Structure-activity relationships for antibacterial to antifungal conversion of kanamycin to amphiphilic analogues

Journal of Organic Chemistry

Volumn 80, Issue 9, 2015, Pages 4398-4411

  Fosso, Marina ^a   AlFindee, Madher N ^a   Zhang, Qian ^a   Nziko, Vincent De Paul Nzuwah ^a   Kawasaki, Yukie ^a   Shrestha, Sanjib K ^a   Bearss, Jeremiah ^a   Gregory, Rylee ^a   Takemoto, Jon Y ^a   Chang, Cheng Wei Tom ^a  

^a UTAH STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL MODIFICATION; FUNGI; FUNGICIDES; LEAD COMPOUNDS; SYNTHETIC APERTURE RADAR;

AMINOGLYCOSIDES; AMPHIPHILICS; ANTI-FUNGAL ACTIVITY; HYDROXYL GROUPS; OCTYL GROUPS; OPTIMAL SITE; PARENT MOLECULES; STRUCTURE-ACTIVITY RELATIONSHIPS;

ANTIFUNGAL AGENTS;

ALKYL GROUP; AMINOGLYCOSIDE DERIVATIVE; AMPHOPHILE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; HYDROXYL GROUP; KANAMYCIN B; KANAMYCIN DERIVATIVE; KANAMYCIN; SURFACTANT;

ALKYLATION; ANTIFUNGAL ACTIVITY; ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; CARBOHYDRATE ANALYSIS; CHEMISTRY; CONFORMATION; DRUG DEVELOPMENT; MOLECULAR GENETICS; SYNTHESIS;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; DRUG DISCOVERY; KANAMYCIN; MOLECULAR SEQUENCE DATA; STRUCTURE-ACTIVITY RELATIONSHIP; SURFACE-ACTIVE AGENTS;

EID: 84928920263     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00248     Document Type: Article

References (33)

1. Fisher, M. C.; Henk, D. A.; Briggs, C. J.; Brownstein, J. S.; Madoff, L. C.; McCraw, S. L.; Gurr, S. J. Nature 2012, 484, 186-194
2. Leonard, P.; Gianessi, L. P.; Reigner, N. The Value of Fungicides in U.S. Crop Production; Crop Protection Research Institute, CropLife Foundation: Washington, DC, 2005.
3. Verweij, P. E.; Snelders, E.; Kema, G. H.; Mellado, E.; Melchers, W. J. Lancet Infect. Dis. 2009, 9, 789-795
4. Review: Umezawa, S.; Tsuchiya, T. In Aminoglycoside Antibiotics; Umezawa, H.; Hooper, I. R., Ed.; Springer-Verlag: New York, 1982; pp 37-110.
5. Mingeot-Leclercq, M.-P.; Glupczynski, Y.; Tulkens, P. M. Antimicrob. Agents Chemother. 1999, 43, 727-737
6. Kotra, L. P.; Haddad, J.; Mobashery, S. Antimicrob. Agents Chemother. 2000, 44, 3249-3256
7. Haddad, J.; Kotra, L. P.; Mobashery, S. In Glycochemistry Principles, Synthesis, and Applications; Wang, P. G.; Bertozzi, C. R., Eds.; Marcel Dekker, Inc.: New York, 2001; pp 353-424.
8. Wang, J.; Chang, C.-W. T. In Aminoglycoside Antibiotics; Arya, D. P., Ed.; John Wiley & Sons, Inc.: New York, 2007; pp 141-180.
9. Fosso, M. Y.; Li, Y.; Gameau-Tsodikova, S. MedChemComm 2014, 5, 1075-1091
10. Bera, S.; Zhanel, G. G.; Schweizer, F. J. Med. Chem. 2008, 51, 6160-6164
11. Zhang, J.; Chiang, F.-I.; Wu, L.; Czyryca, P. G.; Li, D.; Chang, C.-W. T. J. Med. Chem. 2008, 51, 7563-7573
12. Bera, S.; Zhanel, G. G.; Schweizer, F. J. Med. Chem. 2010, 53, 3626-3631
13. Bera, S.; Zhanel, G. G.; Schweizer, F. Bioorg. Med. Chem. Lett. 2010, 20, 3031-3035
14. Bera, S.; Zhanel, G. G.; Schweizer, F. Bioorg. Med. Chem. Lett. 2010, 22, 1499-1503
15. Berkov-Zrihen, Y.; Herzog, I. M.; Feldman, M.; Fridman, M. Org. Lett. 2013, 15, 6144-6147
16. Sainlos, M.; Belmont, P.; Vigneron, J.-P.; Lehn, P.; Lehn, J.-M. Eur. J. Org. Chem. 2003, 2764-2774
17. Ouberai, M.; Garch, F. E.; Bussiere, A.; Riou, M.; Alsteens, D.; Lins, L.; Baussanne, I.; Dufrêne, Y. F.; Brasseur, R.; Decout, J.-L.; Mingeot-Leclercq, M.-P. Biochim. Biophys. Acta 2011, 1808, 1716-1727
18. Herzog, I. M.; Green, K. D.; Berkov-Zrihen, Y.; Feldman, M.; Vidavski, R. R.; Eldar-Boock, A.; Satchi-Fainaro, R.; Eldar, A.; Gameau-Tsodikova, S.; Fridman, M. Angew. Chem., Int. Ed. 2012, 51, 5652-5656
19. Chang, C.-W. T.; Fosso, M.; Kawasaki, Y.; Shrestha, S.; Bensaci, M. F.; Wang, J.; Evans, C. K.; Takemoto, J. Y. J. Antibiot. 2010, 63, 667-672
20. Shrestha, S.; Grilley, M.; Fosso, M.-Y.; Chang, C.-W. T.; Takemoto, J. Y. PLoS One 2013, 8, e73843
21. Chang, C.-W. T.; Takemoto, J. Y. MedChemComm 2014, 5, 1048-1057
22. Blom, P.; Ruttens, B.; van Hoof, S.; Hubrecht, I.; van der Eycken, J. J. Org. Chem. 2005, 70, 10109-10112
23. Nicolaou, K. C.; Randall, J. L.; Furst, G. T. J. Am. Chem. Soc. 1985, 107, 5556-5558
24. He, X.; Chan, T. H. Synthesis 2006, 10, 1645-1651
25. Huestis, M. P.; Aish, G. A.; Hui, J. P. M.; Soo, E. C.; Jakeman, D. L. Org. Biomol. Chem. 2008, 6, 477-484
26. Franais, A.; Urban, D.; Beau, J.-M. Angew. Chem., Int. Ed. 2007, 46, 8662-8665
27. Li, J.; Wang, J.; Czyryca, P. G.; Chang, H.; Orsak, T. W.; Evanson, R.; Chang, C.-W. T. Org. Lett. 2004, 6, 1381-1384
28. Li, J.; Chen, H.-N.; Chang, H.; Wang, J.; Chang, C.-W. T. Org. Lett. 2005, 7, 3061-3064
29. Dinkelar, J.; de Jong, A. R.; van Meer, R.; Somers, M.; Lodder, G.; Overkleeft, H. S.; Codee, J. D. C.; van der Marcl, G. A. J. Org. Chem. 2009, 74, 4982-4991
30. Greenberg, W. A.; Priestley, E.s.; Sears, P. S.; Alper, P. B.; Rosenbohm, C.; Hendrix, M.; Hung, S.-C.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 6527-6541
31. Rai, R.; Chang, H.; Chen, H.-N.; Chang, C.-W. T. J. Carbohydr. Chem. 2005, 24, 131-143
32. Wang, J.; Li, J.; Chen, H.-N.; Chang, H.; Tanifum, C. T.; Liu, H.-H.; Czyryca, P. G.; Chang, C.-W. T. J. Med. Chem. 2005, 48, 6271-6285
33. Shrestha, S.; Chang, C.-W. T.; Meissner, N.; Oblad, J.; Shrestha, J. P.; Sorensen, K.; Grilley, M.; Takemoto, J. Y. Front. Microbiol. 2014, 5, 1-12