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博来霉素中古洛糖-甘露糖部分在铁-分子氧复合物激活中的作用。

The role of the gulose-mannose part of bleomycin in activation of iron-molecular oxygen complexes.

作者信息

Kénani A, Bailly C, Helbecque N, Catteau J P, Houssin R, Bernier J L, Hénichart J P

机构信息

Unité INSERM N. 16, Lille, France.

出版信息

Biochem J. 1988 Jul 15;253(2):497-504. doi: 10.1042/bj2530497.

DOI:10.1042/bj2530497
PMID:2460080
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1149325/
Abstract

A comparison of the complexing properties of metal ions and O2 activation by bleomycin-A2 (BLM-A2) and deglyco-BLM-A2 is presented. Deglyco-BLM-A2 is obtained from the parent derivative by HF cleavage of the sugar moiety followed by h.p.l.c. purification. Complexing of Cu(II) and Fe(III) is studied by using c.d. and e.s.r. spectroscopy. Spin-trapping experiments in the presence of phenyl N-t-butylnitrone indicated lower production of free radicals by deglyco-BLM-A2. Finally, a proposal is made to explain this discrepancy, focusing on the probable role of the gulose-mannose moiety acting as a protecting pocket, comparable with the pocket and picket-fence porphyrins described for haemoproteins.

摘要

本文介绍了博来霉素A2(BLM-A2)和去糖基博来霉素A2的金属离子络合特性及O2活化的比较。去糖基博来霉素A2是通过对母体衍生物的糖部分进行HF裂解,然后进行高效液相色谱纯化而得到的。通过圆二色光谱(c.d.)和电子自旋共振光谱(e.s.r.)研究了Cu(II)和Fe(III)的络合情况。在苯基N-叔丁基硝酮存在下的自旋捕获实验表明,去糖基博来霉素A2产生的自由基较少。最后,提出了一个解释这种差异的建议,重点关注古洛糖-甘露糖部分可能作为保护口袋的作用,这与血红蛋白中描述的口袋和栅栏卟啉类似。

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The role of the gulose-mannose part of bleomycin in activation of iron-molecular oxygen complexes.博来霉素中古洛糖-甘露糖部分在铁-分子氧复合物激活中的作用。
Biochem J. 1988 Jul 15;253(2):497-504. doi: 10.1042/bj2530497.
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本文引用的文献

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The iron-oxygen bond in human oxyhaemoglobin.
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Iron-bleomycin-deoxyribonucleic acid system. Evidence of deoxyribonucleic acid interaction with the alpha-amino group of the beta-aminoalanine moiety.
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Synthetic analogues and biosynthetic intermediates of bleomycin. Metal-binding, dioxygen interaction, and implication for the role of functional groups in bleomycin action mechanism.
J Biol Chem. 1983 Jan 25;258(2):1328-36.
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Deglyco-bleomycin. Degradation of DNA and formation of a structurally unique Fe(II) . CO complex.
J Biol Chem. 1982 Feb 25;257(4):1606-9.
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Activated bleomycin. A transient complex of drug, iron, and oxygen that degrades DNA.活化博来霉素。一种由药物、铁和氧形成的短暂复合物,可降解DNA。
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Structural implications derived from the analysis of electron paramagnetic resonance spectra of natural and artificial copper proteins.通过对天然和人工铜蛋白的电子顺磁共振光谱分析得出的结构含义。
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The chemistry of bleomycin. 8. The structure of the sugar moiety of bleomycin A 2 .博来霉素的化学。8. 博来霉素A2糖部分的结构。
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9
Copper(I)-bleomycin: structurally unique complex that mediates oxidative DNA strand scission.
Biochemistry. 1985 Jan 1;24(1):81-92. doi: 10.1021/bi00322a013.
10
Copper(II)- and iron(II)-complexes of methyl 2-(2-aminoethyl)-aminomethyl-pyridine-6-carboxyl-histidinate (AMPHIS), a peptide mimicking the metal-chelating moiety of bleomycin. An ESR investigation.2-(2-氨基乙基)-氨基甲基-吡啶-6-羧基组氨酸甲酯(AMPHIS)的铜(II)和铁(II)配合物,一种模拟博来霉素金属螯合部分的肽。电子自旋共振研究。
Biochem Biophys Res Commun. 1985 Feb 15;126(3):1036-41. doi: 10.1016/0006-291x(85)90289-x.