A small molecular pH-dependent fluorescent probe for cancer cell imaging in living cell.

A novel pH-dependent two-photon fluorescent molecular probe ABMP has been prepared based on the fluorophore of 2, 4, 6-trisubstituted pyridine. The probe has an absorption wavelength at 354 nm and corresponding emission wavelength at 475 nm with the working pH range from 2.20 to 7.00, especially owning a good liner response from pH = 2.40 to pH = 4.00. ABMP also has excellent reversibility, photostability and selectivity which promotes its ability in analytical application. The probe can be excited with a two-photon fluorescence microscopy and the fluorescence cell imaging indicated that the probe can distinguish Hela cancer cells out of normal cells with a two-photon fluorescence microscopy which suggested its potential application in tumor cell detection.

[1]  Hongyuan Chen,et al.  A BODIPY-derived fluorescent probe for cellular pH measurements. , 2013, Analytical biochemistry.

[2]  Jing Liu,et al.  Highly selective and sensitive pH-responsive fluorescent probe in living Hela and HUVEC cells , 2013 .

[3]  Yixiang Cheng,et al.  Synthesis and fluorescence study of conjugated polymers based on 2,4,6-triphenylpyridine moieties , 2016 .

[4]  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.

[5]  M. Vendrell,et al.  Multicomponent reactions for de novo synthesis of BODIPY probes: in vivo imaging of phagocytic macrophages. , 2013, Journal of the American Chemical Society.

[6]  Maotian Xu,et al.  Lanthanide coordination polymer probe for time-gated luminescence sensing of pH in undiluted human serum. , 2017, Talanta.

[7]  R. Gottlieb,et al.  Apoptosis induced in Jurkat cells by several agents is preceded by intracellular acidification. , 1996, Proceedings of the National Academy of Sciences of the United States of America.

[8]  R. Xu,et al.  Design and investigation of a series of rhodamine-based fluorescent probes for optical measurements of pH. , 2010, Organic letters.

[9]  Xuezheng Song,et al.  A unique red-emitting two-photon fluorescent probe with tumor-specificity for imaging in living cells and tissues. , 2017, Talanta.

[10]  M. Lan,et al.  The study of a curcumin-resembling molecular probe for the pH-responsive fluorometric assay and application in cell imaging. , 2016, Talanta.

[11]  Ashutosh Kumar Singh,et al.  A reversible fluorescence "off-on-off" sensor for sequential detection of aluminum and acetate/fluoride ions. , 2015, Talanta.

[12]  T. Nishi,et al.  The vacuolar (H+)-ATPases — nature's most versatile proton pumps , 2002, Nature Reviews Molecular Cell Biology.

[13]  S. Khodadoust,et al.  Design of an optically stable pH sensor based on immobilization of Giemsa on triacetylcellulose membrane. , 2015, Materials science & engineering. C, Materials for biological applications.

[14]  Sergio Grinstein,et al.  Sensors and regulators of intracellular pH , 2010, Nature Reviews Molecular Cell Biology.

[15]  C. Unaleroglu,et al.  Colorimetric and fluorometric pH sensor based on bis(methoxycarbonyl)ethenyl functionalized BODIPY , 2015 .

[16]  Guang-Jie Song,et al.  A ratiometric lysosomal pH probe based on the imidazo[1,5-a]pyridine–rhodamine FRET and ICT system , 2016 .

[17]  Huan Yu,et al.  An intramolecular charge transfer process based fluorescent probe for monitoring subtle pH fluctuation in living cells. , 2017, Talanta.

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

[19]  T. Hayat,et al.  Sensitive determination of endogenous hydroxyl radical in live cell by a BODIPY based fluorescent probe. , 2017, Talanta.

[20]  Dong Liu,et al.  Detection of trace levels of Pd2+ in pure water using a fluorescent probe assisted by surfactants , 2016 .

[21]  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.

[22]  L. Gerweck,et al.  Cellular pH gradient in tumor versus normal tissue: potential exploitation for the treatment of cancer. , 1996, Cancer research.

[23]  Zhihong Liu,et al.  Fluorescein–formaldehyde oligomeric pH indicator: Facile synthesis, characterization, and potential application , 2005 .

[24]  Huimin Ma,et al.  Fluorescent probes and nanoparticles for intracellular sensing of pH values , 2014, Methods and applications in fluorescence.

[25]  Xuan Zhang,et al.  New fluorescent pH probes for acid conditions , 2015 .

[26]  H. Uramoto,et al.  Cellular pH regulators: potentially promising molecular targets for cancer chemotherapy. , 2003, Cancer treatment reviews.

[27]  Kevin Burgess,et al.  Fluorescent indicators for intracellular pH. , 2010, Chemical reviews.

[28]  Robert J Gillies,et al.  Acidity generated by the tumor microenvironment drives local invasion. , 2013, Cancer research.

[29]  Yuqing Wu,et al.  A highly selective and sensitive fluorescence dual-responsive pH probe in water , 2012 .

[30]  S. Luis,et al.  Turn-on fluorescent probes for nitric oxide sensing based on the ortho-hydroxyamino structure showing no interference with dehydroascorbic acid. , 2014, Chemical communications.

[31]  Juan Zhang,et al.  A fluorescent sensor for low pH values based on a covalently immobilized rhodamine–napthalimide conjugate , 2012 .

[32]  Tao Zhang,et al.  A ratiometric lysosomal pH probe based on the naphthalimide-rhodamine system. , 2015, Journal of materials chemistry. B.

[33]  Wei Feng,et al.  A ratiometric fluorescent sensor for pH fluctuation and its application in living cells with low dark toxicity , 2017 .

[34]  R. V. Omkumar,et al.  A protein–dye hybrid system as a narrow range tunable intracellular pH sensor , 2016, Chemical science.

[35]  T. Jeong,et al.  2,4,6-Trisubstituted pyridines: Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship. , 2007, Bioorganic & medicinal chemistry.

[36]  Yufen Chen,et al.  An easily Prepared Fluorescent pH Probe Based on Dansyl , 2016, Journal of Fluorescence.

[37]  Aifeng Liu,et al.  One-pot synthesis of a new rhodamine-based dually-responsive pH sensor and its application to bioimaging , 2014 .

[38]  Zhihong Liu,et al.  A ratiometric two-photon fluorescent probe for imaging hydrogen sulfide in lysosomes. , 2017, Talanta.

[39]  Chuan Dong,et al.  An indole-carbazole-based ratiometric emission pH fluorescent probe for imaging extreme acidity , 2015 .

[40]  D. Bornhop,et al.  Recent advances in receptor-targeted fluorescent probes for in vivo cancer imaging. , 2012, Current medicinal chemistry.

[41]  A. Jain,et al.  An iron(III) ion-selective sensor based on a mu-bis(tridentate) ligand. , 2007, Talanta.

[42]  H. Stoeckli-Evans,et al.  ICT based ratiometric fluorescent pH sensing using quinoline hydrazones , 2014 .

[43]  Roger Y. Tsien,et al.  Changes in intramitochondrial and cytosolic pH: early events that modulate caspase activation during apoptosis , 2000, Nature Cell Biology.

[44]  Yingfu Li,et al.  A novel far-visible and near-infrared pH probe for monitoring near-neutral physiological pH changes: imaging in live cells. , 2013, Journal of materials chemistry. B.

[45]  Jianbin Chao,et al.  A novel ''donor-π-acceptor'' type fluorescence probe for sensing pH: mechanism and application in vivo. , 2017, Talanta.

[46]  Yan Song,et al.  A novel "turn-on" thiooxofluorescein-based colorimetric and fluorescent sensor for Hg2+ and its application in living cells. , 2017, Talanta.

[47]  Bao-Xiang Zhao,et al.  A rhodamine B-based lysosomal pH probe. , 2015, Journal of materials chemistry. B.

[48]  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.