Static and time-resolved fluorescence investigations of tryptophan analogues - a solvent study

Lotte K, Plessow R, Brockhinke A (2004)

Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Lotte, Kirsten; Plessow, Regina; Brockhinke, AndreasUniBi
Abstract / Bemerkung
The fluorescence properties of tryptophan, polytryptophan and seven of its analogues (7-azatryptophan, 5-hydroxytryptophan, 5-methoxytryptophan, 5-fluorotryptophan, 5-methyltryptophan, 5-bromotryptophan, and 6-fluorotryptophan) are studied using two novel fluorescence spectroscopic techniques for a wide range of solvent polarities. Two-dimensional mapping of all emission and all fluorescence spectra using excitation-emission spectroscopy (EES) has been used to determine quantum yields, positions of emission maxima, full widths at half maximum (FWHMs) as well as Stokes' shifts. Additionally, fluorescence lifetimes obtained from time-resolved experiments using a picosecond laser system are presented and compared with the data acquired from the static setup. This systematic study of the fluorescence characteristics is a prerequisite to assess the potential of these analogues to act as structure-conserving substitutes for tryptophan in protein fluorescence experiments. The potential of these analogues, to act as probes for the local environment, and allow estimation of the polarity in the vicinity of the fluorophore and its exposure to the solvent, is discussed.
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Lotte K, Plessow R, Brockhinke A. Static and time-resolved fluorescence investigations of tryptophan analogues - a solvent study. PHOTOCHEMICAL AND PHOTOBIOLOGICAL SCIENCES. 2004;3(4):348-359.
Lotte, K., Plessow, R., & Brockhinke, A. (2004). Static and time-resolved fluorescence investigations of tryptophan analogues - a solvent study. PHOTOCHEMICAL AND PHOTOBIOLOGICAL SCIENCES, 3(4), 348-359.
Lotte, K., Plessow, R., and Brockhinke, A. (2004). Static and time-resolved fluorescence investigations of tryptophan analogues - a solvent study. PHOTOCHEMICAL AND PHOTOBIOLOGICAL SCIENCES 3, 348-359.
Lotte, K., Plessow, R., & Brockhinke, A., 2004. Static and time-resolved fluorescence investigations of tryptophan analogues - a solvent study. PHOTOCHEMICAL AND PHOTOBIOLOGICAL SCIENCES, 3(4), p 348-359.
K. Lotte, R. Plessow, and A. Brockhinke, “Static and time-resolved fluorescence investigations of tryptophan analogues - a solvent study”, PHOTOCHEMICAL AND PHOTOBIOLOGICAL SCIENCES, vol. 3, 2004, pp. 348-359.
Lotte, K., Plessow, R., Brockhinke, A.: Static and time-resolved fluorescence investigations of tryptophan analogues - a solvent study. PHOTOCHEMICAL AND PHOTOBIOLOGICAL SCIENCES. 3, 348-359 (2004).
Lotte, Kirsten, Plessow, Regina, and Brockhinke, Andreas. “Static and time-resolved fluorescence investigations of tryptophan analogues - a solvent study”. PHOTOCHEMICAL AND PHOTOBIOLOGICAL SCIENCES 3.4 (2004): 348-359.

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PMID: 28533371
Solvent Dependence of Cyanoindole Fluorescence Lifetime.
Hilaire MR, Mukherjee D, Troxler T, Gai F., Chem Phys Lett 685(), 2017
PMID: 29225366
A spectroscopic survey of substituted indoles reveals consequences of a stabilized 1Lb transition.
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PMID: 22882557
Solvent effects on the steady state photophysics of estrone and 17β-estradiol.
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PMID: 22191459
Antimicrobial activity of peptides derived from human ß-amyloid precursor protein.
Papareddy P, Mörgelin M, Walse B, Schmidtchen A, Malmsten M., J Pept Sci 18(3), 2012
PMID: 22249992
Minimalist probes for studying protein dynamics: thioamide quenching of selectively excitable fluorescent amino acids.
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PMID: 22471784
Urea facilitates the translocation of single-stranded DNA and RNA through the alpha-hemolysin nanopore.
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PMID: 20441749
Boosting antimicrobial peptides by hydrophobic oligopeptide end tags.
Schmidtchen A, Pasupuleti M, Mörgelin M, Davoudi M, Alenfall J, Chalupka A, Malmsten M., J Biol Chem 284(26), 2009
PMID: 19398550
Oligotryptophan-tagged antimicrobial peptides and the role of the cationic sequence.
Strömstedt AA, Pasupuleti M, Schmidtchen A, Malmsten M., Biochim Biophys Acta 1788(9), 2009
PMID: 19505433
Enzymatic digestion and antioxidant activity of the native and molten globule states of camel α-lactalbumin: Possible significance for use in infant formula
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PMID: IND44217551
Real-time cellular uptake of serotonin using fluorescence lifetime imaging with two-photon excitation.
Botchway SW, Parker AW, Bisby RH, Crisostomo AG., Microsc Res Tech 71(4), 2008
PMID: 18080329
The five bromotryptophans.
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PMID: 17031473
Single- and multi-photon excited fluorescence from serotonin complexed with beta-cyclodextrin.
Bisby RH, Botchway SW, Dad S, Parker AW., Photochem Photobiol Sci 5(1), 2006
PMID: 16395437
Identification and reactivity of the triplet excited state of 5-hydroxytryptophan.
Dad S, Bisby RH, Clark IP, Parker AW., J Photochem Photobiol B 78(3), 2005
PMID: 15708522
Platinum(II) 1,10-phenanthroline complexes of acetylides containing redox-active groups.
Siemeling U, Bausch K, Fink H, Bruhn C, Baldus M, Angerstein B, Plessow R, Brockhinke A., Dalton Trans (14), 2005
PMID: 15995744

64 References

Daten bereitgestellt von Europe PubMed Central.

Holzwarth, 1995

Lakowicz, 1999

Brockhinke, Appl. Phys. B: Lasers Opt. B71(), 2000

Brockhinke, Phys. Chem. Chem. Phys. 5(), 2003
Hydrophobic clustering in acid-denatured IL-2 and fluorescence of a Trp NH-pi H-bond.
Nanda V, Liang SM, Brand L., Biochem. Biophys. Res. Commun. 279(3), 2000
PMID: 11162427
Aromatic amino acids are critical for stability of the bicoid homeodomain.
Subramaniam V, Jovin TM, Rivera-Pomar RV., J. Biol. Chem. 276(24), 2001
PMID: 11294843

Il'ichev, J. Phys. Chem. B 106(), 2002
Characterization of the emulsification properties of 2S albumins from sunflower seed.
Burnett GR, Rigby NM, Mills EN, Belton PS, Fido RJ, Tatham AS, Shewry PR., J Colloid Interface Sci 247(1), 2002
PMID: 16290454
Probing the role of the F-helix in serpin stability through a single tryptophan substitution.
Cabrita LD, Whisstock JC, Bottomley SP., Biochemistry 41(14), 2002
PMID: 11926819

Chen, J. Phys. Chem. 97(), 1993

Chen, J. Phys. Chem. 98(), 1994

Smirnov, J. Phys. Chem. B 101(), 1997

Rich, Photochem. Photobiol. 58(), 1993

Rich, J. Am. Chem. Soc. 117(), 1995

Guharay, Spectrochim. Acta, Part A 54(), 1998
A continuous fluorescence assay for tryptophan hydroxylase.
Moran GR, Fitzpatrick PF., Anal. Biochem. 266(1), 1999
PMID: 9887224

Steward, J. Am. Chem. Soc. 119(), 1997
Fluorescence properties of recombinant tropomyosin containing tryptophan, 5-hydroxytryptophan and 7-azatryptophan.
Das K, Ashby KD, Smirnov AV, Reinach FC, Petrich JW, Farah CS., Photochem. Photobiol. 70(5), 1999
PMID: 10568167

Negrerie, J. Phys. Chem. 95(), 1991

Chen, Chem. Phys. Lett. 222(), 1994

Reichardt, Chem. Rev 94(), 1994

Plessow, J. Phys. Chem. B 104(), 2000

Beechem, 1991

Burstein, Photochem. Photobiol. 64(), 1996
Fluorescence quenching and isotope effect of tryptophan.
Eisinger J, Navon G., J Chem Phys 50(5), 1969
PMID: 5777485

Demas, J. Phys. Chem. 75(), 1971

Hermans, J. Opt. Soc. Am. 41(), 1951

Gilmore, J. Chem. Phys. 23(), 1955

Gilmore, J. Chem. Phys. 20(), 1952

Lippert, Z. Elektrochem. 61(), 1957

Taft, J. Am. Chem. Soc. 98(), 1976

Kamlet, Chem. Phys. Lett. 77(), 1981

Eftink, J. Phys. Chem. 94(), 1990

Twine, 2003

Guzow, Helv. Chim. Acta 84(), 2001

Ross, 1997

Kelepouris, J. Phys. Chem. A 104(), 2000

Borin, Chem. Phys. 262(), 2000

Catalan, J. Mol. Struct. 142(), 1986

Sengupta, Spectrochim. Acta, Part A 56(), 2000

Catalan, Chem. Phys. Lett. 368(), 2003

Kamlet, J. Am. Chem. Soc. 98(), 1976

Serrano-Andres, Int. J. Quantum Chem. 84(), 2001

Chapman, J. Phys. Chem. 96(), 1992

Eftink, J. Phys. Chem. 99(), 1995

Maroncelli, J. Chem. Phys. 86(), 1987
Fluorescence and the location of tryptophan residues in protein molecules.
Burstein EA, Vedenkina NS, Ivkova MN., Photochem. Photobiol. 18(4), 1973
PMID: 4583619

Lippert, Z. Naturforsch. A 10(), 1955

Kumar, Indian J. Pure Appl. Phys. 23(), 1985


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