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

Photochemical and Photobiological Sciences

Volumn 3, Issue 4, 2004, Pages 348-359

  Lotte, Kirsten ^a   Plessow, Regina ^a   Brockhinke, Andreas ^a  

^a BIELEFELD UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

5 BROMOTRYPTOPHAN; 5 FLUOROTRYPTOPHAN; 5 HYDROXYTRYPTOPHAN; 5 METHOXYTRYPTOPHAN; 5 METHYLTRYPTOPHAN; 7 AZATRYPTOPHAN; AROMATIC AMINO ACID; POLYTRYPTOPHAN; TRYPTOPHAN DERIVATIVE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; CALIBRATION; CHEMICAL ANALYSIS; CONTROLLED STUDY; CORRELATION COEFFICIENT; FLAME PHOTOMETRY; FLUORESCENCE ANALYSIS; FLUORESCENCE SPECTROSCOPY; MATHEMATICAL COMPUTING; NONHUMAN; PRIORITY JOURNAL; QUANTUM YIELD; REVIEW; ULTRAVIOLET RADIATION;

EID: 3042545181     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b312436c     Document Type: Article

References (64)

1. A. R. Holzwarth, Time-Resolved Fluorescence Spectroscopy, in Methods in Enzymology, ed. K. Sauer, Academic Press, New York, 1995, vol. 246, pp. 334–362.
2. J. R. Lakowicz, Principles of Fluorescence Spectroscopy, Plenum Press, New York, 1999.
3. A. Brockhinke R. Plessow P. Dittrich K. Kohse-Höinghaus Analysis of the local conformation of proteins with two-dimensional fluorescence techniques Appl. Phys. B: Lasers Opt. 2000 B71 755-763.
4. A. Brockhinke R. Plessow K. Kohse-Höinghaus C. Herrmann Structural changes in the Ras protein revealed by fluorescence spectroscopy Phys. Chem. Chem. Phys. 2003 5 3498-3506.
5. V. Nanda S. M. Liang L. Brand Hydrophobic clustering in acid-denatured IL-2 and fluorescence of a Trp NH·π H-bond Biochem. Biophys. Res. Commun. 2000 279 770-778.
6. V. Subramaniam T. M. Jovin R. V. Rivera-Pomar Aromatic amino acids are critical for stability of the bicoid homeodomain J. Biol. Chem. 2001 276 21506-21511.
7. Y. V. Il’ichev J. L. Perry J. D. Simon Interaction of ochratoxin A with human serum albumin. Preferential binding of the dianion and pH effects J. Phys. Chem. B 2002 106 452-459.
8. G. R. Burnett N. M. Rigby E. N. C. Mills P. S. Belton R. J. Fido A. S. Tatham P. R. Shewry Characterization of the emulsification properties of 2S albumins from sunflower seed J. Colloid Interface Sci. 2002 247 177-185.
9. D. J. Tew S. P. Bottomley Probing the equilibrium denaturation of the serpin alpha(1)-antitrypsin with single tryptophan mutants; Evidence for structure in the urea unfolded state J. Mol. Biol. 2001 313 1161-1169.
10. S. Chakraborty V. Ittah P. Bai L. Luo E. Haas Z. Y. Peng Structure and dynamics of the alphalactalbumin molten globule: Fluorescence studies using proteins containing a single tryptophan residue Biochemistry 2001 40 7228-7238.
11. B. R. Rami J. B. Udgaonkar pH-jump-induced folding and unfolding studies of barstar: Evidence for multiple folding and unfolding pathways Biochemistry 2001 40 15267-15279.
12. L. D. Cabrita J. C. Whisstock S. P. Bottomley Probing the role of the F-helix in serpin stability through a single tryptophan substitution Biochemistry 2002 41 4575-4581.
13. S. Schlesinger The effect of amino acid analogues on alkaline phosphate formation in Escherichia coli K-12 J. Biol. Chem. 1968 243 3877-3883.
14. Y. Chen R. L. Rich F. Gai J. W. Petrich Fluorescent species of 7-azaindole and 7-azatryptophan in water J. Phys. Chem. 1993 97 1770-1780.
15. Y. Chen F. Gai J. W. Petrich Single-exponential decay of the nonnatural amino-acid 7-azatryptophan and the nonexponential fluorescence decay of tryptophan in water J. Phys. Chem. 1994 98 2203-2209.
16. A. V. Smirnov D. S. English R. L. Rich J. Lane L. Teyton A. W. Schwabacher S. Luo R. W. Thornburg J. W. Petrich Photophysics and biological applications of 7-azaindole and its analogs J. Phys. Chem. B 1997 101 2758-2769.
17. R. L. Rich M. Negrerie J. Li S. Elliott R. W. Thornburg J. W. Petrich The photophysical probe, 7-azatryptophan, in synthetic peptides Photochem. Photobiol. 1993 58 28-30.
18. R. L. Rich F. Gai J. W. Lane J. W. Petrich A. W. Schwabacher Using 7-azatryptophan to probe small molecule-protein interactions on the picosecond time-scale – the complex of yvidin and biotinylated 7-azatryptophan J. Am. Chem. Soc. 1995 117 733-739.
19. P. Soumillion L. Jespers J. Vervoort J. Fastrez Biosynthetic incorporation of 7-azatryptophan into the phage-lambda lysozyme – estimation of tryptophan accessibility, effect on enzymatic activity and protein stability Protein Eng. 1995 8 451-456.
20. F. Shen S. J. Triezenberg P. Hensley D. Porter J. R. Knutson Transcriptional activation domain of the herpesvirus protein VP16 becomes conformationally constrained upon interaction with basal transcription factors J. Biol. Chem. 1996 271 4827-4837.
21. J. Guharay B. Sengupta P. K. Sengupta An assessment of the usefulness of 5-hydroxytryptophan as an optical probe Spectrochim. Acta, Part A 1998 54 185-190.
22. G. R. Moran P. F. Fitzpatrick A continuous fluorescence assay for tryptophan hydroxylase Anal. Biochem. 1999 266 148-152.
23. C. W. V. Hogue A. G. Szabo Characterization of aminoacyl-adenylates in bacillus-subtilis tryptophanyl-transfer RNA-synthase, by the fluorescence of tryptophan analogos 5-hydroxytryptophan and 7-azatryptophan Biophys. Chem. 1993 48 159-169.
24. L. E. Steward C. S. Collins M. A. Gilmore J. E. Carlson J. B. A. Ross A. R. Chamberlin In vitro site-specific incorporation of fluorescent probes into beta-galactosidase J. Am. Chem. Soc. 1997 119 6-11.
25. C. S. Farah F. C. Reinach Regulatory properties of recombinant tropomyosins containing 5-hydroxytryptophan: Ca2+-binding to troponin results in a conformational change in a region of tropomyosin outside the troponin binding site Biochemistry 1999 38 10543-10551.
26. K. Das K. D. Ashby A. V. Smirnov F. C. Reinach J. W. Petrich C. S. Farah Fluorescence properties of recombinant tropomyosin containing tryptophan, 5-hydroxytryptophan and 7-azatryptophan Photochem. Photobiol. 1999 70 719-730.
27. C. W. V. Hogue S. Doublie H. Xue J. T. Wong C. W. Carter A. G. Szabo A concerted tryptophanyl-adenylate-dependent conformational change in Bacillus subtilis tryptophanyl-tRNA synthetase revealed by the fluorescence of Trp92 J. Mol. Biol. 1996 260 446-466.
28. A. Ozarowski J. Q. Wu A. H. Maki Study of complexes of a tryptophan-free mutant of E. coli trp aporepressor with tryptophan analogues using optically detected magnetic resonance (ODMR) FEBS Lett. 1998 422 52-56.
29. C. Y. Wong M. R. Eftink Incorporation of tryptophan analogues into staphylococcal nuclease: Stability toward thermal and guanidine-HCl induced unfolding Biochemistry 1998 37 8947-8953.
30. C. Y. Wong M. R. Eftink Incorporation of tryptophan analogues into staphylococcal nuclease, its V66W mutant, and Delta 137–149 fragment: Spectroscopic studies Biochemistry 1998 37 8938-8946.
31. A. Ozarowski J. Q. Wu S. K. Davis C. Y. Wong M. R. Eftink A. H. Maki Phosphorescence and optically detected magnetic resonance characterization of the environments of tryptophan analogues in staphylococcal nuclease, its V66W mutant, and Delta 137–149 fragment Biochemistry 1998 37 8954-8964.
32. M. Negrerie F. Gai S. M. Bellefeuille J. W. Petrich Photophysics of a novel optical probe – 7-azaindole J. Phys. Chem. 1991 95 8663-8670.
33. Y. Chen F. Gai J. W. Petrich Solvation and excited-state proton-transfer of 7-azaindole in alcohols Chem. Phys. Lett. 1994 222 329-334.
34. C. Reichardt Solvatochromic dyes as solvent polarity indicators Chem. Rev 1994 94 2319-2358.
35. R. Plessow A. Brockhinke W. Eimer K. Kohse-Höinghaus Intrinsic time- and wavelength-resolved fluorescence of oligonucleotides: A systematic investigation using a novel picosecond laser approach J. Phys. Chem. B 2000 104 3695-3704.
36. J. M. Beechem, E. Gratton, M. Ameloot, J. R. Knutson and L. Brand, The Global Analysis of Fluorescence Intensity and Anisotropy Decay Data: Second-Generation Theory and Programs, in Topics in Fluorescence Spectroscopy, ed. J. R. Lakowicz, Plenum Press, New York–London, 1991, vol. 2, Principles, pp. 250–305.
37. E. A. Burstein S. M. Abornev Y. K. Reshetnyak Decomposition of protein tryptophan fluorescence spectra into log–normal components. I. Decomposition algorithms Biophys. J. 2001 81 1699-1709.
38. E. A. Burstein V. I. Emelyanenko Log-normal description of fluorescence spectra of organic fluorophores Photochem. Photobiol. 1996 64 316-320.
39. J. Eisinger G. Navon Fluorescence quenching and isotope effect of tryptophan J. Chem. Phys. 1969 50 2069-2077.
40. J. N. Demas G. A. Crosby Measurement of photoluminescence quantum yields – Review J. Phys. Chem. 1971 75 991-&.
41. J. J. Hermans S. Levinson Some geometric factors in light-scattering apparatus J. Opt. Soc. Am. 1951 41 460-465.
42. E. H. Gilmore Correction J. Chem. Phys. 1955 23 399.
43. E. H. Gilmore G. E. Gibson D. S. McClure Absolute quantum efficiencies of luminescence of organic molecules in solid solution J. Chem. Phys. 1952 20 829-836.
44. E. Lippert Habilitationsschrift zur Erlangung der Lehrberechtigung (Venia Legendi) für das Fach Physikalische Chemie an der Technischen Hochschule Stuttgart – Spektroskopische Bestimmung des Dipolmomentes aromatischer Verbindungen im ersten angeregten Singulettzustand Z. Elektrochem. 1957 61 962-975.
45. R. W. Taft M. J. Kamlet Solvatochromic Comparison Method. 2. Alpha-Scale of Solvent Hydrogen-Bond Donor (Hbd) Acidities J. Am. Chem. Soc. 1976 98 2886-2894.
46. M. J. Kamlet C. Dickinson R. W. Taft Linear Solvation Energy Relationships – Solvent Effects on Some Fluorescence Probes Chem. Phys. Lett. 1981 77 69-72.
47. G. R. Moran R. S. Phillips P. F. Fitzpatrick Influence of steric bulk and electrostatics on the hydroxylation regiospecificity of tryptophan hydroxylase: Characterization of methyltryptophans and azatryptophans as substrates Biochemistry 1999 38 16283-16289.
48. M. R. Eftink L. A. Selvidge P. R. Callis A. A. Rehms Photophysics of Indole-Derivatives – Experimental Resolution of la and Lb Transitions and Comparison with Theory J. Phys. Chem. 1990 94 3469-3479.
49. S. M. Twine and A. G. Szabo, Fluorescent amino acid analogs, in Methods in Enzymology, Academic Press, New York, 2003, pp. 104–127.
50. K. Guzow M. Szabelski J. Malicka W. Wiczk Synthesis of a new, highly fluorescent amino acid derivative: N-[(tert-butoxy)carbonyl]-3-[2-(1H-indol-3-yl)benzoxazol-5-yl]-L-alanine methyl ester Helv. Chim. Acta 2001 84 1086-1092.
51. J. B. A. Ross, A. G. Szabo and C. W. V. Hogue, Enhancement of Protein Spectra with Tryptophan Analogs: Fluorescence Spectroscopy of Protein–Proteon and Protein–Nucleic Acid Interactions, in Methods in Enzymology, Academic Press, New York, 1997, vol. 278, pp. 151–190.
52. L. Kelepouris G. J. Blanchard Lifetime and reorientation measurements of 7-azaindole and 7-azatryptophan in aqueous adipic acid solutions: The significance of pendant functionalities in solution phase association processes J. Phys. Chem. A 2000 104 7261-7267.
53. A. C. Borin L. Serrano-Andres A theoretical study of the absorption spectra of indole and its analogs: indene, benzimidazole, and 7-azaindole Chem. Phys. 2000 262 253-265.
54. J. Catalan P. Perez A. U. Acuna Indole Spectroscopy – the Location of the 1la and 1Lb Electronic States and the Absorption-Spectrum J. Mol. Struct. 1986 142 179-182.
55. B. Sengupta J. Guharay P. K. Sengupta Luminescence behaviour of 5-hydroxyindole in different environments Spectrochim. Acta, Part A 2000 56 1213-1221.
56. J. Catalan C. Diaz First reported evidence that solvent polarity induces an L-1(b)<-> L-1(a) inversion in the indole chromophore Chem. Phys. Lett. 2003 368 717-723.
57. M. J. Kamlet R. W. Taft Solvatochromic Comparison Method. 1. Beta-Scale of Solvent Hydrogen-Bond Acceptor (Hba) Basicities J. Am. Chem. Soc. 1976 98 377-383.
58. L. Serrano-Andres M. Merchan A. C. Borin J. Stalring Theoretical studies on the spectroscopy of the 7-azaindole monomer and dimer Int. J. Quantum Chem. 2001 84 181-191.
59. C. F. Chapman M. Maroncelli Excited-state tautomerization of 7-azaindole in water J. Phys. Chem. 1992 96 8430-8441.
60. M. R. Eftink Y. W. Jia D. Hu C. A. Ghiron Fluorescence quenching studies with tryptophan analogs – excited-state interactions involving the side-chain amino group J. Phys. Chem. 1995 99 5713-5723.
61. M. Maroncelli G. R. Fleming Picosecond solvation dynamics of coumarin 153: the importance of molecular aspects of solvation J. Chem. Phys. 1987 86 6221-6239.
62. E. A. Burstein N. S. Vedenkina M. N. Ivkova Fluorescence and the location of tryptophan residues in protein molecules Photochem. Photobiol. 1973 18 263-279.
63. E. Lippert Dipolmoment und Elektronenstruktur von angeregten Molekülen Z. Naturforsch. A 1955 10 541-545.
64. O. M. Kumar M. K. Machwe Fluorescence of tryptophan in solvents of varying dipole moments Indian J. Pure Appl. Phys. 1985 23 155-157.