Structural Determinants of High-Affinity Binding of Ryanoids to the Vertebrate Skeletal Muscle Ryanodine Receptor: A Comparative Molecular Field Analysis

Biochemistry

Volumn 33, Issue 20, 1994, Pages 6074-6085

  Welch, William ^a   Ahmad, Syed ^a   Airey, Judith A ^a   Sutko, John L ^a   Gerzon, Koert ^b   Humerickhouse, Rod A ^b   Besch, Henry R ^b   Ruest, Luc ^c   Deslongchamps, Pierre ^c  

^a UNIVERSITY OF NEVADA   (United States)

^b INDIANA UNIVERSITY   (United States)

^c UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CALCIUM; HYDROXYL GROUP; MEMBRANE PROTEIN; PYRROLE; RYANODINE; RYANODINE RECEPTOR;

ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CHICKEN; DISSOCIATION CONSTANT; HYDROPHOBICITY; ION PERMEABILITY; MOLECULAR DYNAMICS; NONHUMAN; PRIORITY JOURNAL; QUANTUM MECHANICS; RABBIT; RECEPTOR BINDING; SKELETAL MUSCLE;

ANIMAL; CALCIUM CHANNELS; CHEMISTRY, PHYSICAL; CHICKENS; COMPARATIVE STUDY; ELECTROCHEMISTRY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; MUSCLE PROTEINS; MUSCLES; RABBITS; RYANODINE; RYANODINE RECEPTOR CALCIUM RELEASE CHANNEL; STRUCTURE-ACTIVITY RELATIONSHIP; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, P.H.S.; THERMODYNAMICS;

ANIMALIA; GALLUS GALLUS; ORYCTOLAGUS CUNICULUS; VERTEBRATA;

EID: 0028227183     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi00186a006     Document Type: Article

References (66)

1. Airey, J. A., Beck, C. F., Murakami, K., Tanksley, S. J., Deerinck, T. J., Ellisman, M. H., & Sutko, J. L. (1990) J. Biol. Chem. 265, 14187–14194.
2. Allen, M. S., Tan, Y., Trudell, M. L., Narayanan, K., Schindler, L. R., Martin, M. J., Schultz, C., Hagen, T. J., Koehler, K., Codding, P. W., Skolnick, R., & Cook, J. M. (1990) J. Med. Chem. 33, 2343–2357.
3. Burkert, U., & Allinger, N. L. (1982) Molecular Mechanics, ACS Monograph 177, American Chemical Society, Washington, DC.
4. Campbell, K. P., Knudson, C. M., Imagawa, T., Leung, A. T., Sutko, J. L., Kahl, S. D., Raab, C. R., & Madson, L. (1987) J. Biol. Chem. 262, 6460–6463.
5. Carroll, F. I., Gao, Y., Rahman, M. A., Abraham, P., Parham, K., Lewin, A. H., Boja, J. W., & Kuhar, M. J. (1991a) J. Med. Chem. 34, 2719–2725.
6. Carroll, S., Skarmeta, J. G., Yu, X., Collins, K. D., & Inesi, G. (1991b) Arch. Biochem. Biophys. 290, 239–247.
7. Chu, A., Diaz-Munoz, M., Hawkes, M. J., Brush, K., & Hamilton, S. L. (1990) Mol. Pharmacol. 37, 735–741.
8. Clark, M. (1990) Tetrahedron Comput. Methodol. 3, 47–59.
9. Cramer, R. D., III, Patterson, D. E., & Bunce, J. D. (1988) J. Am. Chem. Soc. 110, 5959–5967.
10. DeVault, G. (1983) New Farm, 25–27 (May/June).
11. Fairhurst, A. S. (1971) J. Labelled Compd. Radiopharm. 7, 133–136.
12. Fairhurst, A. S. (1974) Am. J. Physiol. 227, 1124–1131.
13. Fairhurst, A., & Hasselbach, W. (1970) Eur. J. Biochem. 13, 504–509.
14. Fleischer, S., Ogunbunmi, E. M., Dixon, M. C., & Fleer, E. A. M. (1985) Proc. Natl. Acad. Sci. U.S.A. 82, 7256–7259.
15. Frank, M., & Sleator, W. W. (1975) Naunyn-Schmeideberg's Arch. Pharmacol. 290, 35–47.
16. Gasteiger, J., & Marsili, M. (1980) Tetrahedron 36, 3219–3228.
17. Gasteiger, J., & Marsili, M. (1981) Org. Magn. Reson. 15, 353–360.
18. Gerzon, K., Humerickhouse, R. A., Besch, H. R., Jr., Bidasee, K. R., Emmick, J. T., Tian, Z., Ruest, L., & Sutko, J. L. (1993) J. Med. Chem. 36, 1319–1323.
19. Hansch, C., & Leo, A. (1979) Substituent Constants for Correlation Analysis in Chemistry and Biology, J. Wiley and Sons, New York.
20. Hilgemann, D. W., Delay, M. J., & Langer, G. A. (1983) Circ. Res. 53, 779–793.
21. Hillyard, I. W., & Procita, L. (1959) J. Pharmacol. Exp. Ther. 127, 22–28.
22. Homans, S. W. (1990) Biochemistry 29, 9110–9118.
23. Humerickhouse, R., Besch, H. R., Jr., Gerzon, K., Ruest, L., Sutko, J. L., & Emmick, J. T. (1993) Mol. Pharmacol. 44, 412–421.
24. Inui, M., Saito, A., & Fleischer, S. (1987) J. Biol. Chem. 262, 1740–1747.
25. Jefferies, P. R., Lam, W.-W., Toia, R. F., & Casida, J. E. (1992) J. Agric. Food Chem. 40, 509–512.
26. Jefferies, P. R., Lehmberg, E., Lam, W.-W., & Casida, J. E. (1993) J. Med. Chem. 36, 1128–1135.
27. Jenden, D. J., & Fairhurst, A. S. (1969) Pharmacol. Rev. 21, 1–25.
28. Jones, L. R., & Cala, S. E. (1981) J. Biol. Chem. 256, 11809–11818.
29. Jones, L. R., Besch, H. R., Jr., Sutko, J. L., & Willerson, J. T. (1979) J. Pharmacol. Exp. Ther. 209, 48–55.
30. Kauzmann, W. (1959) Adv. Protein Chem. 14, 1–63.
31. Kaye, P. T., Macrae, R., Meakins, G. D., & Patterson, C. H. (1980) J. Chem. Soc., Perkin Trans. 2, 1631–1635.
32. Kellogg,G.E.,Semus,S. F., & Abraham,D. J. (1991) J. Comput.-Aided Mol. Des. 5, 545–552.
33. Kim, K. H., & Martin, Y. (1991a) J. Org. Chem. 56, 2723–2729.
34. Kim, K. H., & Martin, Y. C. (1991b) J. Med. Chem. 34, 2056–2060.
35. Lai, F. A., Erickson, H. P., Rousseau, E., Liu, Q.-Y., & Meissner, G. (1988) Nature 331, 315–319.
36. Lai, F. A., Misra, M., Xu, L., Smith, H. A., & Meissner, G. (1989) J. Biol. Chem. 264, 16776–16785.
37. Lattanzio, F. A., Jr., Schlatterer, R. G., Nicar, M., Campbell, K. P., & Sutko, J. L. (1987) J. Biol. Chem. 262, 2711–2718.
38. Liu, Q.-Y., Lai, F. A., Rousseau, E., Jones, R. V., & Meissner, G. (1989) Biophys. J. 55, 415–424.
39. Maret, G., El Tayar, N., Carrupt, P. A., Testa, B., Jenner, P., & Baird, M. (1990) Biochem. Pharmacol. 40, 783–792.
40. Marshall, G. R., & Cramer, R. D., III (1988) Trends Pharmacol. Sci. 9, 285–289.
41. Marsili, M., & Gasteiger, J. (1980) Croat. Chem. Acta 53, 601–614.
42. Meissner, G. (1986) J. Biol. Chem. 261, 6300–6306.
43. Nakai, J., Imagawa, T., Hakamata, Y., Shigekawa, M., Takeshima, H., & Numa, S. (1990) FEBS Lett. 271, 169–177.
44. Nayler, W. G., Daile, P., Chipperfield, D., & Gan, K. (1970) Am. J. Physiol. 219, 1620–1626.
45. Nozaki, Y., & Tanford, C. (1971) J. Biol. Chem. 246, 2211–2217.
46. Otsu, K., Willard, H. F., Khanna, V. K., Zorzato, F., Green, N. M., & MacLennan, D. H. (1990) J. Biol. Chem. 265, 13472–13483.
47. Penefsky, Z. J. (1974) Pfluegers Arch. 347, 173–184.
48. Penefsky, Z. J., & Kahn, M. (1970) Am. J. Physiol. 218, 1682–1686.
49. Pessah, I. N., & Zimanyi, I. (1991) Mol. Pharmacol. 39, 679–689.
50. Pessah, I. N., Waterhouse, A. L., & Casida, J. E. (1985) Biochem. Biophys. Res. Commun. 128, 449–456.
51. Pessah, I. N., Francini, A. O., Scales, D. J., Waterhouse, A. L., & Casida, J. E. (1986) J. Biol. Chem. 261, 8643–8648.
52. Powell, M. J. D. (1977) Math. Program. 12, 241–254.
53. Press, W. H., Flannery, B. P., Teukolsky, S. A., & Vetterling, W. T. (1988) Numerical Recipes in C, The Art of Scientific Computing, pp 301–327, Cambridge University Press, Cambridge.
54. Rogers, E. F., Koniuszy, F. R., Shavel, J., Jr., & Folkers, K. (1948) J. Am. Chem. Soc. 70, 3086–3088.
55. Rousseau, E., Smith, J. S., & Meissner, G. (1987) Am. J. Physiol. 253, C364–C368.
56. Ruest, L., Taylor, D. R., & Deslongchamps, P. (1985) Can. J. Chem. 63, 2840–2843.
57. Silipo, C., & Vittoria, A., Eds. (1991) Pharmacochemistry Library, Vol. 16, Elsevier, Amsterdam.
58. Smith, J. S., Imagawa, T., Ma, J., Fill, M., Campbell, K. P., & Coronado, R. (1988) J. Gen. Physiol. 92, 1–26.
59. Sutko, J. L., Willerson, J. T., Templeton, G. H., Jones, L. R., & Besch, H. R., Jr. (1979) J. Pharmacol. Exp. Ther. 209,37–47.
60. Sutko, J. L., Ito, K., & Kenyon, J. L. (1985) Fed. Proc. 44, 2984–2988.
61. Sutko, J. L., Thompson, L. J., Schlatterer, R. G., Lattanzio, F. A., Fairhurst, A. S., Campbell, C., Martin, S. F., Deslongchamps, P., Ruest, L., & Taylor, D. R. (1986) J. Labelled Compd. Radiopharm. 23, 215–222.
62. Takeshima, H., Nishimura, S., Matsumoto, T., Ishida, H., Kangawa, K., Minamino, N., Matsuo, H., Ueda, M., Hanaoka, M., Hirose, T., & Numa, S. (1989) Nature 339, 439–445.
63. Tinker, A., Sutko, J. L., Ruest, L., Welch, W., Airey, J. A., Gerzon, K., Bidasee, K., Besch, H. R., Jr., & Williams, A. J. (1994) Biophys. J. 66, A315.
64. Waterhouse, A. L., Holden, I., & Casida, J. E. (1984) J. Chem. Soc., Chem. Commun. 118, 1265–1266.
65. Waterhouse, A. L., Pessah, I. N., Francini, A. O., & Casida, J. E. (1987) J. Med. Chem. 30, 710–716.
66. Zorzato, F., Fujii, J., Otsu, K., Phillips, M., Green, M. N., Lai, F. A., Meissner, G., & MacLennan, D. H. (1990) J. Biol. Chem. 265, 2244–2256.