Interaction mode of the phe-phenyl group of thrombin receptor-tethered ligand SFLLRNP in receptor activation

Journal of Biochemistry

Volumn 124, Issue 2, 1998, Pages 354-358

  Nose, Takeru ^a   Fujita, Tsugumi ^a   Nakajima, Masahide ^b   Inoue, Yoshihisa ^b   Costa, Tommaso ^c   Shimohigashi, Yasuyuki ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b Green Cross Company   (South Korea)

^c ISTITUTO SUPERIORE DI SANITÀ   (Italy)

Author keywords

Para fluorophenylalanine; Receptor recognition; Tethered ligand peptide; Thrombin; Thrombin receptor

Indexed keywords

4 FLUOROPHENYLALANINE; BENZENE; FLUORINE; HYDROGEN; HYDROXYL GROUP; LIGAND; NITRO DERIVATIVE; PHENYLALANINE; THROMBIN RECEPTOR;

AMINO ACID SUBSTITUTION; ARTICLE; CHEMICAL MODIFICATION; DIPOLE; EPITHELIUM CELL; HUMAN; HUMAN CELL; MOLECULAR INTERACTION; STEREOCHEMISTRY; THROMBOCYTE AGGREGATION;

EID: 0031661719     PISSN: 0021924X     EISSN: None     Source Type: Journal    
DOI: 10.1093/oxfordjournals.jbchem.a022119     Document Type: Article

References (30)

1. Shimohigashi, Y. (1986) Design principles: Enkephalins with predictable mu/delta receptor specificity in Opioid Peptides: Medicinal Chemistry (Rapaka, R.S., Barnett, G., and Hawks, R.L., eds.) NIDA Research Monograph 69, pp. 65-100, NIDA-DHHS, US Government Printing Office, Rockville
2. Hruby, V.J., Li, G., Haskell-Luevano, C., and Shenderovich, M. (1997) Design of peptides, proteins, and peptidomimetics in chi space. Biopolymers 43, 219-266
3. Vu, T.-K.H., Hung, D.T., Wheaton, V.I., and Coughlin, S.R. (1991) Molecular cloning of a functional thrombin receptor reveals a novel proteolytic mechanism of receptor activation. Cell 64, 1057-1068
4. Hui, K.Y., Jakubowski, J.A., Wyss, V.L., and Angleton, E.L. (1992) Minimal sequence requirement of thrombin receptor agonist peptide. Biochem. Biophys. Res. Commun. 184, 790-796
5. Chao, B.H., Kalkunte, S., Maraganore, J.M., and Stone, S.R. (1992) Essential groups in synthetic agonist peptides for activation of the platelet thrombin receptor. Biochemistry 31, 6175-6178
6. Vassallo, R.R., Jr., Kieber-Emmons, T., Cichowsky, K., and Brass, L.F. (1992) Structure-function relationships in the activation of platelet thrombin receptors by receptor derived peptides. J. Biol. Chem. 267, 6081-6085
7. Scarborough, R.M., Naughton, M.A., Teng, W., Hung, D.T., Rose, J., Vu, T.-K.H., Wheaton, V.I., Turck, C.W., and Coughlin, S.R. (1992) Tethered ligand agonist peptides. J. Biol. Chem. 267, 13146-13149
8. Sabo, T., Gurwitz, D., Motola, L., Brodt, P., Barak, R., and Elhanaty, E. (1992) Structure-activity studies of the thrombin receptor activating peptide. Biochem. Biophys. Res. Commun. 188, 604-610
9. Sakaguchi, K., Kodama, H., Ogino, Y., Costa, T., Nose, T., and Shimohigashi, Y. (1994) Structural essentials of Ser-1 in tethered peptide ligand of human thrombin receptor for phosphoinositide hydrolysis. Bull. Chem. Soc. Jpn. 67, 1659-1663
10. Nose, T., Shimohigashi, Y., Okazaki, M., Satoh, Y., Costa, T., Shimizu, N., Ogino, Y., and Ohno, M. (1995) Different roles of two consecutive leucine residues in a receptor-tethered ligand peptide (SFLLRNP) in thrombin receptor activation. Bull. Chem. Soc. Jpn. 68, 2695-2698
11. Nose, T., Shimohigashi, Y., Ohno, M., Costa, T., Shimizu, N., and Ogino, Y. (1993) Enhancement of thrombin receptor activation by thrombin receptor-derived heptapeptide with para-fluorophenylalanine in place of phenylalanine. Biochem. Biophys. Res. Commun. 193, 694-699
12. Feng, D.-M., Veber, D.F., Connolly, T.M., Condra, C., Tang, M.-J., and Nutt, R.F. (1995) Development of a potent thrombin receptor ligand. J. Med. Chem. 38, 4125-4130
13. Shimohigashi, Y., Nose, T., Okazaki, M., Satoh, Y., Ohno, M., Costa, T., Shimizu, N., and Ogino, Y. (1994) Differential roles of two consecutive phenylalanine residues in thrombin receptor-tethered ligand peptides (SFFLRNP) in thrombin receptor activation. Biochem. Biophys. Res. Commun. 203, 366-372
14. Bernatowicz, M.S., Klimas, C.E., Hartl, K.S., Peluso, M., Allegretto, N.J., and Seiler, S.M. (1996) Development of potent thrombin receptor antagonist peptides. J. Med. Chem. 39, 4879-4887
15. Ahn, H.-S., Foster, C., Boykow, G., Arik, L., Smith-Torhan, A., Hesk, D., and Chatterjee, M. (1997) Binding of a thrombin receptor tethered ligand analogue to human platelet thrombin receptor. Mol. Pharmacol. 51, 350-356
16. Moroder, L., Hallet, E., Wünsch, E., Keller, O., and Wersin, G. (1976) Di-tert.-butyldicarbonat-ein vorteihaftes reagenz zur ëinführung der tert.-butyloxycarbonyl-schutzgruppe. Hoppe Seyler's Z. Physiol. Chem. 357, 1651-1653
17. Kollonitsch, J., Barash, L., Kahan, F.M., and Kropp, H. (1973) New antibacterial agent via photofluorination of a bacterial cell wall constituent. Nature 243, 346-347
18. Thaisrivongs, S., Pals, D.T., Kati, W.M., Turner, S.R., Thomasco, L.M., and Watt, W. (1986) Design and synthesis of potent and specific renin inhibitors containing difluorostatine, difluorostatone, and related analogues. J. Med. Chem. 29, 2080-2087
19. Ljungqvist, A., Feng, D.-M., Tang, P.-F.L., Kubota, M., Okamoto, T., Zhang, Y.W., Bowers, C.Y., Hook, W.A., and Folkers, K. (1987) Design, synthesis, and bioassays of antagonists of LHRH which have antiovulatory activity and release negligible histamine. Biochem. Biophys. Res. Commun. 148, 849-856
20. 5]-enkephalin analogues with increased affinity and selectivity for δ opioid receptors. J. Med. Chem. 33, 249-253
21. Maeda, I., Shimohigashi, Y., Ikesue, K., Nose, T., Ide, Y., Kawano, K., and Ohno, M. (1996) Chymotrypsin inhibition induced by side chain-side chain intramolecular CH/π interaction in D-Thr-L-Phe benzylamide. J. Biochem. 119, 870-877
22. Fenton, J.W., II (1988) Regulation of thrombin generation and functions. Semi. Thromb. Hemost. 14, 234-240
23. Davey, M.G. and Luscher, E.F. (1967) Actions of thrombin and other coagulant and proteolytic enzymes on blood platelets. Nature 216, 857-858
24. Bar-Shavit, R., Kahn, A., Wilner, G.D., and Fenton, J.W., II (1983) Monocyte chemotaxis: Stimulation by specific exocite region in thrombin. Science 220, 728-731
25. 2+ mobilization. FEBS Lett. 288, 123-128
26. Zhong, C., Hayzer, D.J., Corson, M.A., and Runge, M.S. (1992) Molecular cloning of the rat vascular smooth muscle thrombin receptor. J. Biol. Chem. 267, 16975-16979
27. Singh, J. and Thornton, J.M. (1985) The interaction between phenylalanine rings in proteins. FEBS Lett. 191, 1-6
28. Hunter, C.A., Singh, J., and Thornton, J.M. (1991) π-π interactions: The geometry and energetics of phenylalanine-phenylalanine interactions in proteins. J. Mol. Biol. 218, 837-846
29. Chipot, C., Jaffe, R., Maigret, B., Pearlman, D.A., and Kollman, P.A. (1996) Benzene dimer: A good model for π-π interactions in proteins? A comparison between the benzene and the toluene dimers in the gas phase and in an aqueous solution. J. Am. Chem. Soc. 118, 11217-11224
30. Nishio, M., Umezawa, Y., Hirota, M., and Takeuchi, Y. (1995) The CH/π interaction: Significance in molecular recognition. Tetrahedron 51, 8665-8701