Modifications of the C6-substituent of penicillin sulfones with the goal of improving inhibitor recognition and efficacy

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 1, 2011, Pages 387-393

  Nottingham, Micheal ^a   Bethel, Christopher R ^b   Pagadala, Sundar Ram Reddy ^a   Harry, Emily ^a   Pinto, Abishai ^a   Lemons, Zachary A ^a   Drawz, Sarah M ^c   Akker, Focco Van Den ^c   Carey, Paul R ^c   Bonomo, Robert A ^b   Buynak, John D ^a  

^a SOUTHERN METHODIST UNIVERSITY   (United States)

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

^c CASE WESTERN RESERVE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Lactamase; Antibiotic; Inhibitor; Penicillin

Indexed keywords

BETA LACTAMASE; BETA LACTAMASE INHIBITOR; PENICILLIN DERIVATIVE; PENICILLIN G; PENICILLIN SULFONE DERIVATIVE; PROTON; SULFONE; UNCLASSIFIED DRUG;

ARTICLE; ENZYME INHIBITION; HYDROGEN BOND; ISOMERIZATION;

BETA-LACTAMASES; BINDING SITES; CATALYTIC DOMAIN; COMPUTER SIMULATION; ENZYME INHIBITORS; PENICILLIN G; PENICILLINS; PROTEIN STRUCTURE, TERTIARY; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONES;

EID: 78650512729     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.10.134     Document Type: Article

References (35)

1. F. Perez, A. Endimiani, K.M. Hujer, and R.A. Bonomo Curr. Opin. Pharmacol. 7 2007 459
2. G.M. Rossolini, M.M. D'Andrea, and C. Mugnaioli Clin. Microbiol. Infect. 14 2008 33
3. K. Bush Clin. Microbiol. Infect. 14 2008 134
4. J. Rodriguez-Bano, and A. Pascual Expert Rev. Anti Infect. Ther. 6 2008 671
5. L. Poirel, J.D. Pitout, and P. Nordmann Future Microbiol. 2 2007 501
6. L. Poirel, T. Naas, and P. Nordmann Antimicrob. Agents Chemother. 54 2010 24
7. A.M. Queenan, and K. Bush Clin. Microbiol. Rev. 20 2007 440
8. F.J. Perez-Llarena, and G. Bou Curr. Med. Chem. 16 2009 3740
9. I. Massova, and S. Mobashery Antimicrob. Agents Chemother. 42 1998 1
10. R.F. Pratt J. Chem. Soc., Perkin Trans. 2 2002 851
11. S.O. Meroueh, G. Minasov, W. Lee, B.K. Shoichet, and S. Mobashery J. Am. Chem. Soc. 125 2003 9612
12. E. Sauvage, F. Kerff, M. Terrak, J.A. Ayala, and P. Charlier FEMS Microbiol. Rev. 32 2008 234
13. E. Gordon, N. Mouz, E. Duee, and O. Dideberg J. Mol. Biol. 299 2000 477
14. Kellogg, M. S. Ger. Pat. DE 3039504 19810430, Chem. Abstr. 1981, 95, 480946.
15. P. Bitha, Z. Li, G.D. Francisco, B.A. Rasmussen, and Y.-I. Lin Bioorg. Med. Chem. Lett. 9 1999 991
16. P. Bitha, Z. Li, G.D. Francisco, Y. Yang, P.J. Petersen, E. Lenoy, and Y.-I. Lin Bioorg. Med. Chem. Lett. 9 1999 997
17. J.D. Buynak, H. Chen, L. Vogeti, V.R. Gadhachanda, C.A. Buchanan, T. Palzkill, R.W. Shaw, J. Spencer, and T.R. Walsh Bioorg. Med. Chem. Lett. 14 2004 1299
18. D. Golemi, L. Maveyraud, A. Ishiwata, S. Tranier, K. Miyashita, T. Nagase, I. Massova, L. Mourey, J.P. Samama, and S. Mobashery J. Antibiot. 53 2000 1022
19. S.A. Testero, P.I. O'Daniel, Q. Shi, M. Lee, D. Hesek, A. Ishiwata, B.C. Noll, and S. Mobashery Org. Lett. 11 2009 2515
20. L. Maveyraud, I. Massova, C. Birck, K. Miyashita, J.-P. Samama, and S. Mobashery J. Am. Chem. Soc. 118 1996 7435
21. L. Mourey, K. Miyashita, P. Swaren, A. Bulychev, J.-P. Samama, and S. Mobashery J. Am. Chem. Soc. 120 1998 9382
22. R.F. Pratt Cell. Mol. Life Sci. 65 2008 2138
23. F. Moosdeen, J.D. Williams, and S. Yamabe Antimicrob. Agents Chemother. 32 1988 925
24. C. Urban, E. Go, N. Mariano, B.J. Berger, I. Avraham, D. Rubin, and J.J. Rahal J. Infect. Dis. 167 1993 448
25. C. Urban, E. Go, N. Mariano, and J.J. Rahal FEMS Microbiol. Lett. 125 1995 193
26. Akkerboom, P. J.; Oldenhof, C. US patent 4,422,971. Chem. Abstr. 1981, 95, 587244.
27. R.A. Volkmann, R.D. Carroll, R.B. Drolet, M.L. Elliott, and B.S. Moore J. Org. Chem. 47 1982 3344
28. J.-M. Rodriguez-Martinez, L. Poirel, and P. Nordmann Antimicrob. Agents Chemother. 53 2009 1766
29. 50 value is ±10%.
30. F.R. Batchelor, J. Cameron-Wood, E.B. Chain, and G.N. Rolinson Proc. R. Soc. London 158 1963 311
31. E. Lobkovsky, P.C. Moews, H. Liu, H. Zhag, J.-M. Frre, and J.R. Knox Proc. Natl. Acad. Sci. U.S.A. 90 1993 11257
32. M. Galleni, and J.-M. Frre Biochem. J. 255 1988 119
33. M. Galleni, G. Amicosante, and J.-M. Frre Biochem. J. 255 1988 123
34. J. Fisher, R.L. Charnas, S.M. Bradley, and J.R. Knowles Biochemistry 20 1981 2726
35. M. Kalp, J.D. Buynak, and P.R. Carey Biochemistry 48 2009 10196