Development of Tyrocidine A analogues with improved antibacterial activity

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 21, 2007, Pages 6667-6677

  Marques, Michael A ^a   Citron, Diane M ^b   Wang, Clay C ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^b LAC USC MEDICAL CENTER   (United States)

Author keywords

Amphipathic peptides; Antibiotics; Cyclopeptide; Gramicidin; Solid phase synthesis; Sulfamylbutyryl resin; Tyrocidine

Indexed keywords

DAPTOMYCIN; GRAMICIDIN S; TYROCIDINE;

AMINO ACID SUBSTITUTION; ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYCLIZATION; DRUG PURIFICATION; ESCHERICHIA COLI; HYDROPHILICITY; HYDROPHOBICITY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; SOLID PHASE SYNTHESIS; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; BACTERIA; DRUG DESIGN; MOLECULAR STRUCTURE; TYROCIDINE;

BACTERIA (MICROORGANISMS); NEGIBACTERIA; POSIBACTERIA;

EID: 34548538972     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.08.007     Document Type: Article

References (65)

1. Chang S., Sievert D.M., Hageman J.C., Boulton M.L., Tenover F.C., Downes F.P., Shah S., Rudrik J.T., Pupp G.R., Brown W.J., Cardo D., and Fridkin S.K. N. Engl. J. Med. 348 (2003) 1342-1347
2. Jones R.N., Farrell D.J., and Morrissey I. Antimicrob. Agents. Chemother. 47 (2003) 2696-2698
3. Sievert D.M., Boulton M.L., Stoltman G., Johnson D., Stobierski M.G., Downes F.P., Somsel P.A., Rudrik J.T., Brown W., Hafeez W., Lundstrom T., Flanagan E., Johnson R., and Mitchell J. JAMA 288 (2002) 824-825
4. Tsiodras S., Gold H.S., Sakoulas G., Eliopoulos G.M., Wennersten C., Venkataraman L., Moellering R.C., and Ferraro M.J. Lancet 358 (2001) 207-208
5. Cui L.Z., Tominaga E., Neoh H.M., and Hiramatsu K. Antimicrob. Agents. Chemother. 50 (2006) 1079-1082
6. Bax R.P. Clin. Infect. Dis. 24 (1997) S151-S153
7. Coates A., Hu Y.M., Bax R., and Page C. Nat. Rev. Drug Dis. 1 (2002) 895-910
8. Cohen M.L. Science 257 (1992) 1050-1055
9. Spratt B.G. Science 264 (1994) 388-393
10. Sefton A.M. Drugs 62 (2002) 557-566
11. Walsh C. Nature 406 (2000) 775-781
12. Silver L., and Bostian K. Eur. J. Clin. Microbiol. Infect. Dis. 9 (1990) 455-461
13. Walsh C. Nat. Rev. Microbiol. 1 (2003) 65-70
14. Rosamund J., and Allsop A. Science 287 (2000) 1973-1976
15. Tettelin F. Drug Dis. Today (2001) 887-892
16. Gonzales R.D., Schreckenberger P.C., Graham M.B., Kelkar S., DenBesten K., and Quinn J.P. Lancet 357 (2001) 1179
17. Pai M.P., Rodvold K.A., Schreckenberger P.C., Gonzales R.D., Petrolatti J.M., and Quinn J.P. Clin. Infect. Dis. 35 (2002) 1269-1272
18. Bax R.P., Anderson R., Crew J., Fletcher P., Johnson T., Kaplan E., Knaus B., Kristinsson K., Malek M., and Strandberg L. Nat. Med. 4 (1998) 545-546
19. Souli M., Kontopidou F.V., Koratzanis E., Antoniadou A., Giannitsioti E., Evangelopoulou P., Kannavaki S., and Giamarellou H. Antimicrob. Agents Chemother. 50 (2006) 3166-3169
20. Rose W.E., and Rybak M.J. Pharmacotherapy 26 (2006) 1099-1110
21. Fraise A.P. J. Infect. 53 (2006) 293-300
22. Doan T.-L., Fung H.B., Mehta D., and Riska P.F. Clin. Therapeutics 28 (2006) 1079-1106
23. Hancock R.E.W., and Chapple D.S. Antimicrob. Agents. Chemother. 43 (1999) 1317-1323
24. Zasloff M. N. Engl. J. Med. 347 (2002) 1199-1200
25. Zasloff M. Nature 415 (2002) 389-395
26. Hotchkiss R.D., and Dubos R.J. J. Biol. Chem. 136 (1940) 803-804
27. Hotchkiss R.D., and Dubos R.J. J. Biol. Chem. 141 (1941) 155-162
28. Jelokhani-Niaraki M., Prenner E.J., Kay C.M., McElhaney R.N., and Hodges R.S. J. Pept. Res. 60 (2002) 23-36
29. Jelokhani-Niaraki M., Prenner E.J., Kondejewski L.H., Kay C.M., McElhaney R.N., and Hodges R.S. Biophys. J. 78 (2000) 286A
30. Jelokhani-Niaraki M., Prenner E.J., Kondejewski L.H., Kay C.M., McElhaney R.N., and Hodges R.S. J. Pept. Res. 58 (2001) 293-306
31. Jones C.R., Sikakana C.T., Hehir S., Kuo M.C., and Gibbons W.A. Biophys. J. 24 (1978) 815-832
32. Jones C.R., Sikakana C.T., Kuo M.C., and Gibbons W.A. J. Am. Chem. Soc. 100 (1978) 5960-5961
33. Kato T., and Izumiya N. Biochimica. Et Biophysica. Acta 493 (1977) 235-238
34. Lewis R., Prenner E.J., Kiricsi M., Jelokhani-Niaraki M., Hodges R.S., and McElhaney R.N. Biophys. J. 88 (2005) 575A
35. Prenner E.J., Jelokhani-Niaraki M., Kondejewski L.H., Hodges R.S., and McElhaney R.N. Biophys. J. 78 (2000) 321A
36. Salgado J., Grage S.L., Kondejewski L.H., Hodges R.S., McElhaney R.N., and Ulrich A.S. J. Biomol. NMR 21 (2001) 191-208
37. Shai Y. Biochimica. Et Biophysica. Acta-Biomembr. 1462 (1999) 55-70
38. Shai Y. Biopolymers 66 (2002) 236-248
39. Prenner E.J., Lewis R., Jelokhani-Niaraki M., Hodges R.S., and McElhaney R.N. Biochimica. Et Biophysica. Acta-Biomembr. 1510 (2001) 83-92
40. Fuchs P.C., Barry A.L., and Brown S.D. Diagn. Microbiol. Infect. Dis. 38 (2000) 51-58
41. Ball L.J., Goult C.M., Donarski J.A., Micklefield J., and Ramesh V. Org. Biomol. Chem. 2 (2004) 1872-1878
42. Ando S., Nishikawa H., Takiguchi H., Lee S., and Sugihara G. Biochimica. Et Biophysica. Acta Biomembr. 1147 (1993) 42-49
43. Jelokhani-Niaraki M., Kondejewski L.H., Farmer S.W., Hancock R.E.W., Kay C.M., and Hodges R.S. Biochem. J. 349 (2000) 747-755
44. Kondejewski L.H., Farmer S.W., Wishart D.S., Hancock R.E.W., and Hodges R.S. Int. J. Pept. Protein. Res. 47 (1996) 460-466
45. Kondejewski L.H., Farmer S.W., Wishart D.S., Kay C.M., Hancock R.E.W., and Hodges R.S. J. Biol. Chem. 271 (1996) 25261-25268
46. Kondejewski L.H., Jelokhani-Niaraki M., Farmer S.W., Lix B., Kay C.M., Sykes B.D., Hancock R.E.W., and Hodges R.S. J. Biol. Chem. 274 (1999) 13181-13192
47. Kondejewski L.H., Lee D.L., Jelokhani-Niaraki M., Farmer S.W., Hancock R.E.W., and Hodges R.S. J. Biol. Chem. 277 (2002) 67-74
48. McInnes C., Kondejewski L.H., Hodges R.S., and Sykes B.D. J. Biol. Chem. 275 (2000) 14287-14294
49. Bu X.Z., Wu X.M., Xie G.Y., and Guo Z.H. Org. Lett. 4 (2002) 2893-2895
50. Kohli R.M., Walsh C.T., and Burkart M.D. Nature 418 (2002) 658-661
51. Qin C.G., Bu X.Z., Wu X.M., and Guo Z.H. J. Comb. Chem. 5 (2003) 353-355
52. Qin C.G., Zhong X.F., Bu X.Z., Ng N.L.J., and Guo Z.H. J. Med. Chem. 46 (2003) 4830-4833
53. Ruttenbe Ma., and Mach B. Biochemistry 5 (1966) 2864
54. Katayama T., Nakao K., Akamatsu M., Ueno T., and Fujita T. J. Pharm. Sci. 83 (1994) 1357-1362
55. Mukhtar T.A., Koteva K.P., and Wright G.D. Chem. Biol. 12 (2005) 229-235
56. Kuo M.C., Drakenberg T., and Gibbons W.A. J. Am. Chem. Soc. 102 (1980) 520-524
57. Kuo M.C., and Gibbons W.A. Biochemistry 18 (1979) 5855-5867
58. Kuo M.C., and Gibbons W.A. J. Biol. Chem. 254 (1979) 6278-6287
59. Kuo M.C., and Gibbons W.A. Biophys. J. 32 (1980) 807-836
60. Trauger J.W., Kohli R.M., and Walsh C.T. Biochemistry 40 (2001) 7092-7098
61. Kohli R.M., Trauger J.W., Schwarzer D., Marahiel M.A., and Walsh C.T. Biochemistry 40 (2001) 7099-7108
62. Trauger J.W., Kohli R.M., Mootz H.D., Marahiel M.A., and Walsh C.T. Nature 407 (2000) 215-218
63. Bax R., Mullan N., and Verhoef J. Int. J. Antimicrob. Agents 16 (2000) 51-59
64. Kay C., Lorthioir O.E., Parr N.J., Congreve M., McKeown S.C., Scicinski J.J., and Ley S.V. Biotech. Bioeng. 71 (2000) 110-118
65. CLSI, Performance Standards for Antimicrobial Susceptibility Testing; Sixteenth Informational Supplement. In CLSI Document M100-S16, 7th ed.; Clinical and Laboratory Standards Institute: Wayne, Pennsylvania, 2006; Vol. 26, pp M100-S16.