title: A rapid response "Turn-On" fluorescent probe for nitroreductase detection and its application in hypoxic tumor cell imaging.
abstract: A novel "Turn-On" fluorescent probe, quaternarized 4-pyridinyl-substituted BODIPY dye by incorporating a 5-nitrofuran moiety, was developed and applied for imaging the hypoxic status of tumor cells by the indirect detection of nitroreductase. The design was based on a nitroreductase-catalyzed reduction of the nitrofuran moiety in the presence of reduced nicotinamide adenine dinucleotide (NADH) as an electron donor and followed by the 1,6-rearrangement-elimination and the release of free 4-pyridinyl-substituted BODIPY dye . This probe displayed desired properties such as high specificity, "Turn-On" fluorescence response with suitable sensitivity, appreciable water solubility and rapid response time (within 5 min). Moreover, as a biocompatible molecule, the probe has been successfully applied for imaging the hypoxic status of tumor cells (e.g. A549 cells) and especially used for real-time determination of nitroreductase produced by Escherichia coli. Therefore, we hope to apply this novel method in the biomedical research fields for the imaging of disease-relevant hypoxia and detection of pathogenic microorganisms.
authors.affiliation: 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, P. R. China. sjshao@licp.cas.cn.
authors.forename: Jian
authors.initials: J
authors.lastname: Xu
authors.forename: Shaobo
authors.initials: S
authors.lastname: Sun
authors.forename: Qian
authors.initials: Q
authors.lastname: Li
authors.forename: Ying
authors.initials: Y
authors.lastname: Yue
authors.forename: Yingdong
authors.initials: Y
authors.lastname: Li
authors.forename: Shijun
authors.initials: S
authors.lastname: Shao
mesh_terms: D001896:Boron Compounds / Q000737:chemistry; D015687:Cell Hypoxia / Q000502:physiology*; D045744:Cell Line, Tumor; D003952:Diagnostic Imaging / Q000379:methods; D004926:Escherichia coli / Q000235:genetics / Q000378:metabolism; D005456:Fluorescent Dyes; D006801:Humans; D009243:NAD / Q000737:chemistry; D009369:Neoplasms / Q000378:metabolism*; D009581:Nitrofurans / Q000737:chemistry / Q000378:metabolism*; D009601:Nitroreductases / Q000032:analysis*
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D005456:Fluorescent Dyes; D009581:Nitrofurans; D009243:NAD; D009601:Nitroreductases