Structure-activity relationship of synthetic phosphoinositolglycans mimicking metabolic insulin action

Biochemistry

Volumn 37, Issue 38, 1998, Pages 13421-13436

  Frick, Wendelin ^a   Bauer, Andrea ^a   Bauer, Jochen ^a   Wied, Susanne ^a   Müller, Günter ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

INSULIN; PHOSPHOINOSITOLGLYCAN; PHOSPHOLIPID; UNCLASSIFIED DRUG;

ARTICLE; GLUCOSE METABOLISM; HORMONE ACTION; INSULIN RESISTANCE; INSULIN RESPONSE; LIPID METABOLISM; LIPOGENESIS; METABOLIC REGULATION; PRIORITY JOURNAL; REGULATORY MECHANISM; STRUCTURE ACTIVITY RELATION;

ADIPOCYTES; ANIMALS; DIAPHRAGM; GLUCOSE; GLYCOSYLPHOSPHATIDYLINOSITOLS; INSULIN; LIPIDS; MALE; PHOSPHOPROTEINS; PHOSPHORYLATION; RATS; RATS, WISTAR; RATS, ZUCKER; RECEPTOR, INSULIN; SIGNAL TRANSDUCTION; STRUCTURE-ACTIVITY RELATIONSHIP; TYROSINE;

EID: 0032558464     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi9806201     Document Type: Article

References (82)

1. Bogardus, C. (1996) in Diabetes Mellitus, Metabolic Abnormalities in the Development of Non-Insulin-Dependent Diabetes Mellitus (LeRoith, D., Taylor, S. I., Olefsky, J. M., Eds.) pp 459-466, Lippincott-Reaven Publishers, Philadelphia, New York.
2. Reaven, G. M. (1996) in Diabetes Mellitus, Insulin Resistance and Its Consequence: Non-Insulin-Dependent Diabetes Mellitus and Coronary Heart Disease (LeRoith, D., Taylor, S. I., Olefsky, J. M., Eds.) pp 509-518, Lippincott-Reaven Publishers, Philadelphia, New York.
3. Baldini, G., Hohman, R., Charron, M. J., and Lodish, H. F. (1991) J. Biol. Chem. 266, 4037-4040.
4. Corvera, S., Jaspers, S., and Pasceri, M. (1991) J. Biol. Chem. 266, 9271-9271.
5. Robinson, L. J., Pang, S., Harris, D. S., Heuser, J., and James, D. E. (1992) J. Cell Biol. 117, 1181-1196.
6. Wheeler, T. J., Fell, R. D., and Hauck, M. A. (1994) Biochim. Biophys. Acta 1196, 191-200.
7. Tsakiridis, T., Vranic, M., and Klip, A. (1995) Biochem. J. 309, 1-5.
8. Chen, D., Elmendorf, J. S., Olson, A. L., Li, X., Earp, H. S., and Pessin, J. E. (1997) J. Biol. Chem. 272, 27401-27410.
9. Varela-Nieto, I., Leon, Y., and Caro, H. N. (1996) Comp. Biochem. Physiol. 115B, 223-241.
10. Müller, G., Schubert, K., Fiedler, F., and Bandlow, W. (1992) J. Biol. Chem. 267, 25337-25346.
11. Müller, G., Gross, E., Wied, S., and Bandlow, W. (1996) Mol. Cell. Biol. 16, 442-456.
12. Müller, G., Wied, S., Crecelius, A., Kessler, A., and Eckel, J. (1997) Endocrinology 8, 3459-3475.
13. Müller, G., Dearey, E.-A., and Pünter, J. (1993) Biochem. J. 289, 509-521.
14. Müller, G., Dearey, E.-A., Korndörfer, A., and Bandlow, W. (1994) J. Cell Biol. 126, 1267-1276.
15. Kessler, A., Müller, G., Wied, S., Crecelius, A., and Eckel, J. (1998) Biochem. J. 330, 277-286.
16. Cross, G. A. M. (1990) Annu. Rev. Cell Biol. 6, 1-39.
17. McConville, M. J., and Ferguson, M. A. J. (1993) Biochem. J. 294, 305-324.
18. Nosjean, O., Briolay, A., and Roux, B. (1997) Biochim. Biophys. Acta 1331, 153-186.
19. Murakata, C., and Ogawa, T. (1990) Tetrahedron Lett. 31, 2439-2442.
20. Murakata, C., and Ogawa, T. (1991) Tetrahedron Lett. 32, 101-104.
21. Murakata, C., and Ogawa, T. (1991) Tetrahedron Lett. 32, 671-674.
22. Murakata, C., and Ogawa, T. (1992) Carbohydr. Res. 234, 75-91.
23. Murakata, C., and Ogawa, T. (1992) Carbohydr. Res. 235, 95-114.
24. Ley, S. V., and Young, L. L. (1992) Synlett 997.
25. Zapata, A., and Martin-Lomas, M. (1992) Carbohydr. Res. 234, 93-106.
26. Frantova, A. Y., Stepanov, A. E., Bushnev, A. S., Zvonkova, E. N., and Sleets, V. I. (1992) Tetrahedron Lett. 33, 3539-3541.
27. Boons, G. J., Grice, P., Leslie, R., Ley, S. V., and Young, L. L. (1993) Tetrahedron Lett. 84, 8523-8526.
28. Khiar, N., and Martin-Lomas, M. (1995) J. Org. Chem. 60, 7071-7021.
29. Roberts, C., Madsen, R., and Fraser-Reid, B. (1995) J. Am. Chem. Soc. 117, 1546-1553.
30. Mootoo, D. R., Konradsson, P., and Fraser-Reid, B. (1989) J. Am. Chem. Soc. 111, 8540-8542.
31. Fraser-Reid, B., Udodong, U. E., Wu, Z., Ottosson, H., Merritt, J. R., Rao, C. S., Roberts, C., and Madsen, R. (1992) Synlett 927.
32. Kratzer, B., Mayer, T. G., and Schmidt, R. R. (1993) Tetrahedron Lett. 34, 6881-6884.
33. Udodong, U. E., Madsen, R., Roberts, C., and Fraser-Reid, B. (1993) J. Am. Chem. Soc. 115, 7886-7887.
34. Burfoot, M. S., Rogers, N. C., Watling, D., Smith, J. M., Pons, S., Paonessaw, G., Campbell, A. S., and Fraser-Reid, B. (1995) J. Am. Chem. Soc. 117, 10387-10388.
35. Madsen, R., Udodong, U. E., Roberts, C., Mootoo, D. R., Konradsson, P., and Fraser-Reid, B. (1995) J. Am. Chem. Soc. 117, 1554-1565.
36. Mayer, T. G., Kratzer, B., and Schmidt, R. R. (1994) Angew. Chem. 106, 2289-2293.
37. Mayer, T. G., Kratzer, B., and Schmidt, R. R. (1994) Angew. Chem., Int. Ed. Engl. 33, 2177-2180.
38. Fonteles, M. C., Huang, L. C., and Larner, J. (1996) Diabetologia 39, 731-734.
39. Cobb, J. E., and Johnson, M. R. (1991) Tetrahedron Lett. 47, 21-30.
40. Berlin, W. K., Zhang, W.-S., and Shen, T. Y. (1991) Tetrahedron Lett. 47, 1-20.
41. Caro, H.-N., Martin-Lomas, M., and Barnabe, M. (1993) Carbohydr. Res. 240, 119-131.
42. Zapata, A., Leon, Y., Mato, J. M., Varela-Nieto, I., Penades, S., and Martin-Lomas, M. (1994) Carbohydr. Res. 264, 21-31.
43. Plourde, R., d'Alarcao, M., and Saltiel, A. R. (1992) J. Org. Chem. 57, 2606-2610.
44. Termin, A., and Schmidt, R. R. (1989) Liebigs Ann. Chem. 789-795.
45. Aneja, R., Aneja, S. G., and Parra, A. (1995) Tetrahedron Asymmetry 6, 17-18.
46. Elie, C. J. J., Verduyn, R., Dreef, C. E., Braunts, D. M., van der Marel, G. A., and van Boom, J. H. (1990) Tetrahedron 46, 8243-8254.
47. Moody, A. J., Stan, M. A., and Stan, M. (1974) Horm. Metab. Res. 6, 12-16.
48. Müller, G., Ertl, J., Gerl, M., and Preibisch, G. (1997) J. Biol. Chem. 272, 10585-10593.
49. Müller, G., and Wied, S. (1993) Diabetes 42, 1852-1867.
50. Vila, M. C., Milligan, G., Standaert, M. L., and Farese, R. V. (1990) Biochemistry 29, 8735-8740.
51. Müller, G., Wied, S., Wetekam, E.-M., Crecelius, A., Unkelbach, A., and Pünter, J. (1994) Biochem. Pharmacol. 58, 985-996.
52. Guinovart, J. J., Salavert, A., Massague, J., Ciudad, C. J., Salsas, E., and Itarte, E. (1979) FEBS Lett. 106, 284-288.
53. Karnieli, E., Zarnowski, M. J., Hissin, P. J., Simpson, J. A., Salans, L. B., and Cushman, S. W. (1981) J. Biol. Chem. 256, 4772-4777.
54. Lawrence, J. C., Jr., Hiken, J. F., and James, D. E. (1990) J. Biol. Chem. 265, 19768-19776.
55. Honnor, R. C., Dhillon, G. S., and Londos, C. (1985) J. Biol. Chem. 260, 15122-15129.
56. Müller, G., Rouveyre, N., Upshon, C., and Bandlow, W. (1998) Biochemistry 37, 8705-8713.
57. Roussel, R., Carlier, P. G., Robert, J.-J., Velho, G., and Bloch, G. (1998) Proc. Natl. Acad. Sci. U.S.A. 95, 1313-1318.
58. Rhea, S., and James, D. E. (1997) Diabetes 46, 1667-1677.
59. Satoh, S., Nishimura, H., Clark, A. E., Kozka, I. J., Vannucci, S. J., Simpson, I. A., Quon, M. J., Cushman, S. W., and Holman, G. D. (1993) J. Biol. Chem. 268, 17820-17829.
60. Vannucci, S. J., Nishimura, H., Satoh, S., Cushman, S. W., Holman, G. D., and Simpson, I. A. (1992) Biochem. J. 288, 325-330.
61. Clarke, J. F., Young, P. W., Yonezawa, K. Kasuga, M., and Holman, G. D. (1994) Biochem. J. 300, 631-635.
62. Smith, O. L. K., and Czech, M. P. (1983) Metabolism 32, 597-602.
63. Terretaz, J., and Jeanrenaud, B. (1983) Endocrinology 112, 1346-1351.
64. Penicaud, L., Issad, T., and Ferre, P. (1988) in Lessons From Animal Diabetes II (Shafrir, E., Renold, A. E., Eds.) pp 438-443, J. Libbey, London, U.K.
65. White, M. F. (1997) Diabetologia 40, S2-S17.
66. Myers, M. G., Sun, X. J. and White, M. F. (1994) Trends Biochem. Sci. 19, 289-293.
67. Holman, G. D., and Kasuga, M. (1997) Diabetologia 40, 991-1003.
68. Stralfors, P. (1997) BioEssciy 19, 327-336.
69. Müller, G., Wied, S., Piossek, C., Bauer, A., Bauer, J., and Frick, W. (1998) Mol. Med. 4, 299-323.
70. Grunberger, G., Zick, Y., and Gordon, P. H. (1984) Science 223, 932-934.
71. Debant, A., Guerre-Millo, M., LeMarchand-Brustel, Y., Freychet, P., Lavar, M., and VanObberghen, E. (1987) Am. J. Physiol. 252, E273-278.
72. Kadowaki, T., Kasuga, M., Akanuma, Y., Ezaki, O., and Takaku, F. (1984) J. Biol. Chem. 259, 14208-14216. Burant, C. F., Trentelaar, M. K., and Buse, M. G. (1986) J. Clin. Invest. 77, 260-270.
73. Kadowaki, T., Kasuga, M., Akanuma, Y., Ezaki, O., and Takaku, F. (1984) J. Biol. Chem. 259, 14208-14216. Burant, C. F., Trentelaar, M. K., and Buse, M. G. (1986) J. Clin. Invest. 77, 260-270.
74. LeMarchand, Y., Gremeany, T., and Ballotti, R. (1985) Nature 315, 676-679.
75. Gremeaux, T., Tanti, J. F., VanObberghen, E., and LeMarchand-Brustel, Y. (1987) Biochimie 69, 387-393.
76. Freidenberg, G. R., Henry, R. R., Klein, H. H., and Olefsky, J. M. (1987) J. Clin. Invest. 79, 240-250.
77. Freidenberg, G. R., Reichart, D., Olefsky, J. M., and Henry, R. R. (1988) J. Clin. Invest. 82, 1398-1406.
78. Arner, P., Pollare, T., Lithell, H., and Livingston, J. N. (1987) Diabetologia 30, 437-440.
79. Caro, J. F., Sinha, M. K., and Raju, S. J. (1987) J. Clin. Invest. 79, 1330-1337.
80. Obermaier-Kusser, B., White, M. F., Pongratz, D., Su, Z., Ermel, B., Mühlbacher, C., and Häring, H. U. (1989) J. Biol. Chem. 264, 9497-9504.
81. Bulangu, L. N., Ossowski, V. M., Bogardus, C., and Mott, D. (1990) Am. J. Physiol. 258, E964-974.
82. Häring, H. U. (1991) Diabetologia 34, 848-861.