Design, synthesis, and evaluation of efflux substrate-metal chelator conjugates as potential antimicrobial agents

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 3, 2007, Pages 707-711

  Zhang, Yanling ^a   Eric Ballard, C ^b   Zheng, Shi Long ^a   Gao, Xingming ^a   Ko, Ko Chun ^a   Yang, Hsiuchin ^a   Brandt, Gary ^a   Lou, Xinhui ^b   Tai, Phang C ^a   Lu, Chung Dar ^a   Wang, Binghe ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

^b NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

Antimicrobial agents; Design; Efflux substrate metal chelator conjugates; Synthesis

Indexed keywords

ANTIINFECTIVE AGENT; CHELATING AGENT; METAL;

ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; BACTERICIDAL ACTIVITY; BIOASSAY; CONTROLLED STUDY; DRUG CONJUGATION; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; GRAM POSITIVE BACTERIUM; HOMEOSTASIS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN;

ANTI-BACTERIAL AGENTS; BACILLUS SUBTILIS; BACTERIA; CHELATING AGENTS; DRUG DESIGN; DRUG RESISTANCE, MULTIPLE, BACTERIAL; ESCHERICHIA COLI; INDICATORS AND REAGENTS; METALS; MICROBIAL SENSITIVITY TESTS; STRUCTURE-ACTIVITY RELATIONSHIP;

BACILLUS SUBTILIS; BACTERIA (MICROORGANISMS); POSIBACTERIA;

EID: 33846188178     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.10.094     Document Type: Article

References (47)

1. Hogan D., and Kolter R. Curr. Opin. Microbiol. 5 (2002) 472
2. Mitscher, L. A.; Pillai, S. P.; Gentry, E. J.; Shankel, D. M. Med. Res. Rev. 1999, 19, 477.
3. Nikaido H. J. Bacteriol. 178 (1996) 5853
4. Nikaido H., and Zgurskaya H.I. Curr. Opin. Infect. Dis. 12 (1999) 529
5. Chakraborti P.K., Bhatt K., Banerjee S.K., and Misra P. Biosci. Rep. 19 (1999) 293
6. Kawamura-Sato K., Shibayama K., Horii T., Iimuma Y., Arakawa Y., and Ohta M. FEMS Microbiol. Lett. 179 (1999) 345
7. Kohler T., Kok M., MicheaHamzehpour M., Plesiat P., Gotoh N., Nishino T., Curty L.K., and Pechere J.C. Antimicrob. Agents Chemother. 40 (1996) 2288
8. Levy S.B. J. Appl. Microbiol. 92 (2002) 65S
9. Loddenkemper R., Sagebiel D., and Brendel A. Eur. Resp. J. 20 (2002) 66S
10. Mizutani T., Kurahashi K., Murakami T., Matsumi N., and Ogoshi H. J. Am. Chem. Soc. (1997) 8991
11. Ouellette M., and Kundig C. Int. J. Antimicrob. Agents 8 (1997) 179
12. van Zuylen L., Nooter K., Sparreboom A., and Verweij J. Invest. New Drugs 18 (2000) 205
13. Kaplan A., and Szabo L.L. Clinical Chemistry: Interpretation and Techniques (1979), Lea & Febiger, Philadelphia
14. Zubercova O., and Babusikova O. Neoplasma 45 (1998) 53
15. Nacsa J., Nagy L., Sharples D., Hever A., Szabo D., Ocsovszki I., Varga A., Konig S., and Molnar J. Anti-Cancer Drug 71 (1998) 3093
16. Lomovskaya O., and Watkins W. J. Mol. Microbiol. Biotechnol. 3 (2001) 225
17. Advani R., Saba H.I., Tallman M., Rowe J.M., Wiernik P.H., Ramek J., Dugan K., Lum B., Villena J., Davis E., Paietta E., Litchman M., Sikic B.I., and Greenberg P.L. Blood 93 (1991) 787
18. Banerjee S.K., Bhatt K., Misra P., and Chakraborti P.K. Mol. Gen. Genet. 262 (2000) 949
19. Dantzig A.H., De Alwis D.P., and Burgess M. Adv. Drug Delivery Rev. 55 (2003) 133
20. Desnottes J.F. Trends Biotech. 14 (1996) 134
21. Schweizer H.P. Genet. Mol. Res. 2 (2003) 48
22. Yu E.W., McDermott G., Zgurskaya H.I., Nikaido H., and Koshland D.E. Science 300 (2003) 976
23. Higgins C.F., and Linton K.J. Science 293 (2001) 1782
24. Borges-Walmsley M.I., McKeegan K.S., and Walmsley A.R. Biochem. J. 376 (2003) 313
25. Esposito B.P., Epsztejn S., Breuer W., and Cabantchik Z.I. Anal. Biochem. 304 (2002) 1
26. Gracio A.M., Gracio A.J.D., Viveiros M., and Amaral L. Int. J. Antimicrob. Agents 22 (2003) 347
27. Kaatz G.W., Moudgal V.V., Seo S.M., Hansen J.B., and Kristiansen J.E. Int. J. Antimicrob. Agents 22 (2003) 254
28. Kaatz G.W., Moudgal V.V., Seo S.M., and Kristiansen J.E. Antimicrob. Agent Chemother. 47 (2003) 719
29. Kolaczkowski M., Michalak K., and Motohashi N. Int. J. Antimicrob. Agents 22 (2003) 279
30. Keshelava N., Tsao-Wei D., and Reynolds C.P. Clin. Cancer Res. 9 (2003) 3492
31. Krishnegowda G., Thimmaiah P., Hegde R., Dass C., Houghton P.J., and Thimmaiah K.N. Bioorg. Med. Chem. 10 (2002) 2367
32. Molnar J., Foldeak S., Nakamura M.J., Rausch H., Domonkos K., and Szabo M. APMIS 100 (1992) 24
33. Molnar J., Hever A., Fakla I., Fischer J., Ocsovski I., and Aszalos A. Anticancer Res. 17 (1997) 481
34. Tierney M.T., and Grinstaff M.W. Org. Lett. 2 (2000) 3413
35. Fanni S., Keyes T.E., Campagna S., and Vos J.G. Inorg. Chem. 37 (1998) 5933
36. Hanson P., Isham W.J., Lewis R.J., and Stockburn W.A. J. Chem. Soc., Perkin Trans. 2 (1981) 1492
37. Mehta G., Sambaiah T., Maiya B.G., Sirish M., and Dattagupta A.. J. Chem. Soc., Perkin Trans. 1 (1995) 295
38. Godefroi E.F., and Wittle E.L. J. Org. Chem. 21 (1956) 1163
39. Fan X., You J., Jiao T., Tan G., and Yu X. Org. Prep. Proced. Int. 32 (2000) 284
40. Bernard H., Yaouanc J.J., Clement J.C., Des Abbayes H., and Handel H. Tetrahedron Lett. 32 (1991) 639
41. Helps I.M., Parker D., Morphy J.R., and Chapman J. Tetrahedron 45 (1989) 219
42. Hancock R.E.W., and Nikaido H. J. Bacteriol. 136 (1978) 381
43. De Silva S.A., Zavaleta A., Baron D.E., Allam O., Isidor E.V., Kashimura N., and Percarpio J.M. Tetrahedron Lett. 38 (1997) 2237
44. Konig B., Pelka M., Klein M., Dix I., Jones P.G., and Lex J. J. Inclusion Phenom. Macrocycl. Chem. 37 (2000) 39
45. Finnery L., and O'Halloran T. Science 300 (2003) 931
46. Hirano T., Kikuchi K., Urano Y., Higuchi T., and Nagano T. Angew. Chem. Int. Ed. 39 (2000) 1052
47. Hyun H.J., Sohn J.H., Ha D.W., Ahn Y.H., Koh J., and Yoon Y.H. Invest. Ophthalmol. Visual Sci. 42 (2001) 460