Interactions of Biapenem with Active-site Serine and Metallo-beta-lactamases

Overview

Journal Antimicrob Agents Chemother

Publisher American Society for Microbiology

Specialty Pharmacology

Date 1995 Jun 1

PMID 7574520

Citations 6

Authors

A Felici

M Perilli

B Segatore

N Franceschini

D Setacci

A Oratore

S Stefani

M Galleni

G Amicosante

Affiliations

Soon will be listed here.

Abstract

Biapenem, formerly LJC 10,627 or L-627, a carbapenem antibiotic, was studied in its interactions with 12 beta-lactamases belonging to the four molecular classes proposed by R. P. Ambler (Philos. Trans. R. Soc. Lond. Biol. Sci. 289:321-331, 1980). Kinetic parameters were determined. Biapenem was readily inactivated by metallo-beta-lactamases but behaved as a transient inhibitor of the active-site serine enzymes tested, although with different acylation efficiency values. Class A and class D beta-lactamases were unable to confer in vitro resistance toward this carbapenem antibiotic. Surprisingly, the same situation was found in the case of class B enzymes from Aeromonas hydrophila AE036 and Bacillus cereus 5/B/6 when expressed in Escherichia coli strains.

Citing Articles

Studies on ternary metallo-beta lactamase-inhibitor complexes using electrospray ionization mass spectrometry.

Selevsek N, Tholey A, Heinzle E, Lienard B, Oldham N, Schofield C J Am Soc Mass Spectrom. 2006; 17(7):1000-4.

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Biapenem.

Perry C, Ibbotson T Drugs. 2002; 62(15):2221-34; discussion 2235.

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Probing substrate binding to metallo-beta-lactamase L1 from Stenotrophomonas maltophilia by using site-directed mutagenesis.

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Biochemical characterization of the Pseudomonas aeruginosa 101/1477 metallo-beta-lactamase IMP-1 produced by Escherichia coli.

LARAKI N, Franceschini N, Rossolini G, Santucci P, Meunier C, De Pauw E Antimicrob Agents Chemother. 1999; 43(4):902-6.

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Interactions of beta-lactamases with sanfetrinem (GV 104326) compared to those with imipenem and with oral beta-lactams.

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References

Bush K, Tanaka S, Bonner D, Sykes R . Resistance caused by decreased penetration of beta-lactam antibiotics into Enterobacter cloacae. Antimicrob Agents Chemother. 1985; 27(4):555-60. PMC: 180094. DOI: 10.1128/AAC.27.4.555. View

Cartwright S, WALEY S . Purification of beta-lactamases by affinity chromatography on phenylboronic acid-agarose. Biochem J. 1984; 221(2):505-12. PMC: 1144066. DOI: 10.1042/bj2210505. View

Cuchural Jr G, MALAMY M, Tally F . Beta-lactamase-mediated imipenem resistance in Bacteroides fragilis. Antimicrob Agents Chemother. 1986; 30(5):645-8. PMC: 176506. DOI: 10.1128/AAC.30.5.645. View

De Meester F, Joris B, Reckinger G, Frere J, WALEY S . Automated analysis of enzyme inactivation phenomena. Application to beta-lactamases and DD-peptidases. Biochem Pharmacol. 1987; 36(14):2393-403. DOI: 10.1016/0006-2952(87)90609-5. View

MONKS J, WALEY S . Imipenem as substrate and inhibitor of beta-lactamases. Biochem J. 1988; 253(2):323-8. PMC: 1149301. DOI: 10.1042/bj2530323. View

Amicosante G, Oratore A, Franceschini N, Maccarrone M, Strom R, Galleni M . Citrobacter diversus ULA-27 beta-lactamases. Improved purification and general properties. Biochem J. 1988; 254(3):885-90. PMC: 1135165. DOI: 10.1042/bj2540885. View

Galleni M, Amicosante G, Frere J . A survey of the kinetic parameters of class C beta-lactamases. Cephalosporins and other beta-lactam compounds. Biochem J. 1988; 255(1):123-9. PMC: 1135199. DOI: 10.1042/bj2550123. View

Fattorini L, Fiorentino D, Amicosante G, Franceschini N, Oratore A, Orefici G . Beta-lactamase production and biological characteristics in nitrosoguanidine induced Mycobacterium fortuitum mutants. Acta Leprol. 1989; 7 Suppl 1:44-7. View

Ubukata K, Hikida M, Yoshida M, Nishiki K, Furukawa Y, Tashiro K . In vitro activity of LJC10,627, a new carbapenem antibiotic with high stability to dehydropeptidase I. Antimicrob Agents Chemother. 1990; 34(6):994-1000. PMC: 171745. DOI: 10.1128/AAC.34.6.994. View

10.

Rasmussen B, Gluzman Y, Tally F . Cloning and sequencing of the class B beta-lactamase gene (ccrA) from Bacteroides fragilis TAL3636. Antimicrob Agents Chemother. 1990; 34(8):1590-2. PMC: 171878. DOI: 10.1128/AAC.34.8.1590. View

11.

Amicosante G, Franceschini N, Segatore B, Oratore A, Fattorini L, Orefici G . Characterization of a beta-lactamase produced in Mycobacterium fortuitum D316. Biochem J. 1990; 271(3):729-34. PMC: 1149623. DOI: 10.1042/bj2710729. View

12.

Watanabe M, Iyobe S, Inoue M, Mitsuhashi S . Transferable imipenem resistance in Pseudomonas aeruginosa. Antimicrob Agents Chemother. 1991; 35(1):147-51. PMC: 244956. DOI: 10.1128/AAC.35.1.147. View

13.

Massidda O, Rossolini G, Satta G . The Aeromonas hydrophila cphA gene: molecular heterogeneity among class B metallo-beta-lactamases. J Bacteriol. 1991; 173(15):4611-7. PMC: 208136. DOI: 10.1128/jb.173.15.4611-4617.1991. View

14.

Lee E, Nicolas M, Kitzis M, Pialoux G, Collatz E, Gutmann L . Association of two resistance mechanisms in a clinical isolate of Enterobacter cloacae with high-level resistance to imipenem. Antimicrob Agents Chemother. 1991; 35(6):1093-8. PMC: 284293. DOI: 10.1128/AAC.35.6.1093. View

15.

Hikida M, Kawashima K, Nishiki K, Furukawa Y, Nishizawa K, Saito I . Renal dehydropeptidase-I stability of LJC 10,627, a new carbapenem antibiotic. Antimicrob Agents Chemother. 1992; 36(2):481-3. PMC: 188463. DOI: 10.1128/AAC.36.2.481. View

16.

Yang Y, Rasmussen B, Bush K . Biochemical characterization of the metallo-beta-lactamase CcrA from Bacteroides fragilis TAL3636. Antimicrob Agents Chemother. 1992; 36(5):1155-7. PMC: 188856. DOI: 10.1128/AAC.36.5.1155. View

17.

Fukasawa M, Sumita Y, Harabe E, Tanio T, Nouda H, Kohzuki T . Stability of meropenem and effect of 1 beta-methyl substitution on its stability in the presence of renal dehydropeptidase I. Antimicrob Agents Chemother. 1992; 36(7):1577-9. PMC: 191626. DOI: 10.1128/AAC.36.7.1577. View

18.

Catchpole C, Wise R, Thornber D, Andrews J . In vitro activity of L-627, a new carbapenem. Antimicrob Agents Chemother. 1992; 36(9):1928-34. PMC: 192211. DOI: 10.1128/AAC.36.9.1928. View

19.

Livermore D . Interplay of impermeability and chromosomal beta-lactamase activity in imipenem-resistant Pseudomonas aeruginosa. Antimicrob Agents Chemother. 1992; 36(9):2046-8. PMC: 192435. DOI: 10.1128/AAC.36.9.2046. View

20.

Felici A, Amicosante G, Oratore A, Strom R, LEDENT P, Joris B . An overview of the kinetic parameters of class B beta-lactamases. Biochem J. 1993; 291 ( Pt 1):151-5. PMC: 1132494. DOI: 10.1042/bj2910151. View