Anthelminthic activity of organotellurium compounds

Ordyntseva, A. P.; Sivovolsva, I. D.; Абакаров, Г. М.; Sadekova, E. I.

doi:10.1007/bf00763667

Cited by 13 publications

(9 citation statements)

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“…[2] Several synthetic tellurium compounds exhibit biological activity. Compounds of the form R 2 TeCl n exhibit anthelmintic activity [3] whereas tellurite ions (TeO 3…”

Section: Introductionmentioning

confidence: 99%

Octa‐O‐bis‐(R,R)‐Tartarate Ditellurane (SAS)—a Novel Bioactive Organotellurium(IV) Compound: Synthesis, Characterization, and Protease Inhibitory Activity

Yosef¹,

Brodsky²,

Sredni³

et al. 2007

ChemMedChem

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Octa-O-bis-(R,R)-Tartarate Ditellurane (SAS) is a new Te(IV) compound, comprised of two tellurium atoms, each liganded by four oxygen atoms from two carboxylates and two alkoxides of two tartaric acids. Unlike many other Te(IV) compounds, SAS was highly stable in aqueous solution. It interacted with thiols to form an unstable Te(SR)(4) product. The product of the interaction of SAS with cysteine was isolated and characterized by mass spectroscopy and elemental analysis. SAS selectively inactivated cysteine proteases, but it did not inactivate other families of proteolytic enzymes. It displayed selectivity towards the cysteine protease cathepsin B, a human enzyme of pharmaceutical interest, with a second order rate constant k(i)/K(i)=5900 M(-1) s(-1).

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“…[2] Several synthetic tellurium compounds exhibit biological activity. Compounds of the form R 2 TeCl n exhibit anthelmintic activity [3] whereas tellurite ions (TeO 3…”

Section: Introductionmentioning

confidence: 99%

Octa‐O‐bis‐(R,R)‐Tartarate Ditellurane (SAS)—a Novel Bioactive Organotellurium(IV) Compound: Synthesis, Characterization, and Protease Inhibitory Activity

Yosef¹,

Brodsky²,

Sredni³

et al. 2007

ChemMedChem

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“…12 Several other tellurium compounds exhibit different biological activities. Compounds of the form R 2 TeCl n exhibit anthelmintic activity 13 while tellurite ions (TeO 3 2-) induce alterations of the erythrocyte membrane. 14 The latter activity is also thioldependent and probably involves intermediates with thioltellurium covalent bonds and various tellurium oxidation states.…”

Section: Introductionmentioning

confidence: 99%

Tellurium Compounds: Selective Inhibition of Cysteine Proteases and Model Reaction with Thiols

et al. 1998

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Ammonium trichloro(dioxoethylene-O,O‘)tellurate (AS101) is an organotellurium(IV) compound that exhibits immunomodulation activity. In light of the unique Te(IV)−thiol chemistry, it was tested as a selective cysteine protease inhibitor. Although no inhibitory activity of serine-, metallo-, or aspartic proteases was observed, AS101 exhibited time- and concentration-dependent inactivation of cysteine proteases. The kinetic parameters of inactivation of papain were K i = 3.5 ± 2.0 μM and k i = (5.1 ± 0.4) × 10-2 min-1. The enzymatic activity could be recovered by treatment with thiols, indicating that the inactivation involves oxidation of the active-site thiol to a disulfide bond (Enz−S−S−R) or to a species containing a Te−S bond such as Enz−S−Te−S−R. Gel permeation chromatography established that the R group is a small molecule and excludes the possibility of dimerization of the enzyme itself. It was further established that some other Te(IV) derivatives could also inactivate cysteine proteases, while Te(VI) derivatives did not exhibit any such inhibitory activity. In order to understand the chemistry underlying the cysteine protease inactivation by AS101 and other organotellurium(IV) compounds, their interaction with the model compound cysteine was studied. While the Te(VI) derivatives did not interact with cysteine, all of the Te(IV) compounds interacted with 4 equiv of cysteine. The kinetics of this interaction is first order in Te and second order in thiol, yielding a third-order rate constant of ∼106 M-2 s-1, as determined for the interaction between AS101 with cysteine. The interactions between Te derivatives and cysteine in DMSO were followed by 125Te and 13C NMR. While Te(VI) compounds did not undergo any changes upon interaction with cysteine, on the basis of their 125Te NMR, the Te(IV) derivatives interacted with 4 equiv of cysteine, yielding new stable Te(IV) compounds. These compounds were tentatively designated as Te(cysteine)4 or its high-valence complex with other components in the reaction mixture. These results expand our understanding of tellurium chemistry and correlate well with its biological activity. Such knowledge can be applied for the development of novel biologically active tellurium compounds.

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“…The antihelminic of four organotelluranes (13-17) was demonstrated against Trichinella spiralis infected mice (Ordyntseva et al 1988). The organotelluranes 13-15 were prepared by the reaction of the aryllithium reagent 12 and TeI 2 followed by the oxidation of the obtained organotellurides with chlorine or bromine.…”

Section: Biological Effects Of Organotellurium Compoundsmentioning

confidence: 99%

A glimpse on biological activities of tellurium compounds

Cunha

Gouvêa

Juliano

2009

An. Acad. Bras. Ciênc.

166

113

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Tellurium is a rare element which has been regarded as a toxic, non-essential trace element and its biological role is not clearly established to date. Besides of that, the biological effects of elemental tellurium and some of its inorganic and organic derivatives have been studied, leading to a set of interesting and promising applications. As an example, it can be highlighted the uses of alkali-metal tellurites and tellurates in microbiology, the antioxidant effects of organotellurides and diorganoditellurides and the immunomodulatory effects of the non-toxic inorganic tellurane, named AS-101, and the plethora of its uses. Inasmuch, the nascent applications of organic telluranes (organotelluranes) as protease inhibitors and its applications in disease models are the most recent contribution to the scenario of the biological effects and applications of tellurium and its compounds discussed in this manuscript.

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Anthelminthic activity of organotellurium compounds

Cited by 13 publications

References 0 publications

Octa‐O‐bis‐(R,R)‐Tartarate Ditellurane (SAS)—a Novel Bioactive Organotellurium(IV) Compound: Synthesis, Characterization, and Protease Inhibitory Activity

Octa‐O‐bis‐(R,R)‐Tartarate Ditellurane (SAS)—a Novel Bioactive Organotellurium(IV) Compound: Synthesis, Characterization, and Protease Inhibitory Activity

Tellurium Compounds: Selective Inhibition of Cysteine Proteases and Model Reaction with Thiols

A glimpse on biological activities of tellurium compounds

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