Crystal structures of biapenem and tebipenem complexed with penicillin-binding proteins 2X and 1A from Streptococcus pneumoniae

Antimicrobial Agents and Chemotherapy

Volumn 52, Issue 6, 2008, Pages 2053-2060

  Yamada, Mototsugu ^a   Watanabe, Takashi ^a   Baba, Nobuyoshi ^a   Takeuchi, Yasuo ^a   Ohsawa, Fukuichi ^a   Gomi, Shuichi ^a  

^a MEIJI SEIKA KAISHA LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM ANTIBIOTIC; BIAPENEM; CARBAPENEM; CEFALOTIN; DEHYDROPEPTIDASE I; DORIPENEM; ERTAPENEM; IMIPENEM; MEMBRANE ENZYME; MEROPENEM; PANIPENEM; PENICILLIN BINDING PROTEIN; PENICILLIN BINDING PROTEIN 1A; PENICILLIN BINDING PROTEIN 2X; PENICILLIN G; TEBIPENEM; TEBIPENEM PIVOXIL; THREONINE; TRYPSIN; TRYPTOPHAN;

ARTICLE; COMPLEX FORMATION; CRYSTAL STRUCTURE; DRUG BIOAVAILABILITY; DRUG PROTEIN BINDING; DRUG STABILITY; DRUG STRUCTURE; ENZYME ACTIVE SITE; HYDROPHOBICITY; NONHUMAN; PRIORITY JOURNAL; STRAIN IDENTIFICATION; STREPTOCOCCUS PNEUMONIAE; STREPTOCOCCUS PNEUMONIAE STRAIN R6;

ANTI-BACTERIAL AGENTS; BACTERIAL PROTEINS; BETA-LACTAMS; BINDING SITES; CARBAPENEMS; CRYSTALLIZATION; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PENICILLIN-BINDING PROTEINS; PEPTIDYL TRANSFERASES; PROTEIN BINDING; STREPTOCOCCUS PNEUMONIAE; THIENAMYCINS;

EID: 44449118389     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.01456-07     Document Type: Article

References (39)

1. Anderson, D. L. 2006. Doripenem. Drugs Today (Barc.) 42:399-404.
2. Asahi, Y., Y. Takeuchi, and K. Ubukata. 1999. Diversity of substitutions within or adjacent to conserved amino acid motifs of penicillin-binding protein 2X in cephalosporin-resistant Streptococcus pneumoniae isolates. Antimicrob. Agents Chemother. 43:1252-1255.
3. Barcus, V. A., K. Ghanekar, M. Yeo, T. J. Coffey, and C. G. Dowson. 1995. Genetics of high level penicillin resistance in clinical isolates of Streptococcus pneumoniae. FEMS Microbiol. Lett. 126:299-303.
4. Bonfiglio, G., G. Maccarone, M. L. Mezzatesta, A. Privitera, V. Carciotto, M. Santagati, S. Stefani, and G. Nicoletti. 1997. In vitro activity of biapenem against recent gram-negative and gram-positive clinical isolates. Chemotherapy 43:393.
5. Contreras-Martel, C., V. Job, A. M. Di Guilmi, T. Vernet, O. Dideberg, and A. Dessen. 2006. Crystal structure of penicillin-binding protein 1a (PBP1a) reveals a mutational hotspot implicated in β-lactam resistance in Streptococcus pneumoniae. J. Mol. Biol. 355:684-696.
6. Dalhoff, A., N. Janjic, and R. Echols. 2006. Redefining penems. Biochem. Pharmacol. 71:1085-1095.
7. Davies, T. A., W. Shang, K. Bush, and R. K. Flamm. 2008. Activity of doripenem and comparator β-lactams against US clinical isolates of Streptococcus pneumoniae with defined mutations in the penicillin-binding domains of pbp1a, pbp2b and pbp2x. J. Antimicrob. Chemother. 61:751-753.
8. Dowson, C. G., T. J. Coffey, and B. G. Spratt. 1994. Origin and molecular epidemiology of penicillin-binding-protein-mediated resistance to β-lactam antibiotics. Trends Microbiol. 2:361-366.
9. Emsley, P., and K. Cowtan. 2004. Coot: model-building tools for molecular graphics. Acta Crystallogr. D Biol. Crystallogr. 60:2126-2132.
10. Garcia-Bustos, J., and A. Tomasz. 1990. A biological price of antibiotic resistance: major changes in the peptidoglycan structure of penicillin-resistant pneumococci. Proc. Natl. Acad. Sci. USA 87:5415-5419.
11. Goa, K. L., and S. Noble. 2003. Panipenem/betamipron. Drugs 63:913-925.
12. Goffin, C., and J. M. Ghuysen. 1998. Multimodular penicillin-binding proteins: an enigmatic family of orthologs and paralogs. Microbiol. Mol. Biol. Rev. 62:1079-1093.
13. Gordon, E., N. Mouz, E. Duée, and O. Dideberg. 2000. The crystal structure of the penicillin-binding protein 2x from Streptococcus pneumoniae and its acyl-enzyme form: implication in drug resistance. J. Mol. Biol. 299:477-485.
14. Hikida, M., K. Itahashi, A. Igarashi, T. Shiba, and M. Kitamura. 1999. In vitro antibacterial activity of LJC 11,036, an active metabolite of L-084, a new oral carbapenem antibiotic with potent antipneumococcal activity. Antimicrob. Agents Chemother. 43:2010-2016.
15. Imuta, M., H. Itani, H. Ona, Y. Hamada, S. Uyeo, and T. Yoshida. 1991. Carbapenem and penem antibiotics. VI. Synthesis and antibacterial activity of 2-heteroaromatic-thiomethyl and 2-carbamoyloxymethyl 1-methylcarbapenems. Chem. Pharm. Bull. (Tokyo) 39:663-671.
16. Isoda, T., H. Ushirogochi, K. Satoh, T. Takasaki, I. Yamamura, C. Sato, A. Mihira, T. Abe, S. Tamai, S. Yamamoto, T. Kumagai, and Y. Nagao. 2006. Syntheses and pharmacokinetic studies of prodrug esters for the development of oral carbapenem, L-084. J. Antibiot. (Tokyo) 59:241-247.
17. Job, V., A. M. Di Guilmi, L. Martin, T. Vernet, O. Dideberg, and A. Dessen. 2003. Structural studies of the transpeptidase domain of PBP1a from Streptococcus pneumoniae. Acta Crystallogr. D Biol. Crystallogr. 59:1067-1069.
18. Josephine, H. R., P. Charlier, C. Davies, R. A. Nicholas, and R. F. Pratt. 2006. Reactivity of penicillin-binding proteins with peptidoglycan-mimetic β-lactams: what's wrong with these enzymes? Biochemistry 45:15873-15883.
19. Keating, G. M., and C. M. Perry. 2005. Ertapenem: a review of its use in the treatment of bacterial infections. Drugs 65:2151-2178.
20. Kobayashi, R., M. Konomi, K. Hasegawa, M. Morozumi, K. Sunakawa, and K. Ubukata. 2005. In vitro activity of tebipenem, a new oral carbapenem antibiotic, against penicillin-nonsusceptible Streptococcus pneumoniae. Antimicrob. Agents Chemother. 49:889-894.
21. Kumar, I., H. R. Josephine, and R. F. Pratt. 2007. Reactions of peptidoglycan-mimetic β-lactams with penicillin-binding proteins in vivo and in membranes. ACS Chem. Biol. 2:620-624.
22. Kumar, I., and R. F. Pratt. 2005. Transpeptidation reactions of a specific substrate catalyzed by the streptomyces R61 DD-peptidase: characterization of a chromogenic substrate and acyl acceptor design. Biochemistry 44:9971-9979.
23. Laskowski, R. A., M. W. MacArthur, D. S. Moss, and J. M. Thornton. 1993. PROCHECK: A program to check the stereochemical quality of protein structures. J. Appl. Crystallogr. 26:283-291.
24. Lee, W., M. A. McDonough, L. P. Kotra, Z. H. Li, N. R. Silvaggi, Y. Takeda, J. A. Kelly, and S. Mobashery. 2001. A 1.2-Å snapshot of the final step of bacterial cell wall biosynthesis. Proc. Natl. Acad. Sci. USA 98:1427-1431.
25. Lowe, M. N., and H. M. Lamb. 2000. Meropenem: an updated review of its use in the management of intra-abdominal infections. Drugs 60:619-646.
26. Macheboeuf, P., C. Contreras-Martel, V. Job, O. Dideberg, and A. Dessen. 2006. Penicillin binding proteins: key players in bacterial cell cycle and drug resistance processes. FEMS Microbiol. Rev. 30:673-691.
27. Macheboeuf, P., A. M. Di Guilmi, V. Job, T. Vernet, O. Dideberg, and A. Dessen. 2005. Active site restructuring regulates ligand recognition in class A penicillin-binding proteins. Proc. Natl. Acad. Sci. USA 102:577-582.
28. McDonough, M. A., J. W. Anderson, N. R. Silvaggi, R. F. Pratt, J. R. Knox, and J. A. Kelly. 2002. Structures of two kinetic intermediates reveal species specificity of penicillin-binding proteins. J. Mol. Biol. 322:111-122.
29. Murshudov, G. N., A. A. Vagin, and E. J. Dodson. 1997. Refinement of macromolecular structures by the maximum-likelihood method. Acta Crystallogr. D Biol. Crystallogr. 53:240-255.
30. Nagao, Y., Y. Nagase, T. Kumagai, H. Matsunaga, T. Abe, O. Shimada, T. Hayashi, and Y. Inoue. 1992. β-Lactams. 3. Asymmetric total synthesis of new non-natural 1β-methylcarbapenems exhibiting strong antimicrobial activities and stability against human renal dehydropeptidase-I. J. Org. Chem. 57:4243-4249.
31. Nishio, M., M. Hirota, and Y. Umezawa. 1998. The CH/π interaction: evidence, nature, and consequences. WILEY-VCH, New York, NY.
32. Pares, S., N. Mouz, Y. Pétillot, R. Hakenbeck, and O. Dideberg. 1996. X-ray structure of Streptococcus pneumoniae PBP2x, a primary penicillin target enzyme. Nat. Struct. Biol. 3:284-289.
33. Perry, C. M., and T. Ibbotson. 2002. Biapenem. Drugs 62:2221-2234.
34. Rodloff, A. C., E. J. Goldstein, and A. Torres. 2006. Two decades of imipenem therapy. J. Antimicrob. Chemother. 58:916-929.
35. Sanbongi, Y., T. Ida, M. Ishikawa, Y. Osaki, H. Kataoka, T. Suzuki, K. Kondo, F. Ohsawa, and M. Yonezawa. 2004. Complete sequences of six penicillin-binding protein genes from 40 Streptococcus pneumoniae clinical isolates collected in Japan. Antimicrob. Agents Chemother. 48:2244-2250.
36. Ubukata, K., M. Hikida, M. Yoshida, K. Nishiki, Y. Furukawa, K. Tashiro, M. Konno, and S. Mitsuhashi. 1990. In vitro activity of LJC10,627, a new carbapenem antibiotic with high stability to dehydropeptidase I. Antimicrob. Agents Chemother. 34:994-1000.
37. Vagin, A., and A. Teplyakov. 1997. MOLREP: an automated program for molecular replacement. J. Appl. Cryst. 30:1022-1025.
38. Yamada, M., T. Watanabe, T. Miyara, N. Baba, J. Saito, Y. Takeuchi, and F. Ohsawa. 2007. Crystal structure of cefditoren complexed with Streptococcus pneumoniae penicillin-binding protein 2X: structural basis for its high antimicrobial activity. Antimicrob. Agents Chemother. 51:3902-3907.
39. Zhao, G., T. I. Meier, J. Hoskins, and K. A. McAllister. 2000. Identification and characterization of the penicillin-binding protein 2a of Streptococcus pneumoniae and its possible role in resistance to β-lactam antibiotics. Antimicrob. Agents Chemother. 44:1745-1748.