Benzoselenazolium-based hemicyanine dye for G-Quadruplex detection.

Zhang-Chi Li, Tian-Ying Wu, Shu-Tang Zeng, Lan Fang, Jun-Xin Mao, Shuo-Bin Chen, Zhi-Shu Huang, Xiu-Cai Chen, Jia-Heng Tan

Bioorganic & medicinal chemistry letters 2022 Aug 15

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Benzothiazolium and benzoxazolium are common groups for the construction of hemicyanine dyes; however, their isosteric analogue benzoselenazolium have rarely been studied. Here, we report the development of the first benzoselenazolium-based hemicyanine dye for the selective detection of G-quadruplexes. This molecule, SEMA-1, was validated as a red-emitting and activatable fluorescent probe whose fluorescence would only be activated in the presence of G-quadruplexes in buffer solution. Consistent with this, SEMA-1 was found to accumulate in nucleoli and could be used to detect the high abundance of nucleolar rDNA and rRNA G-quadruplexes in fixed HeLa cells. On the other hand, due to the retained mitochondrial membrane potential in live HeLa cells, SEMA-1 was captured by mitochondria and had the potential to detect the mitochondrial G-quadruplexes. Collectively, this work demonstrates the value of developing G-quadruplex-specific fluorescent probes from novel benzoselenazolium-based hemicyanine scaffold. Copyright © 2022 Elsevier Ltd. All rights reserved.

Citation

Zhang-Chi Li, Tian-Ying Wu, Shu-Tang Zeng, Lan Fang, Jun-Xin Mao, Shuo-Bin Chen, Zhi-Shu Huang, Xiu-Cai Chen, Jia-Heng Tan. Benzoselenazolium-based hemicyanine dye for G-Quadruplex detection. Bioorganic & medicinal chemistry letters. 2022 Aug 15;70:128801