Bis(picolinato) complexes of vanadium and zinc as potential antidiabetic agents: synthesis, structural elucidation and <i>in vitro</i> insulin-mimetic activity study

Koleša-Dobravc, Tanja; Maejima, Keiichi; Yoshikawa, Yutaka; Meden, Anton; Yasui, Hiroyuki; Perdih, Franc

doi:10.1039/c7nj04189f

Cited by 26 publications

(13 citation statements)

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“…[V IV O(pic) 2 (H 2 O)] and [V V O 2 (picFF/picCN/picOH) 2 ] − , where picFF, picCN, and picOH are 3,5-difluoropicolinato, 5-cyanopicolinato, and 3-hydroxypicolinato, are strong inhibitors of fatty acid mobilization and effective in the treatment of rats affected by diabetes induced with streptozotocin. 10 , 11 …”

Section: Introductionmentioning

confidence: 99%

“…Among several VCs exhibiting insulin-enhancing properties, species with the stoichiometry V IV O(carrier) 2 /V V O 2 (carrier) 2 with carrier = maltolato (ma), 1,2-dimethyl-3-hydroxy-4(1 H )-pyridinonato (dhp), picolinato (pic), and dipicolinato (dipic) have been extensively studied. ,,, V IV and V V complexes with the picolinato ligand and its derivatives are very promising potential drugs (Scheme ). [V IV O(pic) 2 (H 2 O)] and [V V O 2 (picFF/picCN/picOH) 2 ] − , where picFF, picCN, and picOH are 3,5-difluoropicolinato, 5-cyanopicolinato, and 3-hydroxypicolinato, are strong inhibitors of fatty acid mobilization and effective in the treatment of rats affected by diabetes induced with streptozotocin. , …”

Section: Introductionmentioning

confidence: 99%

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Spectroscopic/Computational Characterization and the X-ray Structure of the Adduct of the V^IVO–Picolinato Complex with RNase A

et al. 2021

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The structure, stability, and enzymatic activity of the adduct formed upon the reaction of the V–picolinato (pic) complex [V IV O(pic) 2 (H 2 O)], with an octahedral geometry and the water ligand in cis to the V=O group, with the bovine pancreatic ribonuclease (RNase A) were studied. While electrospray ionization-mass spectrometry, circular dichroism, and ultraviolet–visible absorption spectroscopy substantiate the interaction between the metal moiety and RNase A, electron paramagnetic resonance (EPR) allows us to determine that a carboxylate group, stemming from Asp or Glu residues, and imidazole nitrogen from His residues are involved in the V binding at acidic and physiological pH, respectively. Crystallographic data demonstrate that the V IV O(pic) 2 moiety coordinates the side chain of Glu111 of RNase A, by substituting the equatorial water molecule at acidic pH. Computational methods confirm that Glu111 is the most affine residue and interacts favorably with the OC -6-23-Δ enantiomer establishing an extended network of hydrogen bonds and van der Waals stabilizations. By increasing the pH around neutrality, with the deprotonation of histidine side chains, the binding of the V complex to His105 and His119 could occur, with that to His105 which should be preferred when compared to that to the catalytically important His119. The binding of the V compound affects the enzymatic activity of RNase A, but it does not alter its overall structure and stability.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Spectroscopic/Computational Characterization and the X-ray Structure of the Adduct of the V^IVO–Picolinato Complex with RNase A

et al. 2021

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“…The electron-spin density around the actinide center ( S An ) is capable of accurately describing the metal oxidation state, which has previously been demonstrated by studying homo- and heterovalent diuranium complexes. ,− Herein, we calculated the electron-spin density ( S ) of atoms and listed them in Table . Electron-spin densities of U(VI) and U(IV) were, respectively, calculated to be approximately 0 and 2 in homovalent U VI (thf) – U VI (thf) , U VI – U VI , U IV (thf) – U IV (thf) , and U IV – U IV and heterovalent U VI (thf) – U IV (thf) .…”

Section: Results and Discussionmentioning

confidence: 99%

Relativistic DFT Probe for Reaction Energies and Electronic/Bonding Properties of Polypyrrolic Hetero-Bimetallic Actinide Complexes: Effects of Uranylendo-Oxo Functionalization

Zheng

Bacha

et al. 2021

Inorg. Chem.

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A series of hetero-bimetallic actinide complexes of the Schiff-base polypyrrolic macrocycle (L), featuring cation− cation interactions (CCIs), were systematically investigated using relativistic density functional theory (DFT). The tetrahydrofuran (THF) solvated complex [(THF)(OU VI OU IV )(THF)(L)] 2+ has high reaction free energy (Δ r G), and its replacement with electrondonating iodine promotes the reaction thermodynamics to obtain uranyl iodide [(I)(OU VI OU IV )(I)(L)] 2+ (U VI −U IV ). Retaining this coordination geometry, calculations have been extended to other An(IV) (An = Th, Pa, Np, Pu), i.e., for the substitution of U(IV) to obtain U VI −An IV . As a consequence, the reaction free energy is appreciably lowered, suggesting the thermodynamic feasibility for the experimental synthesis of these bimetallic complexes. Among all U VI −An IV , the electron-spin density and high-lying occupied orbitals of U VI −Pa IV show a large extent of electron transfer from electron-rich Pa(IV) to electron-deficient U(VI), leading to a more stable U V −Pa V oxidation state. Additionally, the shortest bond distance and the comparatively negative E int of the Pa−O endo bond suggest more positive and negative charges (Q) of Pa and endooxo atoms, respectively. As a result of the enhanced Pa−O endo bond and strong CCI in U VI −Pa IV along with the corresponding lowest reaction free energy among all of the optimized complexes, uranyl species is a better candidate for the experimental synthesis in the ultimate context of environmental remediation.

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“…2 All of listed characteristics of zinc as a central ion in combination with various ligands lead to new compounds with interesting antimicrobial, antidiabetic, optical, magnetic and other physical properties. [3][4][5][6][7][8][9][10] On the other hand, salicylic acid (H 2 sal; Fig. 1) has been found in numerous plant species where it acts as a phytohormone necessary for plant growth and development.…”

Section: Introductionmentioning

confidence: 99%

New Zinc Coordination Compound with Simple Salicylato and Pyridine Ligands: Synthesis, Crystal Structure and Hirshfeld Surface Analysis

Kitanovski

Počkaj

2021

ACSi

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A novel mononuclear zinc coordination compound with formula [Zn(Hsal)2(Py)2] (H2sal = salicylic acid, Py = pyridine) was prepared by mixing aqueous solutions of sodium salicylate and zinc sulfate in 1:1 molar ratio, and to the resulting solution pyridine was added dropwise. The obtained compound was characterized by elemental analysis, IR spectroscopy, and its crystal structure was determined by single-crystal X-ray diffraction method. X-ray structure analysis has shown that the central zinc ion is four-coordinated by two monodentate salicylato ligands and two pyridine molecules, forming a distorted tetrahedron. Since the asymmetric unit consists of two halves of coordination molecules, orthorhombic Ibca space group symmetry leads to two coordination molecules with slightly different geometry. The comparison between the two is given in terms of interatomic distances and angles, and also in terms of differences in intermolecular interactions obtained as a result of Hirshfeld surface analysis. With the assistance of C−H…O interactions, the adjacent molecules are linked into chains and further connected into three-dimensional network.

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Bis(picolinato) complexes of vanadium and zinc as potential antidiabetic agents: synthesis, structural elucidation and in vitro insulin-mimetic activity study

Abstract: The studied vanadium(iv), vanadium(v) and zinc(ii) complexes show inhibition of the free fatty acid release from rat adipocytes.

Cited by 26 publications

References 88 publications

Spectroscopic/Computational Characterization and the X-ray Structure of the Adduct of the V^IVO–Picolinato Complex with RNase A

Spectroscopic/Computational Characterization and the X-ray Structure of the Adduct of the V^IVO–Picolinato Complex with RNase A

Relativistic DFT Probe for Reaction Energies and Electronic/Bonding Properties of Polypyrrolic Hetero-Bimetallic Actinide Complexes: Effects of Uranylendo-Oxo Functionalization

New Zinc Coordination Compound with Simple Salicylato and Pyridine Ligands: Synthesis, Crystal Structure and Hirshfeld Surface Analysis

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Bis(picolinato) complexes of vanadium and zinc as potential antidiabetic agents: synthesis, structural elucidation and in vitro insulin-mimetic activity study

Abstract: The studied vanadium(iv), vanadium(v) and zinc(ii) complexes show inhibition of the free fatty acid release from rat adipocytes.

Cited by 26 publications

References 88 publications

Spectroscopic/Computational Characterization and the X-ray Structure of the Adduct of the VIVO–Picolinato Complex with RNase A

Spectroscopic/Computational Characterization and the X-ray Structure of the Adduct of the VIVO–Picolinato Complex with RNase A

Relativistic DFT Probe for Reaction Energies and Electronic/Bonding Properties of Polypyrrolic Hetero-Bimetallic Actinide Complexes: Effects of Uranylendo-Oxo Functionalization

New Zinc Coordination Compound with Simple Salicylato and Pyridine Ligands: Synthesis, Crystal Structure and Hirshfeld Surface Analysis

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Product

Resources

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Spectroscopic/Computational Characterization and the X-ray Structure of the Adduct of the V^IVO–Picolinato Complex with RNase A

Spectroscopic/Computational Characterization and the X-ray Structure of the Adduct of the V^IVO–Picolinato Complex with RNase A