Recent progress in the synthesis of firefly luciferin derivatives. (November 2019)

• Record Type: Journal Article
• Authors: Podsiadły, Radosław; Grzelakowska, Aleksandra; Modrzejewska, Julia; Siarkiewicz, Przemysław; Słowiński, Daniel; Szala, Marcin; Świerczyńska, Małgorzata
• Is Part Of: Dyes and pigments. Volume 170(2019)
• Publication Date: 2019-11
• Subjects: Luciferin -- Bioluminescence -- Synthesis -- Spectroscopic properties; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2019.107627
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: Bioluminescent is a standard noninvasive technique for in vivo imaging. Bioluminescent screenings are based on the generation of light during interaction of luciferase with an appropriate substrate: D-luciferin (LH 2 ), aminoluciferin (NH 2 -LH 2 ) or theirs derivatives. Although there has been meaningful progress in the synthesis of theLH 2, H 2 N-LH 2 and their analogues, still a major synthetic challenge is to obtain luciferins, with red shifted luminescence and emission efficiency comparable to that of native luciferin emission. Over the last decade, by using different methods, a lot of analogues of luciferin/aminoluciferin have been synthesized, and therefore, in this review, we have summarized the recent progress in the design and synthesis of synthetic luciferins in a manner that all readers can be inspired to use, and/or design, and/or develop the useful far red/NIR bioluminescent substrates for luciferase. Highlights: Improvements in D-luciferin and aminoluciferin preparation. Luciferins with additional substituent(s) at benzothiazole ring. Luciferins without benzothiazole and/or thiazoline moiety(ies). Luciferins with additional π-conjugated double bond(s).