Formation and hydrolysis of pyridoxal-5′-phosphate hydrazones and Schiff bases: Prediction of equilibrium and rate constants

Гамов, Г. А.; Киселев, А. Н.; Завалишин, М. Н.; Yarullin, Daniil N.

doi:10.1016/j.molliq.2022.120961

Cited by 7 publications

(9 citation statements)

References 52 publications

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“…[4][5][6]). We observed that hydrazones derived from pyridoxal 5'-phosphate were ~2 log units more stable (in terms of the logarithm of formation equilibrium constant) than the analogous Schiff bases [3]. The latter being dissolved in water at three different pH values (4.5; 7.4; 9.5) with a final concentration of base 10 -4 mol L -1 underwent fast hydrolysis in 10 min.…”

Section: Introductionmentioning

confidence: 91%

“…The ligand synthesized by Authors [2] is a Schiff base obtained as a result of a condensation reaction between pyridoxal and 2-aminoethanol. It happened that recently we studied the equilibria of formation reactions of Schiff bases and hydrazones derived from pyridoxal 5'-phosphate as well as the kinetics of their formation and hydrolysis [3] (other authors also paid a lot of attention to these systems; see, e.g. [4][5][6]).…”

Section: Introductionmentioning

confidence: 99%

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Comment on the Paper “Water-Soluble Pyridine-Based Colorimetric Chemosensor for Naked Eye Detection of Silver Ions: Design, Synthesis, Spectral and Theoretical Investigation”, Anal. Methods 2014, 6, 9610-9614 by B. Annaraj and M. A. Neelakantan

2023

Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol.

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В статье (Anal. Methods 2014, 6, 9610-9614) сообщалось, что основание Шиффа, образованное пиридоксалем и 2-аминоэтанолом (моноэтаноламином), может быть использовано как колориметрический и флуоресцентный индикатор ионов Ag + в водном растворе. В настоящей работе мы демонстрируем, что это основание Шиффа подвергается быстрому гидролизу в водном растворе. Кроме того, мы сообщаем, что нам не удалось воспроизвести результаты работы (Anal. Methods 2014, 6, 9610-9614) в части открытия ионов серебра(I) в водном растворе при помощи флуоресцентного индикатора -основания Шиффа пиридоксаля и 2-аминоэтанола. Настоящий комментарий был направлен первоначально в журнал Королевского химического общества Analytical Methods, где и была опубликована в 2014 году критикуемая работа. Через некоторое время мы получили отказ в опубликовании критической заметки, мотивированный тем, что наша рукопись не содержит новой информации либо новой интерпретации результатов, опубликованных ранее на страницах Analytical Methods. Вместо этого мы лишь ставим под сомнение ранее опубликованные данные. Редколлегия Analytical Methods обещала связаться с авторами критикуемой статьи и отозвать ее, если те не смогут удовлетворительно ответить на критические замечания. Отметим, что на момент подачи настоящей рукописи, критикуемая работа не отмечена, как вызвавшая сомнение, и доступна на странице журнала. Мы полагаем, что полученные нами в рамках данной работы результаты представляют интерес для научной общественности. Мы приветствуем предоставленную возможность вести научную дискуссию на страницах журнала «Известия высших учебных заведений. Химия и химическая технология», если авторы работы (Anal. Methods 2014, 6, 9610-9614) пожелают в ней участвовать.

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Section: Introductionmentioning

confidence: 91%

Section: Introductionmentioning

confidence: 99%

Comment on the Paper “Water-Soluble Pyridine-Based Colorimetric Chemosensor for Naked Eye Detection of Silver Ions: Design, Synthesis, Spectral and Theoretical Investigation”, Anal. Methods 2014, 6, 9610-9614 by B. Annaraj and M. A. Neelakantan

2023

Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol.

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“…The mass change of the hydrogel in the environment with low pH values is mainly controlled by degradation. Previous studies have shown that the hydrolysis of Schiff base under acidic conditions is a quasi-first-order reaction. , Thus, kinetic equations such as eq can be obtained, where P n is the molar concentration of a polymer with n imine bonds. k is the rate constant, and [ H + ] is the concentration of hydrogen ions.…”

Section: Theoretical and Computational Modelmentioning

confidence: 99%

Novel Injectable, Self-Healing, Long-Effective Bacteriostatic, and Healed-Promoting Hydrogel Wound Dressing and Controlled Drug Delivery Mechanisms

Li,

Chen,

Zhang

et al. 2024

ACS Appl. Mater. Interfaces

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Multivalent ion cross-linking has been used to form hydrogels between sodium alginate (SA) and hyaluronic acid (HA) in previous studies. However, more stable and robust covalent cross-linking is rarely reported. Herein, we present a facile approach to fabricate a SA and HA hydrogel for wound dressings with injectable, good biocompatibility, and high ductility. HA was first reacted with ethylenediamine to graft an amino group. Then, it was cross-linked with oxidized SA with dialdehyde to form hydrogel networks. The dressing can effectively promote cell migration and wound healing. To increase the antibacterial property of the dressing, we successfully loaded tetracycline hydrochloride into the hydrogel as a model drug. The drug can be released slowly in the alkaline environment of chronic wounds, and the hydrogel releases drugs again in the more acidic environment with wound healing, achieving a long-term antibacterial effect. In addition, one-dimensional partial differential equations based on Fickian diffusion with time-varying diffusion coefficients and hydrogel thicknesses were used to model the entire complex drug release process and to predict drug release.

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“…PIH prevented *OH‐mediated strand breaks in plasmid pUC‐18 DNA, chelating Fe(II) from the solution [45]. Recent studies predicted equilibrium and rate constants for pyridoxal‐5′‐phosphate hydrazones and Schiff bases under varying pH conditions [46]. In vitro, microsomal metabolism studies indicated that aldehyde derivatives were susceptible to metabolic hydrolysis, while ketone derivatives remained stable [47].…”

Section: Introductionmentioning

confidence: 99%

Evaluation of novel pyridoxal isonicotinoyl hydrazone (PIH) derivatives as potential anti‐tuberculosis agents: An in silico investigation

Hossain,

Al Abbad,

Alsunaidi

et al. 2024

Int J of Quantum Chemistry

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This investigation employed computational methodologies to assess the therapeutic potential of derivatives (1–16) of pyridoxal isonicotinoyl hydrazone (PIH) as potential treatments for tuberculosis. Various computational techniques, including molecular dynamics simulation, molecular docking, density functional theory, and global chemical descriptors, were employed to analyze the interactions between the ligands and target proteins. Docking results indicated that ligands 6, 7, 8, and rifampin exhibited binding affinities of −8.4, −7.4, −9.2, and − 7.2 kcal mol−1, respectively, against mycobacterium tuberculosis enoyl acyl carrier protein reductase (INHA), with ligand 8 demonstrating superior inhibition. Molecular dynamics (MD) simulations were utilized to assess the stability of protein‐ligand interactions. Remarkably, the Root Mean Square Deviation (RMSD) of the INHA‐ligand 8 complex remained minimal, with peak values at .40, .56, .37, and .50 nm at temperatures of 300, 305, 310, and 320 K, respectively. This suggests superior stability compared to the reference drug rifampin and INHA complex, which exhibited an RMSD range of .2 to .8 nm at 300 K. Furthermore, analysis using Frontier Molecular Orbital (FMO) revealed that the Egap value of ligand 8 (4.407 eV) is lower than all the reference drugs except rifampin. This comprehensive theoretical analysis positions ligand 8 as a promising candidate for anti‐tuberculosis drug development, underscoring the need for further exploration through in vitro and in vivo studies.

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Formation and hydrolysis of pyridoxal-5′-phosphate hydrazones and Schiff bases: Prediction of equilibrium and rate constants

Cited by 7 publications

References 52 publications

Comment on the Paper “Water-Soluble Pyridine-Based Colorimetric Chemosensor for Naked Eye Detection of Silver Ions: Design, Synthesis, Spectral and Theoretical Investigation”, Anal. Methods 2014, 6, 9610-9614 by B. Annaraj and M. A. Neelakantan

Comment on the Paper “Water-Soluble Pyridine-Based Colorimetric Chemosensor for Naked Eye Detection of Silver Ions: Design, Synthesis, Spectral and Theoretical Investigation”, Anal. Methods 2014, 6, 9610-9614 by B. Annaraj and M. A. Neelakantan

Novel Injectable, Self-Healing, Long-Effective Bacteriostatic, and Healed-Promoting Hydrogel Wound Dressing and Controlled Drug Delivery Mechanisms

Evaluation of novel pyridoxal isonicotinoyl hydrazone (PIH) derivatives as potential anti‐tuberculosis agents: An in silico investigation

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