Design of a naphthalimide-based probe for acrolein detection in foods and cells

Abstract

Acrolein is a highly toxic agent that can be generated exogenously and endogenously. Therefore, a highly specific and sensitive probe for acrolein with potential applications in acrolein detection must be developed. In this research, a novel fluorescent probe named “probe for acrolein detection” (Pr-ACR) was designed and synthesized based on a naphthalimide fluorophore skeleton, and a thiol group (-SH) was introduced into its structure for acrolein recognition. The -SH traps acrolein via Michael addition and the resultant interaction product of the probe inhibits the photoinduced electron transfer process and produce a strong fluorescence at 510 nm. The probe showed high sensitivity and specificity for acrolein. HPLC-MS/MS analysis verified that it can be used to quantify acrolein in foods, such as soda crackers, red wine, and baijiu, with a fluorescence spectrophotometer. After methyl esterification, the methyl esterified probe (mPr-ACR) successfully visualised acrolein in Hela cells under a laser scanning confocal microscope. This finding proved that Pr-ACR and mPr-ACR are potential tools for the detection and visualisation of acrolein from different sources.