THE COMPARATIVE INVITRO PHARMACOLOGY OF LEUKOTRIENE-D4 AND ITS ISOMERS

被引:24
作者
BAKER, SR
BOOT, JR
JAMIESON, WB
OSBORNE, DJ
SWEATMAN, WJF
机构
关键词
D O I
10.1016/0006-291X(81)90258-8
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
The 5R,6S and 5S,6R isomers of a component of slow reacting substance of anaphylaxis, leukotriene D4 (LTD4), 9-cis-LTD4, 9-cis, 11-trans-LTD4 and 11-trans-LTD4 were synthesized for comparative pharmacological studies on guinea pig intestinal and respiratory smooth muscle preparations. The 5S,6R isomers are biologically active, modification of the double bond stereochemistry causing only a moderate reduction in activity. The 5R,6S isomers possess approximately 1% the biological activity of their respective 5S,6R forms.
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页码:1258 / 1264
页数:7
相关论文
共 11 条
[1]   SELECTIVE INHIBITOR OF SLOW REACTING SUBSTANCE OF ANAPHYLAXIS [J].
AUGSTEIN, J ;
FARMER, JB ;
LEE, TB ;
SHEARD, P ;
TATTERSALL, ML .
NATURE-NEW BIOLOGY, 1973, 245 (146) :215-217
[2]   SYNTHESIS, SEPARATION AND NMR-SPECTRA OF 3 DOUBLE-BOND ISOMERS OF LEUKOTRIENE A METHYL-ESTER [J].
BAKER, SR ;
JAMIESON, WB ;
MCKAY, SW ;
MORGAN, SE ;
RACKHAM, DM ;
ROSS, WJ ;
SHRUBSALL, PR .
TETRAHEDRON LETTERS, 1980, 21 (42) :4123-4126
[3]   SPIRALLY CUT TRACHEAL STRIP PREPARATION [J].
CONSTANTINE, JW .
JOURNAL OF PHARMACY AND PHARMACOLOGY, 1965, 17 (06) :384-+
[4]   TOTAL SYNTHESIS OF SLOW REACTING SUBSTANCES (SRS) - LEUKOTRIENE C-2 (11-TRANS-LEUKOTRIENE-C)-(3) AND LEUKOTRIENE-D-(4) [J].
COREY, EJ ;
CLARK, DA ;
MARFAT, A ;
GOTO, G .
TETRAHEDRON LETTERS, 1980, 21 (33) :3143-3146
[5]   TOTAL SYNTHESIS OF SLOW REACTING SUBSTANCES (SRSS) - 6-EPI-LEUKOTRIENE-C AND 6-EPI-LEUKOTRIENE-D [J].
COREY, EJ ;
GOTO, G .
TETRAHEDRON LETTERS, 1980, 21 (36) :3463-3466
[6]   COMPARATIVE RESPONSES OF TRACHEAL SPIRALS AND PARENCHYMAL STRIPS TO HISTAMINE AND CARBACHOL INVITRO [J].
DRAZEN, JM ;
SCHNEIDER, MW .
JOURNAL OF CLINICAL INVESTIGATION, 1978, 61 (06) :1441-1447
[7]   SLOW REACTING SUBSTANCES OF ANAPHYLAXIS - IDENTIFICATION OF LEUKOTRIENES-C-1 AND LEUKOTRIENES-D FROM HUMAN AND RAT SOURCES [J].
LEWIS, RA ;
AUSTEN, KF ;
DRAZEN, JM ;
CLARK, DA ;
MARFAT, A ;
COREY, EJ .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1980, 77 (06) :3710-3714
[8]   IDENTIFICATION OF THE C(6)-S-CONJUGATE OF LEUKOTRIENE-A WITH CYSTEINE AS A NATURALLY-OCCURRING SLOW REACTING SUBSTANCE OF ANAPHYLAXIS (SRS-A) - IMPORTANCE OF THE 11-CIS-GEOMETRY FOR BIOLOGICAL-ACTIVITY [J].
LEWIS, RA ;
DRAZEN, JM ;
AUSTEN, KF ;
CLARK, DA ;
COREY, EJ .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1980, 96 (01) :271-277
[9]   SEMI-PREPARATIVE HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY AND SPECTROSCOPIC CHARACTERIZATION OF 8 GEOMETRIC ISOMERS OF LEUKOTRIENE-A METHYL-ESTER [J].
MCKAY, SW ;
MALLEN, DNB ;
SHRUBSALL, PR ;
SMITH, JM ;
BAKER, SR ;
JAMIESON, WB ;
ROSS, WJ ;
MORGAN, SE ;
RACKHAM, DM .
JOURNAL OF CHROMATOGRAPHY, 1981, 214 (02) :249-256
[10]  
MORRIS HR, 1980, PROSTAG OTH LIPID M, V20, P601, DOI 10.1016/0090-6980(80)90047-7