A water-soluble BODIPY derivative as a highly selective "Turn-On" fluorescent sensor for H2O2 sensing in vivo.
A type of BODIPY derivatives was designed and synthesized by the N-alkylation reaction of meso-(4-pyridinyl)-substituted BODIPY. The water-solubility of entire molecule was improved to a large extent as a result of the formation of cationic quaternary ammonium salt, while the strong fluorescence inherent to the BODIPY dye fragment is extinguished on alkylation of the pyridine N atom due to the photo-induced electron transfer (PET) process. The N-alkylated BODIPY derivative 4, as a novel water-soluble "Turn-On" fluorescent probe for the discrimination of H2O2, was constructed by incorporating 4-(Bromomethyl)benzeneboronic acid pinacol ester moiety, which showed highly selective fluorescent response to H2O2 against other interferences of ROS and RNS species under physiological conditions, and the reaction mechanism of boronate oxidation was conﬁrmed by (1)H NMR, mass spectrum and optical spectroscopy analysis. As a biocompatible probe in biological systems, probe 4 was successfully applied for monitoring and imaging of H2O2 both in vitro and in vivo using HepG2/LO2 cells and angelfish.
Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, PR China; University of Chinese Academy of Sciences, Beijing 100039, PR China.
Jian
J
Xu
Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, PR China.
Qian
Q
Li
Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, PR China.
Ying
Y
Yue
Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, PR China.
Yong
Y
Guo
Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, PR China. Electronic address: sjshao@licp.cas.cn.
Shijun
S
Shao
D000478:Alkylation; D000818:Animals; D015374:Biosensing Techniques / Q000379:methods; D001896:Boron Compounds / Q000737:chemistry*; D023681:Cichlids / Q000378:metabolism; D005456:Fluorescent Dyes / Q000737:chemistry*; D056945:Hep G2 Cells; D006801:Humans; D006861:Hydrogen Peroxide / Q000032:analysis*; D061848:Optical Imaging / Q000379:methods; D011725:Pyridines / Q000737:chemistry; D012995:Solubility; D013050:Spectrometry, Fluorescence / Q000379:methods; D014867:Water / Q000737:chemistry
C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D005456:Fluorescent Dyes; D011725:Pyridines; D014867:Water; D006861:Hydrogen Peroxide; C023666:pyridine
Fluorescent sensor; H(2)O(2); In vitro and in vivo imaging; N-alkylpyridinium substituted BODIPY derivatives; Water-soluble fluorescent probe