Synthesis and combinational antibacterial study of 5″-modified neomycin

Journal of Antibiotics

Volumn 62, Issue 10, 2009, Pages 539-544

  Zhang, Jianjun ^a   Keller, Katherine ^a   Takemoto, Jon Y ^a   Bensaci, Mekki ^a   Litke, Anthony ^a   Czyryca, Przemyslaw Greg ^b   Chang, Cheng Wei Tom ^a  

^a UTAH STATE UNIVERSITY   (United States)

^b Allosterix Pharmaceuticals   (United States)

Author keywords

Aminoglycoside; Antibiotic; MRSA; Synergism; VRE

Indexed keywords

5'' DEOXY 5'' DODECANAMIDONEOMYCIN B; 5'' DEOXY 5'' TETRADECANAMIDONEOMYCIN B; 5''DEOXY 5'' DECANAMIDONEOMYCIN B; AMIKACIN; FRAMYCETIN; NEOMYCIN; UNCLASSIFIED DRUG; VANCOMYCIN;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; DRUG SYNTHESIS; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; VANCOMYCIN RESISTANT ENTEROCOCCUS;

ANTI-BACTERIAL AGENTS; DRUG SYNERGISM; DRUG THERAPY, COMBINATION; ENTEROCOCCUS; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; HUMANS; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS; MICROBIAL SENSITIVITY TESTS; MOLECULAR CONFORMATION; NEOMYCIN; STRUCTURE-ACTIVITY RELATIONSHIP; VANCOMYCIN RESISTANCE;

METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS;

EID: 70449090218     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2009.66     Document Type: Article

References (23)

1. Umezawa, S & Tsuchiya, T. in Aminoglycoside Antibiotics (eds Umezawa, H. & Hooper, I. R.) 37-110 (Springer-Verlag, New York, 1982).
2. Haddad, J., Kotra, L. P. & Mobashery, S. in Glycochemistry Principles, Synthesis, and Applications (eds Wang, P. G. & Bertozzi, C. R.) 353-424 (Marcel Dekker Inc., New York/Basel, 2001).
3. Wang, J. & Chang, C.-W. T. in Aminoglycoside Antibiotics (ed. Arya, D. P.) 141-180 (John Wiley & Sons, Inc., 2007).
4. Wang, J. et al. Glycodiversification for optimization of the kanamycin class aminoglycosides. J. Med. Chem. 48, 6271-6285 (2005).
5. Li, J., Chiang, F.-I., Chen, H.-N. & Chang, C.-W. T. Investigation of the regioselectivity for Staudinger reaction and its application for the synthesis of aminoglycosides with N-1 modification. J. Org. Chem. 72, 4055-4066 (2007).
6. Fong, D. H. & Berghuis, A. M. Substrate promiscuity of an aminoglycoside antibiotic resistance enzyme via target mimicry. EMBO J. 21, 2323-2331 (2002).
7. Zhang,J. et al. Surprising alteration of antibacterial activity of 500-modified neomycin against resistant bacteria. J. Med. Chem. 51, 7563-7573 (2008).
8. Bera, S., Zhanel, G. G. & Schweizer, F. Design, synthesis, and antibacterial activities of neomycin-lipid conjugates: polycationic lipids with potent Gram-positive activity. J. Med. Chem. 51, 6160-6164 (2008).
9. Ida, T. et al. Identification of aminoglycoside-modifying enzymes by susceptibility testing: epidemiology of methicillin-resistant Staphylococcus aureus in Japan. J. Clin. Microbiol. 39, 3115-3121 (2001).
10. Swenson, J. M. et al. Molecular characterization and multilaboratory evaluation of Enterococcus faecalis ATCC 51299 for quality control of screening tests for vancomycin and high-level aminoglycoside resistance in Enterococci. J. Clin. Microbiol. 33, 3019-3021 (1995).
11. Cetinkaya, Y., Falk, P. & Mayhall, C. G. Vancomycin-resistant enterococci. Clin. Microbiol. Rev. 13, 686-707 (2000).
12. Barna, J. C. J. & Williams, D. H. The structure and mode of action of glycopeptide antibiotics of the vancomycin group. Ann. Rev. Microbiol. 38, 339-357 (1984).
13. Fridkin, S. K. et al. Monitoring antimicrobial use and resistance: comparison with a national benchmark on reducing vancomycin use and vancomycin-resistant enterococci. Emerg. Infect. Dis. 8, 702-707 (2002).
14. Kling, D., Hesek, D., Shi, Q. & Mobashery, S. Design and synthesis of a structurally constrained aminoglycoside. J. Org. Chem. 72, 5450-5453 (2007).
15. Hachiler, H., Santanam, P. & Kayser, F. H. Sequence and characterization of a novel chromosomal aminoglycoside phosphotransferase gene, aph (3¢)-IIb, in Pseudomonas aeruginosa. Antimicrob. Agents Chemother. 40, 1254-1256 (1996).
16. Neu, H. C. & Gootz, T. D. in Medical Microbiology (ed. Baron, S.) 4th edn. 183-185 (The University of Texas Medical Branch at Galvaston, 1996).
17. Cottagnoud, P., Cottagnoud, M. & Tauber, M. G. Vancomycin acts synergistically with gentamicin against penicillin-resistant pneumococci by increasing the intracellular penetration of gentamicin. Antimicrob. Agents Chemother. 40, 144-147 (2003).
18. Eliopoulos, G. M. & Moellering, R. C. Jr. in Antibiotics in Laboratory Medicine (ed. Lorian, V.) 330-396 (Williams & Wikins, New York, 1996).
19. Zhu, W. et al. Vancomycin-resistant Staphylococcus aureus isolates associated with Inc18-Like vanA plasmids in Michigan. Antimicrob. Agents Chemother. 52, 452-457 (2008).
20. Tenover, F. C. et al. Vancomycin-resistant Staphylococcus aureus isolate from a patient in pennsylvania. Antimicrob. Agents Chemother. 48, 275-280 (2004).
21. The procedure was modified from Methods for Dilution Antimicrobial Susceptibility Testing for Bacteria that Grow Aerobically Approved standard M7-A5, and Performance Standards for Antimicrobial Disk Susceptibility Tests. Approved standard M2-A7, National Committee for Clinical Laboratory Standards, Wayne, PA.
22. Dartois, V. et al. Systemic antibacterial activity of novel synthetic cyclic peptides. Antimicrob. Agents Chemother. 49, 3302-3310 (2005).
23. Sorensen, K. N., Kim, K. H. & Takemoto, J. Y. In vitro antifungal and fungicidal activities and erythrocyte toxicities of cyclic lipodepsinonapeptides produced by Pseudomonas syringae pv. Syringae. Antimicrob. Agents Chemother. 40, 2710-2713 (1996).