Spectral fine tuning of cyanine dyes: electron donor-acceptor substituted analogues of thiazole orange.
Spectral fine tuning of cyanine dyes: electron donor-acceptor substituted analogues of thiazole orange.
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DOI：
10.1039/c5pp00117j
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发表时间：
2015-09-26
期刊：
影响因子：
--
通讯作者：
Armitage BA
中科院分区：
文献类型：
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作者：
Rastede EE;Tanha M;Yaron D;Watkins SC;Waggoner AS;Armitage BA
在荧光花青染料上的战略位置引入电子供体和受体基团可以微调吸收和发射光谱，同时保留染料与生物分子宿主（例如双链 DNA 和最初选择用于与母体未取代染料噻唑橙 (TO) 结合的单链抗体片段）结合的能力。观察到的光谱位移与计算的 HOMO-LUMO 能隙一致，反映了 LUMO 中 TO 的喹啉一半上的电子密度局域化。苯并噻唑环和喹啉环上分别带有供甲氧基和撤回三氟甲基的染料将吸收光谱移动到足够长的波长，以允许在绿色波长下激发，而不是母体染料，母体染料在蓝色中最佳激发。
The introduction of electron donor and acceptor groups at strategic locations on a fluorogenic cyanine dye allows fine-tuning of the absorption and emission spectra while preserving the ability of the dye to bind to biomolecular hosts such as double-stranded DNA and a single-chain antibody fragment originally selected for binding to the parent unsubstituted dye, thiazole orange (TO). The observed spectral shifts are consistent with calculated HOMO-LUMO energy gaps and reflect electron density localization on the quinoline half of TO in the LUMO. A dye bearing donating methoxy and withdrawing trifluoromethyl groups on the benzothiazole and quinoline rings, respectively, shifts the absorption spectrum to sufficiently longer wavelengths to allow excitation at green wavelengths as opposed to the parent dye, which is optimally excited in the blue.