Semicarbazide-based fluorescent probe for detection of Cu2+ and formaldehyde in different channels

Yuting He; Hao Wang; Xinhang Fang; Weibing Zhang; Jingyuan Zhang; Junhong Qian

doi:10.1016/j.saa.2023.122818

Semicarbazide-based fluorescent probe for detection of Cu²⁺ and formaldehyde in different channels

Spectrochim Acta A Mol Biomol Spectrosc. 2023 Oct 15:299:122818. doi: 10.1016/j.saa.2023.122818. Epub 2023 May 5.

Authors

Yuting He¹, Hao Wang¹, Xinhang Fang¹, Weibing Zhang¹, Jingyuan Zhang², Junhong Qian³

Affiliations

¹ Shanghai Key Laboratory of Functional Materials Chemistry, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China.
² Department of Chemistry, Faculty of Science, University of Alberta, Edmonton, Alberta t6g2r3, Canada.
³ Shanghai Key Laboratory of Functional Materials Chemistry, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China. Electronic address: junhongqian@ecust.edu.cn.

PMID: 37167742
DOI: 10.1016/j.saa.2023.122818

Abstract

Two fluorescent sensors with the receptor semicarbazide respectively at 7- (CAA) and 3-position (CAB) of coumarin were designed and synthesized. CAA exhibits fluorescence turn-on response to Cu²⁺ by triggering the intramolecular charge transfer (ICT) process via Cu²⁺-catalyzed hydrolysis, and can detect formaldehyde (FA) at different channel by inhibiting the photo-induced electron transfer (PET). However, CAB displays quite different responses: the photophysical properties hardly changed in the presence of FA; while a three-stage fluorescence response of fast quenching, steady increasing and slowly decreasing was found upon addition of Cu²⁺. The high selectivity enabled CAA a good candidate for quantification of Cu²⁺ and formaldehyde as well as bioimaging Cu²⁺ in living cells. Good linear relationships between the fluorescence intensity and analyte concentration were observed in the range of 0.1-30 μM for Cu²⁺ and 1.0-50 μM for FA, and their detection limits (LOD) were calculated to be 0.43 μM and 1.92 μM (3δ/k), respectively.

Keywords: Coumarin; Cu(2+); Fluorescent discrimination; Formaldehyde; Semicarbazide.

MeSH terms

Electron Transport
Fluorescent Dyes* / pharmacology
Formaldehyde*
HeLa Cells
Humans
Spectrometry, Fluorescence / methods

Substances

Fluorescent Dyes
Formaldehyde