Molecular design and biological activities of protein-tyrosine phosphatase inhibitors

Pharmacology and Therapeutics

Volumn 99, Issue 1, 2003, Pages 15-24

  Umezawa, Kazuo ^a   Kawakami, Mariko ^a   Watanabe, Takumi ^b  

^a KEIO UNIVERSITY   (Japan)

^b INSTITUTE OF MICROBIAL CHEMISTRY   (Japan)

Author keywords

Cbl; CH interaction; Dephostatin; Diabetes mellitus; Insulin; Protein tyrosine phosphatase

Indexed keywords

2 MORPHOLINO 8 PHENYLCHROMONE; 4 (4 FLUOROPHENYL) 2 (4 METHYLSULFINYLPHENYL) 5 (4 PYRIDYL)IMIDAZOLE; ANONAINE; ANTIDIABETIC AGENT; APORPHINE DERIVATIVE; DEOXYGLUCOSE; DEPHOSTATIN; ET 3,4 DEPHOSTATIN; GLUCOSE TRANSPORTER 4; HEXYLMETHOXIME 3,4 DEPHOSTAIN; INSULIN RECEPTOR SUBSTRATE 1; METHOXIME 3,4 DEPHOSTATIN; NITROSAMINE; NORNUCIFERINE; PHOSPHATIQUINONE; PROTEIN TYROSINE PHOSPHATASE INHIBITOR; PULCHELLALACTAM; RK 682; UNCLASSIFIED DRUG; VANADATE SODIUM;

ADIPOCYTE; ARTICLE; CELL MEMBRANE; COMPETITIVE INHIBITION; CYTOPLASM; DIABETES MELLITUS; DRUG ACTIVITY; DRUG DESIGN; DRUG EFFECT; DRUG MECHANISM; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; GLUCOSE BLOOD LEVEL; GLUCOSE TRANSPORT; IC 50; IN VIVO STUDY; MOLECULAR WEIGHT; NONHUMAN; PRIORITY JOURNAL; PROTEIN PHOSPHORYLATION; STRUCTURE ACTIVITY RELATION;

EID: 0038201764     PISSN: 01637258     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0163-7258(03)00050-0     Document Type: Article

References (41)

1. Alvi K.A., Casey A., Nair B.G. Pulchellalactam: a CD45 protein tyrosine phosphatase inhibitor from the marine fungus Corollospora pulchella. J Antibiot. 51:1998;515-517.
2. Arabaci G., Guo X.-C., Beebe K.D., Coggeshall K.M., Pei D. α-Haloacetophenone derivatives as photoreversible covalent inhibitors of protein tyrosine phosphatases. J Am Chem Soc. 121:1999;5085-5086.
3. Baumann C.A., Ribon V., Kanzaki M., Thurmond D.C., Mora S., Shigematsu S., Bickel P.E., Pessin J.E., Saltiel A.R. CAP defines a second signalling pathway required for insulin-stimulated glucose transport. Nature. 407:2000;202-207.
4. 2Pmp. Biochem Biophys Res Commun. 204:1994;129-134.
5. Burke T.R. Jr., Ye B., Akamatsu M., Ford H. Jr., Yan X., Kole H.K., Wolf G., Shoelson S.E., Roller P.P. 4′-O-[2-(2-fluoromalonyl)]-L-tyrosine: a phosphotyrosyl mimic for the preparation for signal transduction inhibitory peptides. J Med Chem. 39:1996;1021-1027.
6. Burke T.R. Jr., Ye B., Yan X., Wang S., Jia Z., Chen L., Zhang Z.-Y., Barford D. Small molecule interactions with protein-tyrosine phosphatase PTP-1B and their use in inhibitor design. Biochemistry. 35:1996;15959-15996.
7. Burke T.R. Jr., Yao Z.J., Zhao H., Milne G.W.A., Wu L., Zhang Z.Y., Voigt J.H. Enantioselective synthesis of nonphosphorus-containing phosphotyrosyl mimetics and their use in the preparation of tyrosine phosphatase inhibitory peptides. Tetrahedron. 54:1998;9981-9994.
8. Cao X., Moran E.J., Siev D., Lio A., Ohashi C., Mjalli A.M.M. Synthesis of N-acyl-α-aminoamides on Rink resin: inhibitors of the hematopoietic protein tyrosine phosphatase (HePTP). Bioorg Med Chem Lett. 5:1995;2953-2958.
9. Charbonneau H., Tonks N.K., Walsh K.A., Fischer E.H. The leukocyte common antigen (CD45): a putative receptor-linked protein tyrosine phosphatase. Proc Natl Acad Sci USA. 85:1988;7182-7186.
10. Druker B.J. ST571 (Gleevec™) as a paradigm for cancer therapy. Trends Mol Med. 8:2002;14-18. (suppl.).
11. Elchebly M., Peyette 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. Increased insulin sensitivity and obesity resistance in mice lacking the protein tyrosine phosphatase-1B gene. Science. 283:1999;1544-1548.
12. Fujiwara S., Watanabe T., Nagatsu T., Gohda J., Imoto M., Umezawa K. Enhancement or induction of neurite formation by a protein tyrosine phosphatase inhibitor, 3,4-dephostatin, in growth factor-treated PC12h cells. Biochem Biophys Res Commun. 238:1997;213-217.
13. Goldstein B. Tyrosine Phosphoprotein Phosphatases. 2nd ed. 1998;Oxford University Press, Oxford.
14. 1 phase. FEBS Lett. 372:1995;54-58.
15. Hamel P., Girard Y. Synthesis of dephostatin, a novel tyrosine phosphatase inhibitor. Tetrahedron Lett. 35:1994;8101-8102.
16. Hiriyanna K.T., Baedke D., Beak K.H., Forney B.A., Kordiyak G., Ingebriisen T.S. Thiophosphorylated substrate analogs are potent active site-directed inhibitors of protein-tyrosine phosphatases. Anal Biochem. 223:1994;54-58.
17. Hiroki A., Hatakeyama H., Kawakami M., Watanabe T., Takei I., Umezawa K. Antidiabetic effect of a nitrosamine-free dephostatin analogue, methoxime-3,4-dephostatin, in db/db mice. Biomed Pharmacother. 56:2002;179-185.
18. Hunter T., Sefton B.M. Transforming gene product of Rous sarcoma virus phosphorylates tyrosine. Proc Natl Acad Sci USA. 77:1980;1311-1315.
19. Imoto M., Kakeya H., Sawa T., Hayashi C., Hamada M., Takeuchi T., Umezawa K. Dephostatin, a novel protein tyrosine phosphatase inhibitor produced by Streptomyces: I. Taxonomy, isolation, and characterization. J Antibiot. 46:1993;1342-1346.
20. Imoto M., Tanaka S., Deguchi A., Hayakawa A., Umezawa K. In situ inhibition of protein-tyrosine phosphatase by dephostatin. Cell Pharmacol. 2:1995;199-203.
21. Kagamizono T., Hamaguchi T., Ando T., Sugawara K., Adachi T., Osada H. Phosphatoquinones A and B, novel tyrosine phosphatase inhibitors produced by Streptomyces sp. J Antibiot. 52:1999;75-80.
22. Kakeya H., Imoto M., Takahashi Y., Naganawa H., Takeuchi T., Umezawa K. Dephostatin, a novel protein tyrosine phosphatase inhibitor produced by Streptomyces: II. Structure determination. J Antibiot. 46:1993;1716-1719.
23. Kendall P.M., Johnson J.V., Cook C.E. Synthetic route to an aromatic analogue of strigol. J Org Chem. 44:1979;1421-1424.
24. Kenner K.A., Anyanwu E., Olefsky J.M., Kusari J. Protein-tyrosine phosphatase 1B is a negative regulator of insulin- and insulin-like growth factor-I-stimulated signaling. J Biol Chem. 271:1996;19810-19816.
25. Laforgia S., Morse B., Levy J., Barnea G., Cannizzaro L.A., Li F., Nowell P.C., Boghosian-Sell L., Glick J., Weston A., Harris C.C., Drabkin H., Patterson D., Croce C.M., Schlessinger J., Huebner K. Receptor protein-tyrosine phosphatase gamma is a candidate tumor suppressor gene at human chromosome region 3p21. Proc Natl Acad Sci USA. 88:1991;5036-5040.
26. Miski M., Shen X., Cooper R., Gillum A.M., Fisher D.K., Miller R.W., Higgins T.J. Aporphine alkaloid, CD45 protein tyrosine phosphatase inhibitors, from Rollina ulei. Bioorg Med Chem Lett. 5:1995;1519-1522.
27. Nishio M., Hirota M., Umezawa Y. The CH/π Interaction. 1998;Wiley-VCH, New York.
28. Ostergaad H.L., Shackelford D.A., Hurley T.R., Johnson P., Hyman R., Sefton B.M., Trowbridge I.S. Expression of CD45 alters phosphorylation of the lck-encoded tyrosine protein kinase in murine lymphoma T-cell lines. Proc Natl Acad Sci USA. 86:1989;8959-8963.
29. Puius Y.A., Zhao Y., Sullivan M., Lawrence D.S., Almo S.C., Zhang Z.-Y. Identification of a second aryl phosphate-binding site in protein-tyrosine phosphatase 1B: a paradigm for inhibitor design. Proc Natl Acad Sci USA. 93:1997;13420-13425.
30. Robinson L.J., Pang S., Harris D.S., Heuser J., James D.E. Translocation of the glucose transporter (GLUT4) to the cell surface in permeabilized 3T3-L1 adipocytes: effects of ATP, insulin, and GTP gamma S and localization of GLUT4 to clathrin lattices. J Cell Biol. 117:1992;1181-1196.
31. Roller P.P., Wu L., Zhang Z.Y., Burke T.R. Jr. Potent inhibition of protein-tyrosine phosphatase-1B using the phosphotyrosyl mimetic fluoro-O-malonyl tyrosine (FOMT). Bioorg Med Chem Lett. 8:1998;2149-2150.
32. Suzuki T., Hiroki A., Watanabe T., Yamashita T., Takei I., Umezawa K. Potentiation of insulin-related signal transduction by a novel protein-tyrosine phosphatase inhibitor, Et-3,4-dephostatin, on cultured 3T3-L1 adipocytes. J Biol Chem. 276:2001;27511-27518.
33. Toi M., Mukaida T., Wada T., Hirabayashi N., Toge T., Hori T., Umezawa K. Antineoplastic effect of erbstatin on human mammary and esophageal tumors in athymic mice. Eur J Cancer. 26:1990;722-724.
34. Tonks N.K., Diltz C.D., Fischer E.H. Purification of the major protein-tyrosine-phosphatases of human placenta. J Biol Chem. 263:1988;6722-6730.
35. Tonks N.K., Diltz C.D., Fischer E.H. Characterization of the major protein-tyrosine-phosphatases of human placenta. J Biol Chem. 263:1988;6731-6737.
36. Umezawa Y., Nishio M. Thymine-methyl/pi interaction implicated in the sequence-dependent deformability of DNA. Nucleic Acids Res. 30:2002;2183-2192.
37. Wary K.K., Lou Z., Buchberg A.M., Siracusa L.D., Druck T., LaForgia S., Huebner K. A homozygous deletion within the carbonic anhydrase-like domain of the Ptprg gene in murine L-cells. Cancer Res. 53:1993;1498-1502.
38. Watanabe T., Takeuchi T., Otsuka M., Umezawa K. Total synthesis of dephostatin, a novel protein tyrosine phosphatase inhibitor. J Chem Soc Chem Commun. 1994:1994;437-438.
39. Watanabe T., Takeuchi T., Otsuka M., Tanaka S., Umezawa K. Synthesis and protein tyrosine phosphatase inhibitory activity of dephostatin analogs. J Antibiot. 48:1995;1460-1466.
40. Watanabe T., Suzuki T., Umezawa Y., Takeuchi T., Otsuka M., Umezawa K. Structure-activity relationship and rational design of 3,4-dephostatin derivatives as protein tyrosine phosphatase inhibitors. Tetrahedron. 56:2000;741-752.
41. Yu L.B., McGill A., Wang P.G., Zhang Z.Y. Synthesis and bioassay of a protein-tyrosine-phosphatase inhibitor, dephostatin. Biomed Chem Lett. 5:1995;1003-1006.