Formation of an unusual pyridoxal derivative: Characterization of Cu(II), Ni(II) and Zn(II) complexes and evaluation of binding to DNA and to human serum albumin was written by Mukherjee, Tirtha;Pessoa, Joao Costa;Kumar, Amit;Sarkar, Asit R.. And the article was included in Inorganica Chimica Acta in 2015.Quality Control of 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride The following contents are mentioned in the article:
The in situ reaction of pyridoxal (pyd) and N-methyl-1,3-diamino propane (mdp) with Cu(II)-, Ni(II)- or Zn(II)-acetate yield binuclear [CuII2(pyd-mdp)(pyd-mmdp)Cl] (1), [NiII2(pyd-mdp)(pyd-mmdp)Cl] (2) and [ZnII2(pyd-mdp)(pyd-mmdp)Cl] (3), resp., where pyd-mdp– is the Schiff base ligand and H2pyd-mmdp is an unexpected compound, 1-((3-(((3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene)amino)propyl)(methyl)amino)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol. A plausible mechanism for the formation of the pyd-mmdp2- ligand is discussed. The mol. structure of 1 is determined by single-crystal x-ray diffraction, while those of 2 and 3 were inferred from the spectroscopic data. The binding of pyd-mmdp2- to the metal centers involves two phenolato-O, imine-N and amine-N atoms, and that of pyd-mdp– ligand one phenolato-O, the imine-N and the amine-N atoms; phenolato-O and chloro-Cl atoms bridge the metal centers. Complexes 1-3 are stable in buffered aqueous solutions at least up to 5 h. The competitive binding of 1-3 with DNA was studied, the apparent binding constants being K = 5.6 × 104, 3.9 × 104, and 5.8 × 104 M-1, resp. Complex 3 shows insulin-enhancing activity with an IC50 value of 0.51 relative to Zn sulfate. The interaction of 1, 2 or 3 as well as related complexes with pyridoxal-diamine derivatives with human serum albumin (HSA) was studied by CD spectra. In the presence of HSA, compounds 1-3 progressively decompose with time, forming monomeric M(Schiff base) HSA adducts. Probably imidazole- or amine-N atoms of the protein are involving in adduct formation. This study involved multiple reactions and reactants, such as 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride (cas: 65-22-5Quality Control of 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride).
3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride (cas: 65-22-5) belongs to alcohols. The oxygen atom of the strongly polarized O―H bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. Converting an alcohol to an alkene requires removal of the hydroxyl group and a hydrogen atom on the neighbouring carbon atom. Dehydrations are most commonly carried out by warming the alcohol in the presence of a strong dehydrating acid, such as concentrated sulfuric acid.Quality Control of 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride
Referemce:
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