Vanadyl-biguanide complexes as potential synergistic insulin mimics.

Abstract:

:Vanadium has well-documented blood-glucose-lowering properties both in vitro and in vivo. The design of new oxovanadium(IV) coordination compounds, intended for use as insulin-enhancing agents in the treatment of diabetes mellitus, can potentially benefit from a synergistic approach, in which the whole complex has more than an additive effect from its component parts. Biguanides, most importantly metformin, are oral hypoglycemic agents used today to treat type 2 diabetes mellitus. In this study, biguanide, metformin, and phenformin, all biguanides, were coordinated to oxovanadium(IV) to form potential insulin-enhancing compounds. Highly colored, air-stable, bis(biguanidato)oxovanadium(IV), [VO(big)2], bis(N'N'-dimethylbiguanidato)oxovanadium(IV), [VO(metf)2], and bis(beta-phenethyl-biguanidato)oxovanadium(IV), [VO(phenf)2], were prepared. Solvation with dimethylsulfoxide occurred with VO(metf)2 to form a six-coordinate complex. Precursor ligands and oxovanadium(IV) coordination complexes were characterized by infrared spectroscopy, mass spectrometry, elemental analyses, magnetic susceptibility, and, where appropriate, 1H NMR spectroscopy. Biological testing with VO(metf)2, a representative compound, for insulin-enhancing potential included acute (72 h) administration, both by intraperitoneal (i.p.) injection and by oral gavage (p.o.) in streptozotocin (STZ)-diabetic rats. VO(metf)2 administration resulted in significant blood-glucose lowering at doses of 0.12 mmol kg-1 i.p. and 0.60 mmol kg-1 p.o. (previously established as ED50 doses for organically chelated oxovanadium(IV) complexes); however, no positive associative effects due to the presence of biguanide in the complex were apparent.

journal_name

J Inorg Biochem

authors

Woo LC,Yuen VG,Thompson KH,McNeill JH,Orvig C

doi

10.1016/s0162-0134(99)00152-x

subject

Has Abstract

pub_date

1999-09-30 00:00:00

pages

251-7

issue

3-4

eissn

0162-0134

issn

1873-3344

pii

S0162-0134(99)00152-X

journal_volume

76

pub_type

杂志文章
  • NMR studies of metal ion binding to the Zn-finger-like HNH motif of colicin E9.

    abstract::The 134 amino acid DNase domain of colicin E9 contains a zinc-finger-like HNH motif that binds divalent transition metal ions. We have used 1D 1H and 2D 1H-15N NMR methods to characterise the binding of Co2+, Ni2+ and Zn2+ to this protein. Data for the Co2+-substituted and Ni2+-substituted proteins show that the metal...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/s0162-0134(99)00235-4

    authors: Hannan JP,Whittaker SB,Hemmings AM,James R,Kleanthous C,Moore GR

    更新日期:2000-04-01 00:00:00

  • Tetra-chloro-(bis-(3,5-dimethylpyrazolyl)methane)gold(III) chloride: An HIV-1 reverse transcriptase and protease inhibitor.

    abstract::The title compound ([3,5-Me(2)bpzaH(2)][AuCl(4)]Cl, 1) (Me(2)bpza=bis(3,5-dimethylpyrazolyl)acetic acid), was prepared by reacting H[AuCl(4)] with 3,5-Me(2)bpza; and spectroscopically and structurally characterized. In the solid state structure of 1, the pyrazolyl ligand is doubly protonated to form two strong charge ...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2008.10.001

    authors: Fonteh PN,Keter FK,Meyer D,Guzei IA,Darkwa J

    更新日期:2009-02-01 00:00:00

  • Phenylthiourea alters toxicity of mercury compounds in zebrafish larvae.

    abstract::In recent years larval stage zebrafish have been emerging as a standard vertebrate model in a number of fields, ranging from developmental biology to pharmacology and toxicology. The tyrosinase inhibitor 1-phenyl-2-thiourea (PTU) is used very widely with larval zebrafish to generate essentially transparent organisms t...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2015.07.003

    authors: MacDonald TC,Nehzati S,Sylvain NJ,James AK,Korbas M,Caine S,Pickering IJ,George GN,Krone PH

    更新日期:2015-10-01 00:00:00

  • Desaturation of trans-octadecenoyl-acyl carrier protein by stearoyl-acyl carrier protein delta9 desaturase.

    abstract::Positional isomers of mono-unsaturated 18:1-ACP have been used as substrates for stearoyl-acyl carrier protein delta9 desaturase to test whether a C-H bond abstraction from either the C-9 or C-10 position could lead to rearranged products diagnostic for the production of an allylic radical intermediate. The reconstitu...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/s0162-0134(99)00199-3

    authors: Broadwater JA,Laundre BJ,Fox BG

    更新日期:2000-01-15 00:00:00

  • The intercalation to DNA of bipyridyl complexes of platinum(II) with thioureas.

    abstract::The non-covalent interaction of the complexes [Pt(bpy)(R,R'NCSNR'',R''')(2)]Cl(2) (bpy=2,2'-bipyridine; R=R'=R''=R'''=H; R=Me, R'=R''=R'''=H; R=n-Bu, R'=R''=R'''=H; R=p-tolyl, R'=R''=R'''=H; R=Et, R'=H, R''=Et, R'''=H) with calf thymus DNA has been studied at pH 7 and 25 degrees C. The processes give rise to: (i) reve...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2004.11.002

    authors: Cusumano M,Di Pietro ML,Giannetto A,Vainiglia PA

    更新日期:2005-02-01 00:00:00

  • Superoxide dismutase inhibition of alkaline hemin-mediated O2 activation.

    abstract::Inhibition of hemin-mediated O2 activation by bovine superoxide dismutase and the copper tetrammine complex has been examined. It is shown that the inhibitory effect of these species is not due to metabolism of O2-., but to a nonspecific inhibition of the process by the Cu2+ ion. We propose that the inhibition occurs ...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(89)80026-1

    authors: Adams C,Adams PA

    更新日期:1989-09-01 00:00:00

  • Hydroperoxide-dependent folic acid degradation by cytochrome c.

    abstract::Folic acid is degraded by cytochrome c in the presence of hydrogen peroxide/tert-butyl hydroperoxide at the C9-N10 bond. The degradation is increased with increasing temperature. When guanidine HCl or benzoate are included in the reaction medium, the amount of folic acid degradation is enhanced. Catalase, formate, and...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(87)80058-2

    authors: Taher MM,Lakshmaiah N

    更新日期:1987-10-01 00:00:00

  • Deletions in the loop surrounding the iron-sulfur cluster of adrenodoxin severely affect the interactions with its native redox partners adrenodoxin reductase and cytochrome P450(scc) (CYP11A1).

    abstract::The redox active iron-sulfur center of bovine adrenodoxin is coordinated by four cysteine residues in positions 46, 52, 55 and 92 and is covered by a loop containing the residues Glu-47, Gly-48, Thr-49, Leu-50 and Ala-51. In plant-type [2Fe-2S] ferredoxins, the corresponding loop consists of only four amino acids. The...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/s0162-0134(02)00463-4

    authors: Zöllner A,Hannemann F,Lisurek M,Bernhardt R

    更新日期:2002-09-20 00:00:00

  • The two modes of binding of Ru(phen)(2)dppz(2+) to DNA: thermodynamic evidence and kinetic studies.

    abstract::The binding of Ru(phen)(2)dppz(2+) (dppz=dipyrido[3,2-a:2',3'-c]phenazine) to DNA was investigated at pH 7.0 and 25 degrees C using stopped-flow and spectrophotometric methods. Equilibrium measurements show that two modes of binding, whose characteristics depend on the polymer to dye ratio (C(P)/C(D)), are operative. ...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2006.11.009

    authors: Biver T,Cavazza C,Secco F,Venturini M

    更新日期:2007-03-01 00:00:00

  • Controllable preparation of Nano-MgO and investigation of its bactericidal properties.

    abstract::Samples of nano-MgO with varying particle sizes were prepared by four different methods using Mg(NO3)2.6H2O, Na2CO3, urea and ammonia as raw materials and characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), low temperature N2 adsorption-desorption measurements and FT-IR spectroscopy. Bact...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2004.12.022

    authors: Huang L,Li DQ,Lin YJ,Wei M,Evans DG,Duan X

    更新日期:2005-05-01 00:00:00

  • A Mössbauer and X-ray powder diffraction study of some ferrous hematinics.

    abstract::Iron deficiency anemia is a relatively common illness that can arise from a number of different causes. Three ferrous salts are usually used in its treatment: ferrous fumarate, gluconate, and sulfate. They are administered orally and are relatively well tolerated. These hematinics have been studied by Mössbauer spectr...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(94)00062-f

    authors: Coe EM,Bowen LH,Bereman RD

    更新日期:1995-06-01 00:00:00

  • Intercalation of bulky Delta,Delta- and Lambda,Lambda-bis-Ru(II) complex between DNA base pairs.

    abstract::Interaction of Delta,Delta- and Lambda,Lambda-bis-Ru(II) complexes with native DNA was investigated by isotropic absorption and polarized spectroscopy including circular and linear dichroism (CD and LD). Despite the steric hindrance originating from its four bulky phenanthroline ligands at both ends of the molecule, t...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2008.06.012

    authors: Jang YJ,Kwon BH,Choi BH,Bae CH,Seo MS,Nam W,Kim SK

    更新日期:2008-10-01 00:00:00

  • Dinuclear macrocyclic polyamine zinc(II) complexes: syntheses, characterization and their interaction with plasmid DNA.

    abstract::The syntheses, characteristics of dinuclear macrocyclic polyamine zinc complexes and their interaction with plasmid DNA are reported. The two cyclen (1,4,7,10-tetraazacyclododecane) moieties are bridged by rigid and flexible linkages. The crystal structures of Zn2C27H43N8O15Cl4 [5c.(ClO4)3.2H2O] and Zn2C30H43N10O13Cl3...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2005.05.008

    authors: Xiang QX,Zhang J,Liu PY,Xia CQ,Zhou ZY,Xie RG,Yu XQ

    更新日期:2005-08-01 00:00:00

  • Theoretical characterization of Al(III) binding to KSPVPKSPVEEKG: Insights into the propensity of aluminum to interact with key sequences for neurofilament formation.

    abstract::Classical molecular dynamic simulations and density functional theory are used to unveil the interaction of aluminum with various phosphorylated derivatives of the fragment KSPVPKSPVEEKG (NF13), a major multiphosphorylation domain of human neurofilament medium (NFM). Our calculations reveal the rich coordination chemi...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2020.111169

    authors: Grande-Aztatzi R,Formoso E,Mujika JI,de Sancho D,Lopez X

    更新日期:2020-09-01 00:00:00

  • Inhibition of protein tyrosine phosphatase 1B and alkaline phosphatase by bis(maltolato)oxovanadium (IV).

    abstract::Vanadate has been recognized as a specific and potent phosphatase inhibitor since its structure is similar to that of phosphate. In this study, we measured the inhibition of glutathione S-transferase-tagged protein tyrosine phosphatase 1B (GST-PTP1B) and alkaline phosphatase (ALP) by the insulin enhancing compounds, b...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2008.06.007

    authors: Li M,Ding W,Baruah B,Crans DC,Wang R

    更新日期:2008-10-01 00:00:00

  • A molecular cytogenetic approach to studying platinum resistance.

    abstract::The technique of comparative genomic hybridisation (CGH) has until recently been used to screen for common genomic abnormalities in fresh tumour material; it has identified previously unrecognised regions of amplification associated with poor prognosis subtypes of breast cancer and lymphoma. Our group has applied this...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/s0162-0134(99)00140-3

    authors: Hiorns LR,Seckl MJ,Paradinas F,Sharp SY,Skelton LA,Brunstrom G,Newlands ES,Kelland LR,Leyland-Jones B

    更新日期:1999-10-01 00:00:00

  • Nickel-quinolones interaction: part 3--Nickel(II) complexes of the antibacterial drug flumequine.

    abstract::Nickel(II) complexes with the first-generation quinolone antibacterial agent flumequine in the presence or absence of nitrogen donor heterocyclic ligands (4-benzylpyridine, pyridine, 2,2'-bipyridine or 1,10-phenanthroline) have been structurally characterized by physicochemical and spectroscopic techniques. The experi...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2010.03.007

    authors: Skyrianou KC,Perdih F,Turel I,Kessissoglou DP,Psomas G

    更新日期:2010-07-01 00:00:00

  • Metal complexes of luteinizing hormone-releasing hormone (LHRH). potentiometric and spectroscopic studies.

    abstract::The results are reported of a potentiometric and spectroscopic study of the H+, Cu2+, and Ni2+ complexes of luteinizing hormone-releasing hormone (LHRH, HL) at 25 degrees C and an ionic strength 0.10 mol dm-3 (KNO3), since there is much evidence that the in vivo release of LHRH is influenced by the concentration of co...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(88)80030-8

    authors: Gerega K,Kozlowski H,Masiukiewicz E,Pettit LD,Pyburn S,Rzeszotarska B

    更新日期:1988-05-01 00:00:00

  • Design, synthesis, and evaluation of phosphorescent Ir(III) complexes with anticancer activity.

    abstract::A range of phosphorescent Ir(III) complexes containing four diverse P^P-chelating ligands of the type [Ir(ppy)2(L)][PF6], (ppy = 2‑phenylpyridine) where L is 1,2‑bis(diphenylphosphino)benzene (L1), 1,2‑bis(diphenylphosphino)ethane (L2), 1,2‑bis(diphenylphosphino)propane(L3) and 1,8‑bis(diphenylphosphino)naphthalene (L...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2019.110703

    authors: Liu Z,Li J,Ge X,Zhang S,Xu Z,Gao W

    更新日期:2019-08-01 00:00:00

  • Carbonic anhydrase inhibitors. Part 11. Coordination compounds of heterocyclic sulfonamides with lanthanides are potent inhibitors of isozymes I and II.

    abstract::A number of 22 lanthanide-containing coordination compounds of sulfonamides 2 and 3 were prepared and characterized by elemental analysis and spectroscopic data. The new compounds proved to be highly potent inhibitors of isozymes I and II of carbonic anhydrase. ...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(93)85019-5

    authors: Supuran CT,Manole G,Andruh M

    更新日期:1993-02-01 00:00:00

  • A suite of citrate-derived siderophores from a marine Vibrio species isolated following the Deepwater Horizon oil spill.

    abstract::Nearly all microbes require iron for growth. The low concentration of iron found in the ocean makes iron acquisition a particularly difficult task. In response to these low iron conditions, many bacteria produce low-molecular-weight iron-binding molecules called siderophores to aid in iron uptake. We report herein the...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2011.10.013

    authors: Gauglitz JM,Zhou H,Butler A

    更新日期:2012-02-01 00:00:00

  • Dimerization and DNA recognition rules of mithramycin and its analogues.

    abstract::The antineoplastic and antibiotic natural product mithramycin (MTM) is used against cancer-related hypercalcemia and, experimentally, against Ewing sarcoma and lung cancers. MTM exerts its cytotoxic effect by binding DNA as a divalent metal ion (Me(2+))-coordinated dimer and disrupting the function of transcription fa...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2015.12.011

    authors: Weidenbach S,Hou C,Chen JM,Tsodikov OV,Rohr J

    更新日期:2016-03-01 00:00:00

  • Synthesis, spectroscopic and magnetic resonance studies of mercury (II) and methylmercury (II) complexes of azathioprine, a biologically active mercaptopurine derivative.

    abstract::Synthetic and spectroscopic studies of the Hg(II) and MeHg(II) complexes of azathioprine (AZA), a biologically active 6-mercaptopurine derivative, were undertaken. The altered coordination behavior of AZA with respect to the parent mercaptopurine, with sulfur no longer being the primary donor atom, was confirmed. As c...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(94)85021-6

    authors: Chifotides HT,Dunbar KR,Katsaros N,Pneumatikakis G

    更新日期:1994-08-15 00:00:00

  • Activation of hydrogen peroxide by copper (II) complexes with some histidine-containing peptides and their SOD-like activities.

    abstract::The reactivities of copper(II) complexes with histidine-containing oligopeptides towards active oxygen species such as hydrogen peroxide (H2O2) and superoxide ion (O2-) were investigated by electron spin resonance (ESR)-spin trapping and thiobarbituric acid (TBA) methods. At physiological pH values, Cu(II) complexes w...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(94)85034-8

    authors: Ueda J,Ozawa T,Miyazaki M,Fujiwara Y

    更新日期:1994-08-01 00:00:00

  • Oxo-vanadium as a spin probe for the investigation of the metal coordination environment of imidazole glycerol phosphate dehydratase.

    abstract::Imidazole glycerol phosphate dehydratase (IGPD) catalyses the dehydration of imidazole glycerol phosphate to imidazole acetol phosphate, an important late step in the biosynthesis of histidine. IGPD, isolated as a low molecular weight and inactive apo-form, assembles with specific divalent metal cations to form a cata...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/s0162-0134(00)00025-8

    authors: Petersen J,Hawkes TR,Lowe DJ

    更新日期:2000-05-30 00:00:00

  • A study of the coordination shell of aluminum(III) and magnesium(II) in model protein environments: thermodynamics of the complex formation and metal exchange reactions.

    abstract::Al(III) toxicity in living organisms is based on competition with other metal cations. Mg(II) is one of the most affected cations, since the size similarity dominates over the charge identity. The slow ligand exchange rates for Al(III) render the ion useless as a metal ion at the active sites of enzymes and provide a ...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2005.12.007

    authors: Rezabal E,Mercero JM,Lopez X,Ugalde JM

    更新日期:2006-03-01 00:00:00

  • Redox reactions via vanadium-induced electron transfer.

    abstract::One-electron reduction and oxidation induced by vanadium complexes are demonstrated to be useful in oxidative and reductive transformations of carbonyl compounds. The redox interaction between vanadium complexes and redox-active ligands is achieved with coenzyme PQQ and polyanilines that afford the corresponding redox...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/s0162-0134(00)00036-2

    authors: Hirao T

    更新日期:2000-05-30 00:00:00

  • Synthesis and characterization of three new Cu(II)-dipeptide complexes.

    abstract::Three new copper(II) complexes of stoichiometry [Cu(L-dipeptide)].nH(2)O, containing as ligands the dipeptides L-alanine-L-isoleucine, L-alanine-L-threonine and L-alanine-L-tyrosine were prepared. They were characterized by single crystal X-ray diffractometry, and electronic and infrared spectroscopy. In all cases, th...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/s0162-0134(02)00367-7

    authors: Facchin G,Torre MH,Kremer E,Piro OE,Castellano EE,Baran EJ

    更新日期:2002-04-28 00:00:00

  • Metalated nucleotide chemisorption on hydroxyapatite.

    abstract::The experiments here reported evidence on the importance of the residual charge of a nucleotide derivative, for the adsorption on nHAP (hydroxyapatite nanocrystals), in water solution. We found that the simple presence of phosphates on the nucleotide derivative does not guarantee adsorption on nHAP. On the other hand,...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2015.04.006

    authors: Benedetti M,Antonucci D,De Castro F,Girelli CR,Lelli M,Roveri N,Fanizzi FP

    更新日期:2015-12-01 00:00:00

  • Stability constants of copper(II) mixed complexes with some 4-quinolone antibiotics and (N-N) donors.

    abstract::Studies of complexation equilibria of the antibiotic anions nalidixate and cinoxacinate with [Cu(phen)]2+ and [Cu(bipy)]2+ are reported. These studies indicate that the stability of this type of complex is strongly related to the metal environment. A correlation between the stability constants, determined here, with t...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(96)00041-4

    authors: Mendoza-Díaz G,Perez-Alonso R,Moreno-Esparza R

    更新日期:1996-11-15 00:00:00