嘧啶基双光子荧光染料的设计合成与生物成像

doi:10.11944/j.issn.1000-0518.2017.12.170319

摘要/Abstract

摘要：

生理条件下光学性质稳定的双光子荧光染料在生物成像领域具有广阔的应用前景。我们使用2,4-二甲基-6-羟基嘧啶与4-(N,N-二甲氨基)苯甲醛进行缩合反应,设计合成了具有双光子荧光性质的化合物2-[(1E)-2-[4-(二甲氨基)苯基]乙烯基]-6-甲基-4(3H)-嘧啶(NHP)。通过质谱(MS)、核磁共振波谱(NMR)、紫外可见吸收光谱和荧光发射光谱等技术手段表征了其结构,研究了其光物理性质,以及外部环境改变对其发射光谱的影响。结果表明,化合物NHP的最佳吸收峰位于400 nm,最佳发射峰位于540 nm左右,且荧光发射不受金属离子、氨基酸和pH等环境因素的影响。生物实验结果表明,化合物NHP细胞毒性较小,且具有很好的活细胞和果蝇脑组织成像效果,是一种较为理想的双光子荧光生物成像染料。

关键词: 嘧啶衍生物, 双光子成像, 荧光探针, 生物成像

Abstract:

In the field of biological imaging, two-photon fluorescent dyes with stable optical properties under physiological conditions have broad application prospects. Herein, we designed and synthesized a two-photon fluorescent dye 2-[(1E)-2-[4-(dimethylamino)phenyl]ethenyl]-6-methyl-4(3H)-pyrimidinone(NHP). NHP was obtained by condensation between 2,4-dismethyl-6-pyrimidinol and 4-dimethylaminobenzaldehyde. The chemical structure and optical properties of NHP was characterized by mass spectrometry(MS), nuclear magnetic resonance spectroscopy(NMR), ultraviolet-visible(UV-Vis) absorption spectra and fluorescence emission spectra method as well as the external environment change effect on the emission spectrum. The results show that the absorption peak of NHP is around 400 nm, and the emission peak of which is around 550 nm. The fluorescence emission of NHP is stable in various pH, ions and amino acids conditions. Furthermore, biological experimental results show that NHP is able to image HepG2/SH-SY5Y cells and Drosophila brains with negligible cytotoxicity. All of those indicate that NHP is an ideal two-photon fluorescence dye for bioimaging.

Key words: pyrimidine derivatives, two-photon imaging, fluorescent probes, bioimaging

周佳, 倪赟, 张承武, 仇兴汉, 赵燕菲, 白磊, 张高宾, 李林. 嘧啶基双光子荧光染料的设计合成与生物成像[J]. 应用化学, 2017, 34(12): 1450-1456.

Jia ZHOU, Yun NI, Chengwu ZHANG, Xinghan QIU, Yanfei ZHAO, Lei BAI, Gaobin ZHANG, Lin LI. Design and Synthesis of Pyrimidine Based Two-Photon Fluorescence Probe and Its Application in Bioimaging[J]. Chinese Journal of Applied Chemistry, 2017, 34(12): 1450-1456.

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