Novel mechanism of inhibiting β-Lactamases by sulfonylation using β-Sultams

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 24, 2003, Pages 4489-4492

  Page, Michael I ^a   Hinchliffe, Paul S ^a   Wood, J Matthew ^a   Harding, Lindsay P ^a   Laws, Andrew P ^a  

^a UNIVERSITY OF HUDDERSFIELD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM ANTIBIOTIC; BETA LACTAMASE; BETA LACTAMASE INHIBITOR; BETA SULTAM; ESTER DERIVATIVE; N BENZOYL BETA SULTAM; SERINE; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ENTEROBACTER CLOACAE; ENZYME ACTIVE SITE; ENZYME INACTIVATION; PH; SULFONYLATION;

ENTEROBACTER; ENTEROBACTER CLOACAE;

EID: 0344308935     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2003.08.082     Document Type: Article

References (16)

1. Waley, S. G. In The Chemistry of β-Lactams; Page, M. I., Ed.; Blackie: Glasgow, 1992; p 198. Frère J.-M. Mol. Microbiol. 16:1995;385.
2. Payne D.J. J. Med. Microbiol. 39:1993;93 Nordmann P., Mariotte P.S., Naas T., Labia R., Nicolas M.H. Antimicrob. Agents Chemother. 37:1993;939 Naas T., Vandel L., Sougakoff W., Livermore D.M., Nordmann P. Antimicrob. Agents Chemother. 38:1994;1262.
3. Bush K., Jacoby G.A., Modeiros A.A. Antimicrob. Agents Chemother. 39:1995;1211 Rasmussen B.A., Bush K. Antimicrob. Agents Chemother. 41:1997;223.
4. Page M.I., Laws A.P. Chem. Commun. 1998;1609.
5. Galleni M., Lamotte-Brassuer J., Rossolini G.M., Spencer J., Dideberg O., Frère J.M. Antimicrob. Agents Chemother. 45:2001;660.
6. Kelly J.A., Dideberg O., Charlier P., Wery J., Libert M., Moews P., Knox J., Duez, Fraipont, Joris B., Dusart J., Frère J.M., Ghuysen J.M. Science. 231:1986;1429 Samraoui B., Sutton B., Todd R., Artmiuk P., Waley S.G., Phillips D. Nature. 320:1986;378 Knox J.R., Moews P.C. J. Mol. Biol. 220:1991;435 Moews P.C., Knox J.R., Dideberg O., Charlier P., Frère J.M. Proteins: Struct., Funct., Genet. 7:1990;156 Herzberg O., Moult J.-M. Science. 236:1987;694 Herzberg O. J. Mol. Biol. 217:1991;701 Dideberg O., Charlier O., Wéry J.P., Dehottay P., Dusart J., Erpicum T., Frère J.M., Ghuysen J.-M. Biochem. J. 245:1987;911 Lamotte-Brasseur J., Dive G., Dideberg O., Charlier P., Frère J.M., Ghuysen J.M. Biochem. J. 279:1991;213 Jelsch C., Mourey L., Masson J.-M., Samama J.-P. Proteins: Struct. Funct. Genet. 16:1993;364.
7. Oefner C., Darcy A., Daly J.J., Gubernator K., Charnas R.L., Heinze I., Hubschwerlen C., Winkler F.K. Nature. 343:1990;284 Lobkovsky E., Moews P.C., Hansong L., Haiching Z., Frère J.M., Knox J.R. Proc. Natl. Acad. Sci. U.S.A. 90:1993;11257 Lobkovsky E., Billings E.M., Moews P.C., Rahill J., Pratt R.F., Knox J.R. Biochemistry. 33:1994;6762 Usher K.C., Blaszczak L.C., Weston G.S., Shoichet B.K., Remington S.J. Biochemistry. 37:1998;16082.
8. Damblon C., Zao G.H., Jamin M., Ledent P., Dubus A., Vanhove M., Raquet X., Christiaens L., Frère J.M. Biochem. J. 309:1995;431 Xu Y., Soto G., Hirsch K.R., Pratt R.F. Biochemistry. 35:1996;3595 Murphy B.P., Pratt R.F. Biochemistry. 30:1991;3640.
9. Page M.I., Vilanova B., Layland N.J. J. Am. Chem. Soc. 117:1995;12092.
10. Page, M. I. Enzyme Inhibition. In Comprehensive Medicinal Chemistry; Sammes, P. G., Ed.; Pergamon: Oxford, 1990; Vol. 2, p 61-87.
11. Wood J.M., Page M.I. Trends Heterocycl. Chem. 8:2002;19.
12. Baxter N.J., Laws A.P., Rigoreau L.J.M., Page M.I. J. Am. Chem. Soc. 112:2000;3375 Baxter N.J., Laws A.P., Rigoreau L.J.M., Page M.I. J. Chem. Soc., Perkin Trans. 2. 1996;2245.
13. Beardsell M., Hinchliffe P.S., Wood J.M., Wilmouth R.C., Schofield C.J., Page M.I. Chem. Commun. 2001;1503.
14. Macdonald S.J.F., Dowle M.D., Harrison L.A., Spooner J.E., Shah P., Johnson M.R., Inglis G.G.A., Clarke G.D.E., Belton D.J., Smith R.A., Molloy C.R., Dixon M., Murkitt G., Godward R.E., Skarzynski T., Singh O.M.P., Kumar K.A., Hodgson, McDonald E.G., Hardy W., Finch H., Fleetwood G., Humphreys D.C. Bioorg. Med. Chem. Lett. 11:2001;243.
15. Page M.I., Laws A.P., Slater M.J., Stone J.R. Pure Appl. Chem. 67:1995;711 Laws A.P., Page M.I., Slater M.J. Bioorg. Med. Chem. Lett. 3:1993;2317.
16. Page M.I., Laws A.P., Slater M.J., Stone J.R. Pure Appl. Chem. 67:1995;711 Laws A.P., Page M.I., Slater M.J. Bioorg. Med. Chem. Lett. 3:1993;2317.