A fast responsive, highly selective and light-up fluorescent probe for the two-photon imaging of carboxylesterase in living cells.

A fast responsive and two photon fluorescent probe (HCyNAc) for carboxylesterase (CaE) has been designed based on the D-π-A structure of hemicyanine and naphthalene derivatives. After enzymatic reaction, HCyNAc enabled light-up fluorescence assay of CaE over other biologically-relevant species and enzymes, including ROS. Two-photon imaging of endogenous CaE was confirmed in HeLa cells using HCyNAc under 800 nm NIR excitation.

[1]  B. Tang,et al.  A simple mitochondrial targeting AIEgen for image-guided two-photon excited photodynamic therapy. , 2018, Journal of materials chemistry. B.

[2]  Weiying Lin,et al.  Unique D-π-A-π-D type fluorescent probes for the two-photon imaging of intracellular viscosity. , 2018, Journal of materials chemistry. B.

[3]  B. Tang,et al.  New AIEgens with delayed fluorescence for fluorescence imaging and fluorescence lifetime imaging of living cells , 2017 .

[4]  Honggang Cui,et al.  Self-assembling prodrugs. , 2017, Chemical Society reviews.

[5]  J. Hua,et al.  A pH-sensitive multifunctional fluorescent probe based on N-annulated perylene for the sensitive and selective detection of hypochlorous acid , 2017 .

[6]  Qin-Hua Song,et al.  Selective and Real-Time Detection of Nitric Oxide by a Two-Photon Fluorescent Probe in Live Cells and Tissue Slices. , 2017, Analytical chemistry.

[7]  Eun Sun Kim,et al.  Two-Photon Probes for pH: Detection of Human Colon Cancer using Two-Photon Microscopy. , 2017, Analytical chemistry.

[8]  Xuezheng Song,et al.  Two-photon red-emissive fluorescent probe for imaging nitroxyl (HNO) in living cells and tissues. , 2017, Journal of materials chemistry. B.

[9]  J. Qin,et al.  A two-dimensional molecule with a large conjugation degree: synthesis, two-photon absorption and charge transport ability , 2017 .

[10]  Xingbin Yang,et al.  Imaging and Detection of Carboxylesterase in Living Cells and Zebrafish Pretreated with Pesticides by a New Near-Infrared Fluorescence Off-On Probe. , 2017, Journal of agricultural and food chemistry.

[11]  Hong-jiang Wang,et al.  Lighting-up breast cancer cells by a near-infrared fluorescent probe based on KIAA1363 enzyme-targeting. , 2017, Chemical communications.

[12]  Xiaobing Zhang,et al.  Selective Visualization of the Endogenous Peroxynitrite in an Inflamed Mouse Model by a Mitochondria-Targetable Two-Photon Ratiometric Fluorescent Probe. , 2017, Journal of the American Chemical Society.

[13]  S. Park,et al.  A carboxylesterase-selective ratiometric fluorescent two-photon probe and its application to hepatocytes and liver tissues† †Electronic supplementary information (ESI) available: Synthesis, additional methods, and figures (Fig. S1–S17, Tables S1 and S2). See DOI: 10.1039/c5sc05001d , 2016, Chemical science.

[14]  Guangbo Ge,et al.  A Two-Photon Ratiometric Fluorescent Probe for Imaging Carboxylesterase 2 in Living Cells and Tissues. , 2015, ACS applied materials & interfaces.

[15]  Tongyi Dou,et al.  A Highly Selective Ratiometric Two-Photon Fluorescent Probe for Human Cytochrome P450 1A. , 2015, Journal of the American Chemical Society.

[16]  Fang Zeng,et al.  A ratiometric fluorescent system for carboxylesterase detection with AIE dots as FRET donors. , 2015, Chemical communications.

[17]  Eunjin Kim,et al.  A cysteamine-selective two-photon fluorescent probe for ratiometric bioimaging. , 2015, Chemical communications.

[18]  Yufang Xu,et al.  A highly selective turn-on fluorescent probe based on semi-cyanine for the detection of nitroreductase and hypoxic tumor cell imaging , 2014 .

[19]  Liang Xu,et al.  A highly selective long-wavelength fluorescent probe for the detection of human carboxylesterase 2 and its biomedical applications. , 2014, Chemical Communications.

[20]  P. Fernandes,et al.  The catalytic mechanism of carboxylesterases: a computational study. , 2014, Biochemistry.

[21]  Guangbo Ge,et al.  A highly selective ratiometric fluorescent probe for in vitro monitoring and cellular imaging of human carboxylesterase 1. , 2014, Biosensors & bioelectronics.

[22]  Jing Zhang,et al.  Molecular engineering of a TBET-based two-photon fluorescent probe for ratiometric imaging of living cells and tissues. , 2014, Journal of the American Chemical Society.

[23]  Ben Zhong Tang,et al.  A fluorescent light-up probe with "AIE + ESIPT" characteristics for specific detection of lysosomal esterase. , 2014, Journal of materials chemistry. B.

[24]  Alexandra T. Wrobel,et al.  A Fast and Selective Near-Infrared Fluorescent Sensor for Multicolor Imaging of Biological Nitroxyl (HNO) , 2014, Journal of the American Chemical Society.

[25]  T. Koch,et al.  Carboxylesterase-2 is a highly sensitive target of the antiobesity agent orlistat with profound implications in the activation of anticancer prodrugs. , 2013, Biochemical pharmacology.

[26]  V. Herring,et al.  The Role of Human Carboxylesterases in Drug Metabolism: Have We Overlooked Their Importance? , 2013, Pharmacotherapy.

[27]  Ariel D. Quiroga,et al.  Deficiency of carboxylesterase 1/esterase‐x results in obesity, hepatic steatosis, and hyperlipidemia , 2012, Hepatology.

[28]  Lin Yuan,et al.  A unique approach to development of near-infrared fluorescent sensors for in vivo imaging. , 2012, Journal of the American Chemical Society.

[29]  Yuichiro Sato,et al.  Simultaneous Absolute Protein Quantification of Carboxylesterases 1 and 2 in Human Liver Tissue Fractions using Liquid Chromatography-Tandem Mass Spectrometry , 2012, Drug Metabolism and Disposition.

[30]  Xiaohua Li,et al.  A spectroscopic off-on probe for simple and sensitive detection of carboxylesterase activity and its application to cell imaging. , 2012, The Analyst.

[31]  T. Nishio,et al.  Design and synthesis of an ER-specific fluorescent probe based on carboxylesterase activity with quinone methide cleavage process. , 2011, Bioorganic & medicinal chemistry letters.

[32]  U. Bornscheuer,et al.  Simulation on the structure of pig liver esterase , 2011, Journal of molecular modeling.

[33]  Ji Hee Han,et al.  A mitochondrial-targeted two-photon probe for zinc ion. , 2011, Journal of the American Chemical Society.

[34]  R. Raines,et al.  Synthesis and utility of fluorogenic acetoxymethyl ethers. , 2011, Chemical science.

[35]  Y. Uto,et al.  Design of a SNARF-based Ratiometric Fluorescent Probe for Esterase , 2010 .

[36]  E. Kool,et al.  DNA-polyfluorophore excimers as sensitive reporters for esterases and lipases. , 2010, Chemical communications.

[37]  Y. Fujikawa,et al.  Development of 2,6-carboxy-substituted boron dipyrromethene (BODIPY) as a novel scaffold of ratiometric fluorescent probes for live cell imaging. , 2009, Chemical communications.

[38]  Hong Yang,et al.  A comparison of HPLC and spectrophotometrical methods to determine the activity of ferulic acid esterase in commercial enzyme products and rumen contents of steers. , 2009 .

[39]  Sung Won Cho,et al.  Human plasma carboxylesterase 1, a novel serologic biomarker candidate for hepatocellular carcinoma , 2009, Proteomics.

[40]  Hazel A. Collins,et al.  Two-photon absorption and the design of two-photon dyes. , 2009, Angewandte Chemie.

[41]  Julie A. Johnson,et al.  Role of carboxylesterase 1 and impact of natural genetic variants on the hydrolysis of trandolapril. , 2009, Biochemical pharmacology.

[42]  B. Cho,et al.  Two-photon probes for intracellular free metal ions, acidic vesicles, and lipid rafts in live tissues. , 2009, Accounts of chemical research.

[43]  A. Rottmann,et al.  Determination of rat serum esterase activities by an HPLC method using S-acetylthiocholine iodide and p-nitrophenyl acetate. , 2008, Analytical biochemistry.

[44]  Takuya Terai,et al.  Fluorescent probes for bioimaging applications. , 2008, Current opinion in chemical biology.

[45]  D. Muñoz-Torrero Acetylcholinesterase inhibitors as disease-modifying therapies for Alzheimer's disease. , 2008, Current medicinal chemistry.

[46]  L. Lavis Ester bonds in prodrugs. , 2008, ACS chemical biology.

[47]  Jeong-Han Kim,et al.  An advanced method for the determination of carboxyl methyl esterase activity using gas chromatography-chemical ionization-mass spectrometry. , 2008, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[48]  S. Vandevoorde Overview of the chemical families of fatty acid amide hydrolase and monoacylglycerol lipase inhibitors. , 2008, Current topics in medicinal chemistry.

[49]  Kazuya Kikuchi,et al.  Time-resolved long-lived luminescence imaging method employing luminescent lanthanide probes with a new microscopy system. , 2007, Journal of the American Chemical Society.

[50]  Pablo Domínguez de María,et al.  Pig Liver Esterase (PLE) as Biocatalyst in Organic Synthesis: From Nature to Cloning and to Practical Applications , 2007 .

[51]  Tetsuo Satoh,et al.  Structure, function and regulation of carboxylesterases. , 2006, Chemico-biological interactions.

[52]  R. Borchardt,et al.  Enzymes involved in the bioconversion of ester-based prodrugs. , 2006, Journal of pharmaceutical sciences.

[53]  W. Denk,et al.  Deep tissue two-photon microscopy , 2005, Nature Methods.

[54]  R. Raines,et al.  Latent fluorophore based on the trimethyl lock. , 2005, Journal of the American Chemical Society.

[55]  K. Hahn,et al.  Activation of Endogenous Cdc42 Visualized in Living Cells , 2004, Science.

[56]  U. Karst,et al.  A tripod ligand as new sensitiser for the enzyme amplified lanthanide luminescence determination of esterase. , 2003, The Analyst.

[57]  W. Webb,et al.  Nonlinear magic: multiphoton microscopy in the biosciences , 2003, Nature Biotechnology.

[58]  H. McLeod,et al.  Human carboxylesterase 2 is commonly expressed in tumor tissue and is correlated with activation of irinotecan. , 2002, Clinical cancer research : an official journal of the American Association for Cancer Research.

[59]  M. Reetz Lipases as practical biocatalysts. , 2002, Current opinion in chemical biology.

[60]  W. Brück,et al.  Concentration-dependent effects of the esterase inhibitor BNPP on macrophage migration and myelin phagocytosis , 2001, Brain Research.

[61]  R. Verger,et al.  Lipases: Interfacial Enzymes with Attractive Applications. , 1998, Angewandte Chemie.

[62]  M Hosokawa,et al.  The mammalian carboxylesterases: from molecules to functions. , 1998, Annual review of pharmacology and toxicology.