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Convergent synthesis and optical properties of near-infrared emitting bioluminescent infra-luciferins

机译：近红外发射生物发光红外荧光素的合成与光学性质

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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.
机译：萤光素是一种与烯烃连接的萤光素类似物，其生物发光发射> 700 nm，具有用于多参数体内成像的潜力。我们在这里报告了高产量，可扩展和收敛的红外荧光素合成，这将允许合成其他缀合的荧光素用于近红外生物发光成像研究。我们通过使用新途径合成萤光素的二烯连接类似物证明了这种潜力，该荧光素的荧光和生物发光特性与 D -萤光素和红外荧光素相比。我们发现，与 D -萤光素相比，与二烯连接子的缀合扩展导致特定的生物发光活性降低了3-4个数量级。与它的荧光发射光谱类似，二烯连接的类似物在其生物发光光谱中表现出两个峰，与天然的 D -荧光素相比，主要的峰有轻微的蓝移，而在 ca处有一个较小的峰。 。 800 nm。还确定了荧光量子产率和荧光的pH依赖性。

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