Route–2; voltammetric and spectral responses as well as binding constant (Kb) and Gibb’s free energy change (ΔG) values revealed strongest and more favorable interaction of anthracycline–AA complex with DNA via Route–1. Kb, s (binding site sizes) and ΔG evaluated from experimental (CV, UV-Vis) and theoretical (molecular docking) findings showed enhanced binding strength of tertiary complexes as compared to binary drug–DNA complexes. The results were found comparatively better at pH 7.4. Consistency was observed in binding parameters evaluated from experimental and theoretical techniques. Diffusion coefficients (Do) and heterogeneous electron transfer rate constant (ks,h) confirmed the formation of complexes via slow diffusion kinetics. Percent cell inhibition (%Cinh) of anthracyclines for non-small cell cancer cell lines (NSCCLs) H-1299 and H-157 were evaluated higher in the presence of AA which further complimented experimental and theoretical results.

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“…These free radicals are involved in the oxidation of deoxyribose unit and also cleavage of sugar phosphate. In complexes these cleavage present slightly and also confirming by the formation of hydroxyl free radicals 16 . …”

Section: Dna Binding and Cleavage Studies Of Complexesmentioning

confidence: 53%

Eco-Friendly Synthesis, Spectral, Bio-Potential, DNA Binding and Antituberculosis Activities of Ni(II) And Cu(II) Complexes

2018

Chem Sci Trans

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Abstract:Microwave technique is one of the eco-friendly techniques used widespread in green synthesis of metal-organic compounds. First transition metal complexes of Ni(II) and Cu(II) synthesized using this technique with organic neutral bidentate ligand isonicotinic acid (INH) and anionic benzoate ion. The synthesized complexes were characterized by micro analytical techniques viz., elemental analysis, metal estimation, magnetic moment (VSM), molar conductance and cyclic voltammeter. The spectral techniques UV-Visible, IR and Far-IR are also used to characterize by the synthesized complexes. The elemental analysis, metal estimation, magnetic moment and UV-Visible spectral data of the complexes indicating their molecular formulae, composition and probable geometry (octahedral for Ni(II) and tetragonally distorted octahedral for Cu(II) complexes). Redox properties and reversibility and feasibility of equilibrium of the synthesized complexes were confirmed by their cyclic voltammogram. Complex formation and metal chelating atom (M-O and M-N) ability of the complexes confirmed by their IR and Far-IR spectral data. The antibacterial and antifungal activities of the ligand (INH) and its complexes were carried out by Agar well diffusion method using Actinobacter, Salmonella, E.coli (bacterial strains) and C. Albicance (Fungal strains). The DNA binding and cleavage studies of the complexes compared with those for pure ligand using Calf-thymus DNA. The complexes can interact with DNA at higher concentration. The antituberculosis of the complexes against M.tuberculosis were performed and compared with the standard and ligand isonicotinic acid.

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Spectroscopic, molecular docking and structural activity studies of (E)-N′-(substituted benzylidene/methylene) isonicotinohydrazide derivatives for DNA binding and their biological screening

Cited by 23 publications

References 43 publications

Sulfonamide-Linked Ciprofloxacin, Sulfadiazine and Amantadine Derivatives as a Novel Class of Inhibitors of Jack Bean Urease; Synthesis, Kinetic Mechanism and Molecular Docking

Sulfonamide-Linked Ciprofloxacin, Sulfadiazine and Amantadine Derivatives as a Novel Class of Inhibitors of Jack Bean Urease; Synthesis, Kinetic Mechanism and Molecular Docking

Electrochemical, spectroscopic and theoretical monitoring of anthracyclines’ interactions with DNA and ascorbic acid by adopting two routes: Cancer cell line studies

Eco-Friendly Synthesis, Spectral, Bio-Potential, DNA Binding and Antituberculosis Activities of Ni(II) And Cu(II) Complexes

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