The synthesis of 7-substituted-3-dinitrostyryl cephalosporins and their ability for detecting extended spectrum beta-lactamases (ESBLs)

Hideaki Hanaki; Hiroaki Yamazaki; Hidenori Harada; Ryoichi Kubo; Takayoshi Kobayashi; Koichiro Atsuda; Keisuke Sunakawa

doi:10.1038/ja.2005.9

The synthesis of 7-substituted-3-dinitrostyryl cephalosporins and their ability for detecting extended spectrum beta-lactamases (ESBLs)

J Antibiot (Tokyo). 2005 Jan;58(1):69-73. doi: 10.1038/ja.2005.9.

Authors

Hideaki Hanaki¹, Hiroaki Yamazaki, Hidenori Harada, Ryoichi Kubo, Takayoshi Kobayashi, Koichiro Atsuda, Keisuke Sunakawa

Affiliation

¹ Research Center for Anti-infective Drugs, Kitasato Institure, Minato-ku, Tokyo 108-8641, Japan.

PMID: 15813184
DOI: 10.1038/ja.2005.9

Abstract

We synthesized 7-substituted-3-(2,4-dinitrostyryl)cephalosporin derivatives which were Nitrocefin analogs, for detecting extended spectrum beta-lactamase (ESBL) specifically. HMRZ-86 which has carboxypropyloxyimino group on 7-aminothiazolacetamide substituent were not hydrolyzed by class A, C and D beta-lactamases, but it was hydrolyzed by ESBL and metallo beta-lactamase (class B), then its color changed from yellow to red. The hydrolysis of metallo beta-lactamase was inhibited by adding sodium mercapto acetic acid (SMA). Therefore HMRZ-86 is a useful chromogenic agent to detect ESBL specifically.

MeSH terms

Cephalosporins / chemical synthesis*
Cephalosporins / chemistry
Cephalosporins / pharmacology
Color
Hydrolysis / drug effects
Microbial Sensitivity Tests
Structure-Activity Relationship
beta-Lactamases / drug effects*

Substances

Cephalosporins
HMRZ 86
beta-Lactamases