NDLI: Synthesis, structure analysis, solution chemistry, and in vitro insulinomimetic activity of novel oxovanadium(IV) complexes with tripodal ligands containing an imidazole group derived from amino acids

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Synthesis, structure analysis, solution chemistry, and in vitro insulinomimetic activity of novel oxovanadium(IV) complexes with tripodal ligands containing an imidazole group derived from amino acids

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Synthesis, structure analysis, solution chemistry, and in vitro insulinomimetic activity of novel oxovanadium(IV) complexes with tripodal ligands containing an imidazole group derived from amino acids

Content Provider	Springer Nature Link
Author	Kawabe, Kenji Sasagawa, Takahiro Yoshikawa, Yutaka Ichimura, Akio Kumekawa, Katsumi Yanagihara, Naohisa Taki, Toshikazu Sakurai, Hiromu Kojima, Yoshitane
Copyright Year	2003
Abstract	Structures, chemical properties, and in vitro insulinomimetic activities of new vanadyl [oxovanadium(IV), VO2+] complexes with five tripodal ligands containing an imidazole functionality were examined. The ligands, N-(carboxymethyl)-N-(4-imidazolylmethyl)amino acids, contain glycine, (S)- and (R)-alanine, and (S)- and (R)-leucine residues. The molecular structures of the latter four alanine- and leucine-containing complexes were determined by X-ray analysis. The coordination geometry around each vanadium center was octahedral, where an imino nitrogen occupied the apical site and two carboxylate oxygens, an imidazole nitrogen, and a water molecule coordinated in the equatorial plane. The spectroscopic properties of the complexes were characterized by means of IR, electronic absorption, and CD spectra. Acid dissociation constants (pK a) and protonation sites of the ligands were determined by a combination of potentiometric titrations and 1H NMR spectra. The potentiometric study demonstrated that stability constants (log β) were not so different among the present complexes (14.0–14.9) and a species of molecular complex with a 1:1 metal:ligand ratio existed predominantly at physiological pH 7.4. EPR parameters indicated that the species at pH 7.4 had an octahedral structure similar to the complex in the solid state. On the other hand, an EPR study in phosphate buffer (pH 7.4) suggested that inorganic phosphate coordinated to the vanadium center instead of the imidazole group in the presence of excess phosphate ion. Cyclic voltammograms in the phosphate buffer showed chemically reversible oxidation waves, whereas irreversible oxidation waves were observed in non-coordinating HEPES buffer. Moreover, the oxidation potential of each complex in phosphate buffer was more positive than that in HEPES buffer. Partition coefficients of the present complexes in a n-octanol/saline system were very low, probably due to hydrophilicity of the imidazole group. The in vitro insulinomimetic activities were estimated on the basis of the ability of the complexes to inhibit epinephrine-stimulated free fatty acid release from isolated rat adipocytes. The achiral glycine-derivative complex exhibited the highest insulinomimetic activity, which was higher than that of VOSO4 as a positive control. Putting our previous observations together, it was found that the vanadyl complexes with tetradentate amino acid derivatives having no alkyl side chain tend to have high in vitro insulinomimetic activity.
Starting Page	893
Ending Page	906
Page Count	14
File Format	PDF
ISSN	09498257
Journal	JBIC Journal of Biological Inorganic Chemistry
Volume Number	8
Issue Number	8
e-ISSN	14321327
Language	English
Publisher	Springer-Verlag
Publisher Date	2003-10-09
Publisher Place	Berlin, Heidelberg
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Amino acid Imidazole Insulinomimetic activity Tripodal ligand Vanadyl complex
Content Type	Text
Resource Type	Article
Subject	Biochemistry Inorganic Chemistry

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