Mechanism of inactivation of β-lactamases by novel 6-methylidene penems elucidated using electrospray ionization mass spectrometry

Journal of Medicinal Chemistry

Volumn 47, Issue 14, 2004, Pages 3674-3688

  Tabei, Keiko ^a   Feng, Xidong ^a   Venkatesan, Aranapakam M ^a   Abe, Takao ^b   Hideki, Ushirogochi ^b   Mansour, Tarek S ^a   Siegel, Marshall M ^a  

^a WYETH RESEARCH   (United States)

^b Medical Research Laboratories   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

6 (5,6 DIHYDRO 4H PYRROLO[1,2 B]PYRAZOL 2 YLMETHYLENE) 7 OXO 4 THIA 1 AZABICYCLO[3.2.0]HEPT 2 ENE 2 CARBOXYLIC ACID; 6 (5,6 DIHYDRO 8H IMIDAZO[2,1 C]OXAZIN 2 YLMETHYLENE) 7 OXO 4 THIA 1 AZABICYCLO[3.2.0]HEPT 2 ENE 2 CARBOXYLIC ACID; 6 (6,7 DIHYDRO 5H CYCLOPENTA[D]IMIDAZO[2,1 B][1,3]THIAZOL 2 YLMETHYLENE) 7 OXO 4 THIA 1 AZABICYCLO[3.2.0]HEPT 2 ENE 2 CARBOXYLIC ACID; 6 METHYLIDENE PENEM DERIVATIVE; 7 OXO 6 (5,6,7,8 TETRAHYDROIMIDAZO[1,2 A]PYRAZIN 2 YLMETHYLENE) 4 THIA 1 AZABICYCLO[3.2.0]HEPT 2 ENE 2 CARBOXYLIC ACID; BETA LACTAMASE; BETA LACTAMASE INHIBITOR; DIHYDRO[1,4]THIAZEPINE; ENAMINE; NITROCEFIN; PENEM DERIVATIVE; SERINE; TAZOBACTAM; TRYPSIN; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CHEMICAL REACTION KINETICS; DRUG BINDING SITE; DRUG MECHANISM; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; ELIMINATION REACTION; ENZYME BINDING; ENZYME INACTIVATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; IN VITRO STUDY; PROTEIN DEGRADATION; X RAY CRYSTALLOGRAPHY;

BACTERIAL PROTEINS; BETA-LACTAMASES; BETA-LACTAMS; BINDING SITES; HYDROLYSIS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 3042643024     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm049903j     Document Type: Article

References (34)

1. Micetich, R. G.; Salama, S. M.; Maiti, S. N.; Reddy, A. V. N.; Singh, R. β-Lactamases and their inhibitors: an update. Curr. Med. Chem. Anti-infective Agents 2002, 1, 193-214.
2. Page, M. G. P. β-lactamase inhibitors. Drug Resist. Updates 2000, 3, 109-125.
3. Sandanayaka, V. P.; Prashad, A. S. Resistance to β-lactam antibiotics: Structure and mechanism based design of β-lactamase inhibitors. Curr. Med. Chem. 2002, 9, 1145-1165.
4. Dizdaroglu, M.; Jaruga, P.; Rodriguez, H. Oxidative damage to DNA: mechanisms of product formation and measurement by mass spectrometric techniques. Crit. Rev. Oxidative Stress Aging 2003, 1, 165-189.
5. Ramtohul, Y. K.; Martin, N. I.; Silkin, L.; James, M. N. G.; Vederas, J. C. Synthesis of pseudoxazolones and their inhibition of the 3C cysteine proteinases from hepatitis A virus and human rhinovirus-14. J. Chem. Soc., Perkin Trans. 2002, 11, 1351-1359.
6. Wang, H.; Wu, Y.; Zhao, Z. Fragmentation study of simvastatin and lovastatin using electrospray ionization tandem mass spectrometry. J. Mass Spectrom. 2001, 36, 58-70.
7. Sandanayaka, V. P.; Prashad, A. S.; Yang, Y.; Williamson, R. T.; Lin, Y. I.; Mansour, T. S. Spirocyclopropyl β-lactams as mechanism-based inhibitors of serine β-lactamases. synthesis by rhodium-catalyzed cyclopropanation of 6-diazopenicillanate sulfone. J. Med. Chem. 2003, 46, 2569-2571.
8. Yang, Y.; Janota, K.; Tabei, K.; Huang, N.; Siegel, M. M.; Lin, Y. I.; Rasmussen, B. A.; Shlaes, D. M. Mechanism of inhibition of the class A β-lactamases PC1 and TEM-1 by tazobactam. Observation of reaction products by electrospray ionization mass spectrometry. J. Biol. Chem. 2000, 275, 26674-26682.
9. Ng, L. M.; Pagan-Rodriguez, D.; Zhou, X.; Simmons, R.; Bonomo, R. A.; Hujer, A. M.; Anderson, V. B. An ESI-MS/LC-MS analysis of the inhibition of SHV-1 β-lactamase with tazobactam. Abstracts of Papers, 224th American Chemical Society National Meeting, Boston, MA, Aug 18-22, 2002; American Chemical Society: Washington, DC, 2002; ANYL-099.
10. Bonomo, R. A.; Liu, J.; Chen, Y.; Ng, L.; Hujer, A. M.; Anderson, V. E. Inactivation of CMY-2 β-lactamase by tazobactam: initial mass spectroscopic characterization. Biochem. Biophys. Acta 2001, 1547, 196-205.
11. Coleman, K.; Griffin, D. R. J.; Page, J. W. J.; Upshon, P. A. In vitro evaluation of BRL 42715, a novel β-lactamase inhibitor. Antimicrob. Agents Chemother. 1989, 33, 1580-1587.
12. Bulychev, A.; Massova, I.; Lerner, S. A.; Mobashery, S. Penem BRL 42715: an effective inactivator for β-lactamases. J. Am. Chem. Soc. 1995, 117, 4797-4801.
13. Farmer, T. H.; Page, J. W. J.; Payne, D. J.; Knowles, D. J. C. Kinetic and physical studies of β-lactamase inhibition by a novel penem, BRL 42715. Biochem. J. 1994, 303, 825-830.
14. Okafo, G. N.; Cutler, P.; Knowles, D. J.; Camilleri, P. Capillary electrophoresis study of the hydrolysis of a β-lactamase inhibitor. Anal. Chem. 1995, 67, 3697-3701.
15. Broom, N. J. P.; Farmer, T. H.; Osborne, N. F.; Tyler, J. W. Studies on the mechanism of action of (5R)-(Z)-6-(1-methyl-1,2,3-triazol-4-ylmethylene) penem-3-carboxylic acid (BRL 42715), a potent inhibitor of bacterial β-lactamase. J. Chem. Soc., Chem. Commun. 1992, 22, 1663-1664.
16. Takao, A.; Hiroshi, M.; Ado, M.; Sato, C.; Ushirogochi H.; Sato, K.; Takasaki, T.; Venkatesan, A. M.; Mansour, T. S. Process for preparing 6-alkylidene penem derivatives. Patent WO2003093277, 2003.
17. Nukaga, M.; Abe, T.; Venkatesan, A. M.; Mansour, T. S.; Bonomo, R. A.; Knox, J. R. Inhibition of class A and class C β-lactamases by penems: crystallographic structures of a novel dihydrothiazepine intermediate. Biochemistry 2003, 42, 13152-13159.
18. Abe, T.; Ushirogochi, H.; Yamamura, I.; Kumagai, T.; Mansour, T. S.; Venkatesan, A. M.; Agarwal, A.; Petersen, P. J.; Weiss, W. J.; Lenoy, E.; Yang, Y.; Shales, D. Novel penems bearing a methylidene linkage as broad spectrum β-lactamase inhibitors. Abstracts of Papers of the 43rd Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC), Chicago, IL, Sept 14-17, 2003, F-538.
19. Gioacchini, A. M.; Traldi, P. Mass spectrometry of β-lactam antibiotics. Targets Heterocycl. Syst. 2001, 5, 327-355.
20. Das, P. R.; Pramanik, B. N.; Girijavallabhan, V. M.; Ganguly, A. K. Ionization of penem β-lactam antibiotics using thermospray (filament-on) mass spectrometry. J. Antibiot. 1988, 41, 1268-1271.
21. Triolo, A.; Bonelli, F. Structural characterization of a new class of penem β-lactam antibiotics by triple quadrupole tandem mass spectrometry. Rapid Commun. Mass Spectrom. 1995, 9, 707-711.
22. Mirgorodskaya, E.; Roepstorff, P.; Zubarev, R. A. Localization of O-glycosylation sites in peptides by electron capture dissociation in a Fourier transform mass spectrometer. Anal. Chem. 1999, 71, 4431-4436.
23. Shi, S. D.-H.; Hemling, M. E.; Carr, S. A.; Horn, D. M.; Lindh, I.; McLafferty, F. W. Phosphopeptide/phosphoprotein mapping by electron capture dissociation mass spectrometry. Anal. Chem. 2001, 73, 19-22.
24. Zubarev, R.A.; Kelleher, N. L.; McLafferty, F. W. Electron capture dissociation of multiply charged protein cations. A nonergodic process. J. Am. Chem. Soc. 1998, 120, 3265-3266.
25. Sutcliffe, J. G. Nucleotide sequence of the ampicillin resistance gene of Escherichia coli plasmid pBR322. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 3731-3741.
26. Rasmussen, B. A.; Gluzman, Y.; Tally, F. P. Escherichia coli chromosomal mutations that permit direct cloning of the Bacteroides fragilis metallo-β-lactamase gene, ccrA. Mol. Microbiol. 1991, 5, 1211-1219.
27. Ambler, R. P.; Coulson, A. F. W.; Frere, J.-M.; Ghuysen, J.-M.; Joris, B.; Forsman, M.; Levesque, R. C.; Tiraby, G.; Waley, S. G. A standard numbering scheme for the class A β-lactamases. Biochem. J. 1991, 276, 269-270.
28. Yang, Y.; Testa, R. T.; Bhachech, N.; Rasmussen, B. A.; Bush, K. Biochemical characterization of novel tetrahydrofuranyl-1-β- methylcarbapenems: stability to hydrolysis by renal dehydropeptidases and bacterial β-lactamases, binding to penicillin binding proteins and permeability properties. Antimicrob. Agents Chemother. 1999, 43, 2904-2909.
29. Bush, K.; Macalintal C.; Rasmussen B. A.; Lee V. J.; Yang Y. Kinetic interactions of tazobactam with beta-lactamases from all major structural classes. Antimicrob. Agents Chemother. 1993, 37, 851-858.
30. O'Callanghan, C. H.; Morris, A.; Kirby, S. M.; Shingler, A. H. Novel method for detection of β-lactamases by using a chromogenic cephalosporin substrate. Antimicrob. Agents Chemother. 1972 1, 283-288.
31. Roepstorff, P.; Fohlman, J. Proposal for a common nomenclature for sequence ions in mass spectra of peptides. Biomed. Mass Spectrom. 1984, 11, 601.
32. Valaskovic, G. A.; Kelleher, N. L. Miniaturized formats for efficient mass spectrometry-based proteomics and therapeutic development. Curr. Topics Med. Chem. (Hilversum, Netherlands) 2002, 2, 1-12.
33. Palmblad, M.; Hakansson, K.; Hakansson, P.; Feng, X.; Cooper, H. J.; Giannakopulos, A. E.; Green, P. S.; Derrick, P. J. A 9.4 T Fourier transform ion cyclotron resonance mass spectrometer: description and performance. Eur. J. Mass Spectrom. 2000, 6, 267-275.
34. Gauthier, J. W.; Trautman, T. R.; Jacobson, D. B. Sustained off-resonance irradiation for collision-activated dissociation involving Fourier transform mass spectrometry. Collision-activated dissociation technique that emulates infrared multiphoton dissociation. Anal. Chim. Acta 1991, 246, 211-225.