title: Molecular engineering of a mitochondrial-targeting two-photon in and near-infrared out fluorescent probe for gaseous signal molecules H2S in deep tissue bioimaging.
abstract: Hydrogen sulfide (H2S), one of the biologically important gaseous signal molecules, plays an essential role in diverse normal biochemical functions and pathological processes. Herein, an efficient two-photon in and near-infrared out mitochondria-targeting dye has been designed, synthesized and characterized. It is easily synthesized by the condensation reaction (C˭C) of 4-hydroxybenzaldehyde and 6-(diethylamino)-1,2,3,4-tetrahydroxanthylium (mitochondria-targeting), which possesses large two-photon action absorption cross-section ~160g and high fluorescence quantum yield ~0.15. Encouraged by the results, we proceeded to conjugate this new dye with a H2S recognition moiety (4-dinitrobenzene-ether, DNB), on the basis of the intramolecular charge transfer (ICT) strategy, to construct a novel H2S fluorescent probe (TP-NIR-HS), which shows a targeting ability with high sensitivity and selectivity, and low cytotoxicity. This new probe was then applied for two-photon imaging of living cells and tissues and showed high imaging resolution and a deep-tissue imaging depth of ~350µm, thus demonstrating its practical application in biological systems, and providing a valuable theoretical basis and technical support for the study of physiological and pathological functions of H2S.
authors.affiliation: College of Food Science and Technology, Central South University of Forestry and Technology Changsha, Hunan 410004, P. R. China; College of Life Sciences and Chemistry, Hunan University of Technology, Hunan 412007, P. R. China. Electronic address: zhouly0817@hut.edu.cn.
authors.forename: Liyi
authors.initials: L
authors.lastname: Zhou
authors.affiliation: Molecular Sciences and Biomedicine Laboratory, State Key Laboratory for Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Collaborative Innovation Center for Chemistry and Molecular Medicine, Hunan University, Changsha 410082, China.
authors.forename: Danqing
authors.initials: D
authors.lastname: Lu
authors.affiliation: Molecular Sciences and Biomedicine Laboratory, State Key Laboratory for Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Collaborative Innovation Center for Chemistry and Molecular Medicine, Hunan University, Changsha 410082, China.
authors.forename: Qianqian
authors.initials: Q
authors.lastname: Wang
authors.affiliation: College of Life Sciences and Chemistry, Hunan University of Technology, Hunan 412007, P. R. China.
authors.forename: Sihua
authors.initials: S
authors.lastname: Liu
authors.affiliation: College of Food Science and Technology, Central South University of Forestry and Technology Changsha, Hunan 410004, P. R. China.
authors.forename: Qinlu
authors.initials: Q
authors.lastname: Lin
authors.affiliation: Department of Biology and Chemistry, City University of Hong Kong, 83 Tat Chee Avenue, Kowloon, Hong Kong, P. R. China.
authors.forename: Hongyan
authors.initials: H
authors.lastname: Sun
mesh_terms: D000818:Animals; D015374:Biosensing Techniques / Q000379:methods; D002460:Cell Line; D005456:Fluorescent Dyes / Q000737:chemistry*; D064426:Gasotransmitters / Q000032:analysis*; D006801:Humans; D006862:Hydrogen Sulfide / Q000032:analysis*; D007259:Infrared Rays; D008819:Mice, Nude; D008856:Microscopy, Fluorescence / Q000379:methods; D008928:Mitochondria / Q000737:chemistry*; D061848:Optical Imaging / Q000379:methods*; D013050:Spectrometry, Fluorescence / Q000379:methods
chemical_list: D005456:Fluorescent Dyes; D064426:Gasotransmitters; D006862:Hydrogen Sulfide
keywords: Bioimaging; Gaseous signal molecules; Mitochondrial-targeting; Near-infrared; Two-photon