Gramicidin S identified as a potent inhibitor for cytochrome bd-type quinol oxidase

FEBS Letters

Volumn 582, Issue 15, 2008, Pages 2299-2302

  Mogi, Tatsushi ^a   Ui, Hideaki ^b   Shiomi, Kazuro ^b   Omura, Satoshi ^b   Kita, Kiyoshi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

Antibiotics; Bacterial membrane; Gramicidin S; Quinol oxidase; Respiratory enzyme

Indexed keywords

2 HEPTYL 4 HYDROXYQUINOLINE 1 OXIDE; ANTIMYCIN A1; CYTOCHROME B; CYTOCHROME D; GRAMICIDIN D; GRAMICIDIN S; OXIDOREDUCTASE; OXIDOREDUCTASE INHIBITOR; PIERICIDIN A;

ARTICLE; BINDING AFFINITY; CONCENTRATION (PARAMETERS); DRUG POTENCY; DRUG SCREENING; ENZYME INHIBITION; ESCHERICHIA COLI; IC 50; NONHUMAN; PRIORITY JOURNAL;

ANTI-BACTERIAL AGENTS; CELL MEMBRANE; CYTOCHROMES; DETERGENTS; ELECTRON TRANSPORT CHAIN COMPLEX PROTEINS; ENZYME INHIBITORS; ESCHERICHIA COLI; ESCHERICHIA COLI PROTEINS; GRAMICIDIN; INHIBITORY CONCENTRATION 50; MICELLES; MODELS, CHEMICAL; OXIDOREDUCTASES;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI;

EID: 44749089929     PISSN: 00145793     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.febslet.2008.05.031     Document Type: Article

References (28)

1. Foster T.J. The Staphylococcus aureus 'superbug'. J. Clin. Invest. 114 (2004) 1693-1696
2. Brown E.D., and Wright G.D. New targets and screening approaches in antimicrobial drug discovery. Chem. Rev. 105 (2005) 759-774
3. Peschel A., and Sahl H.-G. The co-evolution of host cationic antimicrobial peptides and microbial resistance. Nat. Rev. Microbiol. 4 (2006) 529-536
4. Bowdish D.M.E., Davidson D.J., and Hancock R.E.W. A re-evaluation of the role of host defense peptides in mammalian immunity. Curr. Protein Pept. Sci. 6 (2005) 35-51
5. Izumiya N., Kato T., Aoyaga H., Waki M., and Kondo M. Synthetic Aspects of Biologically Active Cyclic Peptides: Gramicidin S and Tyrocidines (1979), Halsted Press, New York
6. Waki M., and Izumiya N. Recent advances in the biotechnology of β-lactams and microbial bioactive peptides. In: Kleinhaug H., and van Doren H. (Eds). Biochemistry of Peptide Antibiotics (1990), Walter de Gruyter Company, Berlin 205-244
7. Xu Y., Sugár I.P., and Krishna N.R. A variable target intensity-restrained global optimization (VARTIGO) procedure for determining three-dimensional structures of polypeptides from NOESY data: application to gramicidin-S. J. Biomol. NMR 5 (1995) 37-48
8. Ando S., Nishikawa H., Takiguchi H., Lee S., and Sugihara G. Antimicrobial specificity and hemolytic activity of cyclized basic amphiphilic β-structural model peptides and their interactions with phospholipid bilayers. Biochim. Biophys. Acta 1147 (1993) 42-49
9. Kondejewski L.H., Farmer S.W., Wishart D., Kay C.M., Hancock R.E.W., and Hodges R.S. Modulation of structure and antibacterial and hemolytic activity by ring size in cyclic gramicidin S analogs. J. Biol. Chem. 271 (1996) 25261-25268
10. Katsu T., Ninomiya C., Kuroko M., Kobayashi H., Hirota T., and Fujita Y. Action mechanism of amphipathic peptides gramicidin S and melittin on erythrocyte membrane. Biochim. Biophys. Acta 939 (1988) 57-63
11. Prenner E.J., Lewis R.N.A.H., Newman K.C., Gruner S.M., Kondejewski L.H., Hodges R.S., and McElhaney R.N. Nonlamellar phases induced by the interaction of gramicidin S with lipid bilayers. A possible relationship to membrane disrupting activity. Biochemistry 36 (1997) 7906-7916
12. 19F-NMR. J. Biomol. NMR 21 (2001) 191-208
13. Rautenbach M., Vlok N.M., Stander M., and Hoppe H.C. Inhibition of malaria parasite blood stages by tyrocidines, membrane-active cyclic peptide antibiotics from Bacillus brevis. Biochim. Biophys. Acta 1768 (2007) 1488-1497
14. Jünemann S. Cytochrome bd terminal oxidase. Biochim. Biophys. Acta 1321 (1997) 107-127
15. Mogi T., Tsubaki M., Hori H., Miyoshi H., Nakamura H., and Anraku Y. Two terminal quinol oxidase families in Escherichia coli: variations on molecular machinery for dioxygen reduction. J. Biochem. Mol. Biol. Biophys. 2 (1998) 79-110
16. Way S.S., Sallustio S., Magliozzo R.S., and Goldberg M.B. Impact of either elevated or decreased levels of cytochrome bd expression on Shigella flexneri virulence. J. Bacteriol. 181 (1999) 1229-1237
17. Endley S., McMurray D., and Ficht T.A. Interruption of the cydB locus in Brucella abortus attenuates intracellular survival and virulence in the mouse model of infection. J. Bacteriol. 183 (2001) 2454-2462
18. Shi L., Sohaskey C.D., Kana B.D., Dawes S., North R.J., Mizrahi V., and Gennaro M.L. Changes in energy metabolism of Mycobacterium tuberculosis in mouse lung and under in vitro conditions affecting aerobic respiration. Proc. Natl. Acad. Sci. USA 102 (2005) 15629-15634
19. Ui H., Ishiyama A., Sekiguchi H., Namatame M., Nishihara A., Takahashi A., Shiomi K., Otoguro K., and Ōmura S. Selective and potent in vitro antimalarial activities found in four microbial metabolites. J. Antibiot. 60 (2007) 220-222
20. Kondejewski L.H., Jelokhani-Niaraki M., Farmer S.W., Lix B., Kay C.M., Sykes B.D., Hancock R.E.W., and Hodges R.S. Dissociation of antimicrobial and hemolytic activities in cyclic peptide diastereomers by systematic alteration in amphipathicity. J. Biol. Chem. 274 (1999) 13181-13192
21. Prenner E.J., Kiricsi M., Jelokhani-Niaraki M., Lewis R.N.A.H., Hodges R.S., and McElhane R.N. Structure-activity relationships of diastereomeric lysine ring size analogs of the antimicrobial peptide gramicidin S. Mechanism of action and discrimination between bacterial and animal cell membrane. J. Biol. Chem. 280 (2005) 2002-2011
22. Yamada K., Shinoda S., Oku H., Komagoe K., Katsu K., and Katakai R. Synthesis of low-hemolytic antimicrobial dehydropeptides based on gramicidin S. J. Med. Chem. 49 (2006) 7592-7595
23. Mogi T., Akimoto S., Endou S., Watanabe-Nakayama T., Mizuochi-Asai E., and Miyoshi H. Probing the ubiquinol-binding site in cytochrome bd by site-directed mutagenesis. Biochemistry 45 (2006) 7924-7930
24. Mogi T., Minagawa J., Hirano T., Sato-Watanabe M., Tsubaki M., Uno T., Hori H., Nakamura H., Nishimura Y., and Anraku Y. Substitutions of conserved aromatic amino acid residues in subunit I perturb the metal centers of the Escherichia coli bo-type ubiquinol oxidase. Biochemistry 37 (1998) 1632-1639
25. 50) of an enzymatic reaction. Biochem. Pharmacol. 22 (1973) 3099-3108
26. Bronnikov G.E., Zhang S.-J., Cannon B., and Nedergaard J. A dual component analysis explains the distinctive kinetics of cAMP accumulation in brown adipocytes. J. Biol. Chem. 274 (1999) 37770-37780
27. 2+ ATPase activities and contractile force development. Can. J. Physiol. Pharmacol. 67 (1989) 546-552
28. Eremin V.A., Bulgakova V.G., Kaprel'iants A.S., Lplin A.N., and Ostrovskii D.N. Compartmentation of gramicidin S in membranes of sensitive bacteria and protein-lipid interactions. Biokhimiia 44 (1979) 548-554