A coumarin-based two-photon probe for hydrogen peroxide

• DOI: 10.1016/j.bios.2014.09.073
• Publication Date: 2014-10-01T00:40:30Z
• Authors: Kai-Ming Zhang; Wei Dou; Peng-Xuan Li; Rong Shen; Jia-Xi Ru; Wei Liu; Yu-Mei Cui; Chun-Yang Chen; Wei-Sheng Liu; De-Cheng Bai
• Keywords: Microscopy, Fluorescence, Multiphoton; Coumarins; Cell Line, Tumor; Humans; Hydrogen Peroxide; Neoplasms, Experimental; 01 natural sciences; Fluorescent Dyes; Molecular Imaging; 0104 chemical sciences

A new fluorescence probe was developed for hydrogen peroxide (H2O2) detection based on donor-excited photo induced electron transfer (D-PET) mechanism, together with the benzil as a quenching and recognizing moiety. The benzil could convert to benzoic anhydride via a Baeyer-Villiger type reaction in the presence of H2O2, followed by hydrolysis of benzoicanhydride to give benzoic acid, and the fluorophore released. The probe was synthesized by a 6-step procedure starting from 4-(diethylamino)salicylaldehyde. A density functional theory (DFT) calculation was performed to demonstrate that the benzil was a fluorescence quencher. The probe was evaluated in both one-photon and two-photon mode, and it exhibited high selectivity toward H2O2 over other reactive oxygen species and high sensitivity with a detection limit of 0.09 μM. Furthermore, the probe was successfully applied to cell imaging of intracellular H2O2 levels with one-photon microscopy and two-photon microscopy. The superior properties of the probe made it of great potential use in more chemical and biological researches.