Convergent synthesis and optical properties of near-infrared emitting bioluminescent infra-luciferins.
Convergent synthesis and optical properties of near-infrared emitting bioluminescent infra-luciferins.
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DOI：
10.1039/c6ra19541e
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发表时间：
2017-01-16
期刊：
影响因子：
3.9
通讯作者：
Tisi L
中科院分区：
文献类型：
--
作者：
Anderson JC;Grounds H;Jathoul AP;Murray JAH;Pacman SJ;Tisi L
一个高产，规模化和收敛的合成红外生物发光蛋白及其潜在的近红外生物发光成像的调查。β-胡萝卜素是胡萝卜素的烯烃连接类似物，其生物发光发射>700 nm，并具有用于多参数体内成像的潜力。我们在这里报告了一个高产，可扩展和收敛的合成infra-tetrain，这将允许合成其他共轭tetrain的研究在近红外生物发光成像。我们证明了这一潜力，通过使用新的路线来合成二烯连接的类似物，其中的荧光和生物发光特性进行了比较，这些d-β-胡萝卜素和红外-胡萝卜素。我们发现，共轭延伸到二烯接头导致的特定的生物发光活性降低了3-4个数量级相比，d-胡萝卜素。与其荧光发射光谱类似，二烯连接的类似物在其生物发光光谱中显示出两个峰，主要的一个与天然d-胡萝卜素相比略微蓝移，并且在约100 nm处有一个次要峰。800纳米。荧光量子产率和荧光的pH依赖性也进行了测定。
A high yielding, scalable and convergent synthesis of infra-luciferins and investigation of their potential for near-infrared bioluminescence imaging. Infra-luciferin, an alkene linked analogue of luciferin, gives bioluminescence emission >700 nm and has the potential to be used for multiparametric in vivo imaging. We report here a high yielding, scalable and convergent synthesis of infra-luciferin which will allow the synthesis of other conjugated luciferins for investigation in near-infrared bioluminescence imaging. We demonstrated this potential by using the new route to synthesise a diene linked analogue of luciferin, the fluorescent and bioluminescent properties of which were compared to those of d-luciferin and infra-luciferin. We found that extension of conjugation to a diene linker resulted in the specific bioluminescence activity being reduced by 3–4 orders of magnitude compared to d-luciferin. Analogous to its fluorescence emission spectrum, the diene linked analogue exhibited two peaks in its bioluminescence spectrum, the major one being slightly blue-shifted compared to natural d-luciferin, and a minor peak at ca. 800 nm. The fluorescence quantum yield and pH dependence of fluorescence were also determined.