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铜与青霉胺的红紫色络合物的性质及其形成反应的进一步深入研究

Properties of the red - violet complex of copper and penicillamine and further insight into its formation reaction.

作者信息

Wright J R, Frieden E

出版信息

Bioinorg Chem. 1975 Jan;4(2):163-75. doi: 10.1016/s0006-3061(00)81025-x.

DOI:10.1016/s0006-3061(00)81025-x
PMID:1125331
Abstract

A characteristic red-violet chromophore which forms in the reaction of cupric ion with beta-sulfhydryl- alpha-amino acids has been attributed by several authors to a mixed-valence Cu3L2 structure. We have isolated and examined the analogous chromophore of the chelating drug penicillamine (beta, beta-dimethyl-cysteine), finding instead a polymeric anion with a mixed valence Cu2L2 repeating unit. Direct evidence for a mixed valence polymer cooroborates earlier conclusions of Wilson and Martin (9). Under oxygen-free conditions the anionic complex forms in essentially quantitative yield according to the following reaction: (see article). It has been established that this reaction is halide ion-dependent. The chromophore may be isolated as a sodium salt. This form was found to be stable, and it possessed no measurable activity as an oxidation catalyst. It was also demonstrated through biological experiments with rabbits that a significant amount of the complex- (between 6 percent and 39 percent) is recovered in the urinary tract following intravenous infusions attaining between 1.8 and 10 ppm copper.

摘要

几位作者认为,铜离子与β-巯基-α-氨基酸反应中形成的特征性红紫色发色团归因于混合价态的Cu3L2结构。我们分离并研究了螯合药物青霉胺(β,β-二甲基半胱氨酸)的类似发色团,结果发现是具有混合价态Cu2L2重复单元的聚合阴离子。混合价态聚合物的直接证据证实了威尔逊和马丁(9)早期的结论。在无氧条件下,阴离子络合物基本上以定量产率根据以下反应形成:(见文章)。已经确定该反应依赖于卤离子。发色团可以分离为钠盐。发现这种形式是稳定的,并且作为氧化催化剂没有可测量的活性。通过对兔子的生物学实验还表明,静脉输注达到1.8至10 ppm铜后,大量的络合物(6%至39%)在尿路中被回收。

相似文献

1
Properties of the red - violet complex of copper and penicillamine and further insight into its formation reaction.铜与青霉胺的红紫色络合物的性质及其形成反应的进一步深入研究
Bioinorg Chem. 1975 Jan;4(2):163-75. doi: 10.1016/s0006-3061(00)81025-x.
2
Complexes of sulfur-containing ligands. I. Factors influencing complex formation between D-penicillamine and copper (II) ion.含硫配体配合物。I. 影响D-青霉胺与铜(II)离子形成配合物的因素。
Bioinorg Chem. 1978 Jul;9(1):47-60. doi: 10.1016/s0006-3061(00)82005-0.
3
Molecular biology of copper. A circular dichroism study on copper complexes of thionein and penicillamine.铜的分子生物学。硫蛋白和青霉胺铜配合物的圆二色性研究。
Hoppe Seylers Z Physiol Chem. 1975 Jun;356(6):755-65. doi: 10.1515/bchm2.1975.356.s1.755.
4
Urinary chelates in penicillamine-induced cupuresis. Negative evidence for the involvement of a red-violet complex of copper and penicillamine in rabbits.青霉胺诱导的尿铜排泄中的尿螯合物。关于兔体内铜与青霉胺的红紫色复合物参与作用的阴性证据。
Physiol Chem Phys. 1976;8(4):337-41.
5
The formation and nature of the mixed valence copper-D-penicillamine-chloride cluster in aqueous solution and its relevance to the treatment of Wilson's disease.
J Inorg Biochem. 1979 Nov;11(3):229-39. doi: 10.1016/s0162-0134(00)80020-3.
6
Effects of oxygen-derived free radicals on connective tissue macromolecules: inhibition by copper-penicillamine complex.氧衍生自由基对结缔组织大分子的影响:铜-青霉胺复合物的抑制作用。
J Rheumatol Suppl. 1981 Jan-Feb;7:9-13.
7
The intravenous distribution of a radiolabeled, potentially useful cluster ion of copper and penicillamine.一种放射性标记的、可能有用的铜与青霉胺簇离子的静脉内分布。
Physiol Chem Phys Med NMR. 1986;18(1):37-40.
8
An investigation into copper catalyzed D-penicillamine oxidation and subsequent hydrogen peroxide generation.关于铜催化D-青霉胺氧化及随后过氧化氢生成的研究。
J Inorg Biochem. 2007 Apr;101(4):594-602. doi: 10.1016/j.jinorgbio.2006.12.007. Epub 2006 Dec 20.
9
Synthesis and possible applications of biotin-linked copper clusters.生物素连接的铜簇合物的合成及其可能的应用
Physiol Chem Phys Med NMR. 1990;22(2):63-72.
10
D-Penicillamine: analysis of the mechanism of copper-catalyzed hydrogen peroxide generation.D-青霉胺:铜催化过氧化氢生成机制的分析
J Immunol. 1985 May;134(5):3371-8.

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Biodistribution of 64Cu in inflamed rats following administration of two anti-inflammatory copper complexes.两种抗炎铜配合物给药后64Cu在炎症大鼠体内的生物分布
Agents Actions. 1985 Oct;17(1):104-11. doi: 10.1007/BF01966692.
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A comparative study of in vitro and in vivo interaction of D-penicillamine and triethylenetetramine with copper.
D-青霉胺和三亚乙基四胺与铜的体外和体内相互作用的比较研究。
Proc R Soc Med. 1977;70 Suppl 3(Suppl 3):13-8. doi: 10.1177/00359157770700S307.