Design of an insulin analog with enhanced receptor binding selectivity: Rationale, structure, and therapeutic implications

Journal of Biological Chemistry

Volumn 284, Issue 46, 2009, Pages 32178-32187

  Zhao, Ming ^a,d   Wan, Zhu Ii ^a   Whittaker, Linda ^a   Xu, Bin ^a,e   Phillips, Nelson B ^a   Katsoyannis, Panayotis G ^b   Ismail Beigi, Farmarz ^c   Whittaker, Jonathan ^a   Weiss, Michael A ^a,c  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

^b NEW YORK UNIVERSITY   (United States)

^c CASE WESTERN RESERVE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d Glycopep Chemicals Inc   (United States)

^e Fred Hutchinson Cancer Research Center   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL STRUCTURE; DISEASES; PATIENT TREATMENT; STRUCTURAL DESIGN;

COLORECTAL CANCER; HORMONE-RECEPTOR INTERFACE; INSULIN CONCENTRATIONS; INSULIN RECEPTORS; INSULIN-LIKE GROWTH FACTOR; PHOTOCROSS-LINKING; TYPE 2 DIABETES MELLITUS; UNNATURAL AMINO ACIDS;

INSULIN;

ALANINE; DIAMINOBUTYRIC ACID; GLUCOSE; GLYCINE; INSULIN; INSULIN DERIVATIVE; INSULIN RECEPTOR; LEUCINE; SOMATOMEDIN C; THREONINE;

ALPHA HELIX; AMINO ACID SUBSTITUTION; ANIMAL EXPERIMENT; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; CROSS LINKING; CRYSTAL STRUCTURE; DIABETES MELLITUS; DRUG DESIGN; DRUG RECEPTOR BINDING; GLUCOSE BLOOD LEVEL; MUTAGENESIS; NONHUMAN; PRIORITY JOURNAL; RAT; SYNTHESIS;

ANIMALIA;

EID: 70450269246     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M109.028399     Document Type: Article

References (72)

1. Saydah, S. H., Loria, C. M., Eberhardt, M. S., and Brancati, F. L. (2003) Am. J. Epidemiol. 157, 1092-1100
2. Berster, J. M., and Göke, B. (2008) Arch. Physiol. Biochem. 114, 84-98
3. LeRoith, D., Novosyadlyy, R., Gallagher, E. J., Lann, D., Vijayakumar, A., and Yakar, S. (2008) Exp. Clin. Endocrinol. Diabetes 116, S4-S6
4. Donovan, E. A., and Kummar, S. (2008) Crit. Rev. Oncol. Hematol. 66, 91-98
5. Pollak, M. (2008) Nat. Rev. Cancer 8, 915-928
6. Yang, Y. X., Hennessy, S., and Lewis, J. D. (2004) Gastroenterology 127, 1044-1050
7. Bowker, S. L., Majumdar, S. R., Veugelers, P., and Johnson, J. A. (2006) Diabetes Care 29, 254-258
8. Chung, Y. W., Han, D. S., Park, K. H., Eun, C. S., Yoo, K. S., and Park, C. K. (2008) Dis. Colon Rectum 51, 593-597
9. Monami, M., Lamanna, C., Pala, L., Bardini, G., Cresci, B., Francesconi, P., Balzi, D., Marchionni, N., Rotella, C. M., and Mannucci, E. (2008) Exp. Clin. Endocrinol. Diabetes 116, 184-189
10. Amos, A. F., McCarty, D. J., and Zimmet, P. (1997) Diabet. Med. 14, S1-S85
11. Wild, S., Roglic, G., Green, A., Sicree, R., and King, H. (2004) Diabetes Care 27, 1047-1053
12. Renehan, A. G., Frystyk, J., and Flyvbjerg, A. (2006) Trends Endocrinol. Metab. 17, 328-336
13. Heald, A., Stephens, R., and Gibson, J. M. (2006) Diabet. Med. 23, Suppl. 1, 19-24
14. Samani, A. A., Yakar, S., LeRoith, D., and Brodt, P. (2007) Endocr. Rev. 28, 20-47
15. Tran, T. T., Naigamwalla, D., Oprescu, A. I., Lam, L., McKeown-Eyssen, G., Bruce, W. R., and Giacca, A. (2006) Endocrinology 147, 1830-1837
16. De Meyts, P., and Whittaker, J. (2002) Nat. Rev. Drug Discov. 1, 769-783
17. Brzozowski, A. M., Dodson, E. J., Dodson, G. G., Murshudov, G. N., Verma, C., Turkenburg, J. P., de Bree, F. M., and Dauter, Z. (2002) Biochemistry 41, 9389-9397
18. Lou, M., Garrett, T. P., McKern, N. M., Hoyne, P. A., Epa, V. C., Bentley, J. D., Lovrecz, G. O., Cosgrove, L. J., Frenkel, M. J., and Ward, C. W. (2006) Proc. Natl. Acad. Sci. U.S.A. 103, 12429-12434
19. Gauguin, L., Klaproth, B., Sajid, W., Andersen, A. S., McNeil, K. A., Forbes, B. E., and De Meyts, P. (2008) J. Biol. Chem. 283, 2604-2613
20. Huang, Z., Bodkin, N. L., Ortmeyer, H. K., Hansen, B. C., and Shuldiner, A. R. (1994) J. Clin. Invest. 94, 1289-1296
21. Kristensen, C., Kjeldsen, T., Wiberg, F. C., Schäffer, L., Hach, M., Havelund, S., Bass, J., Steiner, D. F., and Andersen, A. S. (1997) J. Biol. Chem. 272, 12978-12983
22. Gauguin, L., Delaine, C., Alvino, C. L., McNeil, K. A., Wallace, J. C., Forbes, B. E., and De Meyts, P. (2008) J. Biol. Chem. 283, 20821-20829
23. Nanjo, K., Sanke, T., Kondo, M., Nishimura, S., Miyano, M., Linuma, J., Miyamura, K., Inouye, K., Given, B. D., Polonsky, K. S., et al. (1986) Trans. Assoc. Am. Physicians 99, 132-142
24. Denley, A., Wang, C. C., McNeil, K. A., Walenkamp, M. J., van Duyvenvoorde, H., Wit, J. M., Wallace, J. C., Norton, R. S., Karperien, M., and Forbes, B. E. (2005) Mol. Endocrinol. 19, 711-721
25. Kurose, T., Pashmforoush, M., Yoshimasa, Y., Carroll, R., Schwartz, G. P., Burke, G. T., Katsoyannis, P. G., and Steiner, D. F. (1994) J. Biol. Chem. 269, 29190-29197
26. Wan, Z., Xu, B., Huang, K., Chu, Y. C., Li, B., Nakagawa, S. H., Qu, Y., Hu, S. Q., Katsoyannis, P. G., and Weiss, M. A. (2004) Biochemistry 43, 16119-16133
27. Wan, Z. L., Huang, K., Xu, B., Hu, S. Q., Wang, S., Chu, Y. C., Katsoyannis, P. G., and Weiss, M. A. (2005) Biochemistry 44, 5000-5016
28. Katsoyannis, P. G. (1966) Science 154, 1509-1514
29. Kochendoerfer, G. G., and Kent, S. B. (1999) Curr. Opin. Chem. Biol. 3, 665-671
30. Wang, L., Xie, J., and Schultz, P. G. (2006) Annu. Rev. Biophys. Biomol. Struct. 35, 225-249
31. Nakagawa, S. H., and Tager, H. S. (1991) J. Biol. Chem. 266, 11502-11509
32. Xu, B., Hu, S. Q., Chu, Y. C., Huang, K., Nakagawa, S. H., Whittaker, J., Katsoyannis, P. G., and Weiss, M. A. (2004) Biochemistry 43, 8356-8372
33. Weiss, M. A., Hua, Q. X., Jia, W., Chu, Y. C., Wang, R. Y., and Katsoyannis, P. G. (2000) Biochemistry 39, 15429-15440
34. Sosnick, T. R., Fang, X., and Shelton, V. M. (2000) Methods Enzymol. 317, 393-409
35. Whittaker, J., and Whittaker, L. (2005) J. Biol. Chem. 280, 20932-20936
36. Whittaker, J., Groth, A. V., Mynarcik, D. C., Pluzek, L., Gadsboll, V. L., and Whittaker, L. J. (2001) J. Biol. Chem. 276, 43980-43986
37. Xu, B., Huang, K., Chu, Y. C., Hu, S. Q., Nakagawa, S., Wang, S., Wang, R. Y., Whittaker, J., Katsoyannis, P. G., and Weiss, M. A. (2009) J. Biol. Chem. 284, 14597-14608
38. Jones, T. A., Zou, J. Y., Cowan, S. W., and Kjeldgaard, M. (1991) Acta Crystallogr. A 47, 110-119
39. Laskowski, R. A., Macarthur, M. W., Moss, D. S., and Thornton, J. M. (1993) J. Appl. Crystallogr. 26, 283-291
40. Brünger, A. T., Adams, P. D., Clore, G. M., DeLano, W. L., Gros, P., Grosse-Kunstleve, R. W., Jiang, J. S., Kuszewski, J., Nilges, M., Pannu, N. S., Read, R. J., Rice, L. M., Simonson, T., and Warren, G. L. (1998) Acta Crystallogr. D Biol. Crystallogr. 54, 905-921
41. Laskowski, R. A. (1995) J. Mol. Graph. 13, 323-330
42. Kaarsholm, N. C., Norris, K., Jørgensen, R. J., Mikkelsen, J., Ludvigsen, S., Olsen, O. H., Sorensen, A. R., and Havelund, S. (1993) Biochemistry 32, 10773-10778
43. Weiss, M. A., Wan, Z., Zhao, M., Chu, Y. C., Nakagawa, S. H., Burke, G. T., Jia, W., Hellmich, R., and Katsoyannis, P. G. (2002) J. Mol. Biol. 315, 103-111
44. Geiger, R., Geisen, K., Summ, H. D., and Langer, D. (1975) Hoppe Seylers Z. Physiol. Chem. 356, 1635-1649
45. Cosmatos, A., Cheng, K., Okada, Y., and Katsoyannis, P. G. (1978) J. Biol. Chem. 253, 6586-6590
46. Geiger, R., Geisen, K., and Summ, H. D. (1982) Hoppe Seylers Z. Physiol. Chem. 363, 1231-1239
47. Wan, Z. L., and Liang, D. C. (1988) Sci. China B 31, 1426-1438
48. Krail, G., Brandenburg, D., and Zahn, H. (1975) Hoppe Seylers Z. Physiol. Chem. 356, 981-996
49. Baker, E. N., Blundell, T. L., Cutfield, J. F., Cutfield, S. M., Dodson, E. J., Dodson, G. G., Hodgkin, D. M., Hubbard, R. E., Isaacs, N. W., and Reynolds, C. D. (1988) Philos. Trans. R. Soc. Lond. B Biol. Sci. 319, 369-456
50. Shoelson, S. E., Lee, J., Lynch, C. S., Backer, J. M., and Pilch, P. F. (1993) J. Biol. Chem. 268, 4085-4091
51. Rotwein, P., Pollock, K. M., Didier, D. K., and Krivi, G. G. (1986) J. Biol. Chem. 261, 4828-4832
52. Dull, T. J., Gray, A., Hayflick, J. S., and Ullrich, A. (1984) Nature 310, 777-781
53. Adams, T. E., Epa, V. C., Garrett, T. P., and Ward, C. W. (2000) Cell. Mol. Life Sci. 57, 1050-1093
54. Schwartz, G. P., Burke, G. T., and Katsoyannis, P. G. (1987) Proc. Natl. Acad. Sci. U.S.A. 84, 6408-6411
55. Milazzo, G., Sciacca, L., Papa, V., Goldfine, I. D., and Vigneri, R. (1997) Mol. Carcinog. 18, 19-25
56. Brange, J., and Volund, A. (1999) Adv. Drug Deliv. Rev. 35, 307-335
57. Katsoyannis, P. G., and Zalut, C. (1972) Biochemistry 11, 1128-1132
58. Kohn, W. D., Micanovic, R., Myers, S. L., Vick, A. M., Kahl, S. D., Zhang, L., Strifler, B. A., Li, S., Shang, J., Beals, J. M., Mayer, J. P., and DiMarchi, R. D. (2007) Peptides 28, 935-948
59. Huang, K., Chan, S. J., Hua, Q. X., Chu, Y. C., Wang, R. Y., Klaproth, B., Jia, W., Whittaker, J., De Meyts, P., Nakagawa, S. H., Steiner, D. F., Katsoyannis, P. G., and Weiss, M. A. (2007) J. Biol. Chem. 282, 35337-35349
60. Giovannucci, E. (2001) J. Nutr. 131, S3109-S3120
61. Giovannucci, E. (1995) Cancer Causes Control 6, 164-179
62. Sandhu, M. S., Dunger, D. B., and Giovannucci, E. L. (2002) J. Natl. Cancer Inst. 94, 972-980
63. Pollak, M. (2008) Best Pract. Res. Clin. Endocrinol. Metab. 22, 625-638
64. Sun, J., and Jin, T. (2008) Cell. Signal. 20, 219-229
65. Clemmons, D. R. (2007) Nat. Rev. Drug Discov. 6, 821-833
66. Weroha, S. J., and Haluska, P. (2008) J. Mammary Gland Biol. Neoplasia 13, 471-483
67. Calle, E. E., Rodriguez, C., Walker-Thurmond, K., and Thun, M. J. (2003) N. Engl. J. Med. 348, 1625-1638
68. Calle, E. E., and Kaaks, R. (2004) Nat. Rev. Cancer 4, 579-591
69. Berti, L., Kellerer, M., Bossenmaier, B., Seffer, E., Seipke, G., and Häring, H. U. (1998) Horm. Metab. Res. 30, 123-129
70. De Meyts, P., Gu, J. L., Shymko, R. M., Kaplan, B. E., Bell, G. I., and Whittaker, J. (1990) Mol. Endocrinol. 4, 409-416
71. Hemkens, L. G., Grouven, U., Bender, R., Günster, C., Gutschmidt, S., Selke, G. W., and Sawicki, P. T. (2009) Diabetologia 52, 1732-1744
72. Pocock, S. J., and Smeeth, L. (2009) Lancet 374, 511-513