Novel vancomycin dimers with activity against vancomycin-resistant enterococci

Journal of the American Chemical Society

Volumn 118, Issue 51, 1996, Pages 13107-13108

  Sundram, Uma N ^a   Griffin, John H ^a   Nicas, Thalia I ^b  

^a STANFORD UNIVERSITY   (United States)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

VANCOMYCIN; VANCOMYCIN DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; DRUG IDENTIFICATION; DRUG SYNTHESIS; ENTEROCOCCUS; GRAM POSITIVE BACTERIUM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MINIMUM INHIBITORY CONCENTRATION; NUCLEAR MAGNETIC RESONANCE; STAPHYLOCOCCUS;

EID: 0030479181     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9621298     Document Type: Article

References (21)

1. (a) Perkins, H. R.; Nieto, M. Pure Appl. Chem. 1973, 35, 371-381.
2. (b) Reynolds, P. E. Eur. J. Clin. Microbiol. Infect. Dis. 1989, 8, 789-803.
3. (a) Mackay, J. P.; Gerhard, U.; Beauregard, D. A.; Maplestone, R. A.; Williams, D. H. J. Am. Chem. Soc. 1994, 116, 4573-4580.
4. (b) Gerhard, U.; Mackay, J. P.; Maplestone, R. A.; Williams, D. H. J. Am. Chem. Soc. 1993, 115, 232-237.
5. (c) Waltho, J. P.; Williams, D. H. J. Am. Chem. Soc. 1989, 111, 2475-2480.
6. Beauregard, D. A.; Williams, D. H.; Gwynn, M. N.; Knowles, D. J. C. Antimicrob. Agents Chemother. 1995, 39, 781-785.
7. Mackay, J. P.; Gerhard, U.; Beauregard, D. A.; Westwell, M. S.; Searle, M. S.; Williams, D. H. J. Am. Chem. Soc. 1994, 116, 4581-4590.
8. Sundram, U. N.; Griffin, J. H. J. Org. Chem. 1995, 60, 1102-1103.
9. (a) Leclerq, R. E.; Derlot, R. E.; Duval, J.; Courvalin, P. N. Engl. J. Med. 1988, 319, 157-161.
10. (b) Uttley, A. H. C.; Collins, C. H.; Naidoo, J.; George, R. C. Lancet 1988, 1, 57-58.
11. (c) Courvalin, P. Antimicrob. Agents Chemother. 1990, 34, 2291-2296.
12. We have observed that vancomycin-cysteamide (obtained by reduction of 1b or 2b with dithiothreitol) exhibits activity against VRE (mean MIC = 91 μg/mL). However, we believe that this activity is due to in situ oxidation of vancomycin-cysteamide to 1b, which occurs with a half-life of less than 24 h.
13. See: Walsh, C. T.; Fisher, S. L.; Park, I.-S.; Zhu, W. Chem. Biol. 1996, 3, 21-28.
14. Popieniek, P. H.; Pratt, R. F. Anal. Biochem. 1987, 165, 108-113.
15. AcK(F)DADA was prepared by a method analogous to that described for the synthesis of the isomer FK(Ac)DADA (Shi, Z.; Griffin, J. H. J. Am. Chem. Soc. 1993, 115, 6482-6486).
16. Sheldrick, G. M.; Paulus, E.; Vertesy, L.; Hahn, F. Acta Crystallogr. Sect. B: Struct. Sci. 1995, 51, 89-98.
17. (a) Nagarajan, R.; Schabel, A. A.; Occolowitz, J. L.; Counter, F. T.; Ott, J. L.; Felty-Duckworth, A. M. J. Antibiotics 1989, 42, 63-72.
18. (b) Nicas, T. I.; Cole, C. T.; Preston, D. A.; Schabel, A. A.; Nagarajan, R. Antimicrob. Agents Chemother. 1989, 33, 1477-1481.
19. (c) Nicas, T. I.; Mullen, D. L.; Flokowitsch, J. E.; Preston, D. A.; Snyder, N. J.; Stratford, R. E.; Cooper, R. D. Antimicrob. Agents Chemother. 1995, 39, 2585-2587.
20. Neu, H. C. Science 1992, 257, 1064-1073.
21. Noble, W. C.; Virani, Z.; Cree, R. G. A. FEMS Microbiol. Lett. 1992, 93, 195-198.