Fluorescence decay time distribution analysis of cyclic enkephalin analogues; Influence of solvent and Leu configuration in position 5 on conformation

• Authors: Joanna Malicka , Robert Ganzynkowicz , Małgorzata Groth , Cezary Czaplewski , Jerzy Karolczak , Adam Liwo , Wiesław Wiczk
• Languages of publication: EN

Abstracts

EN

Lifetime distribution analysis were performed to study the influence of Leu configuration in position 5 on changes of the peptide chain of cyclic analogues of enkephalins containing a fluorescence donor and acceptor in different solvents. The configuration change of Leu5 in all the analogues of enkephalins studied which contain donor-acceptor pairs has no apparent influence on Trp lifetime distributions. In contrast, there is a significant solvent effect on the shape of lifetime distribution.

Keywords

EN

lifetime distribution; fluorescence; energy transfer; conformation; enkephalin

• Publisher: Polish Biochemical Society
• Journal: Acta Biochimica Polonica
• Year: 2001
• Volume: 48
• Issue: 1
• Pages: 95-102

Dates

published

2001

revised

2001-02-13

accepted

2001-02-15

Contributors

author

Joanna Malicka

• Faculty of Chemistry, University of Gdańsk, Gdańsk, Poland

author

Robert Ganzynkowicz

• Faculty of Chemistry, University of Gdańsk, Gdańsk, Poland

author

Małgorzata Groth

• Faculty of Chemistry, University of Gdańsk, Gdańsk, Poland

author

Cezary Czaplewski

• Faculty of Chemistry, University of Gdańsk, Gdańsk, Poland

author

Jerzy Karolczak

• Quantum Electronic Laboratory, Faculty of Physics, Adam Mickiewicz University, Poznań, Poland

author

Adam Liwo

• Faculty of Chemistry, University of Gdańsk, Gdańsk, Poland

author

Wiesław Wiczk

• Faculty of Chemistry, University of Gdańsk, Gdańsk, Poland

References

• 1. Schiller, P.W. & DiMaio, J. (1982) Opiate receptor subclasses differ in their conformational requirements. Nature 297, 74-76.
• 2. DiMaio, J., Nguyen, T.M.-D., Lemieux, C. & Schiller, P.W. (1982) Synthesis and pharmacological characterization in vitro of cyclic enkephalin analogues: Effect of conformational constraints on opiate receptor selectivity. J. Med. Chem. 25, 1432-1438.
• 3. Mierke, D.F., Lucietto, P., Schiller, P.W. & Goodman, M. (1987) Conformational studies of diastereomeric cyclic enkephalins by 1H-NMR and computer simulations. Biopolymers 26, 1573- 1586.
• 4. Wilkes, B.C. & Schiller, P.W. (1987) Theoretical conformational analysis of a μ-selective cyclic opioid peptide analog. Biopolymers 26, 1431-1444.
• 5. Yamazaki, T., Said-Nejad, O.E., Schiller, P.W. & Goodman, M. (1991) Conformational studies of stereoisomeric 14-membered cyclic enkephalin analogues containing 1-naphthylalanine at the fourth position: Chirality effect of leucine at the fifth position on biological activity and receptor selectivity. Biopolymers 31, 877-898.
• 6. Yamazaki, T., Mierke, D.F., Said-Nejad, O.E., Felder, E.R. & Goodman, M. (1992) 14-Membered cyclic opioids related to dermorphin and their partially retro-inverso modified analogues. II. Preferred conformations in solution as studied by 1H-NMR spectroscopy. Int. J. Pept. Protein Res. 39, 161-181.
• 7. Wilkes, B.C., Zelent, B., Malak, H., Schmidt, R. & Schiller, P.W. (1999) Interpretation of the fluorescence decay characteristic of cyclic β-casomorphin analogs based on theoretically calculated ensembles of their low energy conformers. Peptides, Fronties of peptide science. Proceedings of the Fifteenth American Peptide Symposium, 1997, Nashville, Tennessee, U.S.A. (Tam, J.P., Kaumaya, P.T. P., eds.) Kluwer Academic Press, Dordrecht, Boston, London.
• 8. Paterlini, M.G., Avitable, F., Ostrowski, B.G., Ferguson, D.M. & Portoghese, P.S. (2000) Stereochemical requirements for receptor recognition of the μ-opioid peptide endomorphin-1. Biophys. J. 78, 590- 599.
• 9. Alcala, J.R., Gratton, E. & Prendegrast, F.G. (1987) Interpretation of fluorescence decays in proteins using continous lifetime distributions. Biophys. J. 51, 925-936.
• 10. Lakowicz, J.R., Gryczynski, I., Wiczk, W. & Johnson, M.L. (1994) Distributions of fluorescence decay times for synthetic melittin in water-methanol mixture and complexed with calmodulin, troponin C, and phosphlipids. J. Fluoresc. 4, 169-177.
• 11. Swaminthan, R., Krishnamoorthy, G. & Periasamy, N. (1994) Similarity of fluorescence lifetime distributions for single tryptophan proteins in the random coil state. Biophys. J. 67, 2013-2023.
• 12. Malicka, J., Groth, M., Czaplewski, C., Liwo, A. & Wiczk, W. (1999) Fluorescence decay time distribution analysis of cyclic enkephalin analogues. Influence of the solvent and configuration of amino acids in position 2 and 3 on changes in conformation. Acta Biochim. Polon. 46, 615-629.
• 13. Szmacinski, H., Wiczk, W., Fishman, M.N., Eis, P.S., Lakowicz, J.R. & Johnson, M.L. (1996) Distance distributions from the tyrosyl to disulfide residues in the oxitocin and [Arg8]-vasopressin measured using frequency-domain fluorescence resonance energy transfer. Eur. Biophys. J. 24, 185-193.
• 14. Wiczk, W., Łankiewicz, L., Kasprzykowski, F., Ołdziej, S., Szmacinski, H., Lakowicz, J.R. & Grzonka, Z. (1997) Fluorescence study of neurohypophyseal hormones and their analogues. Distance distributions in series of arginine- vasopressin analogues. Eur. Biophys. J. 26, 183-193.
• 15. Mierke, D.F., Schiller, P.W. & Goodman, M. (1990) A conformational comparison of two stereoisomeric cyclic dermorphin analogues employing NMR and computer simulation. Biopolymers 29, 943-952.
• 16. Lakowicz, J.R., Cherek, H., Gryczynski, I., Joshi, N. & Johnson, M.L. (1987) Analysis of fluorescence decay kinetics measured in the frequency-domain using distributions of decay times. Biophys. Chem. 28, 35-50.
• 17. Gryczynski, I., Wiczk, W., Lakowicz, J.R. & Johnson, M.L. (1989) Decay time distribution analysis of Yt-base in benzene-methanol mixtures. J. Photochem. Photobiol., B: Biology 4, 159-170.
• 18. Ferreira, S.T., Stella, L. & Gratton, E. (1994) Conformational dynamics of bovine Cu, Zn superoxide dismutase revealed by time-resolved fluorescence spectroscopy of the single tyrosine residue. Biophys. J. 66, 1185-1196.
• 19. Livesy, A.K. & Brochon, J.-C. (1987) Analyzing the distribution of decay constants in pulse-fluorimetry using the maximum entropy method. Biophys. J. 52, 693-706.
• 20. Remacle, F. & Levine, R.D. (1993) Time-domain information from frequency- or time-resolved experiments using maximum entropy. J. Phys. Chem. 97, 12553-12560.
• 21. Brochon, J.-C. (1994) Maximum entropy method of data analysis in time-resolved spectroscopy. Methods Enzymol. 240, 262-311.
• 22. Swaminathan, R. & Perisamy, N. (1996) Analysis of fluorescence decay by the maximum entropy method: Influence of noise and analysis parameters of the width of the distribution of lifetimes. Proc. Indian Acad. Sci. (Chem. Sci.) 108, 39-49.
• 23. Siemiarczuk, A., Wagner, B.D. & Ware, W.R. (1990) Comparison of the entropy and exponential series methods for recovery of distributions of lifetimes from fluorescence lifetime data. J. Phys. Chem. 94, 1661-1666.
• 24. Landl, G., Langthaler, T., Engl, H.W. & Kauffman, H.F. (1991) Distribution of event time in time-resolved fluorescence: The exponential series approach-algorithm, regularization, analysis. J. Comput. Phys. 95, 1-28.
• 25. Fields, G.B. & Noble, R.L. (1990) Solid phase peptide synthesis utilizing 9-fluorenylomethoxycarbonyl amino acids. Int. J. Pept. Protein Res. 35, 161-214.
• 26. Schmidt, R. & Neubert, K. (1991) Cyclization studies with tetra- and pentapeptide sequences corresponding to beta-casomorphins. Int. J. Pept. Protein Res. 37, 502-507.
• 27. Karolczak, J., Komar, D., Kubicki, J., Szymański, M., Wróżowo, T. & Maciejewski, A. (1999) Fluorescence dynamics spectrometer of single-picosecond resolution: Optimisation of experimental performance. Bull. Pol. Acad. Sci. Chem. 47, 361-380.
• 28. Lakowicz, J.R. (1999) Protein fluorescence; in Principles of Fluorescence Spectroscopy (2nd edn.) pp. 446-486, Kluwer Academic/Plenum Publishers, New York, Boston, Dordrecht, London, Moscow.