Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Monosaccharide as a Central Scaffold Toward the Construction of Salicylate-Based Bidentate PTP1B Inhibitors via Click Chemistry

  • Tang, Yan-Hui (Key Laboratory for Advanced Materials and Institute of Fine Chemicals, and School of Pharmacy, East China University of Science and Technology) ;
  • Hu, Min (Key Laboratory for Advanced Materials and Institute of Fine Chemicals, and School of Pharmacy, East China University of Science and Technology) ;
  • He, Xiao-Peng (Key Laboratory for Advanced Materials and Institute of Fine Chemicals, and School of Pharmacy, East China University of Science and Technology) ;
  • Fahnbulleh, Sando (Key Laboratory for Advanced Materials and Institute of Fine Chemicals, and School of Pharmacy, East China University of Science and Technology) ;
  • Li, Cui (Key Laboratory for Advanced Materials and Institute of Fine Chemicals, and School of Pharmacy, East China University of Science and Technology) ;
  • Gao, Li-Xin (National Center for Drug Screening, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institutes of Biological Sciences, Chinese Academy of Sciences) ;
  • Sheng, Li (National Center for Drug Screening, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institutes of Biological Sciences, Chinese Academy of Sciences) ;
  • Tang, Yun (Key Laboratory for Advanced Materials and Institute of Fine Chemicals, and School of Pharmacy, East China University of Science and Technology) ;
  • Li, Jia (National Center for Drug Screening, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institutes of Biological Sciences, Chinese Academy of Sciences) ;
  • Chen, Guo-Rong (Key Laboratory for Advanced Materials and Institute of Fine Chemicals, and School of Pharmacy, East China University of Science and Technology)
  • Received : 2010.11.01
  • Accepted : 2011.01.21
  • Published : 2011.03.20
Download PDF
⟨ Previous Next ⟩

Abstract

The discovery of carbohydrate-based bioactive compounds has recently received considerable interest in the drug development. This paper stresses on the application of 1-methoxy-O-glucoside as the central scaffold, whereas salicylic pharmacophores were introduced with diverse spatial orientations probing into the structural preference of an enzymatic target, i.e. protein tyrosine phosphatase 1B (PTP1B). By employing regioselective protection and deprotection strategy, 2,6-, 3,4-, 4,6- and 2,3-di-O-propynyl 1-methoxy-O-glucosides were previously synthesized and then coupled with azido salicylate via click chemistry in forming the desired bidentate salicylic glucosides with high yields. The inhibitory assay of the obtained triazolyl derivatives leads to the identification of the 2,3-disubstituted salicylic 1-methoxy-O-glucoside as the structurally privileged PTP1B inhibitor among this bidentate compound series with micromole-ranged $IC_{50}$ value and reasonable selectivity over other homologous PTPs tested. In addition, docking simulation was conducted to propose a plausible binding mode of this authorized inhibitor with PTP1B. This research might furnish new insight toward the construction of structurally different bioactive compounds based on the monosaccharide scaffold.

Keywords

References

  1. Ernst, B.; Magnani, J. L. Nat. Rev. Drug Discov. 2009, 8, 661. https://doi.org/10.1038/nrd2852
  2. Meutermans, W.; Le, G. T.; Becker, B. ChemMedChem 2006,1, 1164. https://doi.org/10.1002/cmdc.200600150
  3. Abdel-Magid, A. F.; Maryanoff, C. A.; Mehrman, S. J. Curr. Opin.Drug Discovery Dev. 2001, 4, 776.
  4. Elchelby, M.; Payette, P.; Michaliszyn, E.; Cromlish, W.; Collins,S.; Loy, A. L.; Normandin, D.; Cheng, A.; Himms-Hagen, J.;Chan, C. C.; Ramachandran, C.; Gresser, M. J.; Tremblay, M. L.;Kennedy, B. P. Science 1999, 283, 1544. https://doi.org/10.1126/science.283.5407.1544
  5. Klaman, L. D.; Boss, O.; Peroni, O. D.; Kim, J. K.; Martino, J. L.;Zabolotny, J. M.; Moghal, N.; Lubkin, M.; Kim, Y. B.; Sharpe, A.H.; Stricker-Krongrad, A.; Shulman, G. I.; Neel, B. G.; Kahn, B.B. Mol. Cell. Biol. 2000, 20, 5479. https://doi.org/10.1128/MCB.20.15.5479-5489.2000
  6. Zhang, S.; Zhang, Z.-Y. Drug Discov. Today 2007, 12, 373. https://doi.org/10.1016/j.drudis.2007.03.011
  7. V. V Vintonyak, A. P Antonchick, D. Rauh, H. Waldmann, Curr. Opin. Chem. Biol. 2009, 13, 272. https://doi.org/10.1016/j.cbpa.2009.03.021
  8. Liu, S.; Zeng, L.-F.; Wu, L.; Yu, X.; Xue, T.; Gunawan, A. M.;Long, Y.-Q.; Zhang, Z.-Y. J. Am. Chem. Soc. 2008, 130, 17075. https://doi.org/10.1021/ja8068177
  9. Yang, J.-W.; Li, C.; He, X.-P.; Zhao, H.; Gao, L.-X.; Zhang, W.;Shi, X.-X.; Tang, Y.; Li, J.; Chen, G.-R. Bull. Korean Chem. Soc.2010, 31, 3359. https://doi.org/10.5012/bkcs.2010.31.11.3359
  10. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B.Angew. Chem. Int. Ed. 2002, 41, 2596 https://doi.org/10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
  11. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B.Angew. Chem. Int. Ed.2002, 114, 2708. https://doi.org/10.1002/1521-3757(20020715)114:14<2708::AID-ANGE2708>3.0.CO;2-0
  12. Le Droumaguet, C.; Wang, C.; Wang, Q. Chem. Soc. Rev.2010, 39, 1233. https://doi.org/10.1039/b901975h
  13. Mamidyala, S. K.; Finn, M. G. Chem. Soc.Rev. 2010, 39, 1252. https://doi.org/10.1039/b901969n
  14. Jewett, J. C.; Bertozzi, C. R. Chem. Soc.Rev. 2010, 39, 1272. https://doi.org/10.1039/b901970g
  15. Deng, Q.; Zheng, R.-R.; Ding, N.-N.; He, X.-P.; Chen, G.-R.Bull. Korean Chem. Soc. 2010, 31, 1055. https://doi.org/10.5012/bkcs.2010.31.04.1055
  16. Lin, L.; Shen, Q.;Chen, G. R.; Xie, J. Bioorg. Med. Chem. 2008, 16, 9757. https://doi.org/10.1016/j.bmc.2008.09.066
  17. Lee,J. W.; Lee, U. Y.; Han, S. C.; Kim J. H. Bull. Korean Chem. Soc.2009, 30, 1001. https://doi.org/10.5012/bkcs.2009.30.5.1001
  18. Song, Y.-J.; Yoo, C.; Hong, J.-T.; Kim, S.-J.;Son, S. U.; Jang, H.-Y. Bull. Korean Chem. Soc. 2008, 29, 1561. https://doi.org/10.5012/bkcs.2008.29.8.1561
  19. Sirion, U.; Lee, J. H.; Bae, Y. J.; Kim, H. J.; Lee, B. S.; Chi, D.Y. Bull. Korean Chem. Soc. 2010, 31, 1843. https://doi.org/10.5012/bkcs.2010.31.7.1843
  20. Zhang, Y.-J.; He,X.-P.; Hu M.; Li, Z.; Shi, X.-X.; Chen, G.-R. Dyes and Pigments2011, 88, 391. https://doi.org/10.1016/j.dyepig.2010.08.010
  21. Puius, Y. A.; Zhao, Y.; Sullivan, M.; Lawrence, D. S.; Almo, S.C.; Zhang, Z.-Y. Proc. Natl. Acad. Sci. U. S. A. 1997, 94, 13420. https://doi.org/10.1073/pnas.94.25.13420
  22. Shrestha, S.; Bharat, R. B.; Lee, K.-H.; Cho, H. Bioorg. Med.Chem. 2007, 15, 6535-6548. https://doi.org/10.1016/j.bmc.2007.07.010
  23. Shrestha, S.; Lee, K.-H.; Cho, H. Bull. Korean Chem. Soc. 2004,25, 1303. https://doi.org/10.5012/bkcs.2004.25.9.1303
  24. Tanaka, N.; Ohnishi, F.; Uchihata, D.; Torii, S.; Nokami, J. TetrahedronLett. 2007, 48, 7383. https://doi.org/10.1016/j.tetlet.2007.08.004
  25. Ortega-Munoz, M.; Perez-Balderas, F.; Morales-Sanfrutos, J.;Hernandez-Mateo, F.; Isac-Garcia, J.; Santoyo-Gonzalez, F. Eur. J. Org. Chem. 2009, 2454.
  26. Halmos, T.; Montserret, R.; Filippi, J.; Antonakis, K. Carbohydr.Res. 1987, 170, 57. https://doi.org/10.1016/0008-6215(87)85005-X
  27. Zhang, W.; Hong, D.; Zhou, Y.-Y.; Zhang, Y.-N.; Shen, Q.; Li,J.-Y.; Hu, L.-H.; Li, J. Biochim. Biophys. Acta 2006, 1760, 1505. https://doi.org/10.1016/j.bbagen.2006.05.009
  28. Shi, L.; Yu, H. P.; Zhou, Y. Y.; Du, J. Q.; Shen, Q.; Li, J. Y.; Li,J. Acta Pharmacol. Sin. 2008, 29, 278. https://doi.org/10.1111/j.1745-7254.2008.00737.x

Cited by

  1. ChemInform Abstract: Monosaccharide as a Central Scaffold Toward the Construction of Salicylate-Based Bidentate PTP1B Inhibitors via Click Chemistry. vol.42, pp.31, 2011, https://doi.org/10.1002/chin.201131180
  2. Bidentate Inhibitors of Protein Tyrosine Phosphatases vol.20, pp.14, 2014, https://doi.org/10.1089/ars.2013.5710
  3. Deoxysugars as Antituberculars and Alpha-Mannosidase Inhibitors vol.58, pp.6, 2014, https://doi.org/10.1128/AAC.02715-13