ANTIMICROBIAL PROPERTIES OF N-3-(IODOACETYL)-L-2,3-DIAMINOPROPANOIC ACID PEPTIDE CONJUGATES

被引:16
作者
ANDRUSZKIEWICZ, R
CHMARA, H
MILEWSKI, S
ZIENIAWA, T
BOROWSKI, E
机构
[1] Department of Pharmaceutical Technology and Biochemistry, Technical University of Gdansk
关键词
D O I
10.1021/jm00172a012
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Six peptide conjugates consisting of either norvaline, methionine, or lysine and A3-(iodoacetyl)-L-2,3-diaminopropanoic acid—a strong, irreversible inactivator of bacterial and fungal glucosamine-6-phosphate synthase—were synthesized and their antibacterial and antifungal activities were evaluated. Antimicrobial potencies of these peptides were correlated with their transport and cleavage rates inside the cells. Bacteriolysis of Bacillus pumilus cells and inhibition of [14C]glucose incorporation into cell-wall polysaccharides of Candida albicans as a result of glucosamine 6-phosphate inactivation were also observed. Reversal of growth inhibitory effect of these peptides by N-acetylglucosamine in bacteria and fungi suggests the effective delivery of 3-iodoacetyl-L-2,3-diaminopropanoic acid into the cell by a peptide-transport system. © 1990, American Chemical Society. All rights reserved.
引用
收藏
页码:2755 / 2759
页数:5
相关论文
共 21 条
[1]   ILLICIT TRANSPORT - OLIGOPEPTIDE PERMEASE [J].
AMES, BN ;
FERROLUZ.G ;
YOUNG, JD ;
TSUCHIYA, D ;
LECOCQ, J .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1973, 70 (02) :456-458
[2]   USE OF ESTERS OF N-HYDROXYSUCCINIMIDE IN PEPTIDE SYNTHESIS [J].
ANDERSON, GW ;
CALLAHAN, FM ;
ZIMMERMAN, JE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (09) :1839-+
[3]   SYNTHESIS AND BIOLOGICAL PROPERTIES OF N-3-(4-METHOXYFUMAROYL)-L-2,3-DIAMINOPROPANOIC ACID DIPEPTIDES, A NOVEL GROUP OF ANTIMICROBIAL AGENTS [J].
ANDRUSZKIEWICZ, R ;
CHMARA, H ;
MILEWSKI, S ;
BOROWSKI, E .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (10) :1715-1719
[4]   ANTICANDIDAL PROPERTIES OF N-3-(4-METHOXYFUMAROYL)-L-2,3-DIAMINOPROPANOIC ACID OLIGOPEPTIDES [J].
ANDRUSZKIEWICZ, R ;
MILEWSKI, S ;
ZIENIAWA, T ;
BOROWSKI, E .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (01) :132-135
[5]  
ANDRUSZKIEWICZ R, 1987, 9TH POL PEPT S WARSZ, P52
[6]  
BOISVERT W, 1986, J BIOL CHEM, V261, P7871
[7]  
CHMARA H, 1986, ACTA MICROBIOL POL, V35, P15
[8]   TRANSPORT OF IMPERMEANT SUBSTANCES IN ESCHERICHIA-COLI BY WAY OF OLIGOPEPTIDE PERMEASE [J].
FICKEL, TE ;
GILVARG, C .
NATURE-NEW BIOLOGY, 1973, 241 (110) :161-163
[9]  
GOPAL P, 1984, J GEN MICROBIOL, V130, P325
[10]   TRIGGERING OF AUTOLYTIC CELL-WALL DEGRADATION IN ESCHERICHIA-COLI BY BETA-LACTAM ANTIBIOTICS [J].
KITANO, K ;
TOMASZ, A .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1979, 16 (06) :838-848