A light-inactivated antibiotic

被引:37
作者
Lee, WL [1 ]
Li, ZH [1 ]
Vakulenko, S [1 ]
Mobashery, S [1 ]
机构
[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
关键词
D O I
10.1021/jm980648a
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Sodium 7 beta-[(R)-2-(N-b-o-nitrobenzyloxycarbonyl)hydrazino-3-phenylpropanamido]cephalosporanate (1) is described as a new type of beta-lactam antibiotic, which undergoes light-induced destruction of its beta-lactam moiety and hence becomes biologically inactive. This type of antibiotic holds the promise of self-destruction over a number of hours of exposure to light, so that it would not allow selection of resistance in the environment.
引用
收藏
页码:128 / 132
页数:5
相关论文
共 29 条
[11]   AMMONOLYSIS OF CEPHAMYCINS - C-13 NMR CHARACTERIZATION OF THE INTERMEDIATES FROM BETA-LACTAM RING CLEAVAGE PRIOR TO LOSS OF THE 3'-GROUP [J].
GRABOWSKI, EJJ ;
DOUGLAS, AW ;
SMITH, GB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (01) :267-268
[12]   Model studies for new o-nitrobenzyl photolabile linkers: Substituent effects on the rates of photochemical cleavage [J].
Holmes, CP .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2370-2380
[13]   THE ALPHA EFFECT - ON THE ORIGIN OF TRANSITION-STATE STABILIZATION [J].
HOZ, S .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (18) :3545-3547
[14]  
Jones RN, 1985, Manual of clinical microbiology, V4th
[15]  
KLOPMAN G, 1984, CROAT CHEM ACTA, V57, P1411
[16]  
Levy S. B., 1992, ANTIBIOTIC PARADOX M, P143
[17]  
Levy SB, 1997, CIBA F SYMP, V207, P1
[18]  
MICETICH RG, 1985, SYNTHESIS-STUTTGART, P693
[19]  
MOBASHERY S, 1986, J BIOL CHEM, V261, P7879
[20]   BUFFER CATALYSIS IN THE HYDRAZINOLYSIS OF BENZYLPENICILLIN [J].
MORRIS, JJ ;
PAGE, MI .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1980, (01) :220-224