Amino acid-derived phthalimide and saccharin derivatives as inhibitors of human leukocyte elastase, cathepsin G, and proteinase 3

被引:27
作者
Groutas, WC [1 ]
Chong, LS [1 ]
Venkataraman, R [1 ]
Kuang, R [1 ]
Epp, JB [1 ]
HouserArchield, N [1 ]
Huang, H [1 ]
Hoidal, JR [1 ]
机构
[1] UNIV UTAH,HLTH SCI CTR,SCH MED,DIV RESP CRIT CARE & OCCUPAT MED,SALT LAKE CITY,UT 84132
关键词
D O I
10.1006/abbi.1996.0350
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Amino acid-derived phthalimide and saccharin derivatives have been investigated for their inhibitory activity toward the serine proteinases human leukocyte elastase, cathepsin G, and proteinase 3. The saccharin derivatives were found to be effective time-dependent inhibitors of elastase and proteinase 3 (k(obs)/[I] values ranged between 180 and 3620 M(-1) s(-1)) and showed weak or no inhibition toward cathepsin G. The corresponding phthalimide derivatives were found to be inactive. (C) 1996 Academic Press, Inc.
引用
收藏
页码:335 / 340
页数:6
相关论文
共 27 条
[1]  
Bernstein P R, 1994, Prog Med Chem, V31, P59, DOI 10.1016/S0079-6468(08)70019-5
[2]  
BODE W, 1986, EMBO J, V5, P2458
[3]   HUMAN NEUTROPHIL PROTEINASE-3 - MAPPING OF THE SUBSTRATE BINDING-SITE USING PEPTIDYL THIOBENZYL ESTERS [J].
BRUBAKER, MJ ;
GROUTAS, WC ;
HOIDAL, JR ;
RAO, NV .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1992, 188 (03) :1318-1324
[4]  
DORING G, 1994, AM J RESP CRIT CARE, V150, pS114
[5]   SYNTHETIC INHIBITORS OF ELASTASE [J].
EDWARDS, PD ;
BERNSTEIN, PR .
MEDICINAL RESEARCH REVIEWS, 1994, 14 (02) :127-194
[6]  
Groutas W C, 1993, Bioorg Med Chem, V1, P273, DOI 10.1016/S0968-0896(00)82132-X
[7]   INHIBITION OF HUMAN-LEUKOCYTE ELASTASE BY DERIVATIVES OF N-HYDROXYSUCCINIMIDE - A STRUCTURE ACTIVITY-RELATIONSHIP STUDY [J].
GROUTAS, WC ;
BRUBAKER, MJ ;
STANGA, MA ;
CASTRISOS, JC ;
CROWLEY, JP ;
SCHATZ, EJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) :1607-1611
[8]   POTENTIAL MECHANISM-BASED INHIBITORS OF PROTEOLYTIC-ENZYMES [J].
GROUTAS, WC ;
BRUBAKER, MJ ;
VENKATARAMAN, R ;
EPP, JB ;
HOUSERARCHIELD, N ;
CHONG, LS ;
MCCLENAHAN, JJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (02) :175-180
[9]   INHIBITORS OF HUMAN NEUTROPHIL CATHEPSIN-G - STRUCTURAL AND BIOCHEMICAL-STUDIES [J].
GROUTAS, WC ;
BRUBAKER, MJ ;
VENKATARAMAN, R ;
EPP, JB ;
STANGA, MA ;
MCCLENAHAN, JJ .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1992, 294 (01) :144-146
[10]   THE GABRIEL-COLMAN REARRANGEMENT IN BIOLOGICAL-SYSTEMS - DESIGN, SYNTHESIS AND BIOLOGICAL EVALUATION OF PHTHALIMIDE AND SACCHARIN DERIVATIVES AS POTENTIAL MECHANISM-BASED INHIBITORS OF HUMAN-LEUKOCYTE ELASTASE, CATHEPSIN-G AND PROTEINASE-3 [J].
GROUTAS, WC ;
CHONG, LS ;
VENKATARAMAN, R ;
EPP, JB ;
KUANG, R ;
HOUSERARCHIELD, N ;
HOIDAL, JR .
BIOORGANIC & MEDICINAL CHEMISTRY, 1995, 3 (02) :187-193