A colorimetric and ratiometric fluorescent probe for thiols and its bioimaging applications.

A naphthalimide-based colorimetric fluorescent probe containing a disulfide group was designed and synthesized, which could detect the physiological level of GSH quantitatively by a ratiometric fluorescence method and was successfully applied to the imaging of thiols in living HeLa cells.

[1]  X. Qian,et al.  A highly selective and sensitive fluorescent chemosensor for Hg2+ in neutral buffer aqueous solution. , 2004, Journal of the American Chemical Society.

[2]  Jianzhang Zhao,et al.  A selective fluorescent sensor for imaging Cd2+ in living cells. , 2007, Journal of the American Chemical Society.

[3]  Terence E. Rice,et al.  New Fluorescent Model Compounds for the Study of Photoinduced Electron Transfer: The Influence of a Molecular Electric Field in the Excited State , 1995 .

[4]  E. Wang,et al.  Sensitive and selective sensor for biothiols in the cell based on the recovered fluorescence of the CdTe quantum dots-Hg(II) system. , 2009, Analytical chemistry.

[5]  G. Rao,et al.  N-Ethylmaleimide Inhibits Platelet-derived Growth Factor BB-stimulated Akt Phosphorylation via Activation of Protein Phosphatase 2A* , 2002, The Journal of Biological Chemistry.

[6]  D. Sem,et al.  Fluorescence-based detection of thiols in vitro and in vivo using dithiol probes. , 2006, Analytical biochemistry.

[7]  Y. Urano,et al.  Development of an iminocoumarin-based zinc sensor suitable for ratiometric fluorescence imaging of neuronal zinc. , 2007, Journal of the American Chemical Society.

[8]  Xiaoling Zhang,et al.  The determination of thiols based using a probe that utilizes both an absorption red-shift and fluorescence enhancement , 2010 .

[9]  Evan W. Miller,et al.  A fluorescent sensor for imaging reversible redox cycles in living cells. , 2007, Journal of the American Chemical Society.

[10]  D. Spring,et al.  A selective and ratiometric Cu2+ fluorescent probe based on naphthalimide excimer-monomer switching. , 2010, Chemical communications.

[11]  B. Tang,et al.  A fast-response, highly sensitive and specific organoselenium fluorescent probe for thiols and its application in bioimaging. , 2009, Chemical communications.

[12]  S. Greenfield,et al.  Multistep Photochemical Charge Separation in Rod-like Molecules Based on Aromatic Imides and Diimides , 1996 .

[13]  Tao Yi,et al.  A highly selective fluorescence turn-on sensor for cysteine/homocysteine and its application in bioimaging. , 2007, Journal of the American Chemical Society.

[14]  Siyuan Zhang,et al.  Critical roles of intracellular thiols and calcium in parthenolide-induced apoptosis in human colorectal cancer cells. , 2004, Cancer letters.

[15]  Y. Gao,et al.  Theoretical Investigation of the Directional Electron Transfer in 4-Aminonaphthalimide Compounds † , 2002 .

[16]  Xiaoling Zhang,et al.  A ratiometric fluorescent probe based on FRET for imaging Hg2+ ions in living cells. , 2008, Angewandte Chemie.

[17]  Ji Hee Han,et al.  A two-photon fluorescent probe for thiols in live cells and tissues. , 2010, Journal of the American Chemical Society.

[18]  M. Tian,et al.  A fluorescent chemodosimeter specific for cysteine: effective discrimination of cysteine from homocysteine. , 2009, Chemical communications.

[19]  Tao Yi,et al.  FRET-based sensor for imaging chromium(III) in living cells. , 2008, Chemical communications.

[20]  Lin Yuan,et al.  A ratiometric fluorescent probe for cysteine and homocysteine displaying a large emission shift. , 2008, Organic letters.

[21]  Chun Liu,et al.  A ratiometric fluorescent sensor with a large Stokes shift for imaging zinc ions in living cells. , 2009, Chemical communications.

[22]  G. Federici,et al.  Determination of blood total, reduced, and oxidized glutathione in pediatric subjects. , 2001, Clinical chemistry.

[23]  B. Tang,et al.  A rhodamine-based fluorescent probe containing a Se-N bond for detecting thiols and its application in living cells. , 2007, Journal of the American Chemical Society.

[24]  D. Spring,et al.  Zn2+-triggered amide tautomerization produces a highly Zn2+-selective, cell-permeable, and ratiometric fluorescent sensor. , 2010, Journal of the American Chemical Society.

[25]  R. Weissleder,et al.  A highly selective fluorescent probe for thiol bioimaging. , 2008, Organic letters.

[26]  Yufang Xu,et al.  Highly selective fluorescent chemosensor with red shift for cysteine in buffer solution and its bioimage: symmetrical naphthalimide aldehyde , 2008 .

[27]  K. Davies.  Oxidative stress: the paradox of aerobic life. , 1995, Biochemical Society symposium.

[28]  Xiu‐Ping Yan,et al.  Photoactivated CdTe/CdSe quantum dots as a near infrared fluorescent probe for detecting biothiols in biological fluids. , 2009, Analytical chemistry.

[29]  Fuyou Li,et al.  Selective phosphorescence chemosensor for homocysteine based on an iridium(III) complex. , 2007, Inorganic chemistry.

[30]  Hae-Jo Kim,et al.  Highly selective fluorescent sensor for homocysteine and cysteine , 2008 .

[31]  Evan W. Miller,et al.  An ICT-based approach to ratiometric fluorescence imaging of hydrogen peroxide produced in living cells. , 2008, Journal of the American Chemical Society.

[32]  J. Perez,et al.  Quantum Dot-Based OFF/ON Probe for Detection of Glutathione , 2009 .

[33]  Z. A. Wood,et al.  Structure, mechanism and regulation of peroxiredoxins. , 2003, Trends in biochemical sciences.

[34]  X. Qian,et al.  Ratiometric and water-soluble fluorescent zinc sensor of carboxamidoquinoline with an alkoxyethylamino chain as receptor. , 2008, Organic letters.

[35]  J. Tusa,et al.  A fluorescent sensor with high selectivity and sensitivity for potassium in water. , 2003, Journal of the American Chemical Society.

[36]  J. Tusa,et al.  A fluorescent chemosensor for sodium based on photoinduced electron transfer. , 2003, Analytical chemistry.

[37]  J. Chmielewski,et al.  Fluorescence imaging of cellular glutathione using a latent rhodamine. , 2008, Organic letters.

[38]  A. Ajayaghosh,et al.  A near-infrared squaraine dye as a latent ratiometric fluorophore for the detection of aminothiol content in blood plasma. , 2008, Angewandte Chemie.

[39]  W. MacNee,et al.  Regulation of redox glutathione levels and gene transcription in lung inflammation: therapeutic approaches. , 2000, Free radical biology & medicine.

[40]  Zhe Lu,et al.  Visible study of mercuric ion and its conjugate in living cells of mammals and plants. , 2005, Chemical research in toxicology.

[41]  Ying Zhou,et al.  Fluorescent and colorimetric probes for detection of thiols. , 2010, Chemical Society reviews.

[42]  Juyoung Yoon,et al.  A thiol-specific fluorescent probe and its application for bioimaging. , 2010, Chemical communications.