CCK8 peptide derivatized with diphenylphosphine for rhenium labelling: Synthesis and molecular mechanics calculations(325 views) Morelli G, De Luca S, Tesauro D, Saviano M, Pedone C, Dolmella A, Visentin R, Mazzi U
Keywords: Cck8 Derivatives, Molecular Mechanics Calculations, Rhenium-Peptide Complex, Solid-Phase Peptide Synthesis, Amide, Chelating Agent, Cholecystokinin A Receptor, Cholecystokinin Derivative, Cholecystokinin Octapeptide, Cholecystokinin Receptor, Coordination Compound, Cysteine, Ligand, Metal Complex, Nitrogen, Phosphine, Phosphine Derivative, Phosphorus, Sulfur, Peptide Fragment, Phenol Derivative, Amino Terminal Sequence, Article, Binding Affinity, Complex Formation, Controlled Study, Isotope Labeling, Molecular Model, Priority Journal, Protein Analysis, Protein Conformation, Protein Interaction, Protein Modification, Protein Structure, Protein Synthesis, Receptor Binding, Amino Acid Sequence, Chemical Structure, Chemistry, Methodology, Molecular Structure, Support, Non-U S Gov,
Affiliations: *** IBB - CNR ***
Centro Interuniversitario Per la Ricerca Sui Peptidi Bioattivi (CIRPEB), Istituto di Biostrutture e Bioimmagini, CNR, 80134 Napoli, Italy
Dipartimento di Scienze Farmaceutiche, Università di Padova, 35131 Padova, Italy
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Kennedy, K., Gigoux, V., Escrieut, C., Maigret, B., Martinez, J., Moroder, L., Frehel, D., Fourmy, D., Identification of two amino acids of the human cholecystokinin-A receptor that interact with the N-terminal moiety of cholecystokinin (1997) J. Biol. Chem, 272, pp. 2920-2926
Ji, Z., Hadak, E.M., Henne, R.M., Patel, S.A., Lybrand, T.P., Miller, L.J., Direct identification of a distinct site of interaction between the carboxyl-terminal residue of cholecystokinin and the type A cholecystokinin receptor using photoaffinity labeling (1997) J. Biol. Chem, 272, pp. 24393-24401
Ragone, R., De Luca, S., Tesauro, D., Pedone, C., Morelli, G., Fluorescence studies on the binding between 1-47 fragment of cholecystokinin receptor CCKA-R(1-47) and nonsulfated cholecystokinin octapeptide CCK8 (2001) Biopolymers, 56, pp. 47-53
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Santimaria, M., Mazzi, U., Gatto, S., Dolmella, A., Bandoli, G., Nicolini, M., Rhenium complexes with phosphine-containing peptides. Synthesis and characterization of oxorhenium(V) complexes with N-{N-[3-(diphenylphosphino)propionyl]glycyl}-L-S-benzylcysteine and its methyl ester (1997) J. Chem. Soc., Dalton Trans, pp. 1765-1771
Visentin, R., Menin, M., Rossin, R., Polo, F., Giron, M.C., Mazzi, U., Nicolini, M., N-[N-[(diphenylphosphino)propinoyl]glycyl]-L-cysteine methyl ester a BFCA for the synthesis of Rhenium and Technetium-99m oxocomplexes (2001) J. Labelled Cpd. Radiopharm, 44 (SUPPL. 1), pp. S45
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Visentin, R., Rossin, R., Giron, M.C., Dolmella, A., Bandoli, G., Mazzi, U., Synthesis and characterization of rhenium(V)-oxo complexes with diphenylphosphine-propionylglycyl-l-cysteine methyl ester. X-ray structure of {ReO[Ph2P(CH2)2C(O)Gly-1-CysOMe,(P,N,N,S)]} Inorg. Chem, , submitted
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Ji, Z., Hadak, E. M., Henne, R. M., Patel, S. A., Lybrand, T. P., Miller, L. J., Direct identification of a distinct site of interaction between the carboxyl-terminal residue of cholecystokinin and the type A cholecystokinin receptor using photoaffinity labeling (1997) J. Biol. Chem, 272, pp. 24393-24401
Miercke, D. F., Pellegrini, M., Molecular complex of chole-cystokinin-8 and N-terminus of the cholecystokinin A receptor by NMR spectroscopy (1999) Biochemistry, 38, pp. 14775-14783
Berman, H. M., Westbrook, J., Feng, Z., Gilliland, G., Bhat, T. N., Weissig, H., Shindyalov, I. N., Bourne, P. E., The Protein Data Bank (2000) Nucleic Acids Res, 28, pp. 235-242
(2000), PC SPARTAN Pro. Version 1. 0. 5. Wavefunction, Inc.: Irvine, CAHalgren, T. A., Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94 (1996) J. Comput. Chem, 17, pp. 490-641
Stewart, J. J. P., MOPAC: A semiempirical molecular orbital program (1990) J. Comput. Aided Mol. Design, 4, pp. 1-105
CCK8 peptide derivatized with diphenylphosphine for rhenium labelling: Synthesis and molecular mechanics calculations
A novel CCK8 derivative bearing a chelating agent at its N- end and its oxo-rhenium(V) complex have been synthesized and characterized. The chelating agent N-{N-[3-(diphenylphosphino)propionyl]glycyl}cysteine (PN2S) ligand, the coordination set of which is made by the phosphorus atom of phosphine, the nitrogen atoms of the two amido groups and the sulphur atom of cysteine, has been used due to its high affinity towards the oxo-rhenium(V) moiety. Molecular modelling studies indicate that the CCK8 peptide adopts the right conformation for cholecystokinin receptor binding, and that modifications on the N-terminal side of CCK8 obtained by introducing chelating agents and its metal complexes should not affect the interaction with CCKA receptor. Copyright (C) 2002 European Peptide Society and John Wiley Sons, Ltd.
CCK8 peptide derivatized with diphenylphosphine for rhenium labelling: Synthesis and molecular mechanics calculations
No results.
CCK8 peptide derivatized with diphenylphosphine for rhenium labelling: Synthesis and molecular mechanics calculations