Zhao Pei, Wu Xiaokang, Li Jie, Dong Gaopan, Sun Yingai, Ma Zhao, Li Minyong, Du Lupei
Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (MOE), School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, Jinan, Shandong 250012, China.
Org Biomol Chem. 2022 May 26;20(20):4224-4230. doi: 10.1039/d1ob02477a.
The firefly luciferase system is the most extensively utilized bioluminescence system in the field of life science at the moment. In this work, we designed and synthesized a series of alkene-conjugated luciferins to develop new firefly bioluminescence substrates, and further evaluated their activities and . It is worth noting that the maximum biological emission wavelength of novel luciferin analogue AL3 ((,)-2-(6-hydroxy-5-(3-methoxy-3-oxoprop-1-en-1-yl)benzo[]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid) is 100 nm red-shifted compared with D-luciferin, while that of analogue AL4 ((,)-2-(5-(2-cyanovinyl)-6-hydroxybenzo[]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid) is 75 nm red-shifted. The new substrate AL2 ((,)-2-(6-hydroxy-7-(3-methoxy-3-oxoprop-1-en-1-yl)benzo[]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid) showed better bioluminescence performance .
萤火虫荧光素酶系统是目前生命科学领域应用最为广泛的生物发光系统。在本研究中,我们设计并合成了一系列烯烃共轭荧光素,以开发新型萤火虫生物发光底物,并进一步评估了它们的活性。值得注意的是,新型荧光素类似物AL3((,)-2-(6-羟基-5-(3-甲氧基-3-氧代丙-1-烯-1-基)苯并[]噻唑-2-基)-4,5-二氢噻唑-4-羧酸)的最大生物发射波长相较于D-荧光素发生了100 nm的红移,而类似物AL4((,)-2-(5-(2-氰基乙烯基)-6-羟基苯并[]噻唑-2-基)-4,5-二氢噻唑-4-羧酸)的最大生物发射波长发生了75 nm的红移。新型底物AL2((,)-2-(6-羟基-7-(3-甲氧基-3-氧代丙-1-烯-1-基)苯并[]噻唑-2-基)-4,5-二氢噻唑-4-羧酸)表现出了更好的生物发光性能。