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二吡咯烷酮的光氧化：与单线态氧的反应及反应中间体的表征

Photooxidation of Dipyrrinones: Reaction with Singlet Oxygen and Characterization of Reaction Intermediates.

作者信息

Madea Dominik, Peňáková Júlia, Mehara Jaya, Akisaka Rikuo, Martínek Marek, Roithová Jana, Klán Petr

机构信息

Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, Brno 625 00, Czech Republic.

RECETOX, Faculty of Science, Masaryk University, Kamenice 5, Brno 625 00, Czech Republic.

出版信息

J Org Chem. 2025 Feb 14;90(6):2403-2420. doi: 10.1021/acs.joc.4c02954. Epub 2025 Feb 5.

DOI:10.1021/acs.joc.4c02954
PMID:39909730
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11833878/
Abstract

Bilirubin (BR) is a water-insoluble product of heme catabolism in mammals. Elevated blood concentrations of BR, especially in the neonatal period, are treated with blue-green light phototherapy. The major mechanism of BR elimination during phototherapy is photoisomerization, while a minor, less studied mechanism of degradation is oxidation. In this work, we studied the oxidation of the bilirubin model tetramethyl-dipyrrinone (-) by singlet oxygen in methanol using UV-vis and ESI-MS spectroscopy, resulting in propentdyopents as the main oxidation products. We also identified two additional intermediates that were formed during the reaction (hydroperoxide and imine ). The structure of the hydroperoxide was confirmed by helium-tagging IR spectroscopy. Such reaction intermediates formed during the oxidation of BR or bilirubin models have not been described so far. We believe that this work can be used as a first step in studying the complex oxidation mechanism of BR during phototherapy.

摘要

胆红素（BR）是哺乳动物血红素分解代谢的水不溶性产物。血液中BR浓度升高，尤其是在新生儿期，可采用蓝绿光光疗进行治疗。光疗期间BR消除的主要机制是光异构化，而次要的、研究较少的降解机制是氧化。在这项工作中，我们使用紫外可见光谱和电喷雾电离质谱对胆红素模型四甲基二吡咯酮（-）在甲醇中被单线态氧氧化进行了研究，主要氧化产物为原卟啉。我们还鉴定出反应过程中形成的另外两种中间体（氢过氧化物和亚胺）。通过氦标记红外光谱证实了氢过氧化物的结构。到目前为止，尚未描述在BR或胆红素模型氧化过程中形成的此类反应中间体。我们认为这项工作可作为研究光疗期间BR复杂氧化机制的第一步。

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