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Chemi- and bioluminescence of coelenterazine analogues with a conjugated group at the C-8 position

✍ Scribed by Chun Wu; Hideshi Nakamura; Akio Murai; Osamu Shimomura

Book ID: 104230411
Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 63 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)00340-9

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✦ Synopsis

The chemiliminescent compound coelenterazine is involved in various bioluminescence reactions as the substrates, causing the luminescence with an emission peak in the range of 450-475 nm. Anticipating the introduction of a bathochromicshift of the luminescence, several new coelenterazine analogues that have conjugated olefins or aromatic groups at the 8-position of imidazopyrazinone ring were synthesized. In the chemiluminescence reaction, the emission spectra of a majority of the compounds synthesized showed a bathochromic shift, giving an emission peak in the range of 520-580 nm. In the bioluminescence catalyzed by Oplophorus luciferase, the bisthienyl analogue of coelenterazine emitted a moderate intensity of luminescence (5% of coelenterazine) with an emission maximum at 528 nm, which was the longest wavelength of all the analogues tested.

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