Discovery of alkene-conjugated luciferins for redshifted and improved bioluminescence imaging in vitro and in vivo. Issue 20 (12th May 2022)

• Record Type: Journal Article
• Authors: Zhao, Pei; Wu, Xiaokang; Li, Jie; Dong, Gaopan; Sun, Yingai; Ma, Zhao; Li, Minyong; Du, Lupei
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 20(2022)
• Page Start: 4224
• Page End: 4230
• Publication Date: 2022-05-12
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob02477a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The firefly luciferase system is the most extensively utilized bioluminescence system in the field of life science at the moment. Abstract : 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 in vitro and in vivo . It is worth noting that the maximum biological emission wavelength of novel luciferin analogue AL3 (( S, E )-2-(6-hydroxy-5-(3-methoxy-3-oxoprop-1-en-1-yl)benzo[ d ]thiazol-2-yl)-4, 5-dihydrothiazole-4-carboxylic acid) is 100 nm red-shifted compared with d -luciferin, while that of analogue AL4 (( S, E )-2-(5-(2-cyanovinyl)-6-hydroxybenzo[ d ]thiazol-2-yl)-4, 5-dihydrothiazole-4-carboxylic acid) is 75 nm red-shifted. The new substrate AL2 (( S, E )-2-(6-hydroxy-7-(3-methoxy-3-oxoprop-1-en-1-yl)benzo[ d ]thiazol-2-yl)-4, 5-dihydrothiazole-4-carboxylic acid) showed better bioluminescence performance in vivo .