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Spectral And Photophysical Studies Of Benzo[c]xanthene Dyes: Dual Emission PH Sensors.

J. Whitaker, R. Haugland, F. Prendergast
Published 1991 · Chemistry, Medicine

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A series of fluorescent, long-wavelength, benzo[c]-xanthene dyes has been characterized for pH measurement in both excitation and emission ratio applications. The two general classes of these indicators are seminaphthofluoresceins (SNAFLs) and seminaphthorhodafluors (SNARFs) which are substituted at the 10-position with oxygen or nitrogen, respectively. These probes show separate emissions from the protonated and deprotonated forms of the fluorophores. The dyes may be excited at 488 or 514 nm with argon ion lasers. Most of the indicators have pKa values between 7.6 and 7.9. Detailed photophysical studies were conducted on the carboxy-SNAFL-1 system and excited-state prototropic reactions were compared to structurally related derivatives, such as the umbelliferones. Membrane permeant esters, such as diacetates and acetoxymethyl esters have also been prepared. The indicators are spectrally well resolved from calcium indicators such as fura-2 and indo-1 and should be suitable for simultaneous determination of pH and Ca2+ transients.
This paper references
10.1007/BF00482235
Fluorimetric analysis
O. Wolfbeis (1983)
10.1016/0968-0004(86)90245-8
Fluorescence ratio imaging: a new window into intracellular ionic signaling
R. Tsien (1986)
10.1016/S0006-3495(85)83805-4
Fluorescence emission spectroscopy of 1,4-dihydroxyphthalonitrile. A method for determining intracellular pH in cultured cells.
I. Kurtz (1985)
10.1016/0003-2697(86)90174-0
Characteristics of fluoroprobes for measuring intracellular pH.
M. Graber (1986)
10.1039/J19680003051
Prototropic equilibria of electronically excited molecules. Part II. 3-, 6-, and 7-Hydroxyquinoline
S. Mason (1968)
Examination of the intracellular ionic environment and of ionophore action by null point measurements employing the fluorescein chromophore.
D. Babcock (1983)
10.1021/J100625A026
Extended Hueckel molecular orbital calculation on 4-methylumbelliferone and its tautomer
J. Huber (1973)
10.1177/38.5.1692055
Activity of the multidrug transporter results in alkalinization of the cytosol: measurement of cytosolic pH by microinjection of a pH-sensitive dye.
Franz Thiebaut (1990)
10.1083/JCB.105.4.1613
Five-parameter fluorescence imaging: wound healing of living Swiss 3T3 cells
R. Debiasio (1987)
10.1016/0005-2736(85)90183-X
Control of free cytoplasmic calcium by intracellular pH in rat lymphocytes.
S. Grinstein (1985)
10.1016/S0065-3160(08)60331-7
Acid-Base Properties of Electronically Excited States of Organic Molecules
J. F. Ireland (1976)
10.1016/0003-2697(87)90178-3
Determination of intracellular pH of BALB/c-3T3 cells using the fluorescence of pyranine.
K. Giuliano (1987)
10.1039/TF9575300646
Determination of the absolute quantum yield of fluorescent solutions
G. Weber (1957)
10.1016/0165-6147(88)90078-8
Regulation of endocytic processes by pH.
D. Yamashiro (1988)
10.1126/SCIENCE.3798116
Cytosolic acidification as an early transductory signal of human neutrophil chemotaxis.
I. Yuli (1987)
10.1021/J100467A005
Tautomerization kinetics of 7-hydroxy-4-methylcoumarin in the lowest excited singlet state
S. Schulman (1979)
10.1016/0014-5793(88)80135-2
Intracellular pH and cell adhesion to solid substrate
L. Margolis (1988)
10.1515/znb-1970-0408
Primary Ionic Events in the Functional Membrane of Photosynthesis
H. Grünhagen (1970)
10.1039/P29770000262
Concerning the fluorescence of some 7-hydroxycoumarins and related compounds
G. Beddard (1977)
A new generation of Ca2+ indicators with greatly improved fluorescence properties.
G. Grynkiewicz (1985)
10.1021/BI00509A019
Pyranine (8-hydroxy-1,3,6-pyrenetrisulfonate) as a probe of internal aqueous hydrogen ion concentration in phospholipid vesicles.
N. Clement (1981)
10.1002/JCP.1041410223
Heterogeneity of the changes in cytoplasmic pH upon serum stimulation of quiescent fibroblasts
G. Bright (1989)
10.1039/JR9630004897
936. Prototropic equilibria of electronically excited molecules. Part I. 3-Hydroxyquinoline
J. Haylock (1963)
10.1002/CYTO.990110813
Improved method for measuring intracellular Ca++ with fluo-3.
G. Rijkers (1990)
10.1246/BCSJ.56.6
Excited-state Reactions of Coumarins in Aqueous Solutions. I. The Phototautomerization of 7-Hydroxycoumarin and Its Derivative
T. Moriya (1983)
10.1021/BI00578A012
Intracellular pH measurements in Ehrlich ascites tumor cells utilizing spectroscopic probes generated in situ.
J. A. Thomas (1979)
10.1016/0024-3205(86)90632-6
Inositol phosphates turnover, cytosolic Ca++ and pH: putative signals for the control of cell growth.
L. Vicentini (1986)
10.1083/JCB.95.1.189
Cytoplasmic pH and free Mg2+ in lymphocytes
T. Rink (1982)
10.1139/V78-206
Excited state acid–base equilibrium of tyrosine
D. Rayner (1978)



This paper is referenced by
10.1385/0-89603-250-7:177
Measurement of membrane fluidity and membrane fusion with fluorescent probes.
C. L. Bashford (1994)
10.1002/1521-3757(20001002)112:19<3580::AID-ANGE3580>3.0.CO;2-5
Design and Synthesis of Intramolecular Resonance-Energy Transfer Probes for Use in Ratiometric Measurements in Aqueous Solution.
Y. Kawanishi (2000)
10.1002/9781118751879.CH2
Basic Microscopic Technique
Keisuke Isobe (2013)
10.1016/J.DYEPIG.2017.04.005
Highly selective and sensitive fluorescent probe for mercury ions based on a novel rhodol-coumarin hybrid dye
K. Huang (2017)
10.1186/1475-2875-11-124
A high-throughput method to detect Plasmodium falciparum clones in limiting dilution microplates
Brian Lyko (2011)
10.1366/0003702991947964
Polarization-Based Sensing with a Self-Referenced Sample
J. Lakowicz (1999)
10.1002/ADMT.201800561
An Optical pH Sensor Based on Diazaoxatriangulenium and Isopropyl‐Bridged Diazatriangulenium Covalently Bound in a Composite Sol–Gel
T. Sørensen (2018)
10.5772/38263
Flow Cytometry as a Powerful Tool for Monitoring Microbial Population Dynamics in Sludge
Audrey Prorot (2012)
10.1023/B:THEC.0000041813.53353.94
Spectral and Acid–Base Properties of Arylidene Derivatives of Dicyclopentano[b,e]pyridines Serving as Fluorescent pH-Indicators
V. F. Valyuk (2004)
Aus der Abteilung Kardiologie und Pneumologie (Prof. Dr. med. G. Hasenfuß)
I. Medizin (2010)
10.1016/0968-4328(93)90035-Y
Intracellular pH mapping with SNARF-1 and confocal microscopy. II: pH gradients within single cultured cells
P. N. Dubbin (1993)
10.1016/J.DYEPIG.2019.02.026
A two-step responsive colorimetric probe for fast detection of formaldehyde in weakly acidic environment
K. Wei (2019)
10.1016/0003-2697(92)90011-U
Fluorescent rhodol derivatives: versatile, photostable labels and tracers.
J. Whitaker (1992)
10.1002/cplu.201900489
A Polarity-Sensitive Fluorescent Amino Acid and its Incorporation into Peptides for the Ratiometric Detection of Biomolecular Interactions.
Hidetomo Yokoo (2019)
10.1007/s00424-013-1234-z
Small-molecule fluorophores and fluorescent probes for bioimaging
Takuya Terai (2013)
10.1016/S0091-679X(02)70014-9
Measurement of intracellular Ca2+ concentration.
N. Demaurex (2002)
10.1038/s41467-017-02065-3
Proton gradients and pH oscillations emerge from heat flow at the microscale
L. Keil (2017)
10.1021/la3017112
Microcosmic mechanisms for protein incomplete release and stability of various amphiphilic mPEG-PLA microspheres.
Yi Wei (2012)
10.1006/ABIO.1997.2164
Time-resolved fluorescence microscopy could correct for probe binding while estimating intracellular pH.
A. Srivastava (1997)
10.1021/ac3011796
Highly Photostable Near-Infrared Fluorescent pH Indicators and Sensors Based on BF2-Chelated Tetraarylazadipyrromethene Dyes
T. Jokic (2012)
10.1016/0952-7915(92)90014-6
Analysis of lymphocyte activation and metabolism by flow cytometry.
C. June (1992)
10.1021/ja302445w
Field effects induce bathochromic shifts in xanthene dyes.
Martha Sibrian-Vazquez (2012)
10.1117/12.841475
Fluorescence lifetime imaging spectroscopy in living cells with particular regards to pH dependence and electric field effect
Nobuhiro Ohta (2010)
10.1117/12.2066132
Novel pH-sensitive probes with a ratiometric detection for intracellular pH
Martin Ipuy (2014)
10.1002/chem.201500355
Aminorhodamine (ARh): A Bichromophore with Three Emission Bands in Low Temperature Glasses.
Thomas Just Sørensen (2015)
10.1016/J.TRAC.2016.05.001
Optical sensing by integration of analyte-sensitive fluorophore to particles
Carolina Carrillo-Carrión (2016)
10.1002/anie.201702140
A Near-Infrared Dye That Undergoes Multiple Interconversions through Acid-Base Equilibrium and Reversible Redox Processes.
Kengo Asai (2017)
10.1385/1-59259-722-X:305
Intracellular pH and pCa measurement.
M. Opas (1999)
10.1016/S1074-5521(99)80059-3
A novel acidotropic pH indicator and its potential application in labeling acidic organelles of live cells.
Z. Diwu (1999)
10.1016/J.CAP.2009.06.043
Immobilization of enzymes within hydrogel microparticles to create optical biosensors for the detection of organophosphorus compounds
Bumsang Kim (2009)
10.1016/J.DYEPIG.2017.06.047
Synthesis of a novel π-extended hybrid rhodamine dye with far-red fluorescence emission and its application in bioimaging
Kun Huang (2017)
10.1039/B706956A
pH-dependent fluorescence of uncharged benzothiazole-based dyes binding to DNA.
Shuji Ikeda (2007)
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