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

• Autorzy: Malicka J. , Ganzynkowicz R. , Groth M. , Czaplewski C. , Karolczak J. , Liwo A. , Wiczk W.
• Języki publikacji: EN

Abstrakty

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.

Słowa kluczowe

EN

peptide chain; cyclic analogue; conformation; fluorescence; natural ligand; enkephalin; opioid system; energy transfer; opioid receptor; life time distribution

• Wydawca: -
• Czasopismo: Acta Biochimica Polonica
• Rocznik: 2001
• Tom: 48
• Numer: 1
• Opis fizyczny: p.95-102,fig.

Twórcy

autor

Malicka J.

• University of Gdansk, J.Sobieskiego 18, 80-952 Gdansk, Poland

autor

Ganzynkowicz R.

autor

Groth M.

autor

Czaplewski C.

autor

Karolczak J.

autor

Liwo A.

autor

Wiczk W.

Bibliografia

• 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, 1573­1586.
• 4.Wilkes, B.C. & Schiller, P.W. (1987) Theoretical conformational analysis of a ^-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 beta-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 ^-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., Lankiewicz, L., Kasprzykowski, F., Oldziej, 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. 27, 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., Szymanski, M., Wrozowo, 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.