Molecular determinants of AcrB-mediated bacterial efflux implications for drug discovery

Journal of Medicinal Chemistry

Volumn 55, Issue 6, 2012, Pages 2532-2537

  Manchester, John I ^a   Buurman, Ed T ^a   Bisacchi, Gregory S ^a   McLaughlin, Robert E ^a  

^a ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AVIBACTAM; AZITHROMYCIN; BACTERIAL PROTEIN; CARBAPENEM; CEPHALOSPORIN; CEPHALOSPORIN DERIVATIVE; FUNCTIONAL GROUP; GSK 2251052; HYDROXAMIC ACID DERIVATIVE; LEVOFLOXACIN; LIPOPOLYSACCHARIDE; MEROPENEM; PROTEIN ACRB; SPECTINOMYCIN; TETRACYCLINE; UNCLASSIFIED DRUG;

ANTIBIOTIC RESISTANCE; ANTIMICROBIAL ACTIVITY; BACTERIAL MEMBRANE; BACTERIAL METABOLISM; BACTERIAL STRAIN; CELL MEMBRANE; CELL TRANSPORT; CYTOSOL; ESCHERICHIA COLI; GRAM NEGATIVE BACTERIUM; HAEMOPHILUS INFLUENZAE; HIGH THROUGHPUT SCREENING; HYDROPHOBICITY; INTRACELLULAR TRANSPORT; MEMBRANE PERMEABILITY; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR WEIGHT; MULTIDRUG RESISTANCE; NONHUMAN; PSEUDOMONAS AERUGINOSA; RETROSPECTIVE STUDY; REVIEW;

ANTI-BACTERIAL AGENTS; BACTERIAL PROTEINS; DRUG DISCOVERY; DRUG RESISTANCE, BACTERIAL; GENE KNOCKOUT TECHNIQUES; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIAL INFECTIONS; HAEMOPHILUS INFLUENZAE; HUMANS; MICROBIAL SENSITIVITY TESTS; MULTIDRUG RESISTANCE-ASSOCIATED PROTEINS;

EID: 84858742553     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm201275d     Document Type: Review

References (51)

1. Boucher, H. W.; Corey, G. R. Epidemiology of Methicillin-Resistant Staphylococcus aureus Clin. Infect. Dis. 2008, 46 (Suppl. 5) S344-S349 (Pubitemid 351717321)
2. National Nosocomial Infections Surveillance (NNIS) System Report, Data Summary from January 1992 through June 2004, Issued October 2004. Am. J. Infect. Control 2004, 32, 470-485.
3. Rosenthal, V. D.; Maki, D. G.; Mehta, A.; álvarez-Moreno, C.; Leblebicioglu, H.; Higuera, F.; Cuellar, L. E.; Madani, N.; Mitrev, Z.; Dueñas, L.; Navoa-Ng, J. A.; Garcell, H. G.; Raka, L.; Hidalgo, R. F.; Medeiros, E. A.; Kanj, S. S.; Abubakar, S.; Nercelles, P.; Pratesi, R. D. International Nosocomial Infection Control Consortium Report, Data Summary for 2002-2007, Issued January 2008 Am. J. Infect. Control 2008, 36, 627-637
4. Bad Bugs, No Drugs: As Antibiotic Discovery Stagnates, a Public Health Crisis Brews; Infectious Diseases Society of America: Arlington, VA, 2004.
5. Boucher, H. W.; Talbot, G. H.; Bradley, J. S.; Edwards, J. E.; Gilbert, D.; Rice, L. B.; Scheld, 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
6. Giske, C. G.; Monnet, D. L.; Cars, O.; Carmeli, Y. ReAct: Action on Antibiotic Resistance Clinical and Economic Impact of Common Multidrug-Resistant Gram-Negative Bacilli Antimicrob. Agents Chemother. 2008, 52, 813-821 (Pubitemid 351358357)
7. Falagas, M. E.; Bliziotis, I. A. Pandrug-Resistant Gram-Negative Bacteria: The Dawn of the Post-Antibiotic Era? Int. J. Antimicrob. Agents 2007, 29, 630-636 (Pubitemid 46710354)
8. Maltezou, H. C. Metallo-β-lactamases in Gram-Negative Bacteria: Introducing the Era of Pan-Resistance? Int. J. Antimicrob. Agents 2009, 33, 405.e1-405.e7
9. Siegel, R. E. Emerging Gram-Negative Antibiotic Resistance: Daunting Challenges, Declining Sensitivities, and Dire Consequences Respir. Care 2008, 53, 471-479
10. Poole, K. Pseudomonas aeruginosa: Resistance to the Max Front. Microbiol. 2011, 2, 1-13
11. Yamane, K.; Wachino, J.; Suzuki, S.; Kimura, K.; Shibata, N.; Kato, H.; Shibayama, K.; Konda, T.; Arakawa, Y. New Plasmid-Mediated Fluoroquinolone Efflux Pump, QepA, Found in an Escherichia coli Clinical Isolate Antimicrob. Agents Chemother. 2007, 51, 3354-3360 (Pubitemid 350067551)
12. Martínez-Martínez, L.; Pascual, A.; Jacoby, G. A. Quinolone Resistance from a Transferable Plasmid Lancet 1998, 351, 797-799 (Pubitemid 28112342)
13. +-Dependent DNA Ligase Inhibitors with Broad-Spectrum Activity and Antibacterial Efficacy in Vivo Antimicrob. Agents Chemother. 2011, 55, 1088-1096
14. Silver, L. L. Challenges of Antibacterial Discovery Clin. Microbiol. Rev. 2011, 24, 71-109
15. Gwynn, M. N.; Portnoy, A.; Rittenhouse, S. F.; Payne, D. J. Challenges of Antibacterial Discovery Revisited Ann. N.Y. Acad. Sci. 2010, 1213, 5-19
16. Yu, E. W.; McDermott, G.; Zgurskaya, H. I.; Nikaido, H.; Koshland, D. E., Jr. Structural Basis of Multiple Drug-Binding Capacity of the AcrB Multidrug Efflux Pump Science 2003, 300, 976-980 (Pubitemid 36548884)
17. Murakami, S.; Yamaguchi, A. Multidrug-Exporting Secondary Transporters Curr. Opin. Struct. Biol. 2003, 13, 443-452 (Pubitemid 37011449)
18. Okusu, H.; Ma, D.; Nikaido, H. AcrAB Efflux Pump Plays a Major Role in the Antibiotic Resistance Phenotype of Escherichia coli Multiple-Antibiotic- Resistance (MAR) Mutants J. Bacteriol. 1996, 178, 306-308 (Pubitemid 26006095)
19. Oethinger, M.; Kern, W. V.; Jellen-Ritter, A. S.; McMurry, L. M.; Levy, S. B. Ineffectiveness of Topoisomerase Mutations in Mediating Clinically Significant Fluoroquinolone Resistance in Escherichia coli in the Absence of the AcrAB Efflux Pump Antimicrob. Agents Chemother. 2000, 44, 10-13 (Pubitemid 30010664)
20. Kriengkauykiat, J.; Porter, E.; Lomovskaya, O.; Wong-Beringer, A. Use of an Efflux Pump Inhibitor To Determine the Prevalence of Efflux Pump-Mediated Fluoroquinolone Resistance and Multidrug Resistance in Pseudomonas aeruginosa Antimicrob. Agents Chemother. 2005, 49, 565-570 (Pubitemid 40175663)
21. Livermore, D. M. Multiple Mechanisms of Antimicrobial Resistance in Pseudomonas aeruginosa: Our Worst Nightmare? Clin. Infect. Dis. 2002, 34, 634-640 (Pubitemid 34165326)
22. Padilla, E.; Llobet, E.; Domenech-Sanchez, A.; Martinez-Martinez, L.; Bengoechea, J. A.; Alberti, S. Klebsiella pneumoniae AcrAB Efflux Pump Contributes to Antimicrobial Resistance and Virulence Antimicrob. Agents Chemother. 2010, 54, 177-183
23. Lien, E. J.; Hansch, C.; Anderson, S. M. Structure-Activity Correlations for Antibacterial Agents on Gram-Positive and Gram-Negative cells J. Med. Chem. 1968, 11, 430-441
24. Yalçin, I.; Şener, E. QSARs of Some Novel Antibacterial Benzimidazoles, Benzoxazoles, and Oxazolopyridines against an Enteric Gram-Negative Rod K. pneumoniae Int. J. Pharm. 1993, 98, 1-8 (Pubitemid 23242384)
25. Aptula, A.; Kühne, R.; Ebert, R.; Cronin, M.; Netzeva, T.; Schüürmann, G. Modeling Discrimination between Antibacterial and Non-Antibacterial Activity Based on 3D Molecular Descriptors QSAR Comb. Sci. 2003, 22, 113-128 (Pubitemid 36717476)
26. Ferreira, M. M. C.; Kiralj, R. QSAR Study of β-Lactam Antibiotic Efflux by the Bacterial Multidrug Resistance Pump AcrB J. Chemom. 2004, 18, 242-252
27. Nieto, M. J.; Alovero, F. L.; Manzo, R. H.; Mazzieri, M. R. Benzenesulfonamide Analogs of fluoroquinolones. Antibacterial Activity and QSAR Studies Eur. J. Med. Chem. 2005, 40, 361-369 (Pubitemid 40460298)
28. O'Shea, R.; Moser, H. E. Physicochemical Properties of Antibacterial Compounds: Implications for Drug Discovery J. Med. Chem. 2008, 51, 2871-2878 (Pubitemid 351706014)
29. Pasha, F. A.; Muddassar, M.; Lee, C.; Cho, S. J. Mechanism Based QSAR Studies of N -Phenylbenzamides as Antimicrobial Agents Environ. Toxicol. Pharmacol. 2008, 26, 128-135
30. Kiralj, R.; Ferreira, M. M. C. A Priori Descriptors in QSAR: A Case of Gram-Negative Bacterial Multidrug Resistance to β-Lactams Croat. Chem. Acta 2008, 81, 579-592
31. Dahlgren, M. K.; Zetterstrom, C. E.; Gylfe, S.; Linusson, A.; Elofsson, M. Statistical Molecular Design of a Focused Salicylidene Acylhydrazide Library and Multivariate QSAR of Inhibition of Type III Secretion in the Gram-Negative Bacterium Yersinia Bioorg. Med. Chem 2010, 18, 2686-2703
32. Nikaido, H. Molecular Basis of Bacterial Outer Membrane Permeability Revisited Microbiol. Mol. Biol. Rev. 2003, 67, 593-656 (Pubitemid 37549772)
33. Methods for Dillution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically; Approved Standard, 9 th ed.; M07-A8; Clinical and Laboratory Standards Institute: Wayne, PA, 2009; Vol. 29, No. 2.
34. Nikaido, H. Porins and Specific Channels of Bacterial Outer Membranes Mol. Microbiol. 1992, 6, 435-442
35. Vachon, V.; Lyew, D. J.; Coulton, J. W. Transmembrane Permeability Channels across the Outer Membrane of Haemophilus influenzae Type b J. Bacteriol. 1985, 162, 918-924 (Pubitemid 15008133)
36. Yoneyama, H.; Nakae, T. A Small Diffusion Pore in the Outer Membrane of Pseudomonas aeruginosa Eur. J. Biochem. 1986, 157, 33-38
37. Ertl, P.; Rohde, B.; Selzer, P. Fast Calculation of Molecular Polar Surface Area as a Sum of Fragment-Based Contributions and Its Application to the Prediction of Drug Transport Properties J. Med. Chem. 2000, 43, 3714-3717
38. Lu, H.; Tonge, P. J. Drug-Target Residence Time: Critical Information for Lead Optimization Curr. Opin. Chem. Biol. 2010, 14, 467-474
39. Hancock, R. E.; Farmer, S. W.; Li, Z. S.; Poole, K. Interaction of Aminoglycosides with the Outer Membranes and Purified Lipopolysaccharide and OmpF Porin of Escherichia coli Antimicrob. Agents Chemother. 1991, 35, 1309-1314
40. Takacs-Novak, K.; Noszal, B.; Hermecz, I.; Kereszturi, G.; Podanyi, B.; Szasz, G. Protonation Equilibria of Quinolone Antibacterials J. Pharm. Sci. 1990, 79, 1023-1028 (Pubitemid 20376198)
41. Booth, I. R. Regulation of Cytoplasmic pH in Bacteria Microbiol. Rev. 1985, 49, 359-378 (Pubitemid 16209979)
42. Nikaido, H.; Thanassi, D. G. Penetration of Lipophilic Agents with Multiple Protonation Sites into Bacterial Cells: Tetracyclines and Fluoroquinolones as Examples Antimicrob. Agents Chemother. 1993, 37, 1393-1399 (Pubitemid 23202359)
43. Zarfl, C.; Matthies, M.; Klasmeier, J. A Mechanistical Model for the Uptake of Sulfonamides by Bacteria Chemosphere 2008, 70, 753-760 (Pubitemid 350141687)
44. Loubeyre, C.; Desnottes, J. F.; Moreau, N. Influence of Sub-Inhibitory Concentrations of Antibacterials on the Surface Properties and Adhesion of Escherichia coli J. Antimicrob. Chemother. 1993, 31, 37-45 (Pubitemid 23078065)
45. Lindner, B.; Wiese, A.; Brandenburg, K.; Seydel, U.; Dalhoff, A. Lack of Interaction of Fluoroquinolones with Lipopolysaccharides Antimicrob. Agents Chemother. 2002, 46, 1568-1570 (Pubitemid 34415347)
46. Marshall, A. J. H.; Piddock, L. J. V. Interaction of Divalent Cations, Quinolones and Bacteria J. Antimicrob. Chemother. 1994, 34, 465-483 (Pubitemid 24344521)
47. Nikaido, H. Multidrug Efflux Pumps of Gram-Negative Bacteria J. Bacteriol. 1996, 178, 5853-5859 (Pubitemid 26337766)
48. Piddock, L. J. V. Clinically Relevant Chromosomally Encoded Multidrug Resistance Efflux Pumps in Bacteria Clin. Microbiol. Rev. 2006, 19, 382-402
49. Lomize, M. A.; Lomize, A. L.; Pogozheva, I. D.; Mosberg, H. I. OPM: Orientations of Proteins in Membranes Database Bioinformatics 2006, 22, 623-625 (Pubitemid 43372827)
50. Hernandez, V.; Akama, T.; Alley, M. R. K.; Baker, S.; Mao, W.; Rock, F.; Zhang, Y. K.; Zhang, Y.; Zhou, Y.; Crepin, T.; Cusack, S.; Palencia, A.; Nieman, J.; Anugula, M.; Baek, M.; Diaper, C.; Ha, C.; Keramane, M.; Lu, X.; Mohammad, R.; Savariraj, K.; Sharma, R.; Singh, R.; Subed, R.; Plattner, J. Discovery and Mechanism of Action of AN3365: A Novel Boron-Containing Antibacterial Agent in Clinical Development of Gram-Negative Infections. Presented at the 50th Interscience Conference on Antimicrobial Agents and Chemotherapy, Sep 12-15, 2010, Boston, MA; Abstract F1-1637.
51. Stachyra, T.; Pechereau, M.-C.; Bruneau, J.-M.; Miossec, C.; Frere, J. M.; Black, M. T. The Nature of Inhibition of TEM-1 beta-Lactamase by the Non-beta-Lactam Inhibitor NXL104. Presented at the 49th Interscience Conference on Antimicrobial Agents and Chemotherapy, Sep 12-15, 2009, San Francisco, CA; Abstract C1-1374.