Inter- and intramolecular fluorescence quenching of organic dyes by tryptophan
Marme N, Knemeyer JP, Sauer M, Wolfrum J (2003)
BIOCONJUGATE CHEMISTRY 14(6): 1133-1139.
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Autor*in
Marme, N;
Knemeyer, JP;
Sauer, MarkusUniBi;
Wolfrum, J
Einrichtung
Abstract / Bemerkung
Steady-state and time-resolved fluorescence measurements were performed to elucidate the fluorescence quenching of oxazine, rhodamine, carbocyanine, and bora-diaza-indacene dyes by amino acids. Among the natural amino acids, tryptophan exhibits the most pronounced quenching efficiency. Especially, the red-absorbing dyes ATTO 655, ATTO 680, and the oxazine derivative MR 121 are strongly quenched almost exclusively by tryptophan due to the formation of weak or nonfluorescent ground-state complexes with association constants, K-ass., ranging from 96 to 206 M-1. Rhodamine, fluorescein, and bora-diaza-indacene derivatives that absorb at shorter wavelengths are also quenched substantially by tyrosine residues. The quenching of carbocyanine dyes, such as Cy5, and Alexa 647 by amino acids can be almost neglected. While quenching of ATTO 655, ATTO 680, and the oxazine derivative MR121 by tryptophan is dominated by static quenching, dynamic quenching is more efficient for the two bora-diaza-indacene dyes Bodipy-FL and Bodipy630/650. Labeling of the dyes to tryptophan, tryptophan-containing peptides, and proteins (streptavidin) demonstrates that knowledge of these fluorescence quenching processes is crucial for the development of fluorescence-based diagnostic assays. Changes in the fluorescence quantum yield of dye-labeled peptides and proteins might be used advantageously for the quantification of proteases and specific binding partners.
Erscheinungsjahr
2003
Zeitschriftentitel
BIOCONJUGATE CHEMISTRY
Band
14
Ausgabe
6
Seite(n)
1133-1139
ISSN
1043-1802
eISSN
1520-4812
Page URI
https://pub.uni-bielefeld.de/record/1609714
Zitieren
Marme N, Knemeyer JP, Sauer M, Wolfrum J. Inter- and intramolecular fluorescence quenching of organic dyes by tryptophan. BIOCONJUGATE CHEMISTRY. 2003;14(6):1133-1139.
Marme, N., Knemeyer, J. P., Sauer, M., & Wolfrum, J. (2003). Inter- and intramolecular fluorescence quenching of organic dyes by tryptophan. BIOCONJUGATE CHEMISTRY, 14(6), 1133-1139. https://doi.org/10.1021/bc0341324
Marme, N, Knemeyer, JP, Sauer, Markus, and Wolfrum, J. 2003. “Inter- and intramolecular fluorescence quenching of organic dyes by tryptophan”. BIOCONJUGATE CHEMISTRY 14 (6): 1133-1139.
Marme, N., Knemeyer, J. P., Sauer, M., and Wolfrum, J. (2003). Inter- and intramolecular fluorescence quenching of organic dyes by tryptophan. BIOCONJUGATE CHEMISTRY 14, 1133-1139.
Marme, N., et al., 2003. Inter- and intramolecular fluorescence quenching of organic dyes by tryptophan. BIOCONJUGATE CHEMISTRY, 14(6), p 1133-1139.
N. Marme, et al., “Inter- and intramolecular fluorescence quenching of organic dyes by tryptophan”, BIOCONJUGATE CHEMISTRY, vol. 14, 2003, pp. 1133-1139.
Marme, N., Knemeyer, J.P., Sauer, M., Wolfrum, J.: Inter- and intramolecular fluorescence quenching of organic dyes by tryptophan. BIOCONJUGATE CHEMISTRY. 14, 1133-1139 (2003).
Marme, N, Knemeyer, JP, Sauer, Markus, and Wolfrum, J. “Inter- and intramolecular fluorescence quenching of organic dyes by tryptophan”. BIOCONJUGATE CHEMISTRY 14.6 (2003): 1133-1139.
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Towards a fluorescent molecular switch for nucleic acid biosensing.
Massey M, Krull UJ., Anal Bioanal Chem 398(4), 2010
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Mansoor SE, Dewitt MA, Farrens DL., Biochemistry 49(45), 2010
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Observing proteins as single molecules encapsulated in surface-tethered polymeric nanocontainers.
Rosenkranz T, Katranidis A, Atta D, Gregor I, Enderlein J, Grzelakowski M, Rigler P, Meier W, Fitter J., Chembiochem 10(4), 2009
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Position-specific incorporation of fluorescent non-natural amino acids into maltose-binding protein for detection of ligand binding by FRET and fluorescence quenching.
Iijima I, Hohsaka T., Chembiochem 10(6), 2009
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Quantifying adsorbed protein on surfaces using confocal fluorescence microscopy.
Togashi DM, Ryder AG, Heiss G., Colloids Surf B Biointerfaces 72(2), 2009
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Measurement of wheat germ agglutinin binding with a fluorescence microscope.
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Synthesis, crystal, absorption and fluorescence spectroscopy of nitro-stilbene derivatives with benzophenones.
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Design of an optical switch for studying conformational dynamics in individual molecules of GroEL.
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Hungerford G, Benesch J, Mano JF, Reis RL., Photochem Photobiol Sci 6(2), 2007
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Mechanism of interactions of alpha-naphthoflavone with cytochrome P450 3A4 explored with an engineered enzyme bearing a fluorescent probe.
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DEVELOPING A FLUORESCENT LATEX MICROPARTICLE IMMUNOASSAY USING ALEXA FLUOR 568 FOR DETECTION OF STAPHYLOCOCCAL ENTEROTOXIN A
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Fluorescence probe techniques to monitor protein adsorption-induced conformation changes on biodegradable polymers.
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Conformational dynamics in the F/G segment of CYP51 from Mycobacterium tuberculosis monitored by FRET.
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Ratiometric analysis of fluorescence lifetime for probing binding sites in albumin with near-infrared fluorescent molecular probes.
Berezin MY, Lee H, Akers W, Nikiforovich G, Achilefu S., Photochem Photobiol 83(6), 2007
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Chimeric peptide beacons: a direct polypeptide analog of DNA molecular beacons.
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A Förster-resonance-energy transfer-based method for fluorescence detection of the protein redox state.
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A fluorescence assay for rapid detection of ligand binding affinity to HIV-1 gp41.
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Squaraine-derived rotaxanes: highly stable, fluorescent near-IR dyes.
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Single-molecule dynamics of phytochrome-bound fluorophores probed by fluorescence correlation spectroscopy.
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Detection of the opening of the bundle crossing in KcsA with fluorescence lifetime spectroscopy reveals the existence of two gates for ion conduction.
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Fluorescence sensing of intermolecular interactions and development of direct molecular biosensors.
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Optimization of fluorescence response in the design of molecular biosensors.
Demchenko AP., Anal Biochem 343(1), 2005
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Excited-state dynamics of the fluorescent probe Lucifer Yellow in liquid solutions and in heterogeneous media.
Fürstenberg A, Vauthey E., Photochem Photobiol Sci 4(3), 2005
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Fürstenberg A, Vauthey E., Photochem Photobiol Sci 4(3), 2005
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Branching out of single-molecule fluorescence spectroscopy: challenges for chemistry and influence on biology.
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Engineering a signal transduction mechanism for protein-based biosensors.
Kohn JE, Plaxco KW., Proc Natl Acad Sci U S A 102(31), 2005
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A close look at fluorescence quenching of organic dyes by tryptophan.
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