Protonation of hydrazones derived from pyridoxal 5′-phosphate: Thermodynamic and structural elucidation

Гамов, Г. А.; Meshkov, A. N.; Завалишин, М. Н.; Khokhlova, Anisya; Gashnikova, A. V.; Aleksandriiskii, V. V.; Шарнин, В. А.

doi:10.1016/j.molliq.2020.112822

Cited by 12 publications

(9 citation statements)

References 35 publications

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“…The constants of the processes (1)–(3) are adopted from [ 46 ] for PLP-INH (log β 1 = 11.37; log β 2 = 19.60; log β 3 = 23.81), PLP-F2H (log β 1 = 11.43; log β 2 = 19.72; log β 3 = 23.79), PLP-T2H (log β 1 = 11.47; log β 2 = 19.75; log β 3 = 24.24), PLP-T3H (log β 1 = 11.48; log β 2 = 19.31; log β 3 = 24.15). The protonation constants of the PLP-F3H hydrazone are unknown; however, we took them to be equal to those of PLP-F2H, taking into account the closeness of the log β i values determined for different hydrazones to each other.…”

Section: Resultsmentioning

confidence: 99%

Complexation of Gold(III) with Pyridoxal 5′-Phosphate-Derived Hydrazones in Aqueous Solution

et al. 2022

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Today, complexes of gold(I) and gold(III) are recognized as promising drugs for the treatment of bacterial infectious diseases and oncological diseases, respectively. It is of interest to broaden the area of potential use of gold(III) compounds to the pathogenic microorganism as well. The first step towards the development of new antibacterial drugs based on Au3+ complexes is the study of their stability in an aqueous solution. The present contribution reports on the investigation of gold(III) complexation with five hydrazones derived from a well-known biologically active compound, pyridoxal 5′-phosphate (one of the aldehyde forms of the B6 vitamin). The complex formation in aqueous solutions was confirmed by mass spectrometry and fluorescent spectroscopy. The stoichiometric composition of the complexes formed and their stability constants were determined using a UV–Vis titration method. The complexes are quite stable at physiological values of pH, as the speciation diagrams show. The results of the paper are helpful for further studies of gold(III) complexes interaction with biomacromolecules.

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Section: Resultsmentioning

confidence: 99%

Complexation of Gold(III) with Pyridoxal 5′-Phosphate-Derived Hydrazones in Aqueous Solution

et al. 2022

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“…According to the protonation constants determined in Ref. 35, PLPderived hydrazones at pH exist predominantly as monoprotonated species (HL 2-). The first proton is added to imine nitrogen -CH=N-NH-, and the structure is stabilized due to intramolecular hydrogen bonds involving protonated imine nitrogen, carbonyl group, and oxygen in site 3 of PLP residue (see Equation 2).…”

Section: Resultsmentioning

confidence: 99%

Dephosphorylation of pyridoxal 5′‐phosphate‐derived Schiff bases in the presence of bovine alkaline phosphatase

Гамов

Murekhina

Aleksandriiskii

2021

Int J of Chemical Kinetics

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The present paper reports on the study of the dephosphorylation of pyridoxal 5′phosphate and four derived hydrazones (containing the residues of pyrazine, 2furan, 2-thiophene, 3-pyridine carboxylic acids) induced by bovine alkaline phosphatase from intestinal mucosa at 298.2 K and pH 10 (0.05 m Tris-HCl buffer).We observed and discussed characteristic changes in the UV-vis and fluorescent spectra of substrates. Michaelis-Menten parameters of the enzymatic dephosphorylation are calculated. The stability of alkaline phosphatase in the presence of hydrazones is confirmed. The dephosphorylation of the Zn(II) complex with pyridoxal 5′-phosphate-derived hydrazone is analyzed.

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“…Examples of the experimental and calculated titration curves are given in Figures S7–S9, along with examples of total data required for stability constant determination (Figure S10, Tables S5, S6). The results of potentiometric, spectrofluorimetric, and 139 La NMR titrations were processed using KEV software. , …”

Section: Methodsmentioning

confidence: 99%

“…The results of potentiometric, spectrofluorimetric, and 139 La NMR titrations were processed using KEV software. 33,34 MS (MALDI TOF) spectra were registered using the Shimadzu Biotech Axima Confidence setup (Shimadzu, USA). Solutions for MS analysis containing 5 mmol L −1 HCl, 50 mmol L −1 Tris, and Ln(III) ion were applied to the plate and dried in air.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

La(III), Ce(III), Gd(III), and Eu(III) Complexation with Tris(hydroxymethyl)aminomethane in Aqueous Solution

et al. 2020

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Lanthanides such as cerium(III), europium(III), and gadolinium(III) are widely used for designing fluorescent probes or magnetic resonance imaging contrasting agents for biological systems. The synthesis and study of lanthanide complexes in buffer solutions imitating biological fluids are often complicated because of a lack of data on the lanthanide interactions with buffer solution components. Therefore, Ln(III) [where Ln(III) = La(III), Ce(III), Gd(III), Eu(III)] complexation with a widely used buffer agent, tris(hydroxymethyl)aminomethane (Tris), in aqueous solution is studied using potentiometry, spectrofluorimetry, and 139 La NMR spectroscopy. The stoichiometric composition of complexes is determined using mass spectrometry. The thermodynamic stability constants of Ln(III)-Tris complexes are calculated from potentiometric and spectral data; the difficulties in the study of these systems, reliability, and accuracy of the obtained constants are discussed. The possible structures of free Tris and its complexes with lanthanides(III) are optimized on the density functional theory/PBE0 level; the peculiarities of metal−ligand bonds were studied by Quantum Theory Atoms in Molecules analysis.

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Protonation of hydrazones derived from pyridoxal 5′-phosphate: Thermodynamic and structural elucidation

Cited by 12 publications

References 35 publications

Complexation of Gold(III) with Pyridoxal 5′-Phosphate-Derived Hydrazones in Aqueous Solution

Complexation of Gold(III) with Pyridoxal 5′-Phosphate-Derived Hydrazones in Aqueous Solution

Dephosphorylation of pyridoxal 5′‐phosphate‐derived Schiff bases in the presence of bovine alkaline phosphatase

La(III), Ce(III), Gd(III), and Eu(III) Complexation with Tris(hydroxymethyl)aminomethane in Aqueous Solution

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