In vivo near-infrared fluorescence imaging of amyloid-β plaques with a dicyanoisophorone-based probe.

A dicyanoisophorone-based probe with two-photon absorption and NIR emission was developed for the in vivo fluorescence imaging of amyloid-β plaques, which exhibited high selectivity toward Aβ aggregates over other intracellular proteins. The detection limit was calculated to be as low as 109 nM. In vivo imaging studies indicated that the probe could penetrate the blood-brain barrier and label Aβ plaques in the living transgenic mice, and its specific binding to cerebral Aβ plaques was further confirmed by one- and two-photon ex vivo fluorescence imaging. All these results featured its promising application prospects for amyloid-β sensing in basic research and biomedical research.

[1]  Boli Liu,et al.  Smart near-infrared fluorescence probes with donor-acceptor structure for in vivo detection of β-amyloid deposits. , 2014, Journal of the American Chemical Society.

[2]  Sung Hoon Baik,et al.  A two-photon fluorescent probe for amyloid-β plaques in living mice. , 2013, Chemical communications.

[3]  Yogesan Kanagasingam,et al.  Innovative diagnostic tools for early detection of Alzheimer's disease , 2015, Alzheimer's & Dementia.

[4]  Hwan Myung Kim,et al.  Small-molecule two-photon probes for bioimaging applications. , 2015, Chemical reviews.

[5]  Koen Clays,et al.  Red emitting neutral fluorescent glycoconjugates for membrane optical imaging. , 2014, Bioconjugate chemistry.

[6]  Ralf Lemke.  KNOEVENAGEL-KONDENSATIONEN IN DIMETHYLFORMAMID , 1974 .

[7]  Jim Euchner.  Design , 2014, Catalysis from A to Z.

[8]  Anna Moore,et al.  Design, synthesis, and testing of difluoroboron-derivatized curcumins as near-infrared probes for in vivo detection of amyloid-beta deposits. , 2009, Journal of the American Chemical Society.

[9]  Juyoung Yoon,et al.  Recent progress in the development of near-infrared fluorescent probes for bioimaging applications. , 2014, Chemical Society reviews.

[10]  Lin Zhu,et al.  PET/SPECT imaging agents for neurodegenerative diseases. , 2014, Chemical Society reviews.

[11]  C. Leung,et al.  A G-quadruplex-selective luminescent probe with an anchor tail for the switch-on detection of thymine DNA glycosylase activity. , 2016, Biosensors & bioelectronics.

[12]  Maria Laura Bolognesi,et al.  Imaging of β-amyloid plaques by near infrared fluorescent tracers: a new frontier for chemical neuroscience. , 2015, Chemical Society reviews.

[13]  Xu Zhang,et al.  Synthesis and fluorescence of dicyanoisophorone derivatives , 2013 .

[14]  C. Andraud,et al.  Near-Infrared Solid-State Emitters Based on Isophorone: Synthesis, Crystal Structure and Spectroscopic Properties.† , 2011 .

[15]  Xu Zhang,et al.  Red fluorescence thin film based on a strong push–pull dicyanoisophorone system , 2015 .

[16]  J. Weuve,et al.  2016 Alzheimer's disease facts and figures , 2016 .

[17]  Alzheimer’s Association,et al.  2016 Alzheimer's disease facts and figures , 2016, Alzheimer's & Dementia.

[18]  M. Wong,et al.  A theranostic agent for in vivo near-infrared imaging of β-amyloid species and inhibition of β-amyloid aggregation. , 2016, Biomaterials.

[19]  Hailiang Zhu,et al.  Imaging of living cells and zebrafish in vivo using a ratiometric fluorescent probe for hydrogen sulfide. , 2015, The Analyst.

[20]  Dik-Lung Ma,et al.  Metal complexes for the detection of disease-related protein biomarkers , 2016 .

[21]  Sung Hoon Baik,et al.  A quadrupolar two-photon fluorescent probe for in vivo imaging of amyloid-β plaques , 2016, Chemical science.

[22]  G. G. Stokes.  "J." , 1890, The New Yale Book of Quotations.

[23]  L. Mucke,et al.  Amyloid-β–induced neuronal dysfunction in Alzheimer's disease: from synapses toward neural networks , 2010, Nature Neuroscience.

[24]  W. Thies,et al.  2013 Alzheimer's disease facts and figures , 2013, Alzheimer's & Dementia.

[25]  N. Cairns,et al.  Characterization of a Brain Permeant Fluorescent Molecule and Visualization of Aβ Parenchymal Plaques, Using Real-Time Multiphoton Imaging in Transgenic Mice , 2014, Organic letters.

[26]  Juyoung Yoon,et al.  Recent progress in the development of fluorescent, luminescent and colorimetric probes for detection of reactive oxygen and nitrogen species. , 2016, Chemical Society reviews.

[27]  C. L. Teoh,et al.  Chemical Fluorescent Probe for Detection of Aβ Oligomers. , 2015, Journal of the American Chemical Society.

[28]  Miss A.O. Penney.  (b) , 1974, The New Yale Book of Quotations.

[29]  Markus Rudin,et al.  In vivo detection of amyloid-β deposits by near-infrared imaging using an oxazine-derivative probe , 2005, Nature Biotechnology.

[30]  Hiroyuki Kimura,et al.  BODIPY-based molecular probe for imaging of cerebral β-amyloid plaques. , 2012, ACS chemical neuroscience.

[31]  C. Jack,et al.  Tracking pathophysiological processes in Alzheimer's disease: an updated hypothetical model of dynamic biomarkers , 2013, The Lancet Neurology.

[32]  Yan-Jiang Wang,et al.  Alzheimer disease: Lessons from immunotherapy for Alzheimer disease , 2014, Nature Reviews Neurology.

[33]  W. Webb,et al.  Measurement of two-photon excitation cross sections of molecular fluorophores with data from 690 to 1050 nm , 1996 .

[34]  Sung Hoon Baik,et al.  Two-Photon Absorbing Dyes with Minimal Autofluorescence in Tissue Imaging: Application to in Vivo Imaging of Amyloid-β Plaques with a Negligible Background Signal. , 2015, Journal of the American Chemical Society.

[35]  P. Hof,et al.  Novel pentameric thiophene derivatives for in vitro and in vivo optical imaging of a plethora of protein aggregates in cerebral amyloidoses. , 2009, ACS chemical biology.

[36]  Boli Liu,et al.  Amyloid-β Deposits Target Efficient Near-Infrared Fluorescent Probes: Synthesis, in Vitro Evaluation, and in Vivo Imaging. , 2016, Analytical chemistry.

[37]  Kaibo Zheng,et al.  Far-red to near infrared analyte-responsive fluorescent probes based on organic fluorophore platforms for fluorescence imaging. , 2013, Chemical Society Reviews.

[38]  N. Peyriéras,et al.  Biocompatible photoresistant far-red emitting, fluorescent polymer probes, with near-infrared two-photon absorption, for living cell and zebrafish embryo imaging. , 2015, Biomaterials.

[39]  Meiling Zheng,et al.  Synthesis of a water soluble red fluorescent dye and its application to living cells imaging , 2015 .

[40]  Denis Jacquemin,et al.  A water soluble probe with near infrared two-photon absorption and polarity-induced fluorescence for cerebral vascular imaging , 2013 .