Discovery of 1-Hydroxypyridine-2(1H)-thione-6-carboxylic Acid as a First-in-Class Low-Cytotoxic Nanomolar Metallo β-Lactamase Inhibitor

ChemMedChem

Volumn 12, Issue 11, 2017, Pages 845-849

  Shin, Woo Shik ^a   Bergstrom, Alexander ^b   Bonomo, Robert A ^c   Crowder, Michael W ^b   Muthyala, Ramaiah ^a   Sham, Yuk Yin ^a,d  

^a UNIVERSITY OF MINNESOTA   (United States)

^b MIAMI UNIVERSITY   (United States)

^c LOUIS STOKES CLEVELAND VA MEDICAL CENTER   (United States)

^d UNIVERSITY OF MINNESOTA   (United States)

Author keywords

1 hydroxypyridine 2(1H) thiones; drug resistance; metallo lactamase; pyrithiones; VIM 2; lactam antibiotics

Indexed keywords

1 HYDROXYPYRIDINE 2(1H)THIONE 6 CARBOXYLIC ACID; AMOXICILLIN; BETA LACTAMASE INHIBITOR; CAPTOPRIL; CARBOXYLIC ACID; CLAVULANIC ACID; METALLO BETA LACTAMASE; NITROCEFIN; PYRIDINE DERIVATIVE; TAZOBACTAM; UNCLASSIFIED DRUG; 1-HYDROXYPYRIDINE-2(1H)-THIONE-6-CARBOXYLIC ACID; BETA LACTAMASE; PICOLINIC ACID DERIVATIVE; THIOKETONE;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC THERAPY; ANTIMICROBIAL ACTIVITY; ARTICLE; BINDING AFFINITY; BIOCHEMICAL ANALYSIS; CONTROLLED STUDY; CYTOTOXICITY; DRUG IDENTIFICATION; DRUG STRUCTURE; EC50; ENZYME INHIBITION; ESCHERICHIA COLI; HUMAN; HUMAN CELL; LIGAND BINDING; MOLECULAR MODEL; NONHUMAN; PRIORITY JOURNAL; PROCESS OPTIMIZATION; THERAPEUTIC INDEX; WHOLE CELL; CELL SURVIVAL; CHEMISTRY; DRUG EFFECTS; HEK293 CELL LINE; IC50; METABOLISM; MICROBIAL SENSITIVITY TEST; PSEUDOMONAS AERUGINOSA; SYNTHESIS;

BETA-LACTAMASE INHIBITORS; BETA-LACTAMASES; CELL SURVIVAL; ESCHERICHIA COLI; HEK293 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; PICOLINIC ACIDS; PSEUDOMONAS AERUGINOSA; THIONES;

EID: 85019959524     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201700182     Document Type: Article

References (23)

1. S. M. Drawz, R. A. Bonomo, Clin. Microbiol. Rev. 2010, 23, 160–201.
2. T. Palzkill, Ann. N. Y. Acad. Sci. 2013, 1277, 91–104.
3. T. Christopeit, T. J. O. Carlsen, R. Helland, H. K. S. Leiros, J. Med. Chem. 2015, 58, 8671–8682.
4. U. Heinz, R. Bauer, S. Wommer, W. Meyer-Klaucke, C. Papamichaels, J. Bateson, H. W. Adolph, J. Biol. Chem. 2003, 278, 20659–20666;
5. J. Brem, S. S. van Berkel, D. Zollman, S. Y. Lee, O. Gileadi, P. J. McHugh, T. R. Walsh, M. A. McDonough, C. J. Schofield, Antimicrob. Agents Chemother. 2016, 60, 142–150.
6. X. H. Zhou, A. L. W. Po, Biochem. Pharmacol. 1994, 47, 1121–1126.
7. F. E. Jacobsen, J. A. Lewis, S. M. Cohen, ChemMedChem 2007, 2, 152–171.
8. J. Z. Yao, H. Q. Liang, S. X. Liao, Acta Pharm. Sin. 1994, 29, 845–850.
9. M. Marcheselli, P. Azzoni, M. Mauri, Aquat. Toxicol. 2011, 102, 39–47;
10. M. Tailler, L. Senovilla, E. Lainey, S. Thepot, D. Metivier, M. Sebert, V. Baud, K. Billot, P. Fenaux, L. Galluzzi, S. Boehrer, G. Kroemer, O. Kepp, Oncogene 2012, 31, 3536–3546;
11. G. Y. Han, B. X. Xu, X. P. Wang, M. Z. Liu, X. Y. Xu, L. N. Meng, Z. L. Chen, D. Y. Zhu, Acta Chim. Sin. 1981, 39, 433–437;
12. M. Qiu, Y. Chen, Y. Chu, S. W. Song, N. Yang, J. Gao, Z. W. Wu, Antiviral Res. 2013, 100, 44–53;
13. B. M. Krenn, E. Gaudernak, B. Holzer, K. Lanke, F. J. M. Van Kuppeveld, J. Seipelt, J. Virol. 2009, 83, 58–64;
14. J. Schwartz, H. Mizoguchi, R. Bacon, J. Am. Acad. Dermatol. 2013, 68, Ab46.
15. R. A. Jones, A. R. Katritzky, J. Chem. Soc. 1960, 2937–2942.
16. R. Muthyala, N. Rastogi, W. S. Shin, M. L. Peterson, Y. Y. Sham, Bioorg. Med. Chem. Lett. 2014, 24, 2535–2538.
17. R. Muthyala, W. S. Shin, J. S. Xie, Y. Y. Sham, Bioorg. Med. Chem. Lett. 2015, 25, 4320–4324.
18. P. Marchiaro, P. E. Tomatis, M. A. Mussi, F. Pasteran, A. M. Viale, A. S. Limansky, A. J. Vila, Antimicrob. Agents Chemother. 2008, 52, 2250–2252.
19. M. Aitha, A. R. Marts, A. Bergstrom, A. J. Moller, L. Moritz, L. Tumer, J. C. Nix, R. A. Bonomo, R. C. Page, D. L. Tierney, M. W. Crowder, Biochemistry 2014, 53, 7321–7331.
20. N. Y. Schrodinger LLCNY, 2014.
21. A. Albert, C. W. Rees, A. J. H. Tomlinson, Br. J. Exp. Pathol. 1956, 37, 500–511.
22. K. Bush, G. A. Jacoby, Antimicrob. Agents Chemother. 2010, 54, 969–976.
23. D. H. Griffin, T. K. Richmond, C. Sanchez, A. J. Moller, R. M. Breece, D. L. Tierney, B. Bennett, M. W. Crowder, Biochemistry 2011, 50, 9125–9134.