Anderson James C, Grounds Helen, Jathoul Amit P, Murray James A H, Pacman Steven J, Tisi Laurence
Department of Chemistry , University College London , 20 Gordon Street , London , WC1H 0AJ , UK . Email:
School of Biosciences , University of Cardiff , Sir Martin Evans Building, Museum Avenue , Cardiff , CF10 3AX , UK.
RSC Adv. 2017 Jan 16;7(7):3975-3982. doi: 10.1039/c6ra19541e.
Infra-luciferin, an alkene linked analogue of luciferin, gives bioluminescence emission >700 nm and has the potential to be used for multiparametric 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 800 nm. The fluorescence quantum yield and pH dependence of fluorescence were also determined.
异鲁米诺，一种与鲁米诺相连的烯烃类似物，发出波长大于700 nm的生物发光，有潜力用于多参数成像。我们在此报告一种高产率、可扩展且收敛的异鲁米诺合成方法，该方法将允许合成其他共轭鲁米诺，用于近红外生物发光成像研究。我们通过使用新路线合成一种与鲁米诺相连的二烯类似物来证明这种潜力，并将其荧光和生物发光特性与d-鲁米诺和异鲁米诺的特性进行了比较。我们发现，与d-鲁米诺相比，共轭扩展到二烯连接体导致比生物发光活性降低3至4个数量级。与其荧光发射光谱类似，与二烯相连的类似物在其生物发光光谱中表现出两个峰，主要峰与天然d-鲁米诺相比略有蓝移，在800 nm处有一个小峰。还测定了荧光量子产率和荧光的pH依赖性。
