水溶性香豆素衍生物之合成及對於重金屬離子螢光探針之應用

屬離子在生物體內扮演極重要的角色，過量或不足均會影響機能的正常，因此如何感測生物體內的金屬離子變成一項不可或缺的研究目的，而具有螢光的化學感測器可作為分析生物體內重要元素的工具。本研究的目的在於利用香豆素(coumarin)衍生物經由光誘導電子轉移機制(Photoinduced Electron Transfer, PET)設計出對特定金屬離子有專一感測能力的螢光感測器。此外，也藉由分子結構上的設計來增加感測器的水溶性，提高未來應用在生物體內的實用性。如下圖所示，CDC-O利用雜氮冠醚作為金屬離子辨識單元，並且利用兩個羧酸基來增加其水溶性，由實驗可知對鉛離子具有選擇性使螢光增強。CDC-S則是把冠醚中的氧原子改成了硫原子，期望會對較軟性的金屬具有辨識效果，實驗結果顯示果然如預期的對比鉛離子較軟的汞離子具有選擇性。此外，CDC-Asp則是利用天冬胺酸(aspartic acid)為辨識單元，希望利用胺基增加與金屬離子的辨識結合位置，此外，天冬胺酸也是已知對汞離子具有辨識能力的接收端，實驗證明也如預期的對汞離子具有選擇性而使螢光增強。CDC-DPA則是以會與鋅離子作選擇性結合的二吡啶甲基胺作為分子辨識單元，成為一水溶性鋅離子螢光探針。

關鍵字

金屬離子；螢光探針；光誘導電子轉移；水溶性

並列摘要

As more critical environment pollution around the world, top consumers in the food chains, such as human, might be expected to accumulate environmental contaminants, especially the toxic heavy metal ions, thus research for sensing heavy metal ions has attracted more concern, particularly for water-soluble probes. Herein we report a series of coumarin-based fluorescent metal ion probes, ketoaminocoumarin is selected as a signal transducing-unit owing to its high photostability and visible excitation wavelength, the fluorescent enhancement can be rationalized via inhibition of photoinduced electron transfer. CDC-O and CDC-S have a dicarboxylate pseudocrown receptor designed to satisfy the size and charge requirements of the metal cation, and improve water compatibility of water. We use sulfer atom in the receptor unit of CDC-S, wish it would sense softer metal ions than CDC-O does. We also use aspartic acid and dipicolylamine as the molecular recognition unit for CDC-Asp and CDC-DPA, which are reported receptor and selectively for mercury and zinc ions.

並列關鍵字

fluorescent probe ； PET ； water-soluble

參考文獻

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水溶性香豆素衍生物之合成及對於重金屬離子螢光探針之應用

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