Hypervalent Organochalcogenanes As Inhibitors of Protein Tyrosine Phosphatases

Overview

Journal Org Biomol Chem

Publisher Royal Society of Chemistry

Specialties Biochemistry
Chemistry

Date 2011 Jan 18

PMID 21240419

Citations 3

Authors

Leandro Piovan

Li Wu

Zhong-Yin Zhang

Leandro H Andrade

Affiliations

Soon will be listed here.

Abstract

A series of organochalcogenanes was synthesized and evaluated as protein tyrosine phosphatases (PTPs) inhibitors. The results indicate that organochalcogenanes inactivate the PTPs in a time- and concentration-dependent fashion, most likely through covalent modification of the active site sulfur-moiety by the chalcogen atom. Consequently, organochalcogenanes represent a new class of mechanism-based probes to modulate the PTP-mediated cellular processes.

Citing Articles

Stability Study of Hypervalent Tellurium Compounds in Aqueous Solutions.

Princival C, Archilha M, Dos Santos A, Franco M, Braga A, Rodrigues-Oliveira A ACS Omega. 2019; 2(8):4431-4439.

PMID: 31457735 PMC: 6641895. DOI: 10.1021/acsomega.7b00628.

Covalent inhibition of protein tyrosine phosphatases.

Ruddraraju K, Zhang Z Mol Biosyst. 2017; 13(7):1257-1279.

PMID: 28534914 PMC: 5663200. DOI: 10.1039/c7mb00151g.

Enzymatic kinetic resolution of tert-butyl 2-(1-hydroxyethyl)phenylcarbamate, a key intermediate to chiral organoselenanes and organotelluranes.

Piovan L, Pasquini M, Andrade L Molecules. 2011; 16(9):8098-109.

PMID: 21934647 PMC: 6264364. DOI: 10.3390/molecules16098098.

References

Cunha R, Gouvea I, Feitosa G, Alves M, Bromme D, Comasseto J . Irreversible inhibition of human cathepsins B, L, S and K by hypervalent tellurium compounds. Biol Chem. 2009; 390(11):1205-12. DOI: 10.1515/BC.2009.125. View

Sanmartin C, Plano D, Antonio Palop J . Selenium compounds and apoptotic modulation: a new perspective in cancer therapy. Mini Rev Med Chem. 2008; 8(10):1020-31. DOI: 10.2174/138955708785740625. View

Carmely A, Meirow D, Peretz A, Albeck M, Bartoov B, Sredni B . Protective effect of the immunomodulator AS101 against cyclophosphamide-induced testicular damage in mice. Hum Reprod. 2009; 24(6):1322-9. DOI: 10.1093/humrep/den481. View

Zhang Z . Mechanistic studies on protein tyrosine phosphatases. Prog Nucleic Acid Res Mol Biol. 2003; 73:171-220. DOI: 10.1016/s0079-6603(03)01006-7. View

Prigol M, Pinton S, Schumacher R, Nogueira C, Zeni G . Convulsant action of diphenyl diselenide in rat pups: measurement and correlation with plasma, liver and brain levels of compound. Arch Toxicol. 2010; 84(5):373-8. DOI: 10.1007/s00204-009-0507-y. View

Jia Z, Barford D, Flint A, Tonks N . Structural basis for phosphotyrosine peptide recognition by protein tyrosine phosphatase 1B. Science. 1995; 268(5218):1754-8. DOI: 10.1126/science.7540771. View

Zhang Z . Protein tyrosine phosphatases: prospects for therapeutics. Curr Opin Chem Biol. 2001; 5(4):416-23. DOI: 10.1016/s1367-5931(00)00223-4. View

Bhabak K, Mugesh G . Amide-based glutathione peroxidase mimics: effect of secondary and tertiary amide substituents on antioxidant activity. Chem Asian J. 2009; 4(6):974-983. DOI: 10.1002/asia.200800483. View

Combs Jr G, Gray W . Chemopreventive agents: selenium. Pharmacol Ther. 1998; 79(3):179-92. DOI: 10.1016/s0163-7258(98)00014-x. View

10.

Prigol M, Schumacher R, WayneNogueira C, Zeni G . Convulsant effect of diphenyl diselenide in rats and mice and its relationship to plasma levels. Toxicol Lett. 2009; 189(1):35-9. DOI: 10.1016/j.toxlet.2009.04.026. View

11.

Wieslander E, Engman L, Svensjo E, Erlansson M, Johansson U, Linden M . Antioxidative properties of organotellurium compounds in cell systems. Biochem Pharmacol. 1998; 55(5):573-84. DOI: 10.1016/s0006-2952(97)00517-0. View

12.

Tonks N . Protein tyrosine phosphatases: from genes, to function, to disease. Nat Rev Mol Cell Biol. 2006; 7(11):833-46. DOI: 10.1038/nrm2039. View

13.

Zhou N, Xiao H, Li T, Nur-E-Kamal A, Liu L . DNA damage-mediated apoptosis induced by selenium compounds. J Biol Chem. 2003; 278(32):29532-7. DOI: 10.1074/jbc.M301877200. View

14.

Sinha R, El-Bayoumy K . Apoptosis is a critical cellular event in cancer chemoprevention and chemotherapy by selenium compounds. Curr Cancer Drug Targets. 2004; 4(1):13-28. DOI: 10.2174/1568009043481614. View

15.

Gundimeda U, Schiffman J, Gottlieb S, Roth B, Gopalakrishna R . Negation of the cancer-preventive actions of selenium by over-expression of protein kinase Cepsilon and selenoprotein thioredoxin reductase. Carcinogenesis. 2009; 30(9):1553-61. DOI: 10.1093/carcin/bgp164. View

16.

Kumar S, Zhou B, Liang F, Wang W, Huang Z, Zhang Z . Activity-based probes for protein tyrosine phosphatases. Proc Natl Acad Sci U S A. 2004; 101(21):7943-8. PMC: 419536. DOI: 10.1073/pnas.0402323101. View

17.

Hayun R, Shpungin S, Malovani H, Albeck M, Okun E, Nir U . Novel involvement of the immunomodulator AS101 in IL-10 signaling, via the tyrosine kinase Fer. Ann N Y Acad Sci. 2007; 1095:240-50. DOI: 10.1196/annals.1397.028. View

18.

FLEMING J, Ghose A, Harrison P . Molecular mechanisms of cancer prevention by selenium compounds. Nutr Cancer. 2002; 40(1):42-9. DOI: 10.1207/S15327914NC401_9. View

19.

McNaughton M, Engman L, Birmingham A, Powis G, Cotgreave I . Cyclodextrin-derived diorganyl tellurides as glutathione peroxidase mimics and inhibitors of thioredoxin reductase and cancer cell growth. J Med Chem. 2003; 47(1):233-9. DOI: 10.1021/jm030916r. View

20.

Cunha R, Urano M, Chagas J, Almeida P, Bincoletto C, Tersariol I . Tellurium-based cysteine protease inhibitors: evaluation of novel organotellurium(IV) compounds as inhibitors of human cathepsin B. Bioorg Med Chem Lett. 2005; 15(3):755-60. DOI: 10.1016/j.bmcl.2004.11.012. View