Anti-biofilm activity and synergism of novel thiazole compounds with glycopeptide antibiotics against multidrug-resistant Staphylococci

Haroon Mohammad; Abdelrahman S Mayhoub; Mark Cushman; Mohamed N Seleem

doi:10.1038/ja.2014.142

journal article Oct 15, 2014

Anti-biofilm activity and synergism of novel thiazole compounds with glycopeptide antibiotics against multidrug-resistant Staphylococci

Haroon Mohammad Abdelrahman S Mayhoub Mark Cushman Mohamed N Seleem

The Journal of Antibiotics Vol. 68 No. 4 pp. 259-266 · Springer Science and Business Media LLC

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References

41

[1]

CDC. Antibiotic Resistance Threats in the United States, 2013, 1–114 (Centers for Disease Control and Prevention, Atlanta, GA, USA, 2013).

[2]

Moran, G. J. et al. Methicillin-resistant S. aureus infections among patients in the emergency department. New Engl. J. Med. 355, 666–674 (2006). 10.1056/nejmoa055356

[3]

Wang, R. et al. Staphylococcus epidermidis surfactant peptides promote biofilm maturation and dissemination of biofilm-associated infection in mice. J. Clin. Invest. 121, 238–248 (2011). 10.1172/jci42520

[4]

Understanding biofilm resistance to antibacterial agents

David Davies

Nature Reviews Drug Discovery 2003 10.1038/nrd1008

[5]

Mah, T. F. & O'Toole, G. A. Mechanisms of biofilm resistance to antimicrobial agents. Trends Microbiol. 9, 34–39 (2001). 10.1016/s0966-842x(00)01913-2

[6]

Chambers, H. F. Community-associated MRSA—resistance and virulence converge. New Engl. J. Med. 352, 1485–1487 (2005). 10.1056/nejme058023

[7]

Moran, G. J., Amii, R. N., Abrahamian, F. M. & Talan, D. A. Methicillin-resistant Staphylococcus aureus in community-acquired skin infections. Emerg. Infect. Dis. 11, 928–930 (2005). 10.3201/eid1106.040641

[8]

Hiramatsu, K. Vancomycin-resistant Staphylococcus aureus: a new model of antibiotic resistance. Lancet Infect. Dis. 1, 147–155 (2001). 10.1016/s1473-3099(01)00091-3

[9]

Hays, S. J. et al. Substituted 2-benzothiazolamine as sodium flux inhibitors—quantitative structure-activity-relationships and anticonvulsant activity. J. Pharm. Sci. 83, 1425–1432 (1994). 10.1002/jps.2600831013

[10]

Das, J. et al. Discovery of 2-amino-heteroaryl-benzothiazole-6-anilides as potent p56(lck) inhibitors. Bioorg. Med. Chem. Lett. 13, 2587–2590 (2003). 10.1016/s0960-894x(03)00511-0

[11]

Hutchinson, I., Bradshaw, T. D., Matthews, C. S., Stevens, M. F. & Westwell, A. D. Antitumour benzothiazoles. Part 20: 3'-cyano and 3'-alkynyl-substituted 2-(4'-aminophenyl)benzothiazoles as new potent and selective analogues. Bioorg. Med. Chem. Lett. 13, 471–474 (2003). 10.1016/s0960-894x(02)00930-7

[12]

Paget, C. J., Kisner, K., Stone, R. L. & DeLong, D. C. Heterocyclic substituted ureas. II. Immunosuppressive and antiviral activity of benzothiazole- and benzoxazoleureas. J. Med. Chem. 12, 1016–1018 (1969). 10.1021/jm00306a011

[13]

Darwish, E. S., Fattah, A. M. A., Attaby, F. A. & Al-Shayea, O. N. Synthesis and antimicrobial evaluation of some novel thiazole, pyridone, pyrazole, chromene, hydrazone derivatives bearing a biologically active sulfonamide moiety. Int. J. Mol. Sci. 15, 1237–1254 (2014). 10.3390/ijms15011237

[14]

Desai, N. C., Bhatt, N., Somani, H. & Trivedi, A. Synthesis, antimicrobial and cytotoxic activities of some novel thiazole clubbed 1,3,4-oxadiazoles. Eur. J. Med. Chem. 67, 54–59 (2013). 10.1016/j.ejmech.2013.06.029

[15]

Sadek, B., Al-Tabakha, M. M. & Fahelelbom, K. M. S. Antimicrobial prospect of newly synthesized 1,3-thiazole derivatives. Molecules 16, 9386–9396 (2011). 10.3390/molecules16119386

[16]

Mohammad, H. et al. Discovery and characterization of potent thiazoles versus methicillin- and vancomycin-resistant staphylococcus aureus. J. Med. Chem. 57, 1609–1615 (2014). 10.1021/jm401905m

[17]

Mayhoub, A. S. et al. An investigation of phenylthiazole antiflaviviral agents. Bioorg. Med. Chem. 19, 3845–3854 (2011). 10.1016/j.bmc.2011.04.041

[18]

Clinical and Laboratory Standards Institute. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically—Seventh Edition: Approved Standard M7-A7 (Wayne, PA, USA, 2011).

[19]

Messick, C. R., Rodvold, K. A. & Pendland, S. L. Modified time-kill assay against multidrug-resistant Enterococcus faecium with novel antimicrobial combinations. J. Antimicrob. Chemoth. 44, 831–834 (1999). 10.1093/jac/44.6.831

[20]

Baldoni, D., Haschke, M., Rajacic, Z., Zimmerli, W. & Trampuz, A. Linezolid alone or combined with rifampin against methicillin-resistant Staphylococcus aureus in experimental foreign-body infection. Antimicrob. Agents. Chemother. 53, 1142–1148 (2009). 10.1128/aac.00775-08

[21]

Nagai, K. et al. In vitro selection of resistance to clinafloxacin, ciprofloxacin, and trovafloxacin in Streptococcus pneumoniae. Antimicrob. Agents. Chemother. 44, 2740–2746 (2000). 10.1128/aac.44.10.2740-2746.2000

[22]

Orhan, G., Bayram, A., Zer, Y. & Balci, I. Synergy tests by E test and checkerboard methods of antimicrobial combinations against Brucella melitensis. J. Clin. Microbiol. 43, 140–143 (2005). 10.1128/jcm.43.1.140-143.2005

[23]

Furlani, R. E., Yeagley, A. A. & Melander, C. A flexible approach to 1,4-disubstituted 2-aminoimidazoles that inhibit and disperse biofilms and potentiate the effects of B-lactams against multi-drug resistant bacteria. Eur. J. Med. Chem. 2013; 62: 59–70. 10.1016/j.ejmech.2012.12.005

[24]

Microtiter Dish Biofilm Formation Assay

George A. O'Toole

Journal of Visualized Experiments 10.3791/2437

[25]

Mohamed, M. F., Hamed, M. I., Panitch, A. & Seleem, M. N. Targeting methicillin-resistant staphylococcus aureus with short salt-resistant synthetic peptides. Antimicrob. Agents Chemother. 58, 4113–4122 (2014). 10.1128/aac.02578-14

[26]

NCCLS. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically. NCCLS Approved Standard M7-A9 (NCCLS: Wayne, PA, USA, 2012).

[27]

Alder, J. & Eisenstein, B. The advantage of bactericidal drugs in the treatment of infection. Curr. Infect. Dis. Rep. 6, 251–253 (2004). 10.1007/s11908-004-0042-1

[28]

Pankey, G. A. & Sabath, L. D. Clinical relevance of bacteriostatic versus bactericidal mechanisms of action in the treatment of Gram-positive bacterial infections. Clin. Infect. Dis. 38, 864–870 (2004). 10.1086/381972

[29]

McDougal, L. K. et al. Pulsed-field gel electrophoresis typing of oxacillin-resistant Staphylococcus aureus isolates from the United States: establishing a national database. J. Clin. Microbiol. 41, 5113–5120 (2003). 10.1128/jcm.41.11.5113-5120.2003

[30]

Deresinski, S. Vancomycin in combination with other antibiotics for the treatment of serious methicillin-resistant Staphylococcus aureus infections. Clin. Infect. Dis. 49, 1072–1079 (2009). 10.1086/605572

[31]

Finberg, R. W. et al. The importance of bactericidal drugs: future directions in infectious disease. Clin. Infect. Dis. 39, 1314–1320 (2004). 10.1086/425009

[32]

Kosowska-Shick, K. et al. Activity of telavancin against staphylococci and enterococci determined by MIC and resistance selection studies. Antimicrob. Agents Chemother. 53, 4217–4224 (2009). 10.1128/aac.00742-09

[33]

Nguyen, H. M. & Graber, C. J. Limitations of antibiotic options for invasive infections caused by methicillin-resistant Staphylococcus aureus: is combination therapy the answer? J. Antimicrob. Chemoth. 65, 24–36 (2010). 10.1093/jac/dkp377

[34]

Dumitrescu, O. et al. Effect of antibiotics, alone and in combination, on Panton-Valentine leukocidin production by a Staphylococcus aureus reference strain. Clin. Microbiol. Infect. 14, 384–388 (2008). 10.1111/j.1469-0691.2007.01947.x

[35]

Stevens, D. L. et al. Impact of antibiotics on expression of virulence-associated exotoxin genes in methicillin-sensitive and methicillin-resistant Staphylococcus aureus. J. Infect. Dis. 195, 202–211 (2007). 10.1086/510396

[36]

Leonidou, L. & Gogos, C. A. Catheter-related bloodstream infections: catheter management according to pathogen. Int. J. Antimicrob. Agents 36, S26–S32 (2010). 10.1016/j.ijantimicag.2010.11.004

[37]

Vuong, C. & Otto, M. Staphylococcus epidermidis infections. Microbes Infect. 4, 481–489 (2002). 10.1016/s1286-4579(02)01563-0

[38]

More, P. G., Karale, N. N., Lawand, A. S., Narang, N. & Patil, R. H. Synthesis and anti-biofilm activity of thiazole Schiff bases. Med. Chem. Res. 23, 790–799 (2014). 10.1007/s00044-013-0672-7

[39]

Rane, R. A., Sahu, N. U. & Shah, C. P. Synthesis and antibiofilm activity of marine natural product-based 4-thiazolidinones derivatives. Bioorg. Med. Chem. Lett. 22, 7131–7134 (2012). 10.1016/j.bmcl.2012.09.073

[40]

Kwong, A. D., Kauffman, R. S., Hurter, P. & Mueller, P. Discovery and development of telaprevir: an NS3-4A protease inhibitor for treating genotype 1 chronic hepatitis C virus. Nat. Biotechnol. 29, 993–1003 (2011). 10.1038/nbt.2020

[41]

Allegrini, P. & Brunoldi, E. Process for the preparation of a viral protease inhibitor in amorphous form. Google Patents WO2013153055 A1 (2013).

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Published: Oct 15, 2014
Vol/Issue: 68(4)
Pages: 259-266
License: View

Authors

H

Haroon Mohammad

A

Abdelrahman S Mayhoub

Cite This Article

Haroon Mohammad, Abdelrahman S Mayhoub, Mark Cushman, et al. (2014). Anti-biofilm activity and synergism of novel thiazole compounds with glycopeptide antibiotics against multidrug-resistant Staphylococci. The Journal of Antibiotics, 68(4), 259-266. https://doi.org/10.1038/ja.2014.142

Anti-biofilm activity and synergism of novel thiazole compounds with glycopeptide antibiotics against multidrug-resistant Staphylococci

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