title: Fluorescent sensors based on [12]aneN3-modified BODIPY: Discrimination of different biological thiols in aqueous solution and living cells.
abstract: Two fluorescent probes, 1 and 2, derived from borondipyrromethene (BODIPY) modified with macrocyclic polyamine [12]aneN3, were synthesized and applied in the discrimination of cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) with absorption and fluorescent spectroscopy in comparison. It was found that Boc-protected 1 showed highly sensitive and selective recognition of GSH over Cys and Hcy; while probe 2 was able to distinguish the three different thiols due to their different reactivities. With its water-solubility, rapid responsiveness, high sensitivity and low cytotoxicity, probe 2 was successfully applied in the fast detection of three biothiols in living cells.
authors.affiliation: Key Laboratory of Theoretical and Computational Photochemistry, Ministry of Education, College of Chemistry, Beijing Normal University, Xinjiekouwai Street 19, Beijing 100875, China.
authors.forename: Yong-Guang
authors.initials: YG
authors.lastname: Gao
authors.affiliation: Key Laboratory of Theoretical and Computational Photochemistry, Ministry of Education, College of Chemistry, Beijing Normal University, Xinjiekouwai Street 19, Beijing 100875, China.
authors.forename: Ying
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Theoretical and Computational Photochemistry, Ministry of Education, College of Chemistry, Beijing Normal University, Xinjiekouwai Street 19, Beijing 100875, China.
authors.forename: You-Di
authors.initials: YD
authors.lastname: Shi
authors.affiliation: Key Laboratory of Theoretical and Computational Photochemistry, Ministry of Education, College of Chemistry, Beijing Normal University, Xinjiekouwai Street 19, Beijing 100875, China.
authors.forename: Hu-Jun
authors.initials: HJ
authors.lastname: Hao
authors.affiliation: Key Laboratory of Theoretical and Computational Photochemistry, Ministry of Education, College of Chemistry, Beijing Normal University, Xinjiekouwai Street 19, Beijing 100875, China.
authors.forename: Bing
authors.initials: B
authors.lastname: Gong
authors.affiliation: Key Laboratory of Theoretical and Computational Photochemistry, Ministry of Education, College of Chemistry, Beijing Normal University, Xinjiekouwai Street 19, Beijing 100875, China. Electronic address: luzl@bnu.edu.cn.
authors.forename: Zhong-Lin
authors.initials: ZL
authors.lastname: Lu
mesh_terms: D001896:Boron Compounds / Q000737:chemistry*; D002470:Cell Survival; D004305:Dose-Response Relationship, Drug; D005456:Fluorescent Dyes / Q000032:analysis* / Q000737:chemistry*; D006367:HeLa Cells; D056945:Hep G2 Cells; D006801:Humans; D015394:Molecular Structure; D012995:Solubility; D012996:Solutions; D013329:Structure-Activity Relationship; D013438:Sulfhydryl Compounds / Q000032:analysis* / Q000737:chemistry*; D014407:Tumor Cells, Cultured; D014867:Water / Q000737:chemistry
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D005456:Fluorescent Dyes; D012996:Solutions; D013438:Sulfhydryl Compounds; D014867:Water
keywords: BODIPY; Sensor; Thiols; [12]aneN(3)