Active transport of siderophore-mimicking antibacterials across the outer membrane

Drug Resistance Updates

Volumn 2, Issue 6, 1999, Pages 363-369

  Braun, Volkmar ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

3 [(1 CARBOXYMETHYL 1H TETRAZOL 5 YL)THIOMETHYL] 7 [2 (6,7 DIHYDROXY 4 OXO 4H 1 BENZOPYRAN 3 CARBOXAMIDO) 2 (4 HYDROXYPHENYL)ACETAMIDO 8 OXO 5 THIA 1 AZABICYCLO[4.2.0]OCT 2 ENE 2 CARBOXYLIC ACID; 7 [2 (2 AMINO 4 THIAZOLYL) 2 (1,4 DIHYDRO 1,5 DIHYDROXY 4 OXO 2 PYRIDYLMETHOXYIMINO)ACETAMIDO] 3 (1,2,3 THIADIAZOL 5 YLTHIOMETHYL) 3 CEPHEM 4 CARBOXYLIC ACID; 7 [2 (2 AMINO 4 THIAZOLYL) 2 [(1 CARBOXY 1 METHYLETHOXY)IMINO]ACETAMIDO] 3 [(2,3 DIHYDRO 5,6 DIHYDROXY 2 METHYL 1H ISOINDOL 2 YL)METHYL] 3 CEPHEM 4 CARBOXYLIC ACID; ANTIINFECTIVE AGENT; BETA LACTAM; CATECHOL DERIVATIVE; CEPHALOSPORIN DERIVATIVE; CGP 4832; FERRIC ION; FERRICHROME; FERRIMYCIN A; FERRIOXAMINE; GR 6915330; GRISEIN; HYDROXAMIC ACID; RIFAMPICIN; RIFAMYCIN DERIVATIVE; SALMYCIN; SIDEROPHORE; SULFONAMIDE; UNCLASSIFIED DRUG;

ACTIVE TRANSPORT; ANTIBIOTIC RESISTANCE; BACTERIAL OUTER MEMBRANE; CRYSTAL STRUCTURE; DRUG CONJUGATION; DRUG PENETRATION; GRAM NEGATIVE BACTERIUM; NONHUMAN; PERMEABILITY BARRIER; PRIORITY JOURNAL; SHORT SURVEY; STRUCTURE ACTIVITY RELATION;

EID: 0033496153     PISSN: 13687646     EISSN: None     Source Type: Journal    
DOI: 10.1054/drup.1999.0107     Document Type: Article

References (36)

1. Nikaido H. Prevention of drug access to bacterial targets: permeability barriers and active efflux. Science. 264:1994;382-388.
2. Benz R. Uptake of solutes through bacterial outer membranes. Ghuysen J-M., Hakenbeck R. Bacterial cell wall. 1994;397-423 Elsevier, Amsterdam.
3. Schirmer T., Keller T. A., Wang Y-F., Rosenbusch J. P. Structural basis for sugar translocation through the maltoporin channels at 3.1 Å resolution. Science. 276:1995;512-514.
4. Braun V., Hantke K., Köster W. Bacterial iron transport: mechanisms, genetics, and regulation. Sigel A., Sigel H. Metal ions in biological systems. 1998;67-145 Marcel Dekker. New York.
5. Drechsel H., Winkelmann G. Iron chelation and siderophores. Winkelmann G., Carrano C. J. Transition metals in microbial metabolism. 1997;1-49 Harwood Academic Publishers, Amsterdam.
6. Higgins C. F. ABC transporters from microorganisms to man. Ann Rev Cell Biol. 8:1992;67-113.
7. Schneider R., Hantke K. Iron hydroxamate uptake systems in Bacillus subtilis: identification of a lipoprotein as part of a binding protein-dependent transport system. Mol Microbiol. 8:1993;111-121.
8. Ferguson A. D., Hofmann E., Coulton J. W., Diederichs K., Welte W. Structural basis for siderophore-mediated iron transport: crystal structure of FhuA with bound lipopolysaccharide. Science. 282:1998;2215-2220.
9. Locher K., Rees B., Koebnik R. Transmembrane signaling across the ligand-gated FhuA receptor: crystal structures of free and ferrichrome-bound states reveal allosteric changes. Cell. 95:1998;771-778.
10. Braun V. Pumping iron through cell membranes. Science. 282:1998;2202-2203.
11. Braun V. Energy-coupled transport and signal transduction through the gram-negative outer membrane via TonB-ExbB-ExbD-dependent receptor proteins. FEMS Microbiol Rev. 16:1995;295-307.
12. Günter K., Braun V. In vivo evidence for FhuA outer membrane interaction with the TonB inner membrane protein TonB. FEBS Lett. 274:1990;85-88.
13. Moeck G. S., Coulton J. W., Postle K. Cell envelope signaling in Escherichia coli. Ligand binding to the ferrichrome-iron receptor FhuA promotes interaction with the energy-transducing protein TonB. J Biol Chem. 272:1997;28391-28397.
14. Schöffler H., Braun V. Transport across the outer membrane of Escherichia coli via the FhuA receptor is regulated by the TonB protein of the cytoplasmic membrane. Mol Gen Genet. 217:1989;378-383.
15. Nikaido H. The role of outer membrane and efflux pumps in the resistance of gram-negative bacteria. Can we improve drug access? Drug Resistance Updates. 1:1998;93-98.
16. 2ε Angew Chem Suppl. 1982;1322-1335.
17. Hartmann A., Fiedler H-P., Braun V. Uptake and conversion of the antibiotic albomycin by Escherichia coli K-12. Eur J Biochem. 99:1979;517-524.
18. Braun V., Günther K., Hantke K., Zimmermann L. Intracellular activation of albomycin in Escherichia coli and Salmonella typhimurium. J Bacteriol. 156:1983;308-315.
19. Ferguson, A. D. Braun, V. Fiedler, H-P. Coulton, J. W. Diederichs, K. Welte, W. Crystal structure of the antibiotic albomycin in complex with the outer membrane transporter FhuA. 2000.
20. Pugsley P. A., Zimmermann W., Wehrli W. Highly efficient uptake of a rifamycin derivative via FhuA-TonB-dependent uptake route in Escherichia coli. J Gen Microbiol. 133:1987;3505-3511.
21. Ferguson, A. D. Ködding, J. Walker, G. Crystal structure of a semisynthetic rifamycin derivative in complex with the active outer membrane transporter FhuA from Escherichia coli K-12. 2000.
22. Braun M., Killmann H., Braun V. The β-barrel domain of FhuAΔ5-160 is sufficient for TonB-dependent FhuA activities of Escherichia coli. Mol Microbiol. 33:1999;1037-1049.
23. Zähner H., Diddens H., Keller-Schierlein W., Nägeli H-U. Some experiments with semisynthetic sideromycins. Jap J Antibiot Suppl. 30:1977;201-206.
24. 5 -hydroxy-L-ornithine-derived siderophore-β-lactam conjugates: iron transport-mediated drug delivery. J Med Chem. 34:1991;868-978.
25. Diarra M. S., Lavoie M. C., Jacques M. Species selectivity of new siderophore-drug conjugates that use specific iron uptake for entry into bacteria. Antimicrobial Agents Chemother. 40:1996;2610-2617.
26. Hantke K. Dihydroxybenzoylserine - a siderophore for E. coli. FEMS Microbiol Lett. 67:1990;5-8.
27. Watanabe N-A., Nagasu T., Katsu K., Kitoh K. E-0702, a new cephalosporin, is incorporated into Escherichia coli cells via the tonB -dependent iron transport system. Antimicrobial Agents Chemother. 31:1987;497-504.
28. Curtiss N. A. C., Eisenstadt R. L., East S. J. Iron regulated outer membrane proteins of Escherichia coli K-12 and mechanisms of action of catechol-substituted cephalosporins. Antimicrobial Agents Chemother. 32:1988;1879-1886.
29. Nikaido H., Rosenberg E. Y. Cir and Fiu proteins in the outer membrane of Escherichia coli catalyze transport of monomeric catechols: study with β-lactam antibiotics containing catechol and analogous groups. J Bacteriol. 172:1990;1361-1367.
30. Silley P., Griffith J. W., Monsey D., Harris A. M. Mode of action of GR69153, a novel catechol-substituted cephalosporin, and its interaction with the tonB -dependent iron transport system. Antimicrobial Agents Chemother. 34:1990;1806-1808.
31. Weissberger B. A., Abruzzo G. K., Fromtling R. A. L-658-310, a new injectable cephalosporin. I. In vitro antibacterial properties. J Antibiotics. 42:1989;795-806.
32. Valiant M. E., Gilfillan E. C., Gadebusch H. H., Pelak B. A. L-658-310 a new injectable cephalosporin. II. In vitro and in vivo interactions between L-658, 310 and various amino glycosides or ciprofloxacin versus clinical isolates of Pseudomonas aeruginos. J Antibiotics. 42:1989;807-814.
33. Gilfillan E. C., Pelak B. A., Weissberger B. A. L-658-310, a new injectable cephalosporin. III. Experimental chemotherapeutics and pharmacokinetics in laboratory animals. J Antibiotics. 42:1989;815-822.
34. Tatsumi Y., Mejima T., Mitsuhashi S. Mechanism of tonB -dependent transport of KP6736, a 1,5-dihydroxy-4-pyridone-substituted cephalosporin, intoEscherichia coli K-12 cells. Antimicrobial Agents Chemother. 39:1995;613-619.
35. Knüsel F., Zimmermann W. Sideromycins. Corcoran J. W., Hahn F. E. Antibiotics III. Mechanisms of action of antimicrobial and antitumor agents. 1975;653-667 Springer, Berlin.
36. Vertesy L., Aretz W., Fehlhaber H-W., Kogler H. Salmycins A-D, antibiotics from Streptomyces violaceus DSM 8286 having a siderophore-aminoglycoside structure. Helv Chim Acta. 78:1995;46-60.