Abstract
Because of high bioluminescence efficiency and independent cofactors, Cypridina bioluminescence has been already developed as an indispensable analytical tool. However, Cypridina only emits blue light which may be absorbed by some biomaterials. To address this problem, we design three series of oxyluciferin derivatives, replacing moiety at three positions, 3-indolyl group at C5 (R1), 3-(1-guanidino) propyl group at C3 (R2) and an (S)-2-butyl group at the acyl part (R3), with phenyl, naphthyl and phenanthryl groups, respectively. The results found that Cypridina oxyluciferin analogues can emit violet, blue, green and yellow light. The maximum wavelength was observed at 562 nm, which achieved only with extending the conjugation effect by phenanthryl group. Moreover, replacing with naphthyl group at the 5-position have more influential to emission wavelength than phenyl and phenanthryl groups. The calculation of the excited state dissociation constant indicates that 2-acetamido-5-naphthyl-3-naphthylpyrazine (B2) can be potential candidate for fluorescent pH probe.
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