Bilirubin oxidation products (BOXes): synthesis, stability and chemical characteristics.
Bilirubin oxidation products (BOXes): synthesis, stability and chemical characteristics.
复制标题
胆红素氧化产物 (BOX)：合成、稳定性和化学特性。
DOI：
10.1007/978-3-211-75718-5_8
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发表时间：
2008
期刊：
影响因子：
--
通讯作者：
Clark,JF
中科院分区：
文献类型：
--
作者：
Wurster,WL;Pyne-Geithman,GJ;Peat,IR;Clark,JF
胆红素氧化产物（BOX）是神经外科研究的一个热点，因为它们与蛛网膜下腔出血引起的脑血管痉挛有关。关于BOXes在血管痉挛中的作用的信息越来越多，然而，关于BOXes的化学和生物化学特征的信息却很少。更清楚地了解BOXes的合成、稳定性和特性对于更好地理解BOXes在蛛网膜下腔出血后的作用将是重要的。使用常规方法如HPLC和质谱法提取和分析BOX。BOXes稳定性的表征表明，光可以光降解BOXes，t1/2高达10 h，这取决于条件。BOXes的混合异构体的表观消光系数为ε= 6985，λ max为310 nm。BOXes是通过胆红素氧化产生的，产生异构体混合物：4-甲基-5-氧代-3-乙烯基-（1，5-二氢吡咯-2-亚基）乙酰胺（BOX A）和3-甲基-5-氧代-4-乙烯基-（1，5-二氢吡咯-2-亚基）乙酰胺（BOX B）。BOX在环境光下发生光降解，可以通过消光系数进行光度分析，也可以通过HPLC或质谱法进行分析。它们的小分子量和光降解可能使它们难以在以前的研究中表征。
Bilirubin oxidation products (BOXes) have been a subject of interest in neurosurgery because they are purported to be involved in subarachnoid hemorrhage induced cerebral vasospasm. There is a growing body of information concerning their putative role in vasospasm; however, there is a dearth of information concerning the chemical and biochemical characteristics of BOXes. A clearer understanding of the synthesis, stability and characteristics of BOXes will be important for a better understanding of the role of BOXes post subarachnoid hemorrhage.We used hydrogen peroxide to oxidize bilirubin and produce BOXes. BOXes were extracted and analyzed using conventional methods such as HPLC and mass spectrometry. Characterization of the stability of BOXes demonstrates that light can photodegrade BOXes with a t1/2of up to 10 h depending upon conditions. Mixed isomers of BOXes have an apparent extinction coefficient ofε= 6985, and aλmaxof 310 nm.BOXes are produced by the oxidation of bilirubin, yielding a mixture of isomers: 4-methyl-5-oxo-3-vinyl-(1,5-dihydropyrrol-2-ylidene)acetamide (BOX A) and 3-methyl-5-oxo-4-vinyl-(1,5-dihydropyrrol-2-ylidene) acetamide (BOX B). The BOXes are photodegraded by ambient light and can be analyzed spectrophotometrically with their extinction coefficient as well as with HPLC or mass spectrometry. Their small molecular weight and photodegradation may have made them difficult to characterize in previous studies.