Dual-acting hybrid antibiotics: a promising strategy to combat bacterial resistance

Bibliography

• Davies J. In the beginning there was streptomycin. In: Arya DP, editor, Aminoglycoside antibiotics. John Wiley & Sons, Inc., Hoboken, New Jersey; 2007. p. 1-15
   Google Scholar
• Gale EF. Correlation between penicillin resistance and assimilation affinity in Staphylococcus aureus. Nature 1947;160(4064):407
   PubMed Web of Science ®Google Scholar
• Palumbi SR. Evolution – humans as the world's greatest evolutionary force. Science 2001;293(5536):1786-90
   PubMed Web of Science ®Google Scholar
• Umezawa H, Okanishi M, Kondo S, Phosphorylative inactivation of aminoglycosidic antibiotics by Escherichia coli carrying R factor. Science 1967;157(796):1559-61
   PubMed Web of Science ®Google Scholar
• Martin CM, Ikari NS, Zimmerman J, A virulent nosocomial Klebsiella with a transferable R factor for gentamicin: emergence and suppression. J Infect Dis 1971;124(Suppl):S24-9
   PubMed Web of Science ®Google Scholar
• Benveniste R, Davies J. R-factor mediated gentamicin resistance: a new enzyme which modifies aminoglycoside antibiotics. FEBS Lett 1971;14(5):293-96
   PubMed Web of Science ®Google Scholar
• Auckland C, Teare L, Cooke F, Linezolid-resistant enterococci: report of the first isolates in the United Kingdom. J Antimicrob Chemother 2002;50(5):743-6
   PubMed Web of Science ®Google Scholar
• Miller JR, Waldrop GL. Discovery of novel antibacterials. Expert Opin Drug Discov 2010;5(2):145-54
   PubMed Web of Science ®Google Scholar
• Giamarellou H, Poulakou G. Multidrug-resistant gram-negative infections: what are the treatment options? Drugs 2009;69(14):1879-901
   PubMed Web of Science ®Google Scholar
• Arias CA, Murray BE. Antibiotic-resistant bugs in the 21st century – a clinical super-challenge. N Engl J Med 2009;360(5):439-43
   PubMed Web of Science ®Google Scholar
• Gillespie SH. Evolution of drug resistance in Mycobacterium tuberculosis: clinical and molecular perspective. Antimicrob Agents Chemother 2002;46(2):267-74
   PubMed Web of Science ®Google Scholar
• Cottarel G, Wierzbowski J. Combination drugs, an emerging option for antibacterial therapy. Trends Biotechnol 2007;25(12):547-55
   PubMed Web of Science ®Google Scholar
• Bremner JB, Ambrus JI, Samosorn S. Dual action-based approaches to antibacterial agents. Curr Med Chem 2007;14(13):1459-77
   PubMed Web of Science ®Google Scholar
• Mitchison DA. Treatment of tuberculosis. The Mitchell lecture 1979. J R Coll Physicians Lond 1980;14(2):91-5, 98-9
   PubMedGoogle Scholar
• Yeh PJ, Hegreness MJ, Aiden AP, Drug interactions and the evolution of antibiotic resistance. Nat Rev Microbiol 2009;7(6):460-6
   PubMed Web of Science ®Google Scholar
• Chait R, Craney A, Kishony R. Antibiotic interactions that select against resistance. Nature 2007;446(7136):668-71
   PubMed Web of Science ®Google Scholar
• Loewe S. The problem of synergism and antagonism of combined drugs. Arzneimittelforschung 1953;3(6):285-90
   PubMed Web of Science ®Google Scholar
• Pillai SK, Moellering RC, Eliopoulos GM. In: Lorian V, editor, Antibiotics in laboratory medicine. Lippincott Williams & Wilkins, Philadelphia; 2005. p. 365-440
   Google Scholar
• Michel JB, Yeh PJ, Chait R, Drug interactions modulate the potential for evolution of resistance. Proc Natl Acad Sci USA 2008;105(39):14918-23
   PubMed Web of Science ®Google Scholar
• Hegreness M, Shoresh N, Damian D, Accelerated evolution of resistance in multidrug environments. Proc Natl Acad Sci USA 2008;105(37):13977-81
   PubMed Web of Science ®Google Scholar
• Bliziotis IA, Samonis G, Vardakas KZ, Effect of aminoglycoside and beta-lactam combination therapy versus beta-lactam monotherapy on the emergence of antimicrobial resistance: a meta-analysis of randomized, controlled trials. Clin Infect Dis 2005;41(2):149-58
   PubMed Web of Science ®Google Scholar
• Long DD, Marquess DG. Novel heterodimer antibiotics: a review of recent patent literature. Future Med Chem 2009;1(6):1037-50
   PubMed Web of Science ®Google Scholar
• Brotz-Oesterhelt H, Brunner NA. How many modes of action should an antibiotic have? Curr Opin Pharmacol 2008;8(5):564-73
   PubMed Web of Science ®Google Scholar
• Barbachyn MR. Recent advances in the discovery of hybrid antibacterial agents. Annu Rep Med Chem 2008;43:281-90
   Web of Science ®Google Scholar
• Radzishevsky IS, Rotem S, Bourdetsky D, Improved antimicrobial peptides based on acyl-lysine oligomers. Nat Biotechnol 2007;25(6):657-9
   PubMed Web of Science ®Google Scholar
• Komp LP, Karlsson A, Hughes D. Mutation rate and evolution of fluoroquinolone resistance in Escherichia coli isolates from patients with urinary tract infections. Antimicrob Agents Chemother 2003;47(10):3222-32
   PubMed Web of Science ®Google Scholar
• Hubschwerlen C, Specklin JL, Baeschlin D, Oxazolidinone-quinolone hybrid antibiotics. US2008027040; 2008
   Google Scholar
• Hubschwerlen C, Specklin JL, Baeschlin DK, Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections. WO2004096221; 2004
   Google Scholar
• Hubschwerlen C, Specklin JL, Baeschlin DK, Structure-activity relationship in the oxazolidinone-quinolone hybrid series: influence of the central spacer on the antibacterial activity and the mode of action. Bioorg Med Chem Lett 2003;13(23):4229-33
   PubMed Web of Science ®Google Scholar
• Hubschwerlen C, Specklin JL, Sigwalt C, Design, synthesis and biological evaluation of oxazolidinone-quinolone hybrids. Bioorg Med Chem 2003;11(10):2313-19
   PubMed Web of Science ®Google Scholar
• Hubschwerlen C, Specklin JL, Baeschlin D, Oxazolidinone-quinolone hybrid antibiotics. WO2005058888; 2005
   Google Scholar
• Bozdogan B, Appelbaum PC. Oxazolidinones: activity, mode of action, and mechanism of resistance. Int J Antimicrob Agents 2004;23(2):113-19
   PubMed Web of Science ®Google Scholar
• Butler MM, Lamarr WA, Foster KA, Antibacterial activity and mechanism of action of a novel anilinouracil-fluoroquinolone hybrid compound. Antimicrob Agents Chemother 2007;51(1):119-27
   PubMed Web of Science ®Google Scholar
• Zhi C, Long ZY, Manikowski A, Hybrid antibacterials. DNA polymerase-topoisomerase inhibitors. J Med Chem 2006;49(4):1455-65
   PubMed Web of Science ®Google Scholar
• Zhi C, Wright GE. Novel heterocyclic antibacterial compounds. WO02102792; 2002
   Google Scholar
• Zhi C, Long ZY, Gambino J, Synthesis of substituted 6-anilinouracils and their inhibition of DNA polymerase IIIC and Gram-positive bacterial growth. J Med Chem 2003;46(13):2731-9
   PubMed Web of Science ®Google Scholar
• Yanachkova MI, Wright GE. Polar ester prodrugs of heterocyclic hybrid antibacterial compounds and salts thereof. WO2008094203; 2008
   Google Scholar
• Robertson GT, Bonventre EJ, Doyle TB, In vitro evaluation of CBR-2092, a novel rifamycin-quinolone hybrid antibiotic: studies of the mode of action in Staphylococcus aureus. Antimicrob Agents Chemother 2008;52(7):2313-23
   PubMed Web of Science ®Google Scholar
• Robertson GT, Bonventre EJ, Doyle TB, In vitro evaluation of CBR-2092, a novel rifamycin-quinolone hybrid antibiotic: microbiology profiling studies with staphylococci and streptococci. Antimicrob Agents Chemother 2008;52(7):2324-34
   PubMed Web of Science ®Google Scholar
• Floss HG, Yu TW. Rifamycin-mode of action, resistance, and biosynthesis. Chem Rev 2005;105(2):621-32
   PubMed Web of Science ®Google Scholar
• Chaisson RE. Treatment of chronic infections with rifamycins: is resistance likely to follow? Antimicrob Agents Chemother 2003;47(10):3037-9
   PubMed Web of Science ®Google Scholar
• Konig DP, Schierholz JM, Munnich U, Treatment of staphylococcal implant infection with rifampicin-ciprofloxacin in stable implants. Arch Orthop Trauma Surg 2001;121(5):297-9
   PubMed Web of Science ®Google Scholar
• Ding CZ, Jin Y, Combrink K, Kim IH. Quinolone carboxylic acid-substituted rifamycin derivatives. WO2009064792; 2009
   Google Scholar
• Sriram D, Yogeeswari P, Senchani G, Newer tetracycline derivatives: synthesis, anti-HIV, antimycobacterial activities and inhibition of HIV-1 integrase. Bioorg Med Chem Lett 2007;17(8):2372-5
   PubMed Web of Science ®Google Scholar
• Neamati N, Hong H, Sunder S, Potent inhibitors of human immunodeficiency virus type 1 integrase: identification of a novel four-point pharmacophore and tetracyclines as novel inhibitors. Mol Pharmacol 1997;52(6):1041-55
   PubMed Web of Science ®Google Scholar
• Labischinski H, Cherian J, Calanasan C, Boyce RS. Hybrid antimicrobial compounds and their use. WO2010025906; 2010
   Google Scholar
• Huovinen P, Wolfson JS, Hooper DC. Synergism of trimethoprim and ciprofloxacin in vitro against clinical bacterial isolates. Eur J Clin Microbiol Infect Dis 1992;11(3):255-7
   PubMed Web of Science ®Google Scholar
• Wright GD, Berghuis AM, Mobashery S. Aminoglycoside antibiotics. Structures, functions, and resistance. Adv Exp Med Biol 1998;456:27-69
   PubMed Web of Science ®Google Scholar
• Mingeot-Leclercq MP, Glupczynski Y, Tulkens PM. Aminoglycosides: activity and resistance. Antimicrob Agents Chemother 1999;43(4):727-37
   PubMed Web of Science ®Google Scholar
• Wright GD. Mechanisms of aminoglycoside antibiotic resistance. In: Lewis K, Salyers AA, Taber HW, Wax RG, editors, Bacterial resistance to antimicrobials. 2nd edition. CRC press, Taylor & Francis group; 2008. p. 71-101
   Google Scholar
• Grapsas I, Lerner SA, Mobashery S. Conjoint molecules of cephalosporins and aminoglycosides. Arch Pharm (Weinheim) 2001;334(8-9):295-301
   PubMed Web of Science ®Google Scholar
• Giamarellou H. Aminoglycosides plus beta-lactams against gram-negative organisms. Evaluation of in vitro synergy and chemical interactions. Am J Med 1986;80(6B):126-37
   PubMed Web of Science ®Google Scholar
• Clark RB, Pakiz CB, Hostetter MK. Synergistic activity of aminoglycoside-beta-lactam combinations against Pseudomonas aeruginosa with an unusual aminoglycoside antibiogram. Med Microbiol Immunol 1990;179(2):77-86
   PubMed Web of Science ®Google Scholar
• Lee J, Kwon M, Lee KH, An approach to enhance specificity against RNA targets using heteroconjugates of aminoglycosides and chloramphenicol (or linezolid). J Am Chem Soc 2004;126(7):1956-7
   PubMed Web of Science ®Google Scholar
• Kwon M, Kim HJ, Lee J, Enhanced binding affinity of neomycin-chloramphenicol (or linezolid) conjugates to A-site model of 16S ribosomal RNA. Bull Kor Chem Soc 2006;27(10):1664-66
   Web of Science ®Google Scholar
• Yu J, Lee J, Kwon M, Shin K. Heterodimeric conjugates of neomycin-chloramphenicol having an enhanced specificity against RNA targets and its preparation. US2005009765; 2005
   Google Scholar
• Yu J, Lee J, Kwon M, Heterodimeric conjugates of neomycin-oxazolidinone, their preparation and their use. US2005222055; 2005
   Google Scholar
• Pokrovskaya V, Belakhov V, Hainrichson M, Design, synthesis, and evaluation of novel fluoroquinolone-aminoglycoside hybrid antibiotics. J Med Chem 2009;52(8):2243-54
   PubMed Web of Science ®Google Scholar
• Bera S, Zhanel GG, Schweizer F. Evaluation of amphiphilic aminoglycoside-peptide triazole conjugates as antibacterial agents. Bioorg Med Chem Lett 2010;20(10):3031-5
   PubMed Web of Science ®Google Scholar
• Selvakumar N, Kumar GS, Azhagan AM, Synthesis, SAR and antibacterial studies on novel chalcone oxazolidinone hybrids. Eur J Med Chem 2007;42(4):538-43
   PubMed Web of Science ®Google Scholar
• Arnusch CJ, Bonvin AMJJ, Verel AM, The vancomycin-nisin(1-12) hybrid restores activity against vancomycin resistant Enterococci. Biochemistry 2008;47(48):12661-63
   PubMed Web of Science ®Google Scholar
• Long DD, Aggen JB, Chinn J, Exploring the positional attachment of glycopeptide/beta-lactam heterodimers. J Antibiot 2008;61(10):603-14
   PubMed Web of Science ®Google Scholar
• Long DD, Aggen JB, Christensen BG, A multivalent approach to drug Discovery for novel antibiotics. J Antibiot 2008;61(10):595-602
   PubMed Web of Science ®Google Scholar
• Christensen B, Moran EJ, Griffin JH, Novel antibacterial agents. US20070134729; 2007
   Google Scholar
• Christensen B, Moran EJ, Griffin JH, Novel antibacterial agents. US2009111737; 2009
   Google Scholar
• Ding CZ, Kim IH. Nitroheteroaryl-containing rifamycin derivatives. WO2008008480; 2008
   Google Scholar
• Edwards DI. Nitroimidazole drugs – action and resistance mechanisms. II. Mechanisms of resistance. J Antimicrob Chemother 1993;31(2):201-10
   PubMed Web of Science ®Google Scholar
• Sanchez M, Meunier B. Hybrid molecules QA where Q is an aminoquinoline and A is an antibiotic residue, the synthesis and uses thereof as antibacterial agents. US2007060558; 2007
   Google Scholar
• Acharya BN, Thavaselvam D, Kaushik MP. Synthesis and antimalarial evaluation of novel pyridine quinoline hybrids. Med Chem Res 2008;17(8):487-94
   Web of Science ®Google Scholar
• Mallea M, Mahamoud A, Chevalier J, Alkylaminoquinolines inhibit the bacterial antibiotic efflux pump in multidrug-resistant clinical isolates. Biochem J 2003;376(Pt 3):801-5
   PubMed Web of Science ®Google Scholar
• Chevalier J, Bredin J, Mahamoud A, Inhibitors of antibiotic efflux in resistant Enterobacter aerogenes and Klebsiella pneumoniae strains. Antimicrob Agents Chemother 2004;48(3):1043-46
   PubMed Web of Science ®Google Scholar
• Morphy R, Rankovic Z. Designed multiple ligands. An emerging drug discovery paradigm. J Med Chem 2005;48(21):6523-43
   PubMed Web of Science ®Google Scholar
• Gediya LK, Njar VCO. Promise and challenges in drug discovery and development of hybrid anticancer drugs. Expert Opin Drug Discov 2009;4(11):1099-111
   PubMed Web of Science ®Google Scholar