Synthesis, characterization, antimicrobial and DNA binding properties of an organic charge transfer complex obtained from pyrazole and chloranilic acid

Khan, Ishaat M.; Islam, Maidul; Shakya, Sonam; Alam, Kehkashan; Alam, Nisat; Shahid, M.

doi:10.1016/j.bioorg.2020.103779

Cited by 49 publications

(10 citation statements)

References 61 publications

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“…Antimicrobial activity was screened by the cup-plate diffusion method. 22 Briefly, NSG and NSG-DDQ were dissolved in dimethyl sulfoxide (DMSO) to give a final concentration 2048 μg mL −1 . The NSG and the CT complex (NSG-DDQ) were tested against Gram-positive bacteria (Staphylococcus aureus ATCC 29213 and Bacillus subtilis ATCC 10400) and Gramnegative bacteria (E. coli ATCC 10418 and Pseudomonas aeruginosa ATCC 27853).…”

Section: Antimicrobial Activity Antimicrobial Screeningmentioning

confidence: 99%

<p>Charge Transfer Complex of Neostigmine with 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone: Synthesis, Spectroscopic Characterization, Antimicrobial Activity, and Theoretical Study</p>

Yousef¹,

Ezzeldin²,

Abdel‐Aziz³

et al. 2020

DDDT

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Background: Electron donor-acceptor interactions are important molecular reactions for the activity of pharmacological compounds. The aim of the study is to develop a charge transfer (CT) complex: synthesis, characterization, antimicrobial activity, and theoretical study. Method and Results: A solid CT complex of neostigmine (NSG) with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) was synthesized and characterized by infrared spectra, NMR, and UV-visible spectroscopy. The results confirm the formation of a CT complex. The stability of the CT complex between NSG and DDQ in acetonitrile was determined in solution via spectrophotometric measurement, ie, by calculating the formation constant, molar extinction coefficient, and different spectroscopic parameters. The stoichiometry of the formed NSG-DDQ complex was determined using Job's method. The absorption band of the NSG-DDQ complex can be used for the quantification of NSG. Conclusion: The DFT geometry optimization of NSG, DDQ, and the CT complex and the UV comparative study of both theoretical and experimental structures are presented. The experimental results confirm the charge transfer structure. The bacterial study shows that the NSG-DDQ complex has good antibacterial activity against both Gram-positive and Gramnegative bacteria as well as antifungal activity against Candida albicans.

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Section: Antimicrobial Activity Antimicrobial Screeningmentioning

confidence: 99%

<p>Charge Transfer Complex of Neostigmine with 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone: Synthesis, Spectroscopic Characterization, Antimicrobial Activity, and Theoretical Study</p>

Yousef¹,

Ezzeldin²,

Abdel‐Aziz³

et al. 2020

DDDT

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“…Charge–transfer (CT) complexation, or electron–donor transfer, is a crucial aspect of biochemical and biological processes such as drug design, enzyme catalysis, and ion sensing [ 9 ]. The pharmacodynamics and thermodynamics of therapeutic substances and biological processes in the human body are studied using charge–transfer complexation interactions [ 10 , 11 , 12 , 13 , 14 ]. In biological systems, charge–transfer complexes may play a crucial function.…”

Section: Introductionmentioning

confidence: 99%

Increasing the Efficacy of Seproxetine as an Antidepressant Using Charge–Transfer Complexes

et al. 2022

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The charge transfer interactions between the seproxetine (SRX) donor and π-electron acceptors [picric acid (PA), dinitrobenzene (DNB), p-nitrobenzoic acid (p-NBA), 2,6-dichloroquinone-4-chloroimide (DCQ), 2,6-dibromoquinone-4-chloroimide (DBQ), and 7,7′,8,8′-tetracyanoquinodi methane (TCNQ)] were studied in a liquid medium, and the solid form was isolated and characterized. The spectrophotometric analysis confirmed that the charge–transfer interactions between the electrons of the donor and acceptors were 1:1 (SRX: π-acceptor). To study the comparative interactions between SRX and the other π-electron acceptors, molecular docking calculations were performed between SRX and the charge transfer (CT) complexes against three receptors (serotonin, dopamine, and TrkB kinase receptor). According to molecular docking, the CT complex [(SRX)(TCNQ)] binds with all three receptors more efficiently than SRX alone, and [(SRX)(TCNQ)]-dopamine (CTcD) has the highest binding energy value. The results of AutoDock Vina revealed that the molecular dynamics simulation of the 100 ns run revealed that both the SRX-dopamine and CTcD complexes had a stable conformation; however, the CTcD complex was more stable. The optimized structure of the CT complexes was obtained using density functional theory (B-3LYP/6-311G++) and was compared.

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“…These compounds contain diverse pharmacological and physiological activities. 21–24 A reduced form of pyrazole, 2-pyrazoline, has been reported to exert potent antimicrobial, 25 anti-inflammatory, 26 anti analgesic, 26 antioxidant, and anti-cancer 27 activities. Several pyrazole-containing drugs have been serving in clinical trials for years, and many are under current research.…”

Section: Introductionmentioning

confidence: 99%

Coumarin–carbazole based functionalized pyrazolines: synthesis, characterization, anticancer investigation and molecular docking

et al. 2021

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Synthesis, characterization, antimicrobial and DNA binding properties of an organic charge transfer complex obtained from pyrazole and chloranilic acid

Cited by 49 publications

References 61 publications

<p>Charge Transfer Complex of Neostigmine with 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone: Synthesis, Spectroscopic Characterization, Antimicrobial Activity, and Theoretical Study</p>

<p>Charge Transfer Complex of Neostigmine with 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone: Synthesis, Spectroscopic Characterization, Antimicrobial Activity, and Theoretical Study</p>

Increasing the Efficacy of Seproxetine as an Antidepressant Using Charge–Transfer Complexes

Coumarin–carbazole based functionalized pyrazolines: synthesis, characterization, anticancer investigation and molecular docking

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