Discovering the distinct inhibitory effects between C4-epimeric glycosyl amino acids: New insight into the development of protein tyrosine phosphatase inhibitors

Glycoconjugate Journal

Volumn 28, Issue 7, 2011, Pages 493-497

  He, Xiao Peng ^a,c   Li, Cui ^a   Wang, Zhi Zhou ^a   Gao, Li Xin ^a   Shi, Xiao Xin ^a   Tang, Yun ^a   Xie, Juan ^c   Li, Jia ^b   Chen, Guo Rong ^a   Chen, Kaixian ^a,b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^c Ecole Normale Superieure de Cachan   (France)

Author keywords

Click chemistry; Epimer; Molecular docking study; PTP inhibitor; Sugar template

Indexed keywords

AMINO ACID; GLUCOPYRANOSIDE; PROTEIN TYROSINE PHOSPHATASE; PROTEIN TYROSINE PHOSPHATASE INHIBITOR;

ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG DEVELOPMENT; DRUG STRUCTURE; ENZYME INHIBITION; EPIMER; IC 50; MOLECULAR DOCKING; PRIORITY JOURNAL; PROTEIN BINDING; SIGNAL TRANSDUCTION;

AMINO ACIDS; BINDING SITES; CDC25 PHOSPHATASES; CELL CYCLE; CLICK CHEMISTRY; DRUG DISCOVERY; ENZYME INHIBITORS; GALACTOSE; GLYCOSIDES; GLYCOSYLATION; HUMANS; INHIBITORY CONCENTRATION 50; ISOMERISM; MODELS, MOLECULAR; PROTEIN BINDING;

EID: 82955187304     PISSN: 02820080     EISSN: 15734986     Source Type: Journal    
DOI: 10.1007/s10719-011-9347-0     Document Type: Article

References (29)

1. Lis, H., Sharon, N.: Lectins: carbohydrate-specific proteins that mediatecellular recognition. Chem. Rev. 98, 637-674(1998) (Pubitemid 128631438)
2. Bertozzi, C. R., Kiessling, L. L.: Chemical glycobiology. Science 291, 2357-2364(2001) (Pubitemid 32231790)
3. Seeberger, P. H.: Exploring life's sweet spot. Nature 437, 1239(2005) (Pubitemid 41568654)
4. Hart, G. W., Copeland, RJ.: Glycomics hits the big time. Cell 143, 672-676(2010)
5. Ernst, B., Magnani, J. L.: From carbohydrate leads to glycomimetic drugs. Nature Rev. Drug Discov. 8, 661-677(2009)
6. Williams, G. J., Yang, J., Zhang, C., Thorson, J. S.: Recombinant E. coli prototype strains for in vivo glycorandomization. ACS Chem. Biol 6, 101-105(2011)
7. Meutermans, W., Le, G. T., Becker, B.: Carbohydrates as scaffolds in drug discovery. ChemMedChem 1, 1164-1194(2006) (Pubitemid 44786923)
8. He, X.-P., Wang, X.-W., Jin, X.-P., Zhou, H., Shi, X.-X., Chen, G.-R., Long, Y.-T.: Epimeric monosaccharide-quinone hybrids on gold electrodes toward the electrochemical probing of specific carbohydrate-protein recognitions. J. Am. Chem. Soc. 133, 3649-3657(2011)
9. Song, S.-X., Zhang, H.-L., Kim, C.-G., Sheng, L., He, X.-P., Long, Y.-T., Li, J., Chen, G.-R.: Expeditious preparation of triazole-linked glycolipids via microwave accelerated click chemistry and their electrochemical and biological assessments. Tetrahedron 66, 9974-9980(2010)
10. Zhang, Y.-J., He, X.-P., Hu, M., Li, Z., Shi, X.-X., Chen, G.-R.: Highly optically selective and electrochemically active chemosensor for copper (II) based on triazole-linked glucosyl anthraquinone. Dyes and Pigments 88, 391-395(2011)
11. Song, Z., He, X.-P., Jin, X.-P., Gao, L.-X., Sheng, L., Zhou, Y.-B., Li, J., Chen, G.-R.: 'Click' to bidentate bis-triazolyl sugar derivatives with promising biological and optical features. Tetrahedron Lett. 52, 894-898(2011)
12. He, X.-P., Song, Z., Wang, Z.-Z., Shi, X.-X., Chen, K., Chen, G.-R.: Creation of 3, 4-bis-triazolocoumarin-sugar conjugates via fluorogenic dual click chemistry and their quenching specificity with silver (I) in aqueous media. Tetrahedron 67, 3343-3347(2011)
13. Rostovtsev, V. V., Green, L. G., Fokin, V. V., Sharpless, K. B.: A stepwise Huisgen cycloaddition process: copper (I)-catalyzed. Angew. Chem. Int. Ed. 41, 2596-2599(2002)
14. Tornøe, C. W., Christensen, C., Meldal, M.: Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper (I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes to azides. J. Org. Chem. 67, 3057-3064(2002) (Pubitemid 34457265)
15. Kolb, H. C., Finn, M. G., Sharpless, K. B.: Click chemistry: diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. 40, 2004-2021(2002)
16. Aragão-Leoneti, V., Campo, V. L., Gomes, A. S., Field, R. A., Carvalho, I.: Application of copper (I)-catalyzed azide-alkyne cycloaddition (CuAAC) 'click chemistry' in carbohydrate drug and neoglycopolymer synthesis. Tetrahedron 66, 9475-9492(2010)
17. Yamaguchi, M., Takagaki, K., Kojima, K., Hayashi, N., Chen, F., Kakizaki, I., Kon, A., Endo, M.: Novel proteoglycan glycotechnology: chemoenzymatic synthesis of chondroitin sulfatecontaining molecules and its application. Glycoconj. J. 27, 189-198(2010)
18. Vintonyak, V. V., Antonchick, A. P., Rauh, D., Waldmann, H.: The therapeutic potential of phosphatase inhibitors. Curr. Opin. Chem. Biol. 13, 272-283(2009)
19. Vintonyak, V. V., Waldmann, H., Rauh, D.: Using small molecules to target protein phosphatases. Bioorg. Med. Chem. 19, 2145-2155(2011)
20. He, X.-P., Li, C., Jin, X.-P., Song, Z., Zhang, H.-L., Zhu, C.-J., Shen, Q., Zhang, W., Sheng, L., Shi, X.-X., Tang, Y., Li, J., Chen, G.-R., Xie, J.: Microwave-assisted construction of triazole-linked amino acid-glucoside conjugates as novel PTP1B inhibitors. New. J. Chem. 35, 622-631(2011)
21. Halmos, T., Montserret, R., Filippi, J., Antonakis, K.: Studies of the selective silylation of methyl α-and β-D-aldohexopyranosides: stability of the partially protected derivatives in polar solvents. Carbohydr. Res. 170, 57-69(1987)
22. Goddard-Borger, E. D., Stick, R. V.: An efficient, inexpensive, and shelf-stable diazotransfer reagent: imidazole-1-sulfonyl azide hydrochloride. Org. Lett. 9, 3797-3800(2007)
23. Kappe, C. O., Van der Eycken, E.: Click chemistry under nonclassical reaction conditions. Chem. Soc. Rev. 39, 1280-1290(2010)
24. Lee, Y. B., Park, S. R., Jeon, H. B., Kim, K. S.: A new solvent system for efficient synthesis of 1, 2, 3-triazoles. Tetrahedron Lett. 47, 5105-5109(2006) (Pubitemid 43867620)
25. Ziegler, T., Hermann, C.: Synthesis of novel multidentate carbohydrate ligands. Tetrahedron Lett. 49, 2166-2169(2008)
26. Li, C., Tang, J., Xie, J.: Synthesis of crosslinking amino acids by click chemistry. Tetrahedron 65, 7935-7941(2009)
27. Zhang, W., Hong, D., Zhou, Y.-Y., Zhang, Y.-N., Shen, Q., Li, J.-Y., Hu, L.-H., Li, J.: Ursolic acid and its derivatives inhibit protein tyrosine phosphatase 1B, enhancing insulin receptor phosphorylation and stimulating glucose uptake. Biochim. Biophys. Acta 1760, 1505-1512(2006) (Pubitemid 44428024)
28. Shi, L., Yu, P. H., Zhou, Y. Y., Du, J. Q., Shen, Q., Li, J. Y., Li, J.: Discovery of a novel competitive inhibitor of PTP1B by high-throughput screening. Acta Pharmacol. Sin. 29, 278-284(2008) (Pubitemid 351178427)
29. Lavecchia, A., Giovanni, C. D., Novellino, E.: Inhibitors of Cdc25 phosphatases as anticancer agents: a patent review. Expert Opin. Ther. Patents 20, 405-425(2010)