Triazole-Linked Glycolipids Enhance the Susceptibility of MRSA to β-Lactam Antibiotics

ACS Medicinal Chemistry Letters

Volumn 6, Issue 7, 2015, Pages 793-797

  Hu, Xi Le ^a   Li, Dan ^b   Shao, Lei ^b   Dong, Xiaojing ^b   He, Xiao Peng ^a   Chen, Guo Rong ^a   Chen, Daijie ^b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b CHINA STATE INSTITUTE OF PHARMACEUTICAL INDUSTRY   (China)

Author keywords

click reaction; MRSA; superbacteria; Triazolyl glycolipid; lactams

Indexed keywords

BETA LACTAM ANTIBIOTIC; GLYCOLIPID; OXACILLIN; TRIAZOLE DERIVATIVE;

ANTIBIOTIC SENSITIVITY; ARTICLE; CLICK CHEMISTRY; CONTROLLED STUDY; DRUG MECHANISM; DRUG SYNTHESIS; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL;

BACTERIA (MICROORGANISMS); METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS;

EID: 84938093493     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/acsmedchemlett.5b00142     Document Type: Article

References (34)

1. Taubes, G. The bacteria fight back Science 2008, 321, 356-361
2. Addicks, J. P.; Uibel, S.; Jensen, A.-M.; Bundschuh, M.; Klingelhoefer, D.; Groneberg, D. A. MRSA: a density-equalizing mapping analysis of the global research architecture Int. J. Environ. Res. Public Health 2014, 11, 10215-10225
3. Chambers, H. F.; DeLeo, F. R. Waves of resistance: staphylococcus aureus in the antibiotic era Nat. Rev. Microbiol. 2009, 7, 629-641
4. Morens, D. M.; Fauci, A. S. Emerging infectious diseases: threats to human health and global stability PLoS Pathog. 2013, 9, e1003467
5. Williams, A. J.; Harland, L.; Groth, P.; Pettifer, S.; Chichester, C.; Willighagen, E. L.; Evelo, C. T.; Blomberg, N.; Ecker, G.; Goble, C.; Mons, B. Open PHACTS: semantic interoperability for drug discovery Drug Discovery Today 2012, 17, 1188-1198
6. Laudano, J. B. Ceftaroline fosamil: a new broad-spectrum cephalosporin J. Antimicrob. Chemother. 2011, 66 (Suppl. 3) iii11-iii18
7. Chait, R.; Craney, A.; Kishony, R. Antibiotic interactions that select against resistance Nature 2007, 446, 668-671
8. Łeski, T. A.; Tomasz, A. Role of penicillin-binding protein 2 (PBP2) in the antibiotic susceptibility and cell wall cross-linking of staphylococcus aureus: evidence for the cooperative functioning of PBP2, PBP4, and PBP2A J. Bacteriol. 2005, 187, 1815-1824
9. Jia, J.; Zhu, F.; Ma, X.; Gao, Z. W.; Li, Y. X.; Chen, Y. Z. Mechanisms of drug combinations: interaction and network perspectives Nat. Rev. Drug Discovery 2009, 8, 111-128
10. Yocum, R. R.; Rasmussen, J. R.; Strominger, J. L. The mechanism of action of penicillin. Penicillin acylates the active site of bacillus stearothermophilus D-alanine carboxypeptidase J. Biol. Chem. 1980, 255, 3977-3986
11. Yocum, R. R.; Waxman, D. J.; Rasmussen, J. R.; Strominger, J. L. Mechanism of penicillin action: penicillin and substrate bind covalently to the same active site serine in two bacterial D-alanine carboxypeptidases Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 2730-2734
12. Zapun, A.; Contreras-Martel, C.; Vernet, T. Penicillin-binding proteins and beta-lactam resistance FEMS Microbiol. Rev. 2008, 32, 361-385
13. Harris, T. L.; Worthington, R. J.; Melander, C. Potent small-molecule suppression of oxacillin resistance in methicillin-resistant staphylococcus aureus Angew. Chem., Int. Ed. 2012, 51, 11254-11257
14. Su, Z.; Yeagley, A. A.; Su, R.; Peng, L.; Melander, C. Structural studies on 4,5-disubstituted 2-aminoimidazole-based biofilm modulators that suppress bacterial resistance to β-lactams ChemMedChem 2012, 7, 2030-2039
15. Stanley, M.; Cattle, N.; McCauley, J.; Martin, S. R.; Rashid, A.; Field, R. A.; Carbain, B.; Streicher, H. 'TamiGold': phospha-oseltamivir-stabilised gold nanoparticles as the basis for influenza therapeutics and diagnostics targeting the neuraminidase (instead of the hemagglutinin) Med. Chem. Commun. 2012, 3, 1373-1376
16. Papp, I.; Sieben, C.; Sisson, A. L.; Kostka, J.; Böttcher, C.; Ludwig, K.; Herrmann, A.; Haag, R. Inhibition of influenza virus activity by multivalent glycoarchitectures with matched sizes ChemBioChem 2011, 12, 887-895
17. Morales-Serna, J. A.; Boutureira, O.; Serra, A.; Matheu, M. I.; Díaz, Y.; Castillón, S. Synthesis of hyperbranched β-galceramide-containing dendritic polymers that bind HIV-1 rgp120 Eur. J. Org. Chem. 2010, 2657-2660
18. Li, C.; He, X.-P.; Zhang, Y.-J.; Li, Z.; Gao, L.-X.; Shi, X.-X.; Xie, J.; Li, J.; Chen, G.-R.; Tang, Y. Click to a focused library of benzyl 6-triazolo(hydroxy)benzoic glucosides: novel construction of PTP1B inhibitors on a sugar scaffold Eur. J. Med. Chem. 2011, 46, 4212-4218
19. Zhang, H.-L.; He, X.-P.; Sheng, L.; Yao, Y.; Zhang, W.; Shi, X.-X.; Li, J.; Chen, G.-R. Mol. Divers. 2011, 15, 889-900
20. Song, S.-X.; Zhang, H.-L.; Kim, C.-G.; Sheng, L.; He, X.-P.; Long, Y.-T.; Li, J.; Chen, G.-R. Synthesis of novel 6-triazologlycolipids via click chemistry and their preliminary cytotoxicity assessments Tetrahedron 2010, 66, 9974-9980
21. Poláková, M.; Beláňová, M.; Mikušová, K.; Lattová, E.; Perreault, H. Synthesis of 1,2,3-triazolo-linked octyl (1→6)-α-D-oligomannosides and their evaluation in mycobacterial mannosyltransferase assay Bioconjugate Chem. 2011, 22, 289-298
22. Azim, A.; Shah, V.; Doncel, G. F.; Peterson, N.; Gao, W.; Gross, R. Amino acid conjugated sophorolipids: a new family of biologically active functionalized glycolipids Bioconjugate Chem. 2006, 17, 1523-1529
23. Ding, N.; Zhang, Z.; Zhang, W.; Chun, Y.; Wang, P.; Qi, H.; Wang, S.; Li, Y. Synthesis and antibacterial evaluation of a series of oligorhamnoside derivatives Carbohydr. Res. 2011, 346, 2126-2135
24. Abalos, A.; Pinazo, A.; Infante, M. R.; Casals, M.; García, F.; Manresa, A. Physicochemical and antimicrobial properties of new rhamnolipids produced by pseudomonas aeruginosa AT10 from soybean oil refinery wastes Langmuir 2001, 17, 1367-1371
25. Thirumurugan, P.; Matosiuk, D.; Jozwiak, K. Chem. Rev. 2013, 113, 4905-4979
26. He, X.-P.; Xie, J.; Tang, Y.; Li, J.; Chen, G.-R. CuAAC click chemistry accelerates the discovery of novel chemical scaffolds as promising protein tyrosine phosphatases inhibitors Curr. Med. Chem. 2012, 19, 2399-2405
27. Salunke, S. B.; Babu, N. S.; Chen, C.-T. Iron(III) chloride as an efficient catalyst for stereoselective synthesis of glycosyl azides and a cocatalyst with Cu(0) for the subsequent click chemistry Chem. Commun. 2011, 47, 10440-10442
28. Cosgrove, K. L.; Bernhardt, P. V.; Ross, B. P.; McGeary, R. P. Determination of the anomeric configurations of 2,3,4,6-Tetra- O -Acetyl-D-mannopyranosyl azide Aust. J. Chem. 2006, 59, 473-476
29. Rostovstsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes Angew. Chem., Int. Ed. 2002, 41, 2596-2599
30. Tornøe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides J. Org. Chem. 2002, 67, 3057-3064
31. Meldal, M.; Tornøe, C. W. Cu-catalyzed azide-alkyne cycloaddition Chem. Rev. 2008, 108, 2952-3015
32. Hu, F.-Q.; Zhang, Y.-Y.; You, J.; Yuan, H.; Du, Y.-Z. pH triggered doxorubicin delivery of PEGylated glycolipid conjugate micelles for tumor targeting therapy Mol. Pharmaceutics 2012, 9, 2469-2479
33. Hitchcock, C. A.; Barrett-Bee, K. J.; Russell, N. J. The lipid composition and permeability to the triazole antifungal antibiotic ICI 153066 of serum-grown mycelial cultures of Candida albicans J. Gen. Microbiol. 1989, 135, 1949-1955
34. Rogers, S. A.; Huigens, R. W., III; Cavanagh, J.; Melander, C. Synergistic effects between conventional antibiotics and 2-aminoimidazole-derived antibiofilm agents Antimicrob. Agents Chemother. 2010, 54, 2112-2118