Theoretical investigation of the Zn2+ detection mechanism based on the quinoline derivative of the Schiff-base receptor

Wen, Jinrong; Xia, Yafeng; Ding, Sha; Liu, Yuejun

doi:10.1016/j.saa.2022.122123

Cited by 10 publications

(4 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…All the DFT calculations of the synthesized azo dyes ( A 1 –A 4 ) have been performed using the Gaussian 09 software package by using a hybrid B3LYP function with 6‐311++G (d, p) basis set [17] and the outcome results were visualized in Gauss view 6 [18] . The Reduced Density Gradient (RDG) calculations were carried out in multi‐wavefunction [19] and the end results were visualized by using NAMD (NAnoscale Molecular Dynamics) [20] and GNU plot software [21] …”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis, Solvatochromic Studies, DFT Calculations, Characterization, and In Silico Molecular Docking Studies of Azo Dyes of 3‐Methyl‐1‐phenyl‐1H‐pyrazol‐5‐amine

Shakuntala,

Keshavayya,

Pampapathi

2024

ChemistrySelect

View full text Add to dashboard Cite

In this work, the four azo dyes (A1–A4) were synthesized using 5‐amino‐3‐methyl‐1‐phenyl pyrazole with four different coupling components by the conventional, simple diazo‐coupling method. These synthesized azo molecules were confirmed by various spectroscopic methods viz, FT‐IR spectra, HR‐MS spectra, 1H NMR spectra, and 13C NMR spectra. The electronic absorption and fluorescence spectra of synthesized azo compounds were recorded at room temperature, with different solvents. The DFT calculations were performed using 6‐311++G (d, p) basis set to evaluate the global reactive parameters of the synthesized azo dyes. The anti‐microbial activities were studied; the compound A1 exhibited a good antibacterial and anti‐fungal activities. The study of in silico molecular docking of the azo compounds revealed that all the compounds found to possess were extraordinary binding affinity as compared to the standards. The anti‐tuberculosis study was carried against mycobacterium tuberculosis and the results have shown that, the compound A2 showed good sensitivity to the studied azo compounds.

show abstract

Section: Methodsmentioning

confidence: 99%

“…[18] The Reduced Density Gradient (RDG) calculations were carried out in multi-wavefunction [19] and the end results were visualized by using NAMD (NAnoscale Molecular Dynamics) [20] and GNU plot software. [21]…”

Section: Computational Studiesmentioning

confidence: 99%

Synthesis, Solvatochromic Studies, DFT Calculations, Characterization, and In Silico Molecular Docking Studies of Azo Dyes of 3‐Methyl‐1‐phenyl‐1H‐pyrazol‐5‐amine

Shakuntala,

Keshavayya,

Pampapathi

2024

ChemistrySelect

View full text Add to dashboard Cite

show abstract

“…Quinoline and its derivatives have wide biological and pharmacological applications, including anticancer and antimicrobial activity [31][32][33][34][35][36][37][38][39][40]. Similar diverse activity has also been shown by transition and other metal complexes of quinoline and its derivatives, such as 8-hydroxyquinoline (Figure 1) [41][42][43][44][45][46][47][48][49][50]. In contrast, quinones with redox properties similar to Q1, but without a chelating center, have shown much less cytotoxic activity toward cancer cells [5].…”

Section: Introductionmentioning

confidence: 92%

Increased Free Radical Generation during the Interaction of a Quinone-Quinoline Chelator with Metal Ions and the Enhancing Effect of Light

et al. 2023

View full text Add to dashboard Cite

Schiff bases and similar molecules forming metal complexes may cause redox effects, which may also be influenced by light. Anthraquinones such as doxorubicin and idarubicin are widely used antitumor agents, which can generate reactive oxygen species (ROS), stimulated by both the presence of iron and copper ions and also by light. The generated ROS can cause DNA scission, cell membrane oxidation, and many other toxic effects. The redox activity of the quinone-quinoline chelator 2-phenyl-4-(butylamino)naphtho [2,3-h]quinoline-7,12-dione (Q1) was investigated in the presence of iron, copper, and zinc. The influence of light in these interactions was also examined. The chemically induced dynamic nuclear polarization (CIDNP), nuclear magnetic resonance (NMR), and electron paramagnetic resonance (EPR) methods were used to elucidate the molecular changes and ROS generation effects of the Q1 metal interactions. A model electron transfer reaction system between 1,4-dihydropyridine and Q1 was utilized to demonstrate that the chelate complexes of Q1 with both Fe(III) and Cu(II) ions were more redox active than Q1 itself. Similarly, CIDNP and NMR data showed that the concentration dependence of the free radicals yield is much higher in the presence of Fe(III) and Cu(II) ions, in comparison to Zn(II), and also that it increased in the presence of light. These findings underline the role of transition metal ions and Q1 in cyclic redox chain reactions and increase the prospect of the development of copper- and iron-based chelating agents, including Q1 and its derivatives, for anticancer therapy. Furthermore, these findings also signify the effect of light on enhancing ROS formation by Q1 and the prospect of utilizing such information for designing target specific anticancer drugs for photodynamic therapy.

show abstract

“…[31][32][33][34] Recently, numerous fluorescein-based cell permeable Zn 2+ sensor molecules have been disclosed. [35][36][37][38][39][40][41][42] The fluorescence approach is excellent for producing various sensor molecules by designing and synthesizing a reactive moiety that is connected to a certain type of metal ion sensor. [43][44][45][46] The fact that the fluorescence quantum yield is low and favourable ensures that the analyte is mostly responsible for the observed fluorescence intensity if the sensor molecule is converted to the fluorescent form.…”

Section: Introductionmentioning

confidence: 99%

Highly selective and sensitive fluorescent “TURN-ON” furan-based Schiff base for zinc(ii) ion probing: chemical synthesis, DFT studies, and X-ray crystal structure

N. R.,

Revanasiddappa,

Yathirajan

et al. 2023

New J. Chem.

View full text Add to dashboard Cite

show abstract

Theoretical investigation of the Zn2+ detection mechanism based on the quinoline derivative of the Schiff-base receptor

Cited by 10 publications

References 44 publications

Synthesis, Solvatochromic Studies, DFT Calculations, Characterization, and In Silico Molecular Docking Studies of Azo Dyes of 3‐Methyl‐1‐phenyl‐1H‐pyrazol‐5‐amine

Synthesis, Solvatochromic Studies, DFT Calculations, Characterization, and In Silico Molecular Docking Studies of Azo Dyes of 3‐Methyl‐1‐phenyl‐1H‐pyrazol‐5‐amine

Increased Free Radical Generation during the Interaction of a Quinone-Quinoline Chelator with Metal Ions and the Enhancing Effect of Light

Highly selective and sensitive fluorescent “TURN-ON” furan-based Schiff base for zinc(ii) ion probing: chemical synthesis, DFT studies, and X-ray crystal structure

Contact Info

Product

Resources

About