Fluorescent properties and in vitro studies of new dehydroabietic acid-based diarylamines fluorescent probes

Abstract

A series of dehydroabietic acid-based diarylamines have been synthesized in order to investigate their fluorescent properties, photostability, cell toxicity and in vitro fluorescence imaging. The geometries as well as their molecular properties were optimized at the B3LYP/6-31G* level using Gaussian 03. The results indicate that molecular geometry, HOMO and LUMO energies, and energy gaps are important to predict absorption and fluorescent properties. Five of the compounds can be effectively taken up by human cervical carcinoma, human hepatocellular carcinoma SMMC-7721, human gastric cancer SGC-7901 and human lung adenocarcinoma A549 cells and strong blue fluorescent signals are detected in these cells. These compounds are potential candidates for fluorescent probes in biological diagnosis.

Keywords

dehydroabietic acid-based diarylamine / DFT study / fluorescent probe / in vitro imaging

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Supplementary materials

The online version of this article at http://dx.doi.org/10.15302/J-FASE-2017133 contains supplementary materials (Figs. S1–S15; Table S1).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (31670576), and Introduction of the International Advanced Forestry Science and Technology Program (2015-4-44).

Compliance with ethics guidelines

Hong Gao, Jie Song, Shibin Shang, and Zhanqian Song declare that they have no conflicts of interest or financial conflicts to disclose.

All applicable institutional and national guidelines for the care and use of animals were followed.

RIGHTS & PERMISSIONS

The Author(s) 2017. Published by Higher Education Press. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0)