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Effect of Bulky Aryl Group on the Optical Properties of Cypridina Oxyluciferin Analogues
Computational and Theoretical Chemistry ( IF 2.8 ) Pub Date : 2019-11-14 , DOI: 10.1016/j.comptc.2019.112659
Qing-Bo Liu , Yan Leng , Kun Dong , Shao-Jun Huang , Chun-Xia Liu , Xi-Kun Yang , Ai-Min Ren , Chun-Gang Min

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.



中文翻译:

庞大的芳基基团对氧化氧化荧光素类似物的光学性质的影响

由于高生物发光效率和独立的辅助因子,赛普里迪纳生物发光已被开发为必不可少的分析工具。但是,赛普里迪纳仅发出蓝光,而某些生物材料可能会吸收蓝光。为解决此问题,我们设计了三个系列的荧光素衍生物,分别替换了三个位置的部分:C5(R1)处的3-吲哚基,C3(R2)处的3-(1-胍基)丙基和(S)-2酰基部分(R3)上的-丁基分别带有苯基,萘基和菲基。结果发现赛普里迪纳氧化荧光素类似物可发出紫,蓝,绿和黄光。在562nm处观察到最大波长,其仅通过扩展菲基的缀合作用而实现。而且,在5位取代萘基比苯基和菲基对发射波长有更大的影响。激发态解离常数的计算表明2-乙酰胺基-5-萘-3-萘并吡嗪(B2)可能是荧光pH探针的潜在候选者。

更新日期:2019-11-14
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