Vanadium Complexes with Biological Activity

After the discovery of the insulin-like effects of simple inorganic vanadium(IV/V) salts, due to the low intestinal absorption of vanadyl(IV) and the toxicity of vanadate(V), intensive research and synthetic work were directed to generate alternative vanadium complexes. Some of them are shown in Figure 8.1.22,23

In accordance with the inorganic chemistry of vanadium (see p. 143), many of the biologically tested vanadium complexes involve O coordination. Pyrone and pyridinone derivatives are the best, most-studied compounds. The trans-VO(IV)(Cys-Me)2, Figure 8.1, was the first orally active vanadium(IV) complex to treat DM in rats.24 One complex from this group, bismaltolatooxovanadium(IV),

VO(IV) complexes 2x(0,0)

VO(IV) complexes 2x(0,0)

ini-i2

VOCI(thiossm) " VO(thiohyd) VO(thioan), VO(Cys-Me),

Figure 8.1 Structural formulae of several vanadium complexes prepared and tested for their toxicity and biological activity (based on Ref. 20) VO(mal)2: VIV0[bis-maltolate], VO(hdp)2: VIV0[bis(l,2-dimethyl-3-hydroxy-4-pyridinone)], VO(hpo)2: YIV0[bis(2-hydroxy-pyridine-A-oxide)], VO(acac)2: VIV0[bis(acetylacetonate)], VO(Phac)2: VIV0[bis(benzoylacetonate)], VO(cf)2: VIV0{bis[l-cyclopropyl-6-fluoro-l,4-dihydroxo-4-oxo-7-(l-piperazinyl)-3-qinolinecarboxylate]}, VO(pic)2: VlyO[bis(picolinate)], V0(S03salen): V^OITVTV'-ethylenebis (salicylideneimine-5-sulphonate)], VO(dipic): VIVO-dipicolinate, VO(mpo)2: VlyO[bis(2-mercapto-pyridine-Ar-oxide)], VOCl(thiosem): VIVOCl(3-methoxysalicylidene-thiosemicarbazonate), VO(thiohyd): VIV0(OEt)[salicylidene-(benzylmercaptothiocarbonyl)hydrazonate], VO(thioan)2: VIV0[bis(2-aminophenolate)], VO(Cys-Me)2: VIV0[bis(cysteinemethyl ester)], V(hydraz)2: {VIY[bis(phenylacetyla-cetonato-benzoylhydrazone)]}, (VO)2(cit)2: {[VIV202(n-citrate)2]}4", (VO)2(OH)2(UDPglu)2: VIV0-(n-OH)2-(uridylglucose pyrophosphate)^ VO(thiohyd): VvO(OEt)[salicylidene(benzylmercapto-thiocarbonyl)hydrazonate]~, Vanadate: [H2Vv02]~, VO(van-His-Ser): {VvO (H20)[Ar-2-oxido-3-methoxysalicylidene]-histidylserine<2_)}, V02 (dipic): [Vv02(dipicolinate)]~, (VO)2(nap-tea)2: [Vv202{naphthalylide-ne[hydroxymethyl-bis-(oxymethyl)]aminomethane}2], VO(py-tris): [VvO{pyridylidene-tris(methoxy)methylamine}], V0(02)cmaa: VY0(02)[carboxymethyl-aspartate]~, V0(02)2Ala-His: [VvO(bis-peroxo)-alanylhistidine]~

ini-i2

VOCI(thiossm) " VO(thiohyd) VO(thioan), VO(Cys-Me),

Figure 8.1 Structural formulae of several vanadium complexes prepared and tested for their toxicity and biological activity (based on Ref. 20) VO(mal)2: VIV0[bis-maltolate], VO(hdp)2: VIV0[bis(l,2-dimethyl-3-hydroxy-4-pyridinone)], VO(hpo)2: YIV0[bis(2-hydroxy-pyridine-A-oxide)], VO(acac)2: VIV0[bis(acetylacetonate)], VO(Phac)2: VIV0[bis(benzoylacetonate)], VO(cf)2: VIV0{bis[l-cyclopropyl-6-fluoro-l,4-dihydroxo-4-oxo-7-(l-piperazinyl)-3-qinolinecarboxylate]}, VO(pic)2: VlyO[bis(picolinate)], V0(S03salen): V^OITVTV'-ethylenebis (salicylideneimine-5-sulphonate)], VO(dipic): VIVO-dipicolinate, VO(mpo)2: VlyO[bis(2-mercapto-pyridine-Ar-oxide)], VOCl(thiosem): VIVOCl(3-methoxysalicylidene-thiosemicarbazonate), VO(thiohyd): VIV0(OEt)[salicylidene-(benzylmercaptothiocarbonyl)hydrazonate], VO(thioan)2: VIV0[bis(2-aminophenolate)], VO(Cys-Me)2: VIV0[bis(cysteinemethyl ester)], V(hydraz)2: {VIY[bis(phenylacetyla-cetonato-benzoylhydrazone)]}, (VO)2(cit)2: {[VIV202(n-citrate)2]}4", (VO)2(OH)2(UDPglu)2: VIV0-(n-OH)2-(uridylglucose pyrophosphate)^ VO(thiohyd): VvO(OEt)[salicylidene(benzylmercapto-thiocarbonyl)hydrazonate]~, Vanadate: [H2Vv02]~, VO(van-His-Ser): {VvO (H20)[Ar-2-oxido-3-methoxysalicylidene]-histidylserine<2_)}, V02 (dipic): [Vv02(dipicolinate)]~, (VO)2(nap-tea)2: [Vv202{naphthalylide-ne[hydroxymethyl-bis-(oxymethyl)]aminomethane}2], VO(py-tris): [VvO{pyridylidene-tris(methoxy)methylamine}], V0(02)cmaa: VY0(02)[carboxymethyl-aspartate]~, V0(02)2Ala-His: [VvO(bis-peroxo)-alanylhistidine]~

"Bare" vanadium

V(hydraz)2

V(V) complexes

V02(dipic)

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