Novel semisynthetic derivative of antibiotic eremomycin active against drug-resistant gram-positive pathogens including Bacillus anthracis

Journal of Medicinal Chemistry

Volumn 50, Issue 15, 2007, Pages 3681-3685

  Maples, Kirk R ^a   Wheeler, Conrad ^a   Ip, Emily ^a   Plattner, Jacob J ^a   Chu, Daniel ^b   Zhang, Yong Kang ^a   Preobrazhenskaya, Maria N ^c   Printsevskaya, Svetlana S ^c   Solovieva, Svetlana E ^c   Olsufyeva, Evgenia N ^c   Heine, Henry ^d   Lovchik, Julie ^e   Lyons, C Richard ^e  

^a PFIZER INC   (United States)

^b Galileo Laboratories Inc   (United States)

^c GAUSE INSTITUTE OF NEW ANTIBIOTICS   (Russian Federation)

^d UNITED STATES ARMY MEDICAL RESEARCH INSTITUTE OF INFECTIOUS DISEASES   (United States)

^e UNIVERSITY OF NEW MEXICO HEALTH SCIENCES CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 ADAMANTANAMINE DERIVATIVE; AN 0900; CIPROFLOXACIN; EREMOMYCIN; GLYCOPEPTIDE; UNCLASSIFIED DRUG; VANCOMYCIN;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTHRAX; ANTIBIOTIC RESISTANCE; ARTICLE; BACILLUS ANTHRACIS; BACTERIAL STRAIN; BACTERIUM ISOLATE; CONTROLLED STUDY; DISEASE MODEL; DRUG DISTRIBUTION; DRUG HALF LIFE; DRUG STRUCTURE; DRUG SYNTHESIS; ENTEROCOCCUS; FEMALE; MINIMUM INHIBITORY CONCENTRATION; MOUSE; NONHUMAN; REACTION ANALYSIS; STAPHYLOCOCCUS; STAPHYLOCOCCUS AUREUS; STRUCTURE ANALYSIS;

ANIMALS; ANTHRAX; ANTI-BACTERIAL AGENTS; BACILLUS ANTHRACIS; DRUG RESISTANCE, BACTERIAL; GLYCOPEPTIDES; GRAM-POSITIVE BACTERIA; MICE; MICROBIAL SENSITIVITY TESTS; STAPHYLOCOCCAL INFECTIONS; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34547596812     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0700058     Document Type: Article

References (15)

1. Brook, I. The prophylaxis and treatment of anthrax. Int. J. Antimicrob. Agents 2002, 20, 320-325.
2. Greenfield, R. A.; Bronze, M. S. Current therapy and the development of therapeutic options for the treatment of diseases due to bacterial agents of potential biowarfare and bioterrorism. Curr. Opin. Invest. Drugs 2004, 5, 135-140.
3. Athamna, A.; Athamna, M.; Abu-Rashed, N.; Medlej, B.; Bast, D. J.; Rubinshtein, E. Selection of Bacillus anthracis isolates resistant to antibiotics. J. Antimicrob. Chemother. 2004, 54, 424-428.
4. Gause, G. F.; Brazhnikova, M. G.; Lomakina, N. N.; Berdnikova, T. F.; Fedorova, G. B.; Tokareva, N. L.; Borisova, V. N.; Batta, G. Y. Eremomycin-New glycopeptide antibiotic: Chemical properties and structure. J. Antibiot. 1989, 42 (12), 1790-1799.
5. Malabarba, A.; Nicas, T. I.; Thompson, R. S. Structural modifications of glycopeptide antibiotics. Med. Res. Rev. 1997, 17, 69-137.
6. Ge, M.; Chen, Z.; Onishi, H. R.; Kohler, J.; Silver, L. L.; Kerns, R.; Fukuzawa, S.; Thompson, C.; Kahne, D. Vancomycin derivatives that inhibit peptidoglycan biosynthesis without binding D-Ala-D-Ala. Science 1999, 284, 507-511.
7. Preobrazhenskaya, M. N.; Olsufyeva, E. N. Patents on glycopeptides of the vancomycin family and their derivatives as antimicrobials. Expert Opin. Ther. Pat. 2004, 14 (2), 141-173.
8. Printsevskaya, S. S.; Pavlov, A. Y.; Olsufyeva, E. N.; Mirchink, E. P.; Isakova, E. B.; Reznikova, M. I; Goldman, R. C.; Brandstrom, A. A.; Baizman, E. R.; Longley, C. B.; Sztaricskai, F.; Batta, G.; Preobrazhenskaya, M. N. Synthesis and mode of action of hydrophobic derivatives of glycopeptide antibiotic eremomycin and des-(N-methyl-D-leucyl)eremomycin against glycopeptide-sensitive and -resistant bacteria. J. Med. Chem. 2002, 45, 1340-1347.
9. 19F} rotational-echo double resonance. Biochemistry 2006, 45, 5235-5250.
10. Balzarini, J.; Pannecouque, C.; DeClercq, E.; Pavlov, A. Y.; Printsevskaya, S. S.; Miroshnikova, O. V.; Reznikova, M. I.; Preobrazhenskaya, M. N. Antiretroviral activity of semisynthetic derivatives of glycopeptide antibiotics. J. Med. Chem. 2003, 46 (13), 2755-2764.
11. Leadbetter, M. R.; Adams, S. M.; Bazzini, B.; Fatheree, P. R.; Karr, D. E.; Krause, K. M.; Lam, B. M. T.; Linsell, M. S.; Nodwell, M. B.; Pace, J. L.; Quast, K.; Shaw, J.-P.; Soriano, E.; Trapp, S. G.; Villena, J. D.; Wu, T. X.; Christensen, B. G.; Judice, J. K. Hydrophobic vancomycin derivatives with improved ADME properties: discovery of telvancin (TD-6424). J. Antibiot. 2004, 57 (5), 326-336.
12. Morosov, I. S.; Petrov, V. I.; Sergeeva, S. A. Pharmacology of Adamanatane; 2001; pp 50-60.
13. Printsevskaya, S. S; Solovieva, S. E.; Olsufyeva, E. N.; Mirchink, E. P.; Isakova, E. B.; De Clercq, E.; Balzarini, J.; Preobrazhenskaya, M. N. Structure-activity relationship studies of a series of antiviral and antibacterial aglycon derivatives of the glycopeptide antibiotics vancomycin, eremomycin, and dechloroeremomycin. J. Med. Chem. 2005, 48 (11), 3885-3890.
14. Miroshnikova, O. V.; Printsevskaya, S. S.; Olsufyeva, E. N.; Nilius, A.; Hensey-Rudloff, D.; Preobrazhenskaya, M. N. Structure-activity relationships in the series of eremomycin carboxamides. J. Antibiot. 2000, 53 (3), 286-293.
15. Lyons, C. R.; Lovchik, J.; Hutt, J.; Lipscomb, M. F.; Wang, E.; Heninger, S.; Berliba, L.; Garrison, K. Murine model of pulmonary anthrax: Kinetics of dissemination, histopathology, and mouse strain susceptibility. Infect. Immun. 2004, 72, 4801-4809.