Design and Synthesis of Dipeptidomimetic Isocyanonaphthalene as Enhanced-Fluorescent Chemodosimeter for Sensing Mercury Ion and Living Cells

Xiao-Juan Wang; Gao-Wei Li; Yi-Peng Cheng; Qiu-Ling Sun; Yuan-Qiang Hao; Chen-Hong Wang; Lan-Tao Liu

doi:10.3389/fchem.2022.813108

Design and Synthesis of Dipeptidomimetic Isocyanonaphthalene as Enhanced-Fluorescent Chemodosimeter for Sensing Mercury Ion and Living Cells

Front Chem. 2022 Mar 4:10:813108. doi: 10.3389/fchem.2022.813108. eCollection 2022.

Authors

Xiao-Juan Wang¹, Gao-Wei Li¹, Yi-Peng Cheng¹, Qiu-Ling Sun¹, Yuan-Qiang Hao¹, Chen-Hong Wang¹, Lan-Tao Liu¹

Affiliation

¹ College of Chemistry and Chemical Engineering, Henan Engineering Laboratory of Green Synthesis for Pharmaceuticals, and Henan Key Laboratory of Biomolecular Recognition and Sensing, Shangqiu Normal University, Shangqiu, China.

Abstract

A novel valine-based isocyanonaphthalene (NpI) was designed and synthesized by using an easy method and enabled the selective fluorescence detection of Hg²⁺. The chemodosimeter can display an immediate turn-on fluorescence response (500-fold) towards target metal ions upon the Hg²⁺-mediated conversion of isocyano to amino within NpI. Based on this specific reaction, the fluorescence-enhancement probe revealed a high sensitivity toward Hg²⁺ over other common metal ions and exhibited excellent aqueous solubility, good antijamming capability, high sensitivity (detection limit: 14.2 nM), and real-time detection. The response mechanism of NpI was supported by NMR spectroscopy, MS analysis and DFT theoretical calculation using various techniques. Moreover, a dipeptidomimetic NpI probe was successfully applied to visualize intracellular Hg²⁺ in living cells and monitor Hg²⁺ in real water samples with good recoveries and small relative standard deviations.

Keywords: cell imaging; dipeptidomimetic; fluorescent probe; isocyanonaphthalene; mercury ion.