腺苷5'-O-(1-硫代二磷酸)的RP和SP非对映异构体对人血小板的作用。
Effects of RP and SP diastereoisomers of adenosine 5'-O-(1-thiodiphosphate) on human platelets.
作者信息
Cusack N J, Hourani S M
出版信息
Br J Pharmacol. 1981 Jun;73(2):409-12. doi: 10.1111/j.1476-5381.1981.tb10437.x.
Abstract
1 RP and SP diastereoisomers of adenosine 5'-O-(1-thiodiphosphate) ((R)-ADP-alpha-S and (S)-ADP-alpha-S), an adenosine 5'-diphosphate (ADP) analogue, were tested on intact human platelets. 2 Each diastereoisomer induced aggregation, (S)-ADP-alpha-S being 5 times more potent than (R)-ADP-alpha-S but they achieved only 75% of the maximal effect of ADP. 3 Aggregation induced by each diastereoisomer was competitively inhibited by ATP (50 microM). 4 Simultaneous addition of each diastereoisomer inhibited aggregation induced by ADP but not by 11 alpha, 9 alpha-epoxymethano prostaglandin H2, a stable endoperoxide analogue. Both diastereoisomers are therefore partial agonists at the ADP receptor mediating aggregation. 5 Unlike ADP, neither diastereoisomer inhibited prostaglandin E1 (PGE1)-stimulated adenylate cyclase, but each competitively inhibited the effect of aDP, with (S)-ADP-alpha-S again being 5 times more potent than (R)-ADP-alpha-S. 6 These are the first reported examples of ADP analogues to induce platelet aggregation without inhibiting PGE1-stimulated adenylate cyclase.
摘要
对腺苷5'-O-(1-硫代二磷酸)（(R)-ADP-α-S和(S)-ADP-α-S）的RP和SP非对映异构体（一种腺苷5'-二磷酸（ADP）类似物）在完整的人血小板上进行了测试。
每种非对映异构体均诱导聚集，(S)-ADP-α-S的效力比(R)-ADP-α-S高5倍，但它们仅达到ADP最大效应的75%。
每种非对映异构体诱导的聚集均受到ATP（50微摩尔）的竞争性抑制。
同时添加每种非对映异构体可抑制ADP诱导的聚集，但不抑制11α,9α-环氧甲撑前列腺素H2（一种稳定的内过氧化物类似物）诱导的聚集。因此，两种非对映异构体在介导聚集的ADP受体上均为部分激动剂。
与ADP不同，两种非对映异构体均不抑制前列腺素E1（PGE1）刺激的腺苷酸环化酶，但每种均竞争性抑制aDP的作用，(S)-ADP-α-S的效力再次比(R)-ADP-α-S高5倍。
这些是首次报道的不抑制PGE1刺激的腺苷酸环化酶而诱导血小板聚集的ADP类似物实例。
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本文引用的文献
1
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Nature. 1961 Nov 11;192:531-2. doi: 10.1038/192531a0.
2
Partial agonist behaviour of adenosine 5'-O-(2-thiodiphosphate) on human platelets.腺苷5'-O-(2-硫代二磷酸)对人血小板的部分激动剂行为。
Br J Pharmacol. 1981 Jun;73(2):405-8. doi: 10.1111/j.1476-5381.1981.tb10436.x.
3
Effect of the rapid shape change of platelets on the transmission and scattering of light through plasma.血小板快速形状变化对光在血浆中传播和散射的影响。
Nat New Biol. 1971 Jun 16;231(24):220-2. doi: 10.1038/newbio231220a0.
4
Interactions of the pharmacological receptors of blood platelets with adenylate cyclase.血小板的药理受体与腺苷酸环化酶的相互作用。
Ser Haematol. 1973;6(3):333-50.
5
High-pressure liquid chromatography of modified purine mononucleotides and nucleosides.修饰嘌呤单核苷酸和核苷的高压液相色谱法
J Chromatogr. 1973 Aug 29;83:395-404. doi: 10.1016/s0021-9673(00)97056-0.
6
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Proc Natl Acad Sci U S A. 1978 Oct;75(10):4798-800. doi: 10.1073/pnas.75.10.4798.
7
Prostaglandin receptors on human platelets. Structure-activity relationships of stimulatory prostaglandins.人血小板上的前列腺素受体。刺激性前列腺素的构效关系。
Biochem J. 1978 Sep 15;174(3):921-9. doi: 10.1042/bj1740921.
8
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Biochemistry. 1976 Apr 20;15(8):1685-91. doi: 10.1021/bi00653a015.
9
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