Synthesis of Firefly Luciferin Analogues and Evaluation of the Luminescent Properties. Issue 27 (24th May 2016)

• Record Type: Journal Article
• Authors: Ioka, Shuji; Saitoh, Tsuyoshi; Iwano, Satoshi; Suzuki, Koji; Maki, Shojiro A.; Miyawaki, Atsushi; Imoto, Masaya; Nishiyama, Shigeru
• Is Part Of: Chemistry. Volume 22:Issue 27(2016)
• Page Start: 9330
• Page End: 9337
• Publication Date: 2016-05-24
• Subjects: biological activity -- firefly luciferase -- luminescence -- structure–activity relationships -- synthesis design; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201600278
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Five new firefly luciferin (1 ) analogues were synthesized and their light emission properties were examined. Modifications of the thiazoline moiety in1 were employed to produce analogues containing acyclic amino acid side chains (2 –4 ) and heterocyclic rings derived from amino acids (5 and6 ) linked to the benzothiazole moiety. Although methyl esters of all of the synthetic derivatives exhibited chemiluminescence activity, only carboluciferin (6 ), possessing a pyrroline‐substituted benzothiazole structure, had bioluminescence (BL) activity ( λ max =547 nm). Results of bioluminescence studies with AMP‐carboluciferin (AMP=adenosine monophosphate) and AMP‐firefly luciferin showed that the nature of the thiazoline mimicking moiety affected the adenylation step of the luciferin–luciferase reaction required for production of potent BL. In addition, BL of6 in living mice differed from that of1 in that its luminescence decay rate was slower. Abstract : All aglow : Luciferin derivatives possessing acyclic amino acid and heterocyclic substituents were synthesized. All synthetic derivatives displayed chemiluminescence, but onlyd ‐carboluciferin showed 0.5 % bioluminescence (BL) activity compared with that of firefly luciferin.d ‐Carboluciferin differed from firefly luciferin in that decay of its BL in live mice was slower than that of the natural luciferin (see figure).