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6-苯甲酰基-5,7-二羟基-4-苯基色原酮的抗 UVC 辐射和金属螯合特性：作为一种抗白内障剂的应用。

Anti-UVC irradiation and metal chelation properties of 6-benzoyl-5,7-dihydroxy-4-phenyl-chromen-2-one: an implications for anti-cataract agent.

机构信息

Institute of Biological Chemistry, Academia Sinica, 128 Academia Road, Section 2, Nankang, Taipei 115, Taiwan; E-Mails:

出版信息

Int J Mol Sci. 2011;12(10):7059-76. doi: 10.3390/ijms12107059. Epub 2011 Oct 21.

DOI:10.3390/ijms12107059
PMID:22072936
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3211027/
Abstract

Coumarin derivative 1, 5,7-dihydroxy-6-(3-methyl-1-butyryl)-4-phenyl-chromen- 2-one, has been reported to possess radical scavenging activity and DNA protection. We have synthesized a series of coumarins with structural modifications at positions C4, C5, C6 and C7 and evaluated them for their anti-UVC properties. Coumarin 7, 6-benzoyl-5,6-dihydroxy-4-phenyl-chromen-2-one, was found to have the most potent activity in protecting porcine γ-crystallin against UVC insults. Results of fluorescence assays indicated that compound 7 was capable of decreasing the loss of intensity while lens crystallins and DNA PUC19 were irradiated with UVC. Presence of compound 7 decreased hydroxyl radical levels determined by probe 1b and the free iron concentrations determined by Ferrozine reagent. The chelation assay showed that compound 7 was chelated to metal via 6-CO and 5-OH on the benzopyrone ring. The observed protective effects of compound 7 towards crystallins from insults of UVC and free radicals may be due to its iron-chelating activity and its peak absorption at 254 nm.

摘要

香豆素衍生物 1,5,7-二羟基-6-(3-甲基-1-丁酰基)-4-苯基-2H-色烯-2-酮，据报道具有自由基清除活性和 DNA 保护作用。我们合成了一系列在 C4、C5、C6 和 C7 位置进行结构修饰的香豆素，并对它们的抗 UVC 特性进行了评估。香豆素 7,6-苯甲酰基-5,6-二羟基-4-苯基-2H-色烯-2-酮，被发现对 UVC 损伤具有最强的保护猪γ-晶状体蛋白的活性。荧光分析结果表明，化合物 7 能够在 UVC 辐照时降低晶状体蛋白和 DNA PUC19 的强度损失。探针 1b 测定表明，化合物 7 能够降低羟基自由基的水平，Ferrozine 试剂测定表明，化合物 7 能够降低游离铁浓度。螯合实验表明，化合物 7 通过苯并吡喃环上的 6-CO 和 5-OH 与金属螯合。化合物 7 对 UVC 和自由基损伤的晶状体蛋白的保护作用可能是由于其铁螯合活性和在 254nm 处的最大吸收峰。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fc7/3211027/d89ce78875d3/ijms-12-07059f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fc7/3211027/7c759c24b697/ijms-12-07059f1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fc7/3211027/7c759c24b697/ijms-12-07059f1.jpg
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