银杏叶聚戊烯醇金属配合物的合成及其光控活性

doi:10.3969/j.issn.0253-2417.2021.02.010

林产化学与工业 ›› 2021, Vol. 41 ›› Issue (2): 73-78.doi: 10.3969/j.issn.0253-2417.2021.02.010

银杏叶聚戊烯醇金属配合物的合成及其光控活性

张昌伟¹^,², 陶冉¹, 齐志文¹, 沈红¹, 薛兴颖¹, 王成章¹^,²^,*()

1. 中国林业科学研究院林产化学工业研究所; 生物质化学利用国家工程实验室; 国家林业和草原局林产化学工程重点实验室; 江苏省生物质能源和材料重点实验室, 江苏南京 210042
2. 中国林业科学研究院林业新技术研究所, 北京 100091

收稿日期:2020-10-26 出版日期:2021-04-28 发布日期:2021-05-08
通讯作者: 王成章 E-mail:wangczlhs@sina.com
作者简介:王成章, 研究员, 博士, 博士生导师, 研究领域为天然产物研究与利用; E-mail: wangczlhs@sina.com
张昌伟(1987-), 男, 河南信阳人, 助理研究员, 博士, 主要从事天然产物的研究与开发
基金资助:
江苏省青年基金(BK20180152)

Synthesis and Light-controlled Activity of Ginkgo biloba Leaves Polyprenols Metal Complex

Changwei ZHANG¹^,², Ran TAO¹, Zhiwen QI¹, Hong SHEN¹, Xingying XUE¹, Chengzhang WANG¹^,²^,*()

1. Institute of Chemical Industry of Forest Products, CAF; National Engineering Lab. for Biomass Chemical Utilization; Key Lab. of Chemical Engineering of Forest Products, National Forestry and Grassland Administration; Key Lab. of Biomass Energy and Material, Jiangsu Province, Nanjing 210042, China
2. Research Institute of Forestry New Technology, CAF, Beijing 100091, China

Received:2020-10-26 Online:2021-04-28 Published:2021-05-08
Contact: Chengzhang WANG E-mail:wangczlhs@sina.com

摘要/Abstract

摘要：

以银杏叶聚戊烯醇（GBP）为原料，通过化学改性手段将其末端羟基替换成氰基，之后将氰基聚戊烯醇与钌多吡啶配合物络合，合成了聚戊烯醇-钌多吡啶配合物，并对其进行表征，考察了配合物的脂水分配系数、光致配体解离能力和光控抗肿瘤活性。核磁共振表征结果表明，氰基聚戊烯醇和聚戊烯醇-钌多吡啶配合物成功合成。合成的配合物具有较好的脂水分配系数（1.35），有利于其穿透细胞膜。此外，合成的配合物在光照下逐渐发生配体解离，在光照条件下，其对A549肿瘤细胞的半数抑制浓度（IC₅₀）为29.3 μmol/L，展示出比聚戊烯醇（IC₅₀=45.8 μmol/L）更好的抗肿瘤活性，且配合物的光控抗肿瘤活性极可能与其DNA结合能力有关。

关键词: 银杏叶, 聚戊烯醇, 钌多吡啶, 金属配合物, 光控活性

Abstract:

Ginkgo biloba leaves polyprenols(GBP) was used as raw material, and its terminal hydroxyl group was replaced with cyano group by chemical modification method. On this basis, cyano-GBP and ruthenium polypyridine complex were utilized as raw materials, the GBP-ruthenium polypyridine metal complex was synthesized and characterized by complex reaction. The lipid-water partition coefficient, photo-induced ligand dissociation ability and light-controlled antitumor activity of the complex were investigated. NMR results showed that the cyano-GBP and GBP-ruthenium polypyridine metal complex were successfully synthesized. The synthesized complex has good lipid-water partition coefficient(1.35), which was conducive to its penetration of cell membranes. In addition, cyano-GBP ligand of the synthesized complex gradually dissociated under light and exhibited better antitumor activity with the half inhibitory concentration(IC₅₀) against A549 tumor cell of 29.3 μmol/L than GBP(IC₅₀=45.8 μmol/L). Moreover, The light-controlled antitumor activity of the complex may be related to its DNA binding ability.

Key words: Ginkgo biloba leaves, polyprenols, ruthenium polypyridine, metal complex, light-controlled activity

中图分类号:

TQ35

张昌伟, 陶冉, 齐志文, 沈红, 薛兴颖, 王成章. 银杏叶聚戊烯醇金属配合物的合成及其光控活性[J]. 林产化学与工业, 2021, 41(2): 73-78.

Changwei ZHANG, Ran TAO, Zhiwen QI, Hong SHEN, Xingying XUE, Chengzhang WANG. Synthesis and Light-controlled Activity of Ginkgo biloba Leaves Polyprenols Metal Complex[J]. Chemistry and Industry of Forest Products, 2021, 41(2): 73-78.

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银杏叶聚戊烯醇金属配合物的合成及其光控活性

Synthesis and Light-controlled Activity of Ginkgo biloba Leaves Polyprenols Metal Complex

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