Structure guided development of potent reversibly binding penicillin binding protein inhibitors

ACS Medicinal Chemistry Letters

Volumn 2, Issue 3, 2011, Pages 219-223

  Woon, Esther C Y ^a   Zervosen, Astrid ^b   Sauvage, Eric ^b   Simmons, Katie J ^c   Živec, Matej ^d   Inglis, Steven R ^a   Fishwick, Colin W G ^c   Gobec, Stanislav ^d   Charlier, Paulette ^b   Luxen, André ^b   Schofield, Christopher J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF LIÈGE   (Belgium)

^c UNIVERSITY OF LEEDS   (United Kingdom)

^d UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

lactams; antibiotic resistance; antibiotics; boronic acids; Penicillin binding proteins; transpeptidase inhibition

Indexed keywords

4 DIMETHYLAMINOPYRIDINE; BETA LACTAM ANTIBIOTIC; BORONIC ACID DERIVATIVE; ELECTROPHILE; METICILLIN; NITROCEFIN; PENICILLIN BINDING PROTEIN; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; BINDING AFFINITY; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; DRUG SYNTHESIS; HUMAN; HYDROGEN BOND; IC 50; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

EID: 79952659295     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml100260x     Document Type: Article

References (17)

1. Macheboeuf, P.; Contreras-Martel, C.; Job, V.; Dideberg, O.; Dessen, A. Penicillin binding proteins: key players in bacterial cell cycle and drug resistance processes FEMS Microbiol. Rev. 2006, 30, 673-691 (Pubitemid 44199345)
2. Sauvage, E.; Kerff, F.; Terrak, M.; Ayala, J. A.; Charlier, P. The penicillin-binding proteins: structure and role in peptidoglycan biosynthesis FEMS Microbiol. Rev. 2008, 32, 234-258 (Pubitemid 351257821)
3. Höltje, J. V. Growth of the stress-bearing and shape-maintaining murein sacculus of Escherichia coli Microbiol. Mol. Biol. Rev. 1998, 62, 181-203
4. Baldwin, J. E.; Schofield, C. J. The biosynthesis of β-lactams. In The Chemistry of β-Lactams; Page, M. I., Ed.; Blackie Academic and Professional: London, 1992; pp 1 - 78.
5. Massova, I.; Mobashery, S. Kinship and diversification of bacterial penicillin-binding proteins and ss-lactamases Antimicrob. Agents Chemother. 1998, 42, 1-17 (Pubitemid 28053319)
6. Fisher, J. F.; Meroueh, S. O.; Mobashery, S. Bacterial resistance to beta-lactam antibiotics: compelling opportunism, compelling opportunity Chem. Rev. 2005, 105, 395-424 (Pubitemid 40351628)
7. Silvaggi, N. R.; Anderson, J. W.; Brinsmade, S. R.; Pratt, R. F.; Kelly, J. A. The crystal structure of phosphonate-inhibited d -Ala- d -Ala peptidase reveals an analogue of a tetrahedral transition state Biochemistry 2003, 42, 1199-1208 (Pubitemid 36184060)
8. Nicola, G.; Peddi, S.; Stefanova, M.; Nicholas, R. A.; Gutheil, W. G.; Davies, C. Crystal structure of Escherichia coli penicillin-binding protein 5 bound to a tripeptide boronic acid inhibitor: a role for Ser-110 in deacylation Biochemistry 2005, 44, 8207-8217 (Pubitemid 40799901)
9. Pechenov, A.; Stefanova, M. E.; Nicholas, R. A.; Peddi, S.; Gutheil, W. G. Potential transition state analogue inhibitors for the penicillin-binding proteins Biochemistry 2003, 42, 579-588 (Pubitemid 36105778)
10. Dzhekieva, L.; Rocaboy, M.; Kerff, F.; Charlier, P.; Sauvage, E.; Pratt, R. F. Crystal structure of a complex between the Actinomadura R39 DD-peptidase and a peptidoglycan-mimetic boronate inhibitor: interpretation of a transition state a nalogue in terms of catalytic mechanism Biochemistry 2010, 49, 6411-6419
11. Inglis, S. R.; Zervosen, A.; Woon, E. C. Y.; Gerards, T.; Teller, N.; Fischer, D. S.; Luxen, A.; Schofield, C. J. Synthesis and evaluation of 3-(dihydroxyboryl)benzoic acids as D,D-carboxypeptidase R39 inhibitors J. Med. Chem. 2009, 52, 6097-6106
12. Sauvage, E.; Herman, R.; Petrella, S.; Duez, C.; Bouillenne, F.; Frere, J.-M.; Charlier, P. Crystal structure of the Actinomadura R39 DD-peptidase reveals new domains in penicillin-binding proteins J. Biol. Chem. 2005, 280, 31249-31256 (Pubitemid 41291862)
13. Gillet, V.; Johnson, A. P.; Mata, P.; Sike, S.; Williams, P. SPROUT-a programme for structure generation J. Comput.-Aided Mol. Des. 1993, 7, 127-153
14. Law, J. M. S.; Fung, D. Y. K.; Zsoldos, Z.; Simon, A.; Szabo, Z.; Csizmadia, I. G.; Johnson, A. P. Validation of the SPROUT de novo design program THEOCHEM 2003, 666, 651-657
15. Matteson, D. S.; Ray, R.; Rocks, R. R.; Tsai, D. J. S. Directed chiral synthesis by way of a-chloro boronic esters Organometallics 1983, 2, 1536-1543
16. Inglis, S. R.; Woon, E. C. Y.; Thompson, A. L.; Schofield, C. J. Observations on the deprotection of pinanediol and pinacol boronate esters via fluorinated intermediates J. Org. Chem. 2010, 75, 468-471
17. Yuen, A. K. L.; Hutton, C. A. Deprotection of pinacolyl boronate esters via hydrolysis of intermediate potassium trifluoroborates Tetrahedron Lett. 2005, 46, 7899-7903 (Pubitemid 41455043)