Design of salt-insensitive glycine-rich antimicrobial peptides with cyclic tricystine structures

Biochemistry

Volumn 39, Issue 24, 2000, Pages 7159-7169

  Tam, James P ^a   Lu, Yi An ^a   Yang, Jin Long ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOPHILE; CYCLOPEPTIDE; CYSTINE;

AMINO ACID SEQUENCE; ARTICLE; CIRCULAR DICHROISM; DISULFIDE BOND; HYDROPHOBICITY; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN BINDING; PROTEIN STRUCTURE;

AMINO ACID SEQUENCE; ANTI-BACTERIAL AGENTS; ANTI-INFECTIVE AGENTS; ANTIMICROBIAL CATIONIC PEPTIDES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CIRCULAR DICHROISM; CYSTINE; DISULFIDES; DNA-BINDING PROTEINS; DRUG DESIGN; ESCHERICHIA COLI; FUNGI; GLYCINE; GRAM-NEGATIVE BACTERIA; HEMOLYSIS; MOLECULAR SEQUENCE DATA; PEPTIDES, CYCLIC; PROTEIN CONFORMATION; PROTEIN STRUCTURE, SECONDARY; SALTS;

EID: 0034691281     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi0003487     Document Type: Article

References (61)

1. Boman, H. G. (1995) Annu. Rev. Immunol. 13, 61-92.
2. Nicolas, P., and Mor, A. (1995) Annu. Rev. Microbiol. 49, 277-304.
3. Zasloff, M. (1992) Curr. Opin. Immunol. 4, 3-7.
4. Hancock, R. E. (1997) Lancet 349, 418-422.
5. Lehrer, R. I., Lichtenstein, A. K., and Ganz, T. (1993) Annu. Rev. Immunol. 11, 105-128.
6. Lehrer, R. I., and Ganz, T. (1999) Curr. Opin. Immunol. 11, 23-27.
7. Maloy, W. L., and Kari, U. P. (1995) Biopolymers 37, 105-122.
8. Wade, D., Boman, A., Wahlin, B., Drain, C. M., Andreu, D., Boman, H. G., and Merrifield, R. B. (1990) Proc. Natl. Acad. Sci. U.S.A. 87, 4761-4765.
9. Merrifield, E. L., Mitchell, S. A., Ubach, J., Boman, H. G., Andreu, D., and Merrifield, R. B. (1995) Int. Pept. Protein Res. 46, 214-220.
10. Kondejewski, L. H., Farmer, S. W., Wishart, D. S., Kay, C. M., Hancock, R. E. W., and Hodges, R. S. (1996) J. Biol. Chem. 271, 25261-25268.
11. Subbalakshmi, C., Krishnakumari, V., Nagaraj, R., and Sitaram, N. (1996) FEBS Lett. 395, 48-52.
12. Oh, J. E., Hong, S. Y., and Lee, K.-H. (1999) J. Pept. Res. 54, 129-136.
13. Andreu, D., Ubach, J., Boman, A., Wahlin, B., Wade, O., Merrifield, R. B., and Boman, H. G. (1992) FEBS Lett. 296, 190-194.
14. Hamuro, Y., Schneider, J. P., and DeGrado, W. F. (1999) J. Am. Chem. Soc. 121, 12200-12201.
15. Yakum, T. C., Elzer, P. H., and McLaughlin, M. L. (1996) J. Med. Chem. 39, 3603-3605.
16. Kondejewski, L. H., Jelokhani-Niaraki, M., Farmer, W. S., Lix, B., Kay, C. M., Sykes, B. D., Hancock, R. E. W., and Hodges, R. B. (1999) J. Biol. Chem. 274, 13181-13192.
17. Dathe, M., Wieprecht, T., Nikolenko, H., Handel, L., Maloy, W. L., MacDonald, K., Beyemann, M., and Bienert, M. (1997) FEBS Lett. 403, 208-212.
18. Blondelle, S. E., and Houghten, R. A. (1992) Biochemistry 31, 12688-12694.
19. Dathe, M., Shumann, M., Wieprecht, T., Winkler, A., Beyermann, M., Krause, E., Matsuzaki, K., Murase, O., and Bienert, M. (1996) Biochemistry 35, 12612-12622.
20. Tang, Y.-Q., Yuan, J., Ösapay, G., Ösapay, K., Tran, D., Miller, C. J., Ouellette, A. J., and Selsted, M. E. (1999) Science 286, 498-502.
21. Tam, J. P., Lu, Y.-A., Yang, J.-L., and Chiu, K.-W. (1999) Proc. Natl. Acad. Sci. U.S.A. 96, 8913-8918.
22. Gustafson, K. R., Sowder, R. C., II, Henderson, L. E., Parsons, I. C., Kashman, Y., Cardellina, J. H., II, McMahon, J. B., Buckheit, R. W., Jr., Pannell, L. K., and Boyd, M. R. (1994) J. Am. Chem. Soc. 116, 9337-9338.
23. Witherup, K. M., Bogusky, M. J., Anderson, P. S., Ramjit, H., Ransom, R. W., Wood, T., and Sardana, M. (1994) J. Nat. Prod. 57, 1619-1625.
24. Gran, L. (1970) Medd. Nor. Farm. Selsk. 12, 173-180.
25. Gran, L. (1972) Medd. Nor. Farm. Selsk. 34, 125-135.
26. Pallaghy, P. K., Niellsen, K. J., Craik, D. J., and Norton, R. S. (1994) Protein Sci. 3, 1833-1839.
27. Kokryakov, V. N., Harwig, S. S. L., Panyutich, E. A., Shevchenko, A. A., Aleshina, G. M., Shamova, O. V., Korneva, H. A., and Lehrer, R. (1993) FEBS Lett. 327, 231-236.
28. Nakamura, T., Furanaka, H., Miyata, T., Tokunaga, F., Muta, T., Iwanaga, S., Niwa, M., Taokao, T., and Shimonishi, Y. (1988) J. Biol. Chem. 263, 16709-16713.
29. Tam, J. P., Lu, Y.-A., and Yang, J.-L. (2000) Biochim. Biophys. Res. Commun. 267, 783-790.
30. Richardson, J. S., and Richardson, D. C. (1988) Science 240, 1648-1652.
31. Merrifield, R. B. (1963) J. Am. Chem. Soc. 85, 2149-2154.
32. Barany, G., and Merrifield, R. B. (1980) in The Peptides (Gross, E., and Meienhofer, J., Eds.) Vol. 2, pp 1-284, Academic Press, New York.
33. Hojo, H., and Aimoto, S. (1991) Bull. Chem. Soc. Jpn. 64, 111-117.
34. Zhang, L., and Tam, J. P. (1997) J. Am. Chem. Soc. 119, 2363-2370.
35. Tam, J. P., and Lu, Y.-A. (1998) Protein Sci. 7, 1583-1592.
36. Zhang, L., and Tam, J. P. (1999) J. Am. Chem. Soc. 121, 3311-3320.
37. Smyth, D. G. (1967) Methods Enzymol. 11, 214-231.
38. Kussmann, M., Nordhoff, E., Rahbek-Nielsen, H., Haebel, S., Rossel-Larsen, M., Jakobsen, L., Gobom, J., Mirgorodskaya, E., Kroll-Kristensen, A., Palm, L., and Roepstorff, P. (1997) J. Mass Spectrom. 32, 593-601.
39. Lehrer, R. I., Rosenman, M., Harwing, S. S., Jackson, R., and Eisenhauer, P. (1991) J. Immunol. Methods 137, 167-173.
40. Fehlbaum, P., Bulet, P., Machaut, L., Lagueux, M., Broekaert, W. F., Hetru, C., and Hoffmann, J. A. (1994) J. Biol. Chem. 269, 33159-33163.
41. Tam, J. P., Lu, Y.-A., and Yu, Q. (1999) J. Am. Chem. Soc. 121, 4316-4324.
42. Zhou, N. E., Mant, C. T., and Hodges, R. S. (1990) Pept. Res. 3, 8-20.
43. Woody, R. W. (1995) Methods Enzymol. 246, 34-71.
44. Oishi, O., Yamashita, S., Nishimoto, E., Lee, S., Sugihara, G., and Ohno, M. (1997) Biochemistry 36, 4352-4359.
45. Tamamura, H., Ikoma, R., Niwa, M., Funakoshi, S., Murakami, T., and Fujii, N. (1993) Chem. Pharm. Bull 41, 978-980.
46. Daly, N. L., Love, S., Alewood, P. F., and Craik, D. J. (1999) Biochemistry 38, 10606-10614.
47. Rao, A. G. (1999) Arch. Biochem. Biophys. 361, 127-134.
48. Yu, Q., Lehrer, R. I., and Tam, J. P. (2000) J. Biol. Chem. 275, 3943-3949.
49. Hibich, C., Kisters-Woike, B., Reed, J., Masters, C. L., and Beyreuther, K. (1991) J. Mol. Biol. 218, 149-163.
50. Matsuzaki, K., Nakayama, M., Fukui, M., Otaka, A., Funakoshi, S., Fujii, N., Bessho, K., and Miyajima, K. (1993) Biochemistry 32, 11704-11710.
51. Bayer, A., Freund, S., Nicholson, G., and Jung, G. (1993) Angew. Chem., Int. Ed. Engl. 32, 1336-1339.
52. Solomon, S., Hu, J., Zhu, Q., Belcourt, D., Bennett, H. P., Bateman, A., and Antakly, T. (1991) J. Steroid Biochem. Mol. Biol. 40, 391-398.
53. Chertov, O., Michiel, D. F., Xu, L., Wang, J. M., Tani, K., Murphy, W. J., Longo, D. L., Taub, D. D., and Oppenheim, J. J. (1996) J. Biol. Chem. 271, 2935-2940.
54. Xu, Y., Tamamura, H., Arakaki, R., Nakashima, H., Zhang, X., Fujii, N., Uchiyama, T., and Hattori, T. (1999) AIDS Res. Hum. Retroviruses 15, 419-427.
55. Yang, D., Chertov, O., Bykovskaia, S. N., Chen, Q., Buffo, M. J., Shogan, J., Anderson, M., Schröder, J. M., Wang, J. M., Howard, O. M. Z., and Oppenheim, J. J. (1999) Science 286, 525-528.
56. Hoffman, J. A., Kafatos, F. C., Janeway, C. A., Jr., and Ezekowitz, R. A. B. (1999) Science 284, 1313-1318.
57. Medzhitov, R., and Janeway, C. A., Jr. (1998) Proc. Natl. Acad. Sci. U.S.A. 95, 429-430.
58. William, M. J. (1997) EMBO J. 16, 6120-6130.
59. Yorgey, P., Lee, J., Kördel, J., Vivas, E., Warner, P., Jebaratnam, D., and Kolter, R. (1994) Proc. Natl. Acad. Sci. U.S.A. 91, 4519-4523.
60. Skerlavaj, B., Romeo, D., and Gennaro, R. (1990) Infect. Immun. 58, 3724-3730.
61. Breukink, E., Wiedemann, I., Kraaij, O. P., Kuipers, O. P., Sahl, H.-G., and de Kruijff, B. (1999) Science 286, 2361-2364.