A coumarin-based two-photon probe for hydrogen peroxide.

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

Journal: Biosensors & bioelectronics 2015;64():542-6

PMID: 25310486

Full Text on Elsevier Science View on PubMed

Abstract

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.

Address: Key Laboratory of Nonferrous Metals Chemistry and Resources Utilization of Gansu Province and State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, PR China.; Key Laboratory of Preclinical Study for New Drugs of Gansu Province and Operative Surgery Institute, School of Basic Medical Sciences, Lanzhou University, Lanzhou 730000, PR China.; Key Laboratory of Nonferrous Metals Chemistry and Resources Utilization of Gansu Province and State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, PR China. Electronic address: [email protected].; Key Laboratory of Preclinical Study for New Drugs of Gansu Province and Operative Surgery Institute, School of Basic Medical Sciences, Lanzhou University, Lanzhou 730000, PR China. Electronic address: [email protected].

DOI: 10.1016/j.bios.2014.09.073

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MeSH Terms: Cell Line, Tumor, Coumarins, Fluorescent Dyes, Humans, Hydrogen Peroxide, Microscopy, Fluorescence, Multiphoton, Molecular Imaging, Neoplasms, Experimental