title: A New Strategy for Fluorogenic Esterase Probes Displaying Low Levels of Non-specific Hydrolysis.
abstract: A new design for fluorescence probes of esterase activity that features a carboxylate-side pro-fluorophore is demonstrated with boron dipyrromethene (BODIPY)-based probes 1 a and 1 b. Because the design relies on the enzyme-catalyzed hydrolysis of an ester group that is not electronically activated, these probes exhibit a stability to background hydrolysis that is far superior to classical alcohol-side profluorophore-based probes, large signal-to-noise ratios, reduced sensitivity to pH variations, and high enzymatic reactivity. The utility of probe 1 a was established with a real-time fluorescence imaging experiment of endogenous esterase activity that does not require washing of the extracellular medium.
authors.affiliation: Department of Chemistry, Institute of Nanosensor and Biotechnology, Dankook University, 152 Jukjeon-ro, Suji-gu, Yongin-si, Gyeonggi-do, 448-701 (Korea), Fax: (+82) 31-8005-3148.
authors.forename: Sungwoo
authors.initials: S
authors.lastname: Kim
authors.affiliation: Molecular Imaging & Therapy Branch, National Cancer Center, 323 Ilsan-ro, Goyang-si, Gyeonggi-do, 410-769 (Korea).
authors.forename: Hyunjin
authors.initials: H
authors.lastname: Kim
authors.affiliation: Molecular Imaging & Therapy Branch, National Cancer Center, 323 Ilsan-ro, Goyang-si, Gyeonggi-do, 410-769 (Korea). ydchoi@ncc.re.kr.
authors.forename: Yongdoo
authors.initials: Y
authors.lastname: Choi
authors.affiliation: Department of Chemistry, Institute of Nanosensor and Biotechnology, Dankook University, 152 Jukjeon-ro, Suji-gu, Yongin-si, Gyeonggi-do, 448-701 (Korea), Fax: (+82) 31-8005-3148. youngmi@dankook.ac.kr.
authors.forename: Youngmi
authors.initials: Y
authors.lastname: Kim
mesh_terms: D055162:Biocatalysis; D001896:Boron Compounds / Q000737:chemistry*; D004950:Esterases / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D006868:Hydrolysis; D013050:Spectrometry, Fluorescence
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D005456:Fluorescent Dyes; D004950:Esterases
keywords: BODIPY; esterase; fluorescent probe; fluorogenic substrate; turn-on