合成兩種光親和性探針用於研究植物之防禦機制以及乳癌用藥泰莫西芬的副作用來源

陳昱竑

doi:10.6342/NTU201700689

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合成两种光亲和性探针用於研究植物之防御机制以及乳癌用药泰莫西芬的副作用来源

Synthesis of Two Photoaffinity Probes to Investigate Defensive Response in Plants and Adverse Side Effects of Tamoxifen

陈昱竑 , 硕士　　导师：陈昭岑　　

繁体中文 DOI： 10.6342/NTU201700689

蛋白质体学；光亲和性探针；光反应基团； CAPE1 ；泰莫西芬；矽罗丹明；同位素编码； proteomics ； photoaffinity probe ； photoreactive group ； CAPE1 ； tamoxifen ； Si rhodamine ； isotope code

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摘要 │ 参考文献 (74) │ 国际计量

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This thesis is mainly divided into two parts. The first part is to study defensive response in plants. Systemin regulates the expression of defensive genes in tomato leaves in response to insect attacks or other severe mechanical wounding. In 2014, Chen et al discover a novel polypeptide plant hormone named CAPE1. CAPE1 shares similar defensive function with systemin, but its binding protein and the detail signal transduction pathway haven’t been fully understood. These peptidic plant hormones have great potential to become biodegradable and environment friendly pesticide. Thus, a photoaffinity probe PhoLeu-CAPE1 with CAPE1 peptide sequence as the recognition part to investigate CAPE1 binding protein was designed and synthesized. After incubation with plant leaves proteome and photoactivation with UV light, this probe can covalently link to the binding protein for further analysis (Figure A). Despite he probe equips photo-leucine as a photoreactive group and biotin as an affinity tag, it can still trigger defensive response as the native CAPE1. The binding protein labeling is still under progress.
The second part is to study the origin of tamoxifen-induced side effect. Tamoxifen is the first-line drug to treat breast cancer patient with estrogen receptor positive. However, the treatment accompanies with many adverse side effects, including hot flashes, vaginal bleeding or discharge, as well as increasing the risk of endometrial cancer. Furthermore, tamoxifen induces apoptosis in estrogen receptor negative cell lines, but the detail mechanism hasn’t been fully understood. The origin of these adverse effects needs to be sought. Herein, a photoaffinity probe 4-OHT-diaz-alkyne with 4-hydroxytamoxifen (4-OHT) as the recognition unit was designed and synthesized (Figure B-a). A two-step labeling concept was introduced in the probe design. To utilize azide-alkyne cycloaddition to attach tag after protein labeling. A multiple functional tag SiRho-N3-Biotin featuring near infarred dye Si-rhodamine with higher quantum yield as fluorophore and the isotope-coded affinity tag for mass spectrometry detection was designed and synthesized (Figure B-b). These photoaffinity　probes were expected to find the unknown binding proteins, followed by coupling with the tag for further purification and identification.

参考文献 ( 74 ) 〈TOP〉

12. Karney, W. L.; Borden, W. T. J. Am. Chem. Soc. 1997, 119, 3347.
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13. Galardy, R. E.; Craig, L. C.; Printz, M. P. Nature New Biol. 1973, 242, 127
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14. Smith, R. A.; Knowles, J. R. J. Am. Chem. Soc. 1973, 95, 5072.
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15. Bayley H., Photogenerated reagents in biochemistry and molecular biology, 1st ed, 1983.
连结：
20. Li, Z.; Hao, P.; Li, L.; Tan, C. Y. J.; Cheng, X.; Chen, G. Y. J.; Sze, S. K.; Shen, H. M.; Yao, S. Q. Angew. Chem. Int. Ed. 2013, 52, 8551 -8556.
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引用含有DOI的文献

DOI可强化引用精确性、增强学术圈连结，并给予使用者跨平台的良好使用经验，目前在全世界已有超过五千万个对象申请DOI。 如想对DOI的使用与概念有进一步了解，请参考 （ ） 。

DOI可强化引用精确性、增强学术圈连结，并给予使用者跨平台的良好使用经验，目前在全世界已有超过五千万个对象申请DOI。如想对DOI的使用与概念有进一步了解，请参考（）。