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PubMed2002

4-Hydroxypyridine-2,6-dicarboxylatodioxovanadate(V) complexes: solid state and aqueous chemistry.

The aqueous solution and solid state properties of (4-hydroxypyridine-2,6-dicarboxylato)dioxovanadate(V) (also referred to as (4-hydroxydipicolinato)dioxovanadate(V) or (chelidamato)dioxovanadate(V) and abbreviated [VO(2)(dipic-OH)](-)) were investigated. By using (1)H, (13)C, (17)O, and (51)V NMR 1D and 2D spectroscopy, the species present in solution, together with pK(a) values, equilibrium constants, and labilities, were characterized. The complex is most stable at acidic pH down to pH 1 where it is protonated. The stability of this complex is higher than that of the parent dipicolinatodioxovanadate(V) complex. The dipic-OH ligand is coordinated in a tridentate manner throughout the pH range studied, and the vanadium(V) atom is five-coordinate. Solid state structures of (NMe(4))[VO(2)(dipic-OH)].H(2)O (monoclinic, P2(1)/n) and Na[VO(2)(dipic-OH)].2H(2)O (triclinic, P1) were determined. The discrete complex anions in (NMe(4))[VO(2)(dipic-OH)].H(2)O are connected by hydrogen bonding between the hydroxyl group, a water molecule, and a carboxylate oxygen atom. Changing the counterion from NMe(4)(+) to sodium ion in Na[VO(2)(dipic-OH)].2H(2)O leads to the formation of a polymeric structure. Dynamic processes in solution were explored by using (1)H and (13)C EXSY NMR spectroscopy; exchange between complex and free ligand below pH 4 was observed. The differences between the dipicolinatodioxovanadate(V) parent complex and the [VO(2)(dipic-OH)](-) complex in the solid state and in solution demonstrate the subtle consequences of the one substitutional difference between the two ligands. The insulin-mimetic properties of this compound are likely to be of mechanistic interest in developing an understanding of the mode of action of the few known insulin-mimetic vanadium(V) complexes.

Crystallography, X-Ray↗
PubMed2006

Vanadium complex of 2-(2'-Pyridyl)-4,5-dicyanoimidazole showing spermicidal and cytotoxic properties.

Two complexes having the formulas VO(DCIPy)2(H2O).1.5H2O and VO(DCIPy)2(H2O).2MeOH have been synthesized and characterized (DCIPy = 2-(2'-pyridyl)-4,5-dicyanoimidazolato). The methanol solvated species has been studied by X-ray diffraction, and single crystals form in the space group P2(1)/n. The hydrated species was studied by electron paramagnetic resonance spectroscopy in both the solid state and in a frozen solution, and the values of A( parallel) examined using the additivity relationship. The hydrated species was shown to exhibit both spermicidal and cytoxic properties.

Antiviral Agents↗
PubMed2000

Electron transfer. 140. Reactions of riboflavin with metal center reductants.

Riboflavin (I) is reduced in separable steps by indium(I), vanadium(II), europium(II), and titanium(III) in 0.02-1.0 M H+, yielding first the radical ion, II (lambdamax = 495 nm), and then the dihydro compound, III. The initial reduction with InI yields 2 equiv of the radical, but kinetic profiles exhibit no irregularity due to intervention of In(II), indicating that participation by the dipositive state is much more rapid than the In(I) reaction. Predominant paths involve the protonated form of the flavin, RbH+, and that of the radical, RbH2.+. Formation of the radical with excess V(II) and Ti(III) (but not with In(I)) is strongly autocatalytic, reflecting rapid comproportionation involving the flavin and the dihydro compound. The V(II) and Ti(III) rates for both steps greatly exceed the substitution-controlled limits for these states and therefore pertain to outer-sphere processes. The very high ratio kEu/kv for the first step, however, points to an inner-sphere reduction by the lanthanide cation. A kinetic inversion is observed for In(I) (kRbH.+ > kRbH2.+), implying a bridged reduction path for the initial step with this center as well.

Electron Transport↗
PubMed2002

Oxovanadium complex-catalyzed aerobic oxidation of propargylic alcohols.

A catalytic system consisting of vanadium oxyacetylacetonate [VO(acac)(2)] and 3 A molecular sieves (MS3A) in acetonitrile works effectively for the aerobic oxidation of propargylic alcohols [R(1)CH(OH)Ctbd1;CR(2)] to the corresponding carbonyl compounds under an atmospheric pressure of molecular oxygen. Although the reactivity of alpha-acetylenic alkanols (R(1) = alkyl) is lower compared to that of the alcohols of R(1) = aryl, alkenyl, and alkynyl, the use of VO(hfac)(2) as a catalyst and the addition of hexafluoroacetylacetone improve the product yield in these cases. A catalytic cycle involving a vanadium(V) alcoholate species and beta-hydrogen elimination from it has been proposed for this oxidation.

Journal Article↗
PubMed2002

Synthesis, characterization, and reactivity of mononuclear O,N-chelated vanadium(IV) and -(III) complexes of methyl 2-Aminocyclopent-1-ene-1-dithiocarboxylate based ligand: reporting an example of conformational isomerism in the solid state.

Vanadium(IV) and -(III) complexes of a tetradentate N(2)OS Schiff base ligand H(2)L [derived from methyl 2-((beta-aminoethyl)amino)cyclopent-1-ene-1-dithiocarboxylate and salicylaldehyde] are reported. In all the complexes, the ligand acts in a bidentate (N,O) fashion leaving a part containing the N,S donor set uncoordinated. The oxovanadium(IV) complex [VO(HL)(2)] (1) is obtained by the reaction between [VO(acac)(2)] and H(2)L. In the solid state, compound 1 has two conformational isomers 1a and 1b; both have been characterized by X-ray crystallography. Compound 1a has the syn conformation that enforces the donor atoms around the metal center to adopt a distorted tbp structure (tau = 0.55). Isomer 1b on the other hand has an anti conformation with almost a regular square pyramidal geometry (tau = 0.06) around vanadium. In solution, however, 1 prefers to be in the square pyramidal form. A second variety of vanadyl complex [VO(L(cyclic))(2)](I(3))(2) (2) with a new bidentate O,N donor ligand involving isothiazolium moiety has been obtained by a ligand-based oxidation of the precursor complex 1 with iodine. Preliminary X-ray and FAB mass spectroscopic data of 2 have supported the formation of a heterocyclic moiety by a ring closure reaction involving a N-S bond. Vanadium(III) complex [V(acac)(HL)(2)] (3) has been obtained through partial ligand displacement of [V(acac)(3)] with H(2)L. Compound 3 has almost a regular octahedral structure completed by two bidentate HL ligands along with an acetylacetonate molecule. Electronic spectra, magnetism, EPR, and redox properties of these compounds are reported.

Journal Article↗
PubMed2001

pH-dependent investigations of vanadium(V)-peroxo-malate complexes from aqueous solutions. In search of biologically relevant vanadium(V)-peroxo species.

The established biochemical potential of vanadium has spurred considerable research interest in our lab, with specific focus on pertinent synthetic studies of vanadium(III) with a biologically relevant, organic, dicarboxylic acid, malic acid, in aqueous solutions. Simple reactions between VCl3 and malic acid in water, at different pH values, in the presence of H2O2, led to the crystalline dimeric complexes (Cat)4[VO(O2)(C4H3O5)]2*nH2O (Cat = K+, n = 4, 1; Cat = NH4+, n = 3, 2) and K2[VO(O2)(C4H4O5)]2*2H2O (3). All three complexes were characterized by elemental analysis, FT-IR, and UV/visible spectroscopies. Compound 1 crystallizes in the monoclinic space group P2(1)/c, with a = 8.380(5) A, b = 9.252(5) A, c = 13.714(8) A, beta = 93.60(2) degrees, V = 1061(1) A3, and Z = 4. Compound 2 crystallizes in the triclinic space group P1, with a = 9.158(4) A, b = 9.669(4) A, c = 14.185(6) A, alpha = 104.81(1) degrees, beta = 90.31(1) degrees, gamma = 115.643(13) degrees, V = 1085.0(7) A(3), and Z = 2. Compound 3 crystallizes in the monoclinic space group P2(1)/c, with a = 9.123(8) A, b = 9.439(8) A, c = 10.640(9) A, beta = 104.58(3) degrees, V = 887(1) A3, and Z = 2. The X-ray structures showed that, in 1 and 2, the dimers consist of two (V(V)=O)2O2 rhombic units to which two malate ligands are attached. The ligands are triply deprotonated and, as such, they coordinate to vanadium(V), promoting a pentagonal bipyramidal geometry. In 3, the dimeric (V(V)=O)2O2 rhombic unit persists, with the two doubly deprotonated malate ligands coordinated to the vanadium(V) ions. UV/vis and EPR spectroscopic studies on the intermediate blue solutions of the synthesis reactions of 1-3 support the existence of vanadyl-containing dimeric species. These species further react with H2O2 to yield oxidation of V(IV)2O2 to V(V)2O2 and coordination of the peroxide to vanadium(V). From the collective data on 1-3, it appears that pH acts as a decisive factor in dictating the structural features of the isolated complexes. The details of the introduced structural differentiation in the reported complexes, and their potential relevance to vanadium(V) dicarboxylate systems in biological media are dwelled on.

Crystallography, X-Ray↗
PubMed2004

Positive regulation of ERK activation and MKP-1 expression by peroxovanadium complex bpV (phen).

Lower micromolar concentrations of peroxovanadium compound potassium bisperoxo(1,10-phenanthroline)oxovanadate (V) [bpV (phen)] stimulate RINm5F cell metabolic activity. 1 and 3 micromol/L bpV (phen) induces strong and sustained activation of extracellular signal-regulated kinase (ERK). However, it seems that bpV (phen) does not effect c-Jun N-terminal kinase (JNK) and p38 mitogen-activated protein kinase (MAPK) phosphorylation. In addition, bpV (phen) induces mitogen-activated protein kinase phosphatase-1 (MKP-1) expression. We found that ERK activation could be completely abolished if RINm5F cells were incubated with both bpV (phen) and PD 98059, a specific inhibitor of upstream ERK kinase MEK1. On the other hand, this combined treatment up-regulated activation of stress kinases, JNK and p38 MAPK, significantly suppressed MKP-1 expression and induced cell death. Thus, our results suggest that the mechanism underlying bpV (phen) survival-enhancing effect could be associated with induced ERK activation and MKP-1 expression.

Animals↗
PubMed1983

Interaction of metals and carbon tetrachloride on lipid peroxidation and hepatotoxicity.

Rats were administered ferrous sulfate, cadmium chloride, or sodium vanadate alone and in combination with carbon tetrachloride (CCl4) to determine if lipid peroxidation is associated with the toxicity of the three metals and to determine if there is an interaction between these metals and CCl4 in producing lipid peroxidation and hepatotoxicity. Expired ethane was used as an index of lipid peroxidation while serum alanine aminotransferase (ALT) and histopathology were used to assess liver damage. Lipid peroxidation did not appear to be associated with the hepatotoxicity of cadmium since no measurable increase in ethane production was observed when serum ALT concentrations were doubled relative to controls. Cadmium did not increase ethane when administered with CCl4 and the increase in ALT was additive. Iron and vanadate produced small significant increases in ethane production but no increase in ALT and only minor histopathologic changes, yet potentiated lipid peroxidation and liver damage when administered with CCl4. Thus, Cd did not produce lipid peroxidation and did not potentiate the lipid peroxidation and hepatotoxicity of CCl4, while iron or vanadate which produced lipid peroxidation alone potentiated the lipid peroxidation and hepatotoxicity of CCl4.

Alanine Transaminase↗
PubMed2006

Preparation and photocatalytic properties of YVO4 nanopowders.

YVO(4) photocatalysts with different grain sizes were obtained by annealing the YVO(4) nanopowders synthesized via microwave irradiation. The products were characterized by X-ray diffractometer (XRD), scanning electron microscope (SEM), transmission electron microscope (TEM), surface area and porosity analyzer, and ultraviolet-visible (UV-vis) spectrophotometer. Photocatalytic measurements showed that the YVO(4) nanopowders with grain size of about 5 nm possess superior photocatalytic properties in decolorization of methyl orange solution.

Azo Compounds↗
PubMed2002

Studies of electron paramagnetic resonance parameters and defect structures for Ti2+ and V3+ ions in CdS crystals.

By applying the high-order perturbation formulas based on the cluster approach for the EPR parameters of 3d2 ions in trigonal symmetry, the zero-field splitting D, g factors gparallel, gperpendicular, and hyperfine structure constants Aparallel, Aperpendicular for Ti2+ and V3+ ions in CdS crystals are studied. From the studies, the defect structures of these paramagnetic impurity centers are obtained and the EPR parameters are also explained reasonably.

Biophysical Phenomena↗
PubMed2006

Synthesis, characterization, and structures of oxovanadium(V) complexes of Schiff bases of beta-amino alcohols as tunable catalysts for the asymmetric oxidation of organic sulfides and asymmetric alkynylation of aldehydes.

Oxovanadium(V) complexes and with general formula VO(L3*)(OR5) were prepared in quantitative yields in alcohol (R5OH) from reactions of VO(O-i-Pr)3 and tridentate Schiff bases of beta-amino alcohols having one or two stereogenic centers, (HO)C*(R1)(R2)C*H(R3)N[double bond, length as m-dash]CH(2-OH-3,5-R4(2)-C6H2) (H2L3*). The alkoxy OR5 ligand exchanges readily with the alcoholic molecule in the solvent. Crystal structures of and were determined to be five-coordinate square pyramidal monomers. However, 1H NMR spectra of the complexes reveal two sets of signals, indicating the presence of two isomers in solution. The two isomers are suggested to be the endo/exo pair or the monomer/dimer pair. Asymmetric oxidations of methyl phenyl sulfide catalyzed by catalyst precursors were demonstrated to afford the chiral sulfoxide in yields and ee values similar to those obtained from the in situ-formed catalytic systems of VO(acac)2 and corresponding Schiff base ligands. Complexes and are also good catalysts for asymmetric alkynyl additions to aldehydes. Structural differences between the oxovanadium complexes, for inducing high stereoselectivities in the asymmetric oxidation of organic sulfides and the asymmetric alkynyl addition to aldehydes, are rationalized.

Aldehydes↗
PubMed1993

Dissimilatory metal reduction.

Microorganisms can enzymatically reduce a variety of metals in metabolic processes that are not related to metal assimilation. Some microorganisms can conserve energy to support growth by coupling the oxidation of simple organic acids and alcohols, H2, or aromatic compounds to the reduction of Fe(III) or Mn(IV). This dissimilatory Fe(III) and Mn(IV) reduction influences the organic as well as the inorganic geochemistry of anaerobic aquatic sediments and ground water. Microorganisms that use U(VI) as a terminal electron acceptor play an important role in uranium geochemistry and may be a useful tool for removing uranium from contaminated environments. Se(VI) serves as a terminal electron acceptor to support anaerobic growth of some microorganisms. Reduction of Se(VI) to Se(O) is an important mechanism for the precipitation of selenium from contaminated waters. Enzymatic reduction of Cr(VI) to the less mobile and less toxic Cr(III), and reduction of soluble Hg(II) to volatile Hg(O) may affect the fate of these compounds in the environment and might be used as a remediation strategy. Microorganisms can also enzymatically reduce other metals such as technetium, vanadium, molybdenum, gold, silver, and copper, but reduction of these metals has not been studied extensively.

Bacteria↗
PubMed1990

Characterization of vanadium bromoperoxidase from Macrocystis and Fucus: reactivity of vanadium bromoperoxidase toward acyl and alkyl peroxides and bromination of amines.

Vanadium bromoperoxidase (V-BrPO) has been isolated and purified from the marine brown algae Fucus distichus and Macrocystis pyrifera. V-BrPO catalyzes the oxidation of bromide by hydrogen peroxide, resulting in the bromination of certain organic acceptors or the formation of dioxygen. V-BrPO from F. distichus and M. pyrifera have subunit molecular weights of 65,000 and 74,000, respectively, and specific activities of 1580 units/mg (pH 6.5) and 1730 units/mg (pH 6) for the bromination of monochlorodimedone, respectively. As isolated, the enzymes contain a substoichiometric vanadium/subunit ratio; the vanadium content and specific activity are increased by addition of vanadate. V-BrPO (F. distichus, M. pyrifera, and Ascophyllum nodosum) also catalyzes the oxidation of bromide using peracetic acid. In the absence of an organic acceptor, a mixture of oxidized bromine species (e.g., hypobromous acid, bromine, and tribromide) is formed. Bromamine derivatives are formed from the corresponding amines, while 5-bromocytosine is formed from cytosine. In all cases, the rate of the V-BrPO-catalyzed reaction is much faster than that of the uncatalyzed oxidation of bromide by peracetic acid, at pH 8.5, 1 mM bromide, and 2 mM peracetic acid. In contrast to hydrogen peroxide, V-BrPO does not catalyze formation of dioxygen from peracetic acid in either the presence or absence of bromide. V-BrPO also uses phenylperacetic acid, m-chloroperoxybenzoic acid, and p-nitroperoxybenzoic acid to catalyze the oxidation of bromide; dioxygen is not formed with these peracids. V-BrPO does not catalyze bromide oxidation or dioxygen formation with the alkyl peroxides ethyl hydroperoxide, tert-butyl hydroperoxide, and cuminyl hydroperoxide.

Amines↗
PubMed2002

Peroxo-bridged divanadate as selective bromide oxidant in bromoperoxidation.

Diperoxovanadate is effective only in presence of free vanadate in vanadium-dependent bromoperoxidation at physiological pH. Peroxide in the form of bridged divanadate complex (VOOV-type), but not the bidentate form as in diperoxovanadate, is proposed to be the oxidant of bromide. In order to obtain direct evidence, peroxo-divanadate complexes with glycyl-glycine, glycyl-alanine and glycyl-asparagine as heteroligands were synthesized. By elemental analysis and spectral studies they were characterized to be triperoxo-divanadates, [V2O,(O2)3(peptide)3] x H2O, with the two vanadium atoms bridged by a peroxide and a heteroligand. The dipeptide seems to stabilize the peroxo-bridge by inter-ligand interaction, possibly hydrogen bonding. This is indicated by rapid degradation of these compounds on dissolving in water with partial loss of peroxide accompanied by release of bubbles of oxygen. The 51V-NMR spectra of such solutions showed diperoxovanadate and decavanadate (oligomerized from vanadate) as the products. Additional oxygen was released on treating these solutions with catalase as expected of residual diperoxovanadate. The solid compounds when added to the reaction mixtures showed transient, rapid bromoperoxidation reaction, but not oxidation of NADH or inactivation of glucose oxidase, the other two activities shown by a mixture of diperoxovanadate and vanadyl. This demonstration of peroxide-bridged divanadate as a powerful, selective oxidant of bromide, active at physiological pH, should make it a possible candidate of mimic in the action of vanadium in bromoperoxidase proteins.

Bromides↗
PubMed1998

Near UV circular dichroism from biomimetic model compounds define the coordination geometry of vanadate centers in MeVi- and MeADPVi-rabbit myosin subfragment 1 complexes in solution.

The circular dichroism (CD) spectrum was measured from vanadate (Vi) cyclic esters of chiral vicinal diols, hydroxycarboxylates, and cyclodextrines as a function of Vi concentration ([Vi]) and at the lowest energy transitions of the vanadium. At low [Vi] and in the presence of excess vicinal diols, hydroxycarboxylates, or cyclodextrines the CD signal intensity scales linearly with [Vi] indicating the predominance of a monomeric cyclic ester. At higher [Vi], the signal intensity in the presence of the vicinal diols and hydroxycarboxylates become nonlinear in [Vi], indicating formation of a dimeric cyclic ester. Vanadium-51 NMR (51V-NMR) indicates the coordination geometry of several of these model Vi centers in solution and identifies the CD signals characteristic to Vi trigonal bipyramidal (tbp) and octahedral (Oh) coordination geometries from monomeric and dimeric species. The CD spectra from monomeric and dimeric forms of the tbp-coordinated model compounds have two apparent transitions with amplitudes of opposite sign at wavelengths > or = 240 nm. Spectra from the monomeric and dimeric Oh coordinated species are distinct from the tbp-type spectra over the same wavelength domain because of the presence of two additional transitions with opposite sign amplitudes. These model spectra were compared to the vanadate CD spectra from Vi bound to rabbit myosin subfragment 1 (S1) in solution, in the presence of divalent metal cations (MeVi-S1) or trapped with MeADP (MeADPVi-S1). Polymeric MeVi binds to the active site of S1 and the vanadate centers in MnVi-S1 or CoVi-S1 produce a CD signal resembling that from the tbp model. The trapped ATPase transition state analog MeADPVi produces a different CD signal resembling that from the Oh model.

Adenosine Triphosphate↗
PubMed2004

Mononuclear and dinuclear monoperoxovanadium(v) complexes with a hetero ligand. 1.(1) Self-decomposition reaction, detection of reactive oxygen species, and oxidizing ability.

A mononuclear peroxovanadium(V) complex with histamine-N,N-diacetate (histada), K[VO(O(2))(histada)], and a dinuclear peroxovanadium(V) complex with 2-oxo-1,3-diaminopropane-N,N,N',N'-tetraacetate (dpot), Cs(3)[(VO)(2)(O(2))(2)(dpot)], were prepared and characterized. The self-decomposition reaction was examined for these peroxovanadium(V) complexes as well as for K[VO(O(2))(cmhist)] (cmhist = N-carboxymethylhistidinate). The reaction profiles depicted by the absorbance change in the UV-vis spectrum show a sigmoid shape with an induction period. The induction period is reduced by the addition of acid, fluoride, thiocyanate, VO(2+), VO(2)(+), and trolox compared to the solution containing perchlorate. On the other hand, the induction period was elongated by the addition of chloride, bromide, and 2-tert-butyl-p-cresol. These behaviors are discussed on the basis of a radical chain mechanism. The self-decomposition reactions have also been followed by the (1)H and (51)V NMR and EPR spectra. These spectral studies as well as the UV-vis spectral study indicate that vanadium(V) is partly reduced to vanadium(IV) in the self-decomposition process. The histada complex yields a mixed-valence dinuclear complex in a concentrated solution, and the dpot complex yields a mixed-valence tetranuclear complex. The reduction of vanadium ion suggests that the peroxo ligand may act as a reducing agent. In order to know the fate of the peroxo ligand, we tried to detect superoxide anion and hydroxyl radical, which were anticipated to be produced in the self-decomposition process. The formation of superoxide anion was spectrophotometrically confirmed using two independent methods, including the reduction of cytochrome c and the reduction of sodium 4-[3-(iodophenyl)-2-(4-nitrophenyl)-2H-5-tetrazolio]-1,3-benzene disulfonate (WST-1). The formation of hydroxyl radical was confirmed by an EPR spin trapping technique. The oxidizing abilities of the peroxovanadium(V) complexes toward bovine serum albumin (BSA) were also evaluated. In the protein carbonyl assay, it was found that the total amount of protein carbonyl in BSA was increased by the reaction with the peroxovanadium complexes in the concentration-dependent manner. In addition, the oxidation of sulfhydryl group in BSA induced by the peroxovanadium complexes was confirmed.

Animals↗
PubMed2000

Chemical and physicochemical characterization of porous hydroxyapatite ceramics made of natural bone.

The properties of a porous hydroxyapatite ceramic produced by sintering of bovine bone were investigated by using a number of physicochemical methods such as scanning electron microscopy (SEM), SEM in combination with energy dispersive X-ray spectroscopy (SEM-EDX), mercury intrusion porosimetry, krypton-adsorption, contact angle measurements, wide angle X-ray diffraction. Fourier transform infrared spectroscopy, thermal analysis, inductively coupled plasma optical atom emissions spectroscopy and flame atomic absorption spectroscopy. The results indicate that there are considerable differences between the ceramic and native bone. However, the most important properties with respect to the use of such ceramics as a biomaterial for filling bone defects namely the high porosity (> or = 57 +/- 2%) and the interconnecting pore system are maintained. While macropores with an average diameter of approx. 300 microm contribute 97% to porosity, micropores with an average diameter of 1.3 microm account for only 3% of the total porosity. The surface area was found to be approx. 0.1 m2/g. The contact angles of water (44.6 +/- 15.4 degrees, n = 5) and tetrahydrofurane (10 degrees) allow the processing of the ceramic to a drug carrier by incubation with aqueous or organic drug solutions. The ceramic is highly crystalline with crystal sizes of 1-7 microm and contains crystal bridges. The investigation of its chemical composition revealed small amounts of other inorganic compounds such as Ca4O(PO4)2, NaCaPO4, Ca3(PO4)2, CaO, and MgO. Besides trace amounts of aluminum, iron, magnesium, potassium, silica, sodium, vanadium and zinc it contains probably carbonated apatite.

Animals↗
PubMed1999

Vanadyl-biguanide complexes as potential synergistic insulin mimics.

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.

Animals↗