The Importance of the trans-Enamine Intermediate as a β-Lactamase Inhibition Strategy Probed in Inhibitor-Resistant SHV β-Lactamase Variants

ChemMedChem

Volumn 7, Issue 6, 2012, Pages 1002-1008

  Ke, Wei ^a   Rodkey, Elizabeth A ^a   Sampson, Jared M ^a   Skalweit, Marion J ^c   Sheri, Anjaneyulu ^d   Pagadala, Sundar Ram Reddy ^d   Nottingham, Michael D ^d   Buynak, John D ^d   Bonomo, Robert A ^b,c   van den Akker, Focco ^a  

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

^b CASE WESTERN RESERVE UNIVERSITY   (United States)

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

^d SOUTHERN METHODIST UNIVERSITY   (United States)

Author keywords

Antibacterial agents; Beta lactamases; Drug resistance; Inhibitors; Protein crystallography

Indexed keywords

2' BETA GLUTAROXYPENICILLINATE SULFONE; BETA LACTAMASE INHIBITOR; BETA LACTAMASE SHV; ENAMINE; M69V BETA LACTAMASE SHV; PROTEIN VARIANT; S130G BETA LACTAMASE SHV; SA 213; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; DEACYLATION; ENZYME ACTIVE SITE; ENZYME INHIBITOR COMPLEX; ENZYME PURIFICATION; ENZYME STABILITY; ESCHERICHIA COLI; MOLECULAR CLONING; MOLECULAR INTERACTION; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN BINDING; PROTEIN CONFORMATION; PROTEIN EXPRESSION; PROTEIN STRUCTURE; SITE DIRECTED MUTAGENESIS; X RAY CRYSTALLOGRAPHY;

BETA-LACTAMASES; BINDING SITES; BIPHENYL COMPOUNDS; CATALYTIC DOMAIN; CRYSTALLOGRAPHY, X-RAY; DRUG RESISTANCE, BACTERIAL; ENZYME INHIBITORS; IMIDAZOLES; ISOMERISM;

EID: 84861553754     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201200006     Document Type: Article

References (31)

1. S. M. Drawz, R. A. Bonomo, Clin. Microbiol. Rev. 2010, 23, 160-201.
2. For Ambler positions, see: (Last accessed: March 8th, 2012).
3. P. S. Padayatti, A. Sheri, M. A. Totir, M. S. Helfand, M. P. Carey, V. E. Anderson, P. R. Carey, C. R. Bethel, R. A. Bonomo, J. D. Buynak, F. vandenAkker, J. Am. Chem. Soc. 2006, 128, 13235-13242.
4. J. Lamotte-Brasseur, G. Dive, O. Dideberg, P. Charlier, J. M. Frère, J. M. Ghuysen, Biochem. J. 1991, 279 (Pt.1), 213-221.
5. S. B. Vakulenko, B. Geryk, L. P. Kotra, S. Mobashery, S. A. Lerner, Antimicrob. Agents Chemother. 1998, 42, 1542-1548.
6. U. Imtiaz, E. M. Billings, J. R. Knox, S. Mobashery, Biochemistry 1994, 33, 5728-5738.
7. A. P. Kuzin, M. Nukaga, Y. Nukaga, A. Hujer, R. A. Bonomo, J. R. Knox, Biochemistry 2001, 40, 1861-1866.
8. B. P. Atanasov, D. Mustafi, M. W. Makinen, Proc. Natl. Acad. Sci. USA 2000, 97, 3160-3165.
9. U. Imtiaz, E. Billings, J. R. Knox, E. K. Manavathu, S. A. Lerner, S. Mobashery, J. Am. Chem. Soc. 1993, 115, 4435-4442.
10. M. S. Helfand, C. R. Bethel, A. M. Hujer, K. M. Hujer, V. E. Anderson, R. A. Bonomo, J. Biol. Chem. 2003, 278, 52724-52729.
11. M. S. Helfand, M. A. Taracila, M. A. Totir, R. A. Bonomo, J. D. Buynak, F. vandenAkker, P. R. Carey, Biochemistry 2007, 46, 8689-8699.
12. V. L. Thomas, D. Golemi-Kotra, C. Kim, S. B. Vakulenko, S. Mobashery, B. K. Shoichet, Biochemistry 2005, 44, 9330-9338.
13. T. Sun, C. R. Bethel, R. A. Bonomo, J. R. Knox, Biochemistry 2004, 43, 14111-14117.
14. D. Pagan-Rodriguez, X. Zhou, R. Simmons, C. R. Bethel, A. M. Hujer, M. S. Helfand, Z. Jin, B. Guo, V. E. Anderson, L. M. Ng, R. A. Bonomo, J. Biol. Chem. 2004, 279, 19494-19501.
15. D. Sulton, D. Pagan-Roderiguez, X. Zhou, Y. Liu, A. M. Hujer, C. R. Bethel, M. S. Helfand, J. M. Thomson, V. E. Anderson, J. D. Buynak, L. M. Ng, R. A. Bonomo, J. Biol. Chem. 2005, 280, 35528-35536.
16. A. P. Kuzin, M. Nukaga, Y. Nukaga, A. M. Hujer, R. A. Bonomo, J. R. Knox, Biochemistry 1999, 38, 5720-5727.
17. M. A. Totir, P. S. Padayatti, M. S. Helfand, M. P. Carey, R. A. Bonomo, P. R. Carey, F. vandenAkker, Biochemistry 2006, 45, 11895-11904.
18. X. Wang, G. Minasov, B. K. Shoichet, J. Biol. Chem. 2002, 277, 32149-32156.
19. M. S. Helfand, A. M. Hujer, F. D. Sonnichsen, R. A. Bonomo, J. Biol. Chem. 2002, 277, 47719-47723.
20. J. M. Sampson, W. Ke, C. R. Bethel, S. R. Pagadala, M. D. Nottingham, R. A. Bonomo, J. D. Buynak, F. vandenAkker, Antimicrob. Agents Chemother. 2011, 55, 2303-2309.
21. L. M. Ellerby, W. A. Escobar, A. L. Fink, C. Mitchinson, J. A. Wells, Biochemistry 1990, 29, 5797-5806.
22. A. M. Hujer, K. M. Hujer, R. A. Bonomo, Biochim. Biophys. Acta Protein Struct. Mol. Enzymol. 2001, 1547, 37-50.
23. S. Lin, M. Thomas, S. Mark, V. Anderson, R. A. Bonomo, Biochim. Biophys. Acta Protein Struct. Mol. Enzymol. 1999, 1432, 125-136.
24. J. W. Pflugrath, Acta Crystallogr. D 1999, 55, 1718-1725.
25. A. J. McCoy, R. W. Grosse-Kunstleve, P. D. Adams, M. D. Winn, L. C. Storoni, R. J. Read, J. Appl. Crystallogr. 2007, 40, 658-674.
26. G. N. Murshudov, A. A. Vagin, E. J. Dodson, Acta Crystallogr. D 1997, 53, 240-255.
27. P. Emsley, K. Cowtan, Acta Crystallogr. D 2004, 60, 2126-2132.
28. A. W. Schüttelkopf, D. M. vanAalten, Acta Crystallogr. D 2004, 60, 1355-1363.
29. F. vandenAkker, W. G. Hol, Acta Crystallogr. D 1999, 55, 206-218.
30. R. A. Laskowski, M. W. MacArthur, D. S. Moss, J. M. Thornton, J. Appl. Crystallogr. 1993, 26, 283-291.
31. Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326.