Bispyrene-fluorescein hybrid based FRET cassette: a convenient platform toward ratiometric time-resolved probe for bioanalytical applications.

Pyrene excimer possesses a large Stokes shift and long fluorescence lifetime and has been widely applied in developing time-resolved biosensing systems to solve the autofluorescence interference problems in biological samples. However, only a few of pyrene excimer-based small molecular probes have been reported so far. Ratiometric probes, on the other hand, can eliminate interferences from environmental factors such as instrumental efficiency and environmental conditions by a built-in correction of the dual emission bands but are ineffective for endogenous autofluorescence in biosystems. In this work, by combining the advantages of time-resolved fluorescence technique with ratiometric probe, we reported a bispyrene-fluorescein hybrid FRET cassette (PF) as a novel ratiometric time-resolved sensing platform for bioanalytical applications, with pH chosen as a biorelated target. The probe PF showed a fast, highly selective, and reversible ratiometric fluorescence response to pH in a wide range from 3.0 to 10.0 in buffered solution. By employing time-resolved fluorescence technique, the pH-induced fluorescence signal of probe PF can be well-discriminated from biological autofluorescence background, which enables us to detect pH in a range of 4.0-8.0 in cell media within a few seconds. It has also been preliminarily applied for ratiometric quantitative monitoring of pH changes in living cells with satisfying results. Since many fluorescein-based fluorescence probes have been developed, our strategy might find wide applications in design ratiometric time-resolved probes for detection of various biorelated targets.

[1]  Juyoung Yoon,et al.  A bispyrene derivative as a selective fluorescent probe for RNA. , 2014, Chemical communications.

[2]  Huimin Ma,et al.  Design strategies for water-soluble small molecular chromogenic and fluorogenic probes. , 2014, Chemical reviews.

[3]  Jian‐mei Lu,et al.  A coumarin-indole-based near-infrared ratiometric pH probe for intracellular fluorescence imaging. , 2013, The Analyst.

[4]  Guoping Li,et al.  Quinoline-based fluorescent probe for ratiometric detection of lysosomal pH. , 2013, Organic letters.

[5]  R. Kumar,et al.  Two-color probe to monitor a wide range of pH values in cells. , 2013, Angewandte Chemie.

[6]  Wei Feng,et al.  Luminescent chemodosimeters for bioimaging. , 2013, Chemical reviews.

[7]  Jiangli Fan,et al.  Energy transfer cassettes based on organic fluorophores: construction and applications in ratiometric sensing. , 2013, Chemical Society reviews.

[8]  Jiangli Fan,et al.  Imaging of lysosomal pH changes with a fluorescent sensor containing a novel lysosome-locating group. , 2012, Chemical communications.

[9]  Yi Lu,et al.  Direct detection of adenosine in undiluted serum using a luminescent aptamer sensor attached to a terbium complex. , 2012, Analytical chemistry.

[10]  Alan S. Waggoner,et al.  Genetically encoded pH sensor for tracking surface proteins through endocytosis. , 2012, Angewandte Chemie.

[11]  Juyoung Yoon,et al.  Fluorescent chemosensors based on spiroring-opening of xanthenes and related derivatives. , 2012, Chemical reviews.

[12]  Lin Yuan,et al.  Development of FRET-based dual-excitation ratiometric fluorescent pH probes and their photocaged derivatives. , 2012, Chemistry.

[13]  B. Davidson,et al.  Clarifying lysosomal storage diseases , 2011, Trends in Neurosciences.

[14]  K. Hanaoka,et al.  Rational design of ratiometric near-infrared fluorescent pH probes with various pKa values, based on aminocyanine. , 2011, Journal of the American Chemical Society.

[15]  Kemin Wang,et al.  Competition-mediated pyrene-switching aptasensor: probing lysozyme in human serum with a monomer-excimer fluorescence switch. , 2010, Analytical chemistry.

[16]  Yanxi Zhang,et al.  Reversible three-state switching of multicolor fluorescence emission by multiple stimuli modulated FRET processes within thermoresponsive polymeric micelles. , 2010, Angewandte Chemie.

[17]  Cuichen Wu,et al.  A general excimer signaling approach for aptamer sensors. , 2010, Biosensors & bioelectronics.

[18]  David A. Rand,et al.  Measurement of single-cell dynamics , 2010, Nature.

[19]  Amitabha Sarkar,et al.  Palladium nanoparticle catalyzed Hiyama coupling reaction of benzyl halides. , 2010, The Journal of organic chemistry.

[20]  Daniel O. Frimannsson,et al.  Azide conjugatable and pH responsive near-infrared fluorescent imaging probes. , 2009, Organic letters.

[21]  Kwang Soo Kim,et al.  Unique sandwich stacking of pyrene-adenine-pyrene for selective and ratiometric fluorescent sensing of ATP at physiological pH. , 2009, Journal of the American Chemical Society.

[22]  Ping Li,et al.  A near-infrared neutral pH fluorescent probe for monitoring minor pH changes: imaging in living HepG2 and HL-7702 cells. , 2009, Journal of the American Chemical Society.

[23]  Jong Seung Kim,et al.  Tren-spaced rhodamine and pyrene fluorophores: Excimer modulation with metal ion complexation , 2009 .

[24]  Erhan Deniz,et al.  Bidirectional switching of near IR emitting boradiazaindacene fluorophores. , 2008, Organic letters.

[25]  C. Niemeyer,et al.  Self-assembled donor comprising quantum dots and fluorescent proteins for long-range fluorescence resonance energy transfer. , 2008, Journal of the American Chemical Society.

[26]  Weihong Tan,et al.  Pyrene excimer signaling molecular beacons for probing nucleic acids. , 2008, Journal of the American Chemical Society.

[27]  X. Cui,et al.  Reagentless aptamer based impedance biosensor for monitoring a neuro-inflammatory cytokine PDGF. , 2007, Biosensors & bioelectronics.

[28]  Yasuhiro Shiraishi,et al.  Effects of metal cation coordination on fluorescence properties of a diethylenetriamine bearing two end pyrene fragments. , 2007, The journal of physical chemistry. B.

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

[30]  Hsiao-Yun Wu,et al.  Characterization and application of single fluorescent nanodiamonds as cellular biomarkers , 2007, Proceedings of the National Academy of Sciences.

[31]  Yasuhiro Shiraishi,et al.  pH- and H2O-driven triple-mode pyrene fluorescence. , 2006, Organic letters.

[32]  E. Beutler.  Lysosomal storage diseases: natural history and ethical and economic aspects. , 2006, Molecular genetics and metabolism.

[33]  S. Jockusch,et al.  Pyrene binary probes for unambiguous detection of mRNA using time-resolved fluorescence spectroscopy , 2006, Nucleic acids research.

[34]  S. Shackney,et al.  A simple correction for cell autofluorescence for multiparameter cell‐based analysis of human solid tumors , 2006, Cytometry. Part B, Clinical cytometry.

[35]  R. Brady.  Enzyme replacement for lysosomal diseases. , 2006, Annual review of medicine.

[36]  Weihong Tan,et al.  Light-switching excimer probes for rapid protein monitoring in complex biological fluids. , 2005, Proceedings of the National Academy of Sciences of the United States of America.

[37]  Takahiko Nojima,et al.  A pyrene-labeled G-quadruplex oligonucleotide as a fluorescent probe for potassium ion detection in biological applications. , 2005, Angewandte Chemie.

[38]  Ehud Y Isacoff,et al.  A selective, cell-permeable optical probe for hydrogen peroxide in living cells. , 2004, Journal of the American Chemical Society.

[39]  J. Lee,et al.  An excimer-based, binuclear, on-off switchable calix[4]crown chemosensor. , 2004, Journal of the American Chemical Society.

[40]  Anthony H. Futerman,et al.  The cell biology of lysosomal storage disorders , 2004, Nature Reviews Molecular Cell Biology.

[41]  Kazuhisa Fujimoto,et al.  Unambiguous detection of target DNAs by excimer-monomer switching molecular beacons. , 2004, The Journal of organic chemistry.

[42]  M. Russo,et al.  Regulation of Intracellular pH Mediates Bax Activation in HeLa Cells Treated with Staurosporine or Tumor Necrosis Factor-α* , 2002, The Journal of Biological Chemistry.

[43]  M. Donowitz,et al.  Subcellular Redistribution Is Involved in Acute Regulation of the Brush Border Na+/H+ Exchanger Isoform 3 in Human Colon Adenocarcinoma Cell Line Caco-2 , 1998, The Journal of Biological Chemistry.

[44]  T. Speake,et al.  Modulation of calcium signals by intracellular pH in isolated rat pancreatic acinar cells , 1998, The Journal of physiology.

[45]  C. Goolsby,et al.  Reducing cellular autofluorescence in flow cytometry: an in situ method. , 1997, Cytometry.

[46]  C. Hidalgo,et al.  LUMINAL PH REGULATES CALCIUM RELEASE KINETICS IN SARCOPLASMIC RETICULUM VESICLES , 1996 .

[47]  R. Gottlieb,et al.  Mutant cystic fibrosis transmembrane conductance regulator inhibits acidification and apoptosis in C127 cells: possible relevance to cystic fibrosis. , 1996, Proceedings of the National Academy of Sciences of the United States of America.

[48]  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.

[49]  S. Muallem,et al.  Na+, K+, and H+/HCO3− Transport in Submandibular Salivary Ducts , 1995, The Journal of Biological Chemistry.

[50]  R. Gottlieb,et al.  Cell acidification in apoptosis: granulocyte colony-stimulating factor delays programmed cell death in neutrophils by up-regulating the vacuolar H(+)-ATPase. , 1995, Proceedings of the National Academy of Sciences of the United States of America.

[51]  M. Donowitz,et al.  Separate C-terminal Domains of the Epithelial Specific Brush Border Na+/H+ Exchanger Isoform NHE3 Are Involved in Stimulation and Inhibition by Protein Kinases/Growth Factors (*) , 1995, The Journal of Biological Chemistry.

[52]  L. Orci,et al.  A view of acidic intracellular compartments , 1988, The Journal of cell biology.

[53]  I Yuli,et al.  Cytosolic acidification as an early transductory signal of human neutrophil chemotaxis. , 1987, Science.

[54]  T. Mosmann.  Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. , 1983, Journal of immunological methods.

[55]  Xianfeng Zhou,et al.  An FRET-based ratiometric chemosensor for in vitro cellular fluorescence analyses of pH. , 2012, Biomaterials.

[56]  R. Gillies,et al.  [Ca2+]i and pHin Homeostasis in Kaposi Sarcoma Cells , 1996 .