Oleanolic acid and its derivatives: New inhibitor of protein tyrosine phosphatase 1B with cellular activities

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 18, 2008, Pages 8697-8705

  Zhang, Yi Nan ^a   Zhang, Wei ^a   Hong, Di ^a   Shi, Lei ^a   Shen, Qiang ^a   Li, Jing Ya ^a   Li, Jia ^a   Hu, Li Hong ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Inhibitor; Oleanolic acid; Protein tyrosine phosphatase 1B; SAR (structure activity relationship)

Indexed keywords

CORNUS OFFICINALIS EXTRACT; INSULIN; INSULIN RECEPTOR; OLEANOLIC ACID; OLEANOLIC ACID DERIVATIVE; PROTEIN TYROSINE PHOSPHATASE 1B; PROTEIN TYROSINE PHOSPHATASE 1B INHIBITOR; TRITERPENOID;

ANIMAL CELL; ARTICLE; CHINESE MEDICINE; CHO CELL; CONTROLLED STUDY; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; GLUCOSE TRANSPORT; HORMONAL REGULATION; MYOTUBE; NONHUMAN; PROTEIN PHOSPHORYLATION; STRUCTURE ACTIVITY RELATION; T LYMPHOCYTE;

ANIMALS; CELL LINE; CHO CELLS; CRICETINAE; CRICETULUS; DIABETES MELLITUS; DRUGS, CHINESE HERBAL; ENZYME INHIBITORS; HUMANS; INSULIN; OBESITY; OLEANOLIC ACID; PHOSPHORYLATION; PROTEIN TYROSINE PHOSPHATASE, NON-RECEPTOR TYPE 1; RECEPTOR, INSULIN; STRUCTURE-ACTIVITY RELATIONSHIP; T-LYMPHOCYTES;

EID: 51449111044     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.07.080     Document Type: Article

References (40)

1. Barford D., Flint A.J., and Tonks N.K. Science 263 (1994) 1397
2. Elchebly M., Payette P., Michaliszyn E., Cromlish W., Colins S., Loy A.L., Normandin D., Chenng A., Himms-Hagen J.C., and Chan C. Science 283 (1999) 1544
3. Klaman L.D., Boss O., Peroni O.D., Kim J.K., Zabotny J.M., Moghal N., Lubkin M., Kim Y.B., Sharpe A.H., Stricker-Krongrad A., Shulman G.I., Neel B.G., and Kahn B.B. Mol. Cell. Biol. 20 (2000) 5479
4. Puius Y.A., Zhao Y., Sullivan M., Lawrence D.S., Almo S.C., and Zhang Z.Y. Proc. Natl. Acad. Sci. 94 (1997) 13420
5. Iversen L.F., Andersen H.S., Branner S., Mortensen S.B., Peters G.H., Norris K., Olsen O.H., Jeppesen C.B., Lundt B.F., Ripka W., Møller K.B., and Møller N.P.H. J. Biol. Chem. 275 (2000) 10300
6. Wiesmann C., Barr K.J., Kung J., Zhu J., Erlanson D.A., Shen W., Fahr B.J., Zhong M., Taylor L., Randal M., McDowell R.S., and Hansen S.K. Nat. Struct. Mol. Biol. 11 (2004) 730
7. Johnson T.O., Ermolieff J., and Jirousek M.R. Nat. Rev. Drug Disc. 1 (2002) 696
8. Liu G. Curr. Med. Chem. 10 (2003) 1407
9. Bialy L., and Waldmann H. Angew. Chem., Int. Ed. 44 (2005) 3814
10. Zhang S., and Zhang Z.Y. Drug Discovery Today 12 (2007) 373
11. Goldman J.M., and Melo J.V. N. Engl. J. Med. 344 (2001) 1084
12. Wilhelm S., Carter C., Lynch M., Lowinger T., Dumas J., Smith R.A., Schwartz B., Simantov R., and Kelley S. Nat. Rev. Drug Disc. 5 (2006) 835
13. Iverson L.F., Møller K.B., Pedersen A.K., Peters G.H., Petersen A.S., Andersen H.S., Branner S., Mortensen S.B., and Møller N.P.H. J. Biol. Chem. 277 (2002) 19982
14. Combs A.P., Zhu W., Crawley M.L., Glass B., Polam P., Sparks R.B., Modi D., Takvorian A., McLaughlin E., Yue E.W., Wasserman Z., Bower M., Wei M., Rupar M., Ala P.J., Reid B.M., Ellis D., Gonneville L., Emm T., Taylor N., Yeleswaram S., Li Y., Wynn R., Burn T.C., Hollis G., Liu P.C.C., and Metcalf B. J. Med. Chem. 49 (2006) 3774
15. Boutselis I.G., Yu X., Zhang Z.Y., and Borch R.F. J. Med. Chem. 50 (2007) 856
16. Wilson D.P., Wan Z.K., Xu W.X., Kirincich S.J., Follows B.C., Joseph-McCarthy D., Foreman K., Moretto A., Wu J., Zhu M., Binnun E., Zhang Y.L., Tam M., Erbe D.V., Tobin J., Xu X., Leung L., Shilling A., Tam S.Y., Mansour T.S., and Lee J. J. Med. Chem. 50 (2007) 4681
17. Cui L., Na M., Oh H., Bae E.Y., Jeong D.G., Ryu S.E., Kim S., Kim B.Y., Ahn J.S., and Oh W.K. Bioorg. Med. Chem. Lett. 16 (2006) 1426
18. Na M., Jang J., Njamen D., Mbafor J.T., Fomum Z.T., Kim B.Y., Oh W.K., and Ahn J.S. J. Nat. Prod. 69 (2006) 1572
19. Wang Y., Shang X.Y., Wang S.J., Mo S.Y., Li S., Yang Y.C., Ye F., Shi J.G., and He L. J. Nat. Prod. 70 (2007) 296
20. Cui L., Ndinteh D.T., Na M., Thuong P.T., Silike-Muruumu J., Njamen D., Mbafor J.T., Fomum Z.T., Ahn J.S., and Oh W.K. J. Nat. Prod. 70 (2007) 1039
21. Gong J.X., Shen X., Yao L.G., Jiang H., Krohn K., and Guo Y.W. Org. Lett. 9 (2007) 1715
22. Chen R.M., Hu L.H., Shen Q., and Li J. Bioorg. Med. Chem. Lett. 12 (2002) 3387
23. Li Y.F., Hu L.H., Lou F.C., Shen Q., and Li J. J. Asian Nat. Prod. Res. 7 (2005) 13
24. Li Y.F., Shen Q., Li J., and Hu L.H. Chem. Biodiv. 4 (2007) 961
25. Zhang W., Hong D., Zhou Y.Y., Zhang Y.N., Shen Q., Li J.Y., Hu L.H., and Li J. Biochim. Biophys. Acta 1760 (2006) 1505
26. Shi L., Zhang W., Zhou Y.Y., Zhang Y.N., Li J.Y., Hu L.H., and Li J. Eur. J. Pharmacol. 584 (2008) 21
27. Chung Y.-H., Jang S.-C., Kim S.-J., and Sung N.-D. J. Appl. Biol. Chem. 50 (2007) 52
28. Lihong, Hu et al. PCT CN2005/000172, 2005.
29. Matsunaga S., Tanaka R., and Akagi M. Phytochemistry 27 (1988) 255
30. Pardhy R.S., and Bhattacharyya S.C. Ind. J. Chem. 16B (1978) 176
31. Shim S.B., Kim N.J., and Kim D.H. Planta Medica 66 (2000) 40
32. Bonte F., Dumas M., Chaudagne C., and Meybeck A. Planta Medica 60 (1994) 133
33. O'Donnell M.J., Boniece J.M., and Earp S.E. Tetrahedron Lett. 19 (1978) 2641
34. Corey E.J., Shibata S., and Bakshi R.K. J. Org. Chem. 53 (1988) 2861
35. Karliner J., and Djerassi C. J. Org. Chem. 31 (1966) 1945
36. Chen Y.T., and Seto C.T. J. Med. Chem. 45 (2002) 3946
37. Liu J., Liu Y., and Parkinson A.J. J. Pharmacol. Exp. Ther. 275 (1995) 768
38. Bourdeau A., Dube N., and Tremblay M.L. Curr. Opin. Cel. Biol. 17 (2005) 203
39. Cheng A., Dube N., Gu F., and Tremblay M.L. Eur. J. Biochem. 269 (2002) 1050
40. DeFronzo R.A., Jacot E., Jequier E., Maeder E., Wahren J., and Felber J.P. Diabetes 30 (1981) 1000