Citation: ZHOU Jia, NI Yun, ZHANG Chengwu, QIU Xinghan, ZHAO Yanfei, BAI Lei, ZHANG Gaobin, LI Lin. 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. doi: 10.11944/j.issn.1000-0518.2017.12.170319 shu

Design and Synthesis of Pyrimidine Based Two-Photon Fluorescence Probe and Its Application in Bioimaging

Key Laboratory of Flexible Electronics(KLOFE) & Institute of Advanced Materials(IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials(SICAM), Nanjing Tech University(Nanjing Tech), Nanjing 211816, China

Corresponding author: ZHANG Chengwu, iamcwzhang@njtech.edu.cn ZHANG Gaobin, iamgbzhang@njtech.edu.cn LI Lin, iamlli@njtech.edu.cn
Received Date: 5 September 2017
Revised Date: 23 October 2017
Accepted Date: 23 October 2017

Fund Project: the National Natural Science Foundation of China 81672508Supported by the National Natural Science Foundation of China(No.81672508, No.61505076), the Major Projects of Natural Science Research in Colleges and Universities in Jiangsu(No.16KJA180004)the National Natural Science Foundation of China 61505076the Major Projects of Natural Science Research in Colleges and Universities in Jiangsu 16KJA180004

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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.
- pyrimidine derivatives,
- two-photon imaging,
- fluorescent probes,
- bioimaging
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