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
[1]   PHOTOSENSITIVE PROTECTING GROUPS OF AMINO-SUGARS AND THEIR USE IN GLYCOSIDE SYNTHESIS - 2-NITROBENZYLOXYCARBONYLAMINO AND 6-NITROVERATRYLOXYCARBONYLAMINO DERIVATIVES [J].
AMIT, B ;
ZEHAVI, U ;
PATCHORN.A .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (02) :192-196
[2]  
ARLTROP JA, 1966, CHEM COMMUN, P822
[3]  
Bush K, 1998, ADV EXP MED BIOL, V456, P71
[4]   Light-activated proteins [J].
Curley, K ;
Lawrence, DS .
CURRENT OPINION IN CHEMICAL BIOLOGY, 1999, 3 (01) :84-88
[5]   ABSENCE OF AN ALPHA-EFFECT IN THE GAS-PHASE NUCLEOPHILIC REACTIONS OF HOO- [J].
DEPUY, CH ;
DELLA, EW ;
FILLEY, J ;
GRABOWSKI, JJ ;
BIERBAUM, VM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (08) :2481-2482
[6]   STEREOSELECTIVE AMINATION OF CHIRAL ENOLATES - A NEW APPROACH TO THE ASYMMETRIC-SYNTHESIS OF ALPHA-HYDRAZINO AND ALPHA-AMINO-ACID DERIVATIVES [J].
EVANS, DA ;
BRITTON, TC ;
DOROW, RL ;
DELLARIA, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6395-6397
[7]   ASYMMETRIC-SYNTHESIS OF THE ENKEPHALINASE INHIBITOR THIORPHAN [J].
EVANS, DA ;
MATHRE, DJ ;
SCOTT, WL .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (11) :1830-1835
[8]   ELIMINATION OF A GOOD LEAVING GROUP FROM THE 3'-POSITION OF A CEPHALOSPORIN NEED NOT BE CONCERTED WITH BETA-LACTAM RING-OPENING - TEM-2 BETA-LACTAMASE-CATALYZED HYDROLYSIS OF PYRIDINE-2-AZO-4'-(N',N'-DIMETHYLANILINE) CEPHALOSPORIN (PADAC) AND OF CEPHALORIDINE [J].
FARACI, WS ;
PRATT, RF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (05) :1489-1490
[9]   Brominated 7-hydroxycoumarin-4-ylmethyls: Photolabile protecting groups with biologically useful cross-sections for two photon photolysis [J].
Furuta, T ;
Wang, SSH ;
Dantzker, JL ;
Dore, TM ;
Bybee, WJ ;
Callaway, EM ;
Denk, W ;
Tsien, RY .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (04) :1193-1200
[10]   Desyl esters of amino acid neurotransmitters. Phototriggers for biologically active neurotransmitters [J].
Gee, KR ;
Kueper, LW ;
Barnes, J ;
Dudley, G ;
Givens, RS .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (04) :1228-1233