Nocathiacin I analogues: Synthesis, in vitro and in vivo biological activity of novel semi-synthetic thiazolyl peptide antibiotics

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 22, 2004, Pages 5573-5577

  Naidu, B Narasimhulu ^a   Sorenson, Margaret E ^a   Zhang, Yunhui ^a   Kim, Oak K ^a   Matiskella, John D ^a   Wichtowski, John A ^a   Connolly, Timothy P ^a   Li, Wenying ^a   Lam, Kin S ^a   Bronson, Joanne J ^a   Pucci, Michael J ^a   Clark, Junius M ^a   Ueda, Yasutsugu ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

Antibacterial activity; Conjugate addition; Frozen water; Nocathiacins

Indexed keywords

ANTIBIOTIC AGENT; NOCATHIACIN I; PEPTIDE DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; IN VIVO STUDY;

AMINES; ANTI-BACTERIAL AGENTS; ENTEROCOCCUS FAECALIS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; PEPTIDES; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS PNEUMONIAE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 5144229218     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.08.058     Document Type: Article

References (20)

1. J. Vandeputte, and J.D. Dutcher Antibiot. Annu. 1955/1956 1956 560 561
2. B. Anderson, D.C. Hodgkin, and M.A. Viswamitra Nature 225 1970 233 235
3. C. Pascard, A. Ducruix, J. Lunel, and T. Prange J. Am. Chem. Soc. 99 1977 6418 6423
4. W. Li, J.E. Leet, H.A. Ax, D.R. Gustavson, D.M. Brown, L. Turner, K. Brown, J. Clark, H. Yang, J. Fung-Tomc, and K.S. Lam J. Antibiot. 56 2003 226 231
5. J.E. Leet, W. Li, H.A. Ax, J.A. Matson, S. Huang, R. Huang, J.L. Cantone, D. Drexler, R.A. Dalterio, and K.S. Lam J. Antibiot. 56 2003 232 242
6. T. Sasaki, T. Otani, H. Matsumoto, N. Unemi, M. Hamada, T. Takeuchi, and M. Hori J. Antibiot. 8 1998 715 721
7. P.T. Northcote, M. Siegel, D.B. Borders, and M.D. Lee J. Antibiot. 47 1994 901 908
8. (a) Ueda, Y.; Barrett, J.; DenBleyker, K.; Fung-Tomc, J.; Discotto, L.; Stickle, T.; Kolek, B.; Pucci, M. Abstracts of Papers, 43rd Annual ICAAC Meeting, Chicago, IL, Sept 14-17; American Society for Microbiology: Washington, DC, 2003; F-1842
9. (b) Yang, H.; Chaniewski, S.; Clark, J.; Ferraro, C.; Gali, V.; Lamb, L.; Medina, I. Abstracts of Papers, 43rd Annual ICAAC Meeting, Chicago, IL, Sept 14-17; American Society for Microbiology: Washington, DC, 2003; B-319
10. Y.Y. Xing, and D.E. Draper Biochemistry 35 1996 1581 1588
11. D.E. Draper D.E. Draper Protein-RNA Recognition in a Highly Conserved Ribosomal Domain Targeted by Thiazole Antibiotics 1998 Academic San Diego 113 125
12. S.E. Heffron, and F. Jurnak Biochemistry 39 2000 37 45
13. P. Hrnciar, Y. Ueda, S. Huang, J.E. Leet, and J.J. Bronson J. Org. Chem. 67 2002 8789 8793
14. A. Regueiro-Ren, B.N. Naidu, X. Zheng, T.W. Hudyma, T.P. Connolly, J.D. Matiskella, Y. Zhang, O.K. Kim, M.E. Sorenson, M. Pucci, J. Clark, J.J. Bronson, and Y. Ueda Bioorg. Med. Chem. Lett. 14 2004 171 175
15. B.N. Naidu, M.E. Sorenson, T.W. Hudyma, X. Zheng, Y. Zhang, J.J. Bronson, M.J. Pucci, J.M. Clark, and Y. Ueda Bioorg. Med. Chem. Lett. 14 2004 3743 3746
16. B.N. Naidu, W. Li, M.E. Sorenson, T.P. Connolly, J.A. Wichtowski, Y. Zhang, O.K. Kim, J.D. Matiskella, K.S. Lam, J.J. Bronson, and Y. Ueda Tetrahedron Lett. 45 2004 1059 1063
17. Conjugate adducts were formed as 1:1 diastereomeric mixture and the antibacterial activity of the individual isomers is comparable to that of the mixture
18. 2O: C, 46.37; H, 4.80; N, 12.67; S, 9.67; Cl, 4.28. Found: C, 46.45; H, 4.76; N, 12.77; S, 9.84; Cl, 4.69
19. 5 CFU/well and was run on microtiter plates. The volume of each well was 100 μL and the plates were inoculated at 35°C for 18 h in ambient air
20. 50s) of the drug-treated animals were determined by the Spearman-Karber nonparametric estimator method. Each experimental group consisted of 10 animals and a minimum of 3 different concentrations of drug was evaluated per compound