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吲哚菁绿的光致分解

Light-induced decomposition of indocyanine green.

作者信息

Engel Eva, Schraml Rüdiger, Maisch Tim, Kobuch Karin, König Burkhard, Szeimies Rolf-Markus, Hillenkamp Jost, Bäumler Wolfgang, Vasold Rudolf

机构信息

Departments of Organic Chemistry, University of Regensburg, Regensburg, Germany.

出版信息

Invest Ophthalmol Vis Sci. 2008 May;49(5):1777-83. doi: 10.1167/iovs.07-0911.

Abstract

PURPOSE

To investigate the light-induced decomposition of indocyanine green (ICG) and to test the cytotoxicity of light-induced ICG decomposition products.

METHODS

ICG in solution was irradiated with laser light, solar light, or surgical endolight. The light-induced decomposition of ICG was analyzed by high-performance liquid chromatography (HPLC) and mass spectrometry. Porcine retinal pigment epithelial (RPE) cells were incubated with the light-induced decomposition products of ICG, and cell viability was measured by trypan blue exclusion assay.

RESULTS

Independent of the light source used, singlet oxygen (photodynamic type 2 reaction) is generated by ICG leading to dioxetanes by [2+2]-cycloaddition of singlet oxygen. These dioxetanes thermally decompose into several carbonyl compounds. The decomposition products were identified by mass spectrometry. The decomposition of ICG was inhibited by adding sodium azide, a quencher of singlet oxygen. Incubation with ICG decomposition products significantly reduced the viability of RPE cells in contrast to control cells.

CONCLUSIONS

ICG is decomposed by light within a self-sensitized photo oxidation. The decomposition products reduce the viability of RPE cells in vitro. The toxic effects of decomposed ICG should be further investigated under in vivo conditions.

摘要

目的

研究吲哚菁绿(ICG)的光诱导分解,并测试光诱导的ICG分解产物的细胞毒性。

方法

用激光、太阳光或手术内光照射溶液中的ICG。通过高效液相色谱(HPLC)和质谱分析ICG的光诱导分解。将猪视网膜色素上皮(RPE)细胞与ICG的光诱导分解产物一起孵育,并通过台盼蓝排斥试验测量细胞活力。

结果

无论使用何种光源,ICG都会产生单线态氧(光动力2型反应),通过单线态氧的[2+2]环加成生成二氧杂环丁烷。这些二氧杂环丁烷热分解成几种羰基化合物。通过质谱鉴定分解产物。通过添加单线态氧猝灭剂叠氮化钠抑制ICG的分解。与对照细胞相比,用ICG分解产物孵育显著降低了RPE细胞的活力。

结论

ICG在自敏化光氧化过程中被光分解。分解产物在体外降低了RPE细胞的活力。分解的ICG的毒性作用应在体内条件下进一步研究。

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