title: Sensing for intracellular thiols by water-insoluble two-photon fluorescent probe incorporating nanogel.
abstract: A novel "turn-on" two-photon fluorescent probe containing a π-conjugated triarylboron luminogen and a maleimide moiety DMDP-M based on the photo-induced electron transfer (PET) mechanism for biothiol detection was designed and synthesized. By simply loading the hydrophobic DMDP-M on a cross-linked Pluronic(®) F127 nanogel (CL-F127), a probing system DMDP-M/CL-F127 was established, which shows quick response, high selectivity and sensitivity to cysteine (Cys), homocysteine (Hcy) and glutathione (GSH) in aqueous phase. The DMDP-M/CL-F127 system presented the fastest response to Cys with a rate constant of 0.56 min(-1), and the detection limit to Cys was calculated to be as low as 0.18 μM. The DMDP-M/CL-F127 system has been successfully applied to the fluorescence imaging of biothiols in NIH/3T3 fibroblasts either with single-photon or two-photon excitation because of its high biocompatibility and cell-membrane permeability. The present work provides a general, simple and efficient strategy for the application of hydrophobic molecules to sensing biothiols in aqueous phase, and a novel sensing system for intracellular biothiols fitted for both single-photon and two-photon fluorescence imaging.
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
authors.forename: Xudong
authors.initials: X
authors.lastname: Guo
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
authors.forename: Xin
authors.initials: X
authors.lastname: Zhang
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
authors.forename: Shuangqing
authors.initials: S
authors.lastname: Wang
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
authors.forename: Shayu
authors.initials: S
authors.lastname: Li
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China. Electronic address: hurui@iccas.ac.cn.
authors.forename: Rui
authors.initials: R
authors.lastname: Hu
authors.affiliation: Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, China. Electronic address: yili@mail.ipc.ac.cn.
authors.forename: Yi
authors.initials: Y
authors.lastname: Li
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China. Electronic address: gqyang@iccas.ac.cn.
authors.forename: Guoqiang
authors.initials: G
authors.lastname: Yang
mesh_terms: D000818:Animals; D005456:Fluorescent Dyes / Q000737:chemistry*; D042541:Intracellular Space / Q000378:metabolism*; D051379:Mice; D041681:NIH 3T3 Cells; D061848:Optical Imaging; D017785:Photons; D020442:Poloxamer / Q000737:chemistry*; D012995:Solubility; D013438:Sulfhydryl Compounds / Q000737:chemistry* / Q000378:metabolism*; D014867:Water / Q000737:chemistry*
chemical_list: D005456:Fluorescent Dyes; D013438:Sulfhydryl Compounds; D014867:Water; D020442:Poloxamer
keywords: Intracellular thiols; Nanogel; Sensing; Two-photon fluorescent probe; Water-insoluble