Dimers of nostocarboline with potent antibacterial activity

Chemotherapy

Volumn 56, Issue 4, 2010, Pages 318-324

  Locher, Hans H ^a   Ritz, Daniel ^a   Pfaff, Philippe ^a   Gaertner, Mika ^a   Knezevic, Andreja ^a   Sabato, Daniela ^a   Schroeder, Susanne ^a   Barbaras, Damien ^b   Gademann, Karl ^c  

^a ACTELION PHARMACEUTICALS LTD   (Switzerland)

^b ETH ZURICH   (Switzerland)

^c UNIVERSITY OF BASEL   (Switzerland)

Author keywords

Cationic antibacterials; Chlorhexidine; Mode of action

Indexed keywords

ADENOSINE TRIPHOSPHATE; ANTIINFECTIVE AGENT; CARBOLINE DERIVATIVE; CHLORHEXIDINE; CIPROFLOXACIN; DIMER; NOSTOCARBOLINE DIMER 1; NOSTOCARBOLINE DIMER 10; NOSTOCARBOLINE DIMER 2; NOSTOCARBOLINE DIMER 3; NOSTOCARBOLINE DIMER 4; NOSTOCARBOLINE DIMER 5; NOSTOCARBOLINE DIMER 6; NOSTOCARBOLINE DIMER 7; NOSTOCARBOLINE DIMER 8; NOSTOCARBOLINE DIMER 9; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BACTERIAL GENE; BACTERIAL MEMBRANE; BACTERIAL STRAIN; BACTERICIDAL ACTIVITY; BACTERIUM ISOLATE; BROTH DILUTION; CHO CELL; CONCENTRATION RESPONSE; CONTROLLED STUDY; DIMERIZATION; DNA METABOLISM; DRUG CYTOTOXICITY; DRUG EFFECT; DRUG MECHANISM; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; ESCHERICHIA COLI; FUNGAL STRAIN; GRAM POSITIVE BACTERIUM; HYDROPHOBICITY; IN VITRO STUDY; MEMBRANE DAMAGE; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR INTERACTION; NONHUMAN; PRIORITY JOURNAL; REPORTER GENE; YEAST;

ALKALOIDS; ANIMALS; ANTI-BACTERIAL AGENTS; ANTI-INFECTIVE AGENTS, LOCAL; CARBOLINES; CHLORHEXIDINE; CHO CELLS; CIPROFLOXACIN; CRICETINAE; CRICETULUS; DIMERIZATION; ESCHERICHIA COLI; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS; MICROBIAL SENSITIVITY TESTS;

EID: 77955530884     PISSN: 00093157     EISSN: None     Source Type: Journal    
DOI: 10.1159/000320033     Document Type: Article

References (28)

1. Boucher HW, Talbot GH, Bradley JS, Edwards JE, Gilbert D, Rice LB, Scheid M, Spellberg B, Bartlett J: Bad bugs, no drugs: no ESKAPE! An update from the Infectious Diseases Society of America. Clin Infect Dis 2009; 48: 1-12.
2. Spellberg B, Guidos R, Gilbert D, Bradley J, Boucher HW, Scheld WM, Bartlett JG, Edwards J Jr, Infectious Diseases Society of America: The epidemic of antibiotic-resistant infections: a call to action for the medical community from the Infectious Diseases Society of America. Clin Infect Dis 2008; 46: 155-164.
3. Al-Tawfik JA, Anani AA: Antimicrobial susceptibility pattern of bacterial pathogens causing urinary tract infections in a Saudi Arabian hospital. Chemotherapy 2009; 55: 127-131.
4. Lange RP, Locher HH, Wyss PC, Then RL: The targets of currently used antibacterial agents: lessons for drug discovery. Curr Pharm Des 2007; 13: 3140-3154.
5. Newman DJ, Cragg GM: Natural products as sources of new drugs over the last 25 years. J Nat Prod 2007; 70: 461-477.
6. Gademann K, Portmann C: Secondary metabolites from cyanobacteria: complex structures and powerful bioactivities. Curr Org Chem 2008; 12: 326-341.
7. Blom JF, Brütsch T, Barbaras D, Bethuel Y, Locher HH, Hubschwerlen C, Gademann K: Potent algicides based on the cyanobacterial alkaloid nostocarboline. Org Lett 2006; 8: 737-740.
8. Portmann C, Blom JF, Gademann K, Jüttner F: Aerucyclamides A and B: isolation and synthesis of toxic ribosomal heterocyclic peptides from the cyanobacterium Microcystis aeruginosa PCC 7806. J Nat Prod 2008; 71: 1193-1196.
9. Becher PG, Beuchat J, Gademann K, Jüttner F: Nostocarboline: isolation and synthesis of a new cholinesterase inhibitor from Nostoc 78-12A. J Nat Prod 2005; 68: 1793-1795.
10. Barbaras D, Kaiser M, Brun R, Gademann K: Potent and selective antiplasmodial activity of the cyanobacterial alkaloid nostocarboline and its dimers. Bioorg Med Chem Lett 2008; 18: 4413-4415.
11. Bonazzi S, Barabaras D, Patiny L, Scopelliti R, Schneider P, Cole ST, Kaiser M, Brun R, Gademann K: Antimalarial and antitubercular nostocarboline and eudistomin derivatives: synthesis, in vitro and in vivo biological evaluation. Bioorg Med Chem 2010; 18: 1464-1476.
12. Winson MK, Swift S, Hill PJ, Sims CM, Griesmayr G, Bycroft BW, Williams P, Stewart GS: Engineering the luxCDABE genes from Photorhabdus luminescens to provide a bioluminescent reporter for constitutive and promoter probe plasmids and mini-Tn 5 constructs. FEMS Microbiol Lett 1998; 163: 193-202.
13. Datsenko KA, Wanner BL: One-step inactivation of chromosomal genes in Escherichia coli K-12 using PCR products. Proc Natl Acad Sci USA 2000; 97: 6640-6645.
14. Gérard F, Pradel N, Wu LF: Bactericidal activity of colicin V is mediated by an inner membrane protein, SdaC, of Escherichia coli. J. Bacteriol 2005; 187: 1945-1950.
15. Miller JH: A Short Course in Bacterial Genetics: A Laboratory Manual and Handbook for Escherichia coli and Related Bacteria. Cold Spring Harbor, Cold Spring Harbor Laboratory, 1992.
16. Clinical and Laboratory Standards Institute: Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically, ed.7.: Approved Standard M7-A7. Wayne, CLSI, 2006.
17. Higgins DL, Chang R, Debabov DV, Leung J, Wu T, Krause KM, Sandvik E, Hubbard JM, Kaniga K, Schmidt DE Jr, Gao Q, Cass RT, Karr DE, Benton BM, Humphrey PP: Telavancin, a multifunctional lipoglycopeptide, disrupts both cell wall synthesis and cell membrane integrity in methicillin-resistant Staphylococcus aureus. Antimicrob Agents Chemother 2005; 49: 1127-1134.
18. McDonnell G, Russell AD: Antiseptics and disinfectants: activity, action, and resistance. Clin Microbiol Rev 1999; 12: 147-179.
19. Gilbert P, Moore LE: Cationic antiseptics: diversity of action under a common epithet. J Appl Microbiol 2005; 99: 703-715.
20. Quillardet P, de Bellecombe C, Hofnung M: The SOS chromotest, a calorimetric assay for genotoxins: validation study with 83 compounds. Mut Res 1985; 147: 79-95.
21. Raivio T: Envelope stress response and Gram-negative pathogenesis. Mol Microbiol 2005; 56: 1119-1128.
22. Andersen CL, Holland IB, Jacq A: Verapamil, a Ca2+ channel inhibitor acts as a local anesthetic and induces the sigma E dependent extra-cytoplasmic stress response in E. coli. Biochim Biophys Acta 2006; 1758: 1587-1595.
23. Zapantis A, Lopez M, Hoffman E, et al: The use of colistin in multidrug-resistant infections. Hosp Pharm 2007; 42: 1127-1138.
24. Friedrich CL, Moyles D, Beveridge T, Hancock REW: Antibacterial action of structurally diverse cationic peptides on Gram-positive bacteria. Antimicrob Agents Chemother 2000; 44: 2086-2092.
25. Jenssen H, Hamill P, Hancock RE: Peptide antimicrobial agents. Clin Microbiol Rev 2006; 19: 491-511.
26. Wu MH, Maier E, Benz R; Hancock RE: Mechanism of interaction of different classes of cationic antimicrobial peptides with planar bilayers and with the cytoplasmic membrane of Escherichia coli. Biochemistry 1999; 38: 7235-7242.
27. van't Hof W, Veerman ECI, Helmerhorst EJ, Amerongen AV: Antimicrobial peptides: properties and applicability. Biol Chem 2001; 382: 597-619.
28. Ryge TS, Frimodt-Moller N, Hansen PR: Antimicrobial activities of twenty lysinepeptoid hybrids against clincaly relevant bacteria and fungi. Chemotherapy 2008; 54: 152-156.