Neomycin-phenolic conjugates: Polycationic amphiphiles with broad-spectrum antibacterial activity, low hemolytic activity and weak serum protein binding

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 4, 2012, Pages 1499-1503

  Findlay, Brandon ^a   Zhanel, George G ^a   Schweizer, Frank ^a  

^a UNIVERSITY OF MANITOBA   (Canada)

Author keywords

Aminoglycosides; Cationic amphiphiles; Huisgen condensation; Phenolic disinfectants; Quaternary ammonium chlorides

Indexed keywords

AMPHOPHILE; AZIDE; CUPROUS ION; FRAMYCETIN; NEOMYCIN; PHENOL DERIVATIVE; POLYCATION;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; BACTERIAL MEMBRANE; CYCLOADDITION; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; HEMOLYSIS; HYDROPHOBICITY; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; NONHUMAN; PLASMA PROTEIN BINDING;

BACTERIA (MICROORGANISMS); METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; NEGIBACTERIA; POSIBACTERIA;

EID: 84856665482     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.01.025     Document Type: Article

References (34)

1. Arias, C. A.; Murray, B. E. N. Eng. J. Med. 2009, 360, 439.
2. Payne, D. J.; Gwynn, M. N.; Holmes, D. J.; Pompliano, D. L. Nat. Rev. Drug Disc. 2007, 6, 29.
3. Vatopoulos, A. C.; Kalapothaki, V.; Legakis, N. J. Emerg. Infect. Dis. 1999, 5, 471.
4. Lowy, F. D. J. Clin. Invest. 2003, 111, 1265.
5. Wright, G. D. Nat. Rev. Microbiol. 2007, 5, 175.
6. Mulvey, M. R.; Simor, A. E. CMAJ 2009, 180, 408.
7. Li, X. Z.; Nikaido, H. Drugs 2004, 64, 159.
8. Bera, S.; Zhanel, G. G.; Schweizer, F. J. Antimicrob. Chemother. 2010.
9. Bera, S.; Zhanel, G. G.; Schweizer, F. J. Med. Chem. 2010.
10. Bera, S.; Zhanel, G. G.; Schweizer, F. Bioorg. Med. Chem. Lett. 2010, 20, 3031.
11. Bera, S.; Zhanel, G. G.; Schweizer, F. J. Med. Chem. 2008, 51, 6160.
12. Findlay, B.; Zhanel, G. G.; Schweizer, F. Antimicrob. Agents Chemother. 2010, 54, 4049.
13. Hanessian, S.; Pachamuthu, K.; Szychowski, J.; Giguere, A.; Swayze, E. E.; Migawa, M. T.; Francois, B.; Kondo, J.; Westhof, E. Bioorg. Med. Chem. Lett. 2010, 20, 7097.
14. Zhang, J.; Chiang, F. I.; Wu, L.; Czyryca, P. G.; Li, D.; Chang, C. W. J. Med. Chem. 2008, 51, 7563.
15. Ouberai, M.; El Garch, F.; Bussiere, A.; Riou, M.; Alsteens, D.; Lins, L.; Baussanne, I.; Dufrene, Y. F.; Brasseur, R.; Decout, J. L.; Mingeot-Leclercq, M. P. Biochim. Biophys. Acta 2011, 1808, 1716.
16. Baussanne, I.; Bussiere, A.; Halder, S.; Ganem-Elbaz, C.; Ouberai, M.; Riou, M.; Paris, J. M.; Ennifar, E.; Mingeot-Leclercq, M. P.; Decout, J. L. J. Med. Chem. 2010, 53, 119.
17. Marr, A. K.; Gooderham, W. J.; Hancock, R. E. Curr. Opin. Pharmacol. 2006, 6, 468.
18. Rotem, S.; Mor, A. Biochim. Biophys. Acta 2008, 1788, 1582.
19. Svenson, J.; Brandsdal, B. O.; Stensen, W.; Svendsen, J. S. J. Med. Chem. 2007, 50, 3334.
20. McDonnell, G.; Russell, A. D. Clin. Microbiol. Rev. 1999, 12, 147.
21. Pokrovskaya, V.; Belakhov, V.; Hainrichson, M.; Yaron, S.; Baasov, T. J. Med. Chem. 2009, 52, 2243.
22. Waring, M. J. Bioorg. Med. Chem. Lett. 2009, 19, 2844.
23. Hancock, R. E.; Bellido, F. J. Antimicrob. Chemother. 1992, 29, 235.
24. Schroeder, R.; Waldsich, C.; Wank, H. EMBO J. 2000, 19, 1.
25. Chen, Y.; Guarnieri, M. T.; Vasil, A. I.; Vasil, M. L.; Mant, C. T.; Hodges, R. S. Antimicrob. Agents Chemother. 2007, 51, 1398.
26. Zhu, L.; Lin, J.; Ma, J.; Cronan, J. E.; Wang, H. Antimicrob. Agents Chemother. 2010, 54, 689.
27. Meldal, M.; Tornoe, C. W. Chem. Rev. 2008, 108, 2952.
28. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2004, 2001, 40.
29. Dickschat, J. S.; Reichenbach, H.; Wagner-Döbler, I.; Schulz, S. Eur. J. Org. Chem. 2005, 2005, 4141.
30. Boer, J.; Blount, K. F.; Luedtke, N. W.; Elson-Schwab, L.; Tor, Y. Angew. Chem., Int. Ed. 2005, 44, 927.
31. Hanessian, S.; Masse, R.; Capmeau, M. L. J. Antibiot. (Tokyo) 1977, 30, 893.
32. Zhanel, G. G.; DeCorby, M.; Laing, N.; Weshnoweski, B.; Vashisht, R.; Tailor, F.; Nichol, K. A.; Wierzbowski, A.; Baudry, P. J.; Karlowsky, J. A.; Lagace-Wiens, P.; Walkty, A.; McCracken, M.; Mulvey, M. R.; Johnson, J.; Hoban, D. J.Canadian Antimicrobial Resistance Alliance (CARA) Antimicrob. Agents Chemother. 2008, 52, 1430.
33. Zhanel, G. G.; Adam, H. J.; Low, D. E.; Blondeau, J.; Decorby, M.; Karlowsky, J. A.; Weshnoweski, B.; Vashisht, R.; Wierzbowski, A.; Hoban, D. J.Canadian Antimicrobial Resistance Alliance (CARA) Microbiol. Infect. Dis. 2011, 69, 291.
34. Stewart, M. J.; Parikh, S.; Xiao, G.; Tonge, P. J.; Kisker, C. J. Mol. Biol. 1999, 290, 859.