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[β-环糊精对梭曼的失活作用]

[Inactivation of soman by beta-cyclodextrin].

作者信息

Saint-André S, Désiré B

出版信息

C R Acad Sci III. 1985;301(3):67-72.

PMID:3930009
Abstract

Soman (pinacolyl methylphosphonofluoridate), a mixture of four stereoisomers, is inactivated appreciably in Tris buffer, pH 7.40, mu = 0.155 at 25 degrees C by beta-cyclodextrin (cycloheptaamylose, beta-CD). Under these conditions, the dissociation constant Kd of the 1:1 complex formed by beta-CD and soman and the rate constant k2 for the phosphonylation of beta-CD by soman are (0.53 +/- 0.05)mM and (5.9 +/- 0.6) X 10(-2) min-1 respectively. It results that the inactivation of soman by the mono-anion of beta-CD is about 2,600 times faster than the hydrolysis of soman by the hydroxide ion. The inactivation of both P(-) isomers of soman by beta-CD proceeds apparently at the same rate but both P(+) isomers react more slowly. Thus the interaction is stereospecific. The inactivation of soman by beta-CD appears to be as fast in human plasma in vitro as in Tris buffer.

摘要

梭曼(频哪基甲基膦酰氟)是四种立体异构体的混合物,在25℃、pH值为7.40、离子强度μ = 0.155的Tris缓冲液中,可被β-环糊精(环庚糖,β-CD)显著灭活。在这些条件下,β-环糊精与梭曼形成的1:1复合物的解离常数Kd以及梭曼对β-环糊精进行膦酰化反应的速率常数k2分别为(0.53 ± 0.05)mM和(5.9 ± 0.6)×10⁻² min⁻¹。结果表明,β-环糊精的单阴离子对梭曼的灭活作用比氢氧根离子对梭曼的水解作用快约2600倍。β-环糊精对梭曼的两种P(-)异构体的灭活作用显然以相同速率进行,但两种P(+)异构体的反应较慢。因此,这种相互作用具有立体特异性。在体外,β-环糊精对梭曼的灭活作用在人血浆中似乎与在Tris缓冲液中一样快。

相似文献

1
[Inactivation of soman by beta-cyclodextrin].[β-环糊精对梭曼的失活作用]
C R Acad Sci III. 1985;301(3):67-72.
2
Interaction of soman with beta-cyclodextrin.梭曼与β-环糊精的相互作用。
Fundam Appl Toxicol. 1986 Nov;7(4):646-57.
3
Inactivation of sarin and soman by cyclodextrins in vitro.环糊精在体外对沙林和梭曼的灭活作用。
Experientia. 1987 Apr 15;43(4):395-7. doi: 10.1007/BF01940424.
4
Absorption, distribution, excretion and metabolism of orally administered 14C-beta-cyclodextrin in rat.大鼠口服14C-β-环糊精后的吸收、分布、排泄及代谢
Arzneimittelforschung. 1985;35(7):1042-7.
5
Intestinal absorption of 14C-labelled beta-cyclodextrin in rats.大鼠对14C标记的β-环糊精的肠道吸收
Arzneimittelforschung. 1980;30(5):808-10.
6
Separation of cefoperazone enantiomers using beta-cyclodextrin as chiral additive by capillary zone electrophoresis.以β-环糊精为手性添加剂,采用毛细管区带电泳法分离头孢哌酮对映体。
Chirality. 2004 Jan;16(1):45-9. doi: 10.1002/chir.10305.
7
Binding and hydrolysis of soman by human serum albumin.人血清白蛋白对梭曼的结合与水解作用
Chem Res Toxicol. 2008 Feb;21(2):421-31. doi: 10.1021/tx700339m. Epub 2007 Dec 29.
8
Internalization of cycloheptaamylose-dansyl chloride complex during labelling of surface membrane in living Paramecium aurelia cells.在活体草履虫细胞表面膜标记过程中环糊精-丹磺酰氯复合物的内化
Basic Appl Histochem. 1985;29(2):121-33.
9
Thermal and pH stability of "beta-benzyme".“β - 本酶”的热稳定性和pH稳定性
Proc Natl Acad Sci U S A. 1987 Feb;84(3):673-4. doi: 10.1073/pnas.84.3.673.
10
Direct detection of stereospecific soman hydrolysis by wild-type human serum paraoxonase.野生型人血清对氧磷酶对立体特异性梭曼水解的直接检测。
FEBS J. 2007 Mar;274(5):1183-91. doi: 10.1111/j.1742-4658.2006.05650.x. Epub 2007 Feb 5.

引用本文的文献

1
Structure-efficiency relationships of cyclodextrin scavengers in the hydrolytic degradation of organophosphorus compounds.环糊精清除剂在有机磷化合物水解降解中的结构-效率关系
Beilstein J Org Chem. 2017 Mar 6;13:417-427. doi: 10.3762/bjoc.13.45. eCollection 2017.
2
Interactions of cyclodextrins and their derivatives with toxic organophosphorus compounds.环糊精及其衍生物与有毒有机磷化合物的相互作用。
Beilstein J Org Chem. 2016 Feb 5;12:204-28. doi: 10.3762/bjoc.12.23. eCollection 2016.
3
Inactivation of sarin and soman by cyclodextrins in vitro.
环糊精在体外对沙林和梭曼的灭活作用。
Experientia. 1987 Apr 15;43(4):395-7. doi: 10.1007/BF01940424.