Biological properties of novel antistaphylococcal quinoline-indole agents

Antimicrobial Agents and Chemotherapy

Volumn 47, Issue 2, 2003, Pages 458-466

  Oliva, Brunello ^a   Miller, Keith ^b   Caggiano, Nico ^b   O'Neill, Alexander J ^b   Cuny, Gregory D ^c,d   Hoemann, Michael Z ^c,e   Hauske, James R ^c   Chopra, Ian ^b  

^a UNIVERSITY OF L'AQUILA   (Italy)

^b UNIVERSITY OF LEEDS   (United Kingdom)

^c SUNOVION PHARMACEUTICALS INC   (United States)

^d The Harvard Center for Neurodegeneration & Repair   (United States)

^e BIOGEN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPICILLIN; ANTIBIOTIC AGENT; BACITRACIN; CHLORAMPHENICOL; CIPROFLOXACIN; CYCLOSERINE; DALFOPRISTIN PLUS QUINUPRISTIN; ERYTHROMYCIN; FOSFOMYCIN; FUSIDIC ACID; IB 367; LINEZOLID; MEROPENEM; NORFLOXACIN; OXACILLIN; OXAZOLIDINONE DERIVATIVE; PENICILLIN G; POLYMYXIN B; PSEUDOMONIC ACID; QUINOLINE INDOLE AGENT; RIFAMPICIN; SEP 118843; SEP 155342; STREPTOMYCIN; TETRACYCLINE DERIVATIVE; UNCLASSIFIED DRUG; VANCOMYCIN;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; BACTERICIDAL ACTIVITY; DRUG MECHANISM; HEMOLYSIS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTI-BACTERIAL AGENTS; CELL MEMBRANE; ESCHERICHIA COLI; HEMOLYSIS; INDOLES; MICE; MICROBIAL SENSITIVITY TESTS; QUINOLINES; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037310293     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.47.2.458-466.2003     Document Type: Article

References (49)

1. Boman, H. G., and D. A. Monner. 1975. Characterization of lipopolysaccharides from Escherichia coli K-12 mutants. J. Bacteriol. 121:455-464.
2. British Society for Antimicrobial Chemotherapy. 1991. A guide to sensitivity testing. Report of the working party on antibiotic sensitivity testing of the British Society for Antimicrobial Chemotherapy. J. Antimicrob. Chemother. 27(Suppl. D):1-50.
3. Chopra, I., J. Hodgson, B. Metcalf, and G. Poste. 1997. The search for antimicrobial agents effective against bacteria resistant to multiple antibiotics. Antimicrob. Agents Chemother. 41:497-503.
4. Chopra, I., R. W. Lacey, and J. Conolly. 1974. Biochemical and genetic basis of tetracycline resistance in Staphylococcus aureus. Antimicrob. Agents Chemother. 6:397-404.
5. Chopra, I., and M. Roberts. 2001. Tetracycline antibiotics: mode of action, applications, molecular biology, and epidemiology of bacterial resistance. Microbiol. Mol. Biol. Rev. 65:232-260.
6. Clark, D. 1984. Novel antibiotic hypersensitive mutants of Escherichia coli: genetic mapping and chemical characterization. FEMS Microbiol. Lett. 21: 189-195.
7. Clark, D. P., and J. P. Beard. 1979. Altered phospholipid composition in mutants of Escherichia coli sensitive or resistant to organic solvents. J. Gen. Microbiol. 113:267-274.
8. Climo, M. W., R. L. Patron, and G. L. Archer. 1999. Combinations of vancomycin and beta-lactams are synergistic against staphylococci with reduced susceptibilities to vancomycin. Antimicrob. Agents Chemother. 43: 1747-1753.
9. Cohen, M. L. 2000. Changing patterns of infectious disease. Nature 406:762-767.
10. Craig, W. A., and S. Gudmundson. 1996. Postantibiotic effect, p. 296-329. In V. Lorian (ed.), Antibiotics in laboratory medicine, 4th ed. The Williams & Wilkins Co., Philadelphia, Pa.
11. Crosse, A. M., D. L. A. Greenway, and R. R. England. 2000. Accumulation of ppGpp and ppGp in Staphylococcus aureus 8325-4 following nutrient starvation. Lett. Appl. Microbiol. 31:332-337.
12. Fernandez-Lopez, S., H. S. Kim, E. C. Choi, M. Delgado, J. R. Granja, A. Khasanov, K. Kraehenbuehl, G. Long, D. A. Weinberger, K. M. Wilcoxen, and M. R. Ghadiri. 2001. Antibacterial agents based on the cyclic D,L-alpha-peptide architecture. Nature 412:452-455.
13. Gale, E. F., E. Cundliffe, P. E. Reynolds, M. H. Richmond, and M. J. Waring. 1981. The molecular basis of antibiotic action, 2nd ed. John Wiley & Sons, London, United Kingdom.
14. Harrington, C. R., and J. Baddiley. 1984. Synthesis of peptidoglycan and teichoic acid in Bacillus subtilis: role of the electrochemical proton gradient. J. Bacteriol. 159:925-933.
15. Hebeisen, P., I. Heinze-Krauss, P. Angehrn, P. Hohl, M. G. P. Page, and R. L. Then. 2001. In vitro and in vivo properties of Ro 63-9141, a novel broad-spectrum cephalosporin with activity against methicillin-resistant staphylococci. Antimicrob. Agents Chemother. 45:825-836.
16. Hecker, S. J., I. S. Cho, T. W. Glinka, Z. J. Zhang, M. E. Price, V. J. Lee, B. G. Christensen, A. Boggs, S. Chamberland, F. Malouin, T. R. Parr, T. Annamalai, J. Blais, E. L. Bond, L. Case, C. Chan, J. Crase, R. Frith, D. Griffith, L. Harford, N. Liu, M. Ludwikow, K. Mathias, D. Rea, and R. Williams. 1998. Discovery of MC-02,331, a new cephalosporin exhibiting potent activity against methicillin-resistant Staphylococcus aureus. J. Antibiot. 51:722-734.
17. Heisler, L. M., H. Suzuki, R. Landick, and C. A. Gross. 1993. Four contiguous amino acids define the target for streptolydigin resistance in the beta subunit of Escherichia coli RNA polymerase. J. Biol. Chem. 268:25369-25375.
18. Hilliard, J. J., R. M. Goldschmidt, L. Licata, E. Z. Baum, and K. Bush. 1999. Multiple mechanisms of action for inhibitors of histidine protein kinases from bacterial two-component systems. Antimicrob. Agents Chemother. 43: 1693-1699.
19. Hoemann, M. Z., G. Kumaravel, R. L. Xie, R. F. Rossi, S. Meyer, A. Sidhu, G. D. Cuny, and J. R. Hauske. 2000. Potent in vitro methicillin-resistant Staphylococcus aureus activity of 2-(1H-indol-3-yl) quinoline derivatives. Bioorg. Med. Chem. Lett. 10:2675-2678.
20. Hsu Chen, C. C., and D. S. Feingold. 1973. The mechanism of polymyxin B action and selectivity toward biologic membranes. Biochemistry 12:2105-2111.
21. Jacoby, G. A. 1996. Antimicrobial-resistant pathogens in the 1990s. Annu. Rev. Med. 47:169-179.
22. Jolliffe, L. K., R. J. Doyle, and U. N. Streips. 1981. The energized membrane and cellular autolysis in Bacillus subtilis. Cell 25:753-763.
23. Kohsaka, M., and A. L. Demain. 1976. Conversion of penicillin N to cephalosporin(s) by cell-free extracts of Cephalosporium acremonium. Biochem. Biophys. Res. Commun. 70:465-473.
24. Labischinski, H., K. Ehlert, and B. Wieland. 1998. Novel antistaphylococcal targets and compounds. Expert Opin. Investig. Drugs 7:1245-1256.
25. Leduc, M., R. Kasra, and J. Vanheijenoort. 1982. Induction and control of the autolytic system of Escherichia coli. J. Bacteriol. 152:26-34.
26. Lee, K. H., and J. E. Oh. 2000. Design and synthesis of novel antimicrobial pseudopeptides with selective membrane-perturbation activity. Bioorg. Med. Chem. 8:833-839.
27. Livermore, D. M. 2000. Antibiotic resistance in staphylococci. Int. J. Antimicrob. Agents 16:S3-S10.
28. Maki, H., K. Miura, and Y. Yamano. 2001. Katanosin B and plusbacin A(3), inhibitors of peptidoglycan synthesis in methicillin-resistant Staphylococcus aureus. Antimicrob. Agents Chemother. 45:1823-1827.
29. Martinez, J. L., and F. Baquero. 2000. Mutation frequencies and antibiotic resistance. Antimicrob. Agents Chemother. 44:1771-1777.
30. Miller, K., A. J. O'Neill, and I. Chopra. 2002. Response of Escherichia coli hypermutators to selection pressure with antimicrobial agents from different classes. J. Antimicrob. Chemother. 49:925-934.
31. Moellering, R. C. 1998. Antibiotic resistance: lessons for the future. Clin. Infect. Dis. 27:S135-S140.
32. Navon-Venezia, S., R. Feder, L. Gaidukov, Y. Carmeli, and A. Mor. 2002. Antibacterial properties of dermaseptin S4 derivatives with in vivo activity. Antimicrob. Agents Chemother. 46:689-694.
33. Novick, R. 1967. Properties of a cryptic high-frequency transducing phage in Staphylococcus aureus. Virology 33:155-166.
34. Nyberg, G. K., and J. Carlsson. 1981. Metabolic inhibition of Peptostreptococcus anaerobius decreases the bactericidal effect of hydrogen peroxide. Antimicrob. Agents Chemother. 20:726-730.
35. Oliva, B., W. M. Maiese, M. Greenstein, D. B. Borders, and I. Chopra. 1993. Mode of action of the cyclic depsipeptide antibiotic LL-AO341-beta(1) and partial characterization of a Staphylococcus aureus mutant resistant to the antibiotic. J. Antimicrob. Chemother. 32:817-830.
36. O'Neill, A. J., J. H. Cove, and I. Chopra. 2001. Mutation frequencies for resistance to fusidic acid and rifampicin in Staphylococcus aureus. J. Antimicrob. Chemother. 47:647-650.
37. Rodionov, D. G., and E. E. Ishiguro. 1995. Direct correlation between overproduction of guanosine 3′,5′-bispyrophosphate (ppgpp) and penicillin tolerance in Escherichia coli. J. Bacteriol. 177:4224-4229.
38. Sambrook, J., and D. W. Russell. 2001. Molecular cloning: a laboratory manual, 3rd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.
39. Sanders, W. E., Jr., and C. C. Sanders. 1979. Toxicity of antibacterial agents: mechanism of action on mammalian cells. Annu. Rev. Pharmacol. Toxicol. 19:53-83.
40. Silverman, J. A., N. Oliver, T. Andrew, and T. Li. 2001. Resistance studies with daptomycin. Antimicrob. Agents Chemother. 45:1799-1802.
41. Steinberg, D. A., M. A. Hurst, C. A. Fujii, A. H. C. Kung, J. F. Ho, F. C. Cheng, D. J. Loury, and J. C. Fiddes. 1997. Protegrin-1: a broad-spectrum, rapidly microbicidal peptide with in vivo activity. Antimicrob. Agents Chemother. 41:1738-1742.
42. Stratton, C. W. 1996. Mechanisms of action for antimicrobial agents: general priniciples and mechanisms for selected classes of antibiotics, p. 579-603. In V. Lorian (ed.), Antibiotics in laboratory medicine, 4th ed. The Williams & Wilkins Co., Philadelphia, Pa.
43. Sukupolvi, S., and M. Vaara. 1989. Salmonella typhimurium and Escherichia coli mutants with increased outer-membrane permeability to hydrophobic compounds. Biochim. Biophys. Acta 988:377-387.
44. Tally, F. P., M. Zeckel, M. W. Wasilewski, C. Carini, C. L. Berman, G. L. Drusano, and F. B. Oleson. 1999. Daptomycin: a novel agent for grampositive infections. Expert Opin. Investig. Drugs 8:1223-1238.
45. Tenover, F. C., J. W. Biddle, and M. V. Lancaster. 2001. Increasing resistance to vancomycin and other glycopeptides in Staphylococcus aureus. Emerg. Infect. Dis 7:327-332.
46. Tsiodras, S., H. S. Gold, G. Sakoulas, G. M. Eliopoulos, C. Wennersten, L. Venkataraman, R. C. Moellering, and M. J. Ferraro. 2001. Linezolid resistance in a clinical isolate of Staphylococcus aureus. Lancet 358:207-208.
47. Tuomanen, E., and A. Tomasz. 1986. Induction of autolysis in nongrowing Escherichia coli. J. Bacteriol. 167:1077-1080.
48. Wilson, M., B. Oliva, R. Cassels, P. J. O'Hanlon, and I. Chopra. 1995. SB-205952, a novel semisynthetic monic acid analog with at least two modes of action. Antimicrob. Agents Chemother. 39:1925-1933.
49. Zhao, W. H., Z. Q. Hu, S. Okubo, Y. Hara, and T. Shimamura. 2001. Mechanism of synergy between epigallocatechin gallate and beta-lactams against methicillin-resistant Staphylococcus aureus. Antimicrob. Agents Chemother. 45:1737-1742.