CCK8 peptide derivatized with diphenylphosphine for rhenium labelling: Synthesis and molecular mechanics calculations (325 views)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2002 Jul; 8(7): 373-381.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 1.691, 5-year impact factor: 1.715
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-0035995967&partnerID=40&md5=1d5616c24e4f4fa7b1aec92d65a79e2d
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
References:
Heppeler, A., Froidevaux, S., Eberle, A.N., Maecke, H.R., Receptor targeting for tumor localisation and therapy with radiopeptides (2000) Curr. Med. Chem, 7, pp. 971-99
Reubi, J.C., Schaer, J.C., Waser, B., Cholecystokinin(CCK)-A and CCK-B/gastrin receptors in human tumors (1997) Cancer Res, 57, pp. 1377-1386
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
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
Giragossian, C., Miercke, D.F., Intermolecular interactions between cholecystokinin-8 and third extracellular loop of cholecystokinin A receptor (2001) Biochemistry, 40, pp. 3804-3809
Santimaria, M., Blok, D., Feitsma, R.I.J., Mazzi, U., Pauwels, E.K.J., Experiments on a new phosphine-peptide chelator for labelling of peptides with Tc-99m (1999) Nucl. Med. Biol, 26, pp. 251-258
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
Lis, T., Jezowska-Trzebiatowska, B., Preparation of oxo-pentachlororhenate(VI) and oxotetrachlororhenate(V). The crystal and molecular structure of AsPh4ReOCl4 (1977) Acta Crystallogr, 33 B, pp. 1248-1250
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
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
Reubi, J. C., Schaer, J. C., Waser, B., Cholecystokinin (CCK) -A and CCK-B/gastrin receptors in human tumors (1997) Cancer Res, 57, pp. 1377-1386
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
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2002 Jul; 8(7): 373-381.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 1.691, 5-year impact factor: 1.715
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-0035995967&partnerID=40&md5=1d5616c24e4f4fa7b1aec92d65a79e2d
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
References:
Heppeler, A., Froidevaux, S., Eberle, A.N., Maecke, H.R., Receptor targeting for tumor localisation and therapy with radiopeptides (2000) Curr. Med. Chem, 7, pp. 971-99
Reubi, J.C., Schaer, J.C., Waser, B., Cholecystokinin(CCK)-A and CCK-B/gastrin receptors in human tumors (1997) Cancer Res, 57, pp. 1377-1386
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
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
Giragossian, C., Miercke, D.F., Intermolecular interactions between cholecystokinin-8 and third extracellular loop of cholecystokinin A receptor (2001) Biochemistry, 40, pp. 3804-3809
Santimaria, M., Blok, D., Feitsma, R.I.J., Mazzi, U., Pauwels, E.K.J., Experiments on a new phosphine-peptide chelator for labelling of peptides with Tc-99m (1999) Nucl. Med. Biol, 26, pp. 251-258
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
Lis, T., Jezowska-Trzebiatowska, B., Preparation of oxo-pentachlororhenate(VI) and oxotetrachlororhenate(V). The crystal and molecular structure of AsPh4ReOCl4 (1977) Acta Crystallogr, 33 B, pp. 1248-1250
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
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
Reubi, J. C., Schaer, J. C., Waser, B., Cholecystokinin (CCK) -A and CCK-B/gastrin receptors in human tumors (1997) Cancer Res, 57, pp. 1377-1386
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.
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
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CCK8 peptide derivatized with diphenylphosphine for rhenium labelling: Synthesis and molecular mechanics calculations
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Accardo A, Mansi R, Morisco A, Mangiapia G, Paduano L, Tesauro D, Radulescu A, Aurilio M, Aloj L, Arra C, Morelli G
* Peptide modified nanocarriers for selective targeting of bombesin receptors (429 views)
Mol Biosyst (ISSN: 1742-206x), 2010 May; 6(5): 878-887.
Impact Factor: 3.825
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Arnesano F, Scintilla S, Calò V, Bonfrate E, Ingrosso C, Losacco M, Pellegrino T, Rizzarelli E, Natile G
* Copper-triggered aggregation of ubiquitin (534 views)
Plosone (ISSN: 1932-6203, 1932-6203electronic, 1932-6203linking), 2009 Sep 16; 4(9): e7052-e7052.
Impact Factor: 4.351
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Accardo A, Tesauro D, Morisco A, Mangiapia G, Vaccaro M, Gianolio E, Heenan RK, Paduano L, Morelli G
* Micelles obtained by aggregation of gemini surfactants containing the CCK8 peptide and a gadolinium complex (398 views)
J Biol Inorg Chem (ISSN: 0949-8257, 1432-1327electronic, 0949-8257linking), 2009 May; 14(4): 587-599.
Impact Factor: 3.415
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Ciaccio C, Tundo GR, Grasso G, Spoto G, Marasco D, Ruvo M, Gioia M, Rizzarelli E, Coletta M
* Somatostatin: a novel substrate and a modulator of insulin-degrading enzyme activity (455 views)
J Mol Biol (ISSN: 1089-8638, 0022-2836, 1089-8638electronic), 2009 Feb 6; 385(5): 1556-1567.
Impact Factor: 3.871
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Vaccaro M, Mangiapia G, Accardo A, Tesauro D, Gianolio E, Frielinghaus H, Morelli G, Paduano L
* Polymerized mixed aggregates containing gadolinium complex and CCK8 peptide (429 views)
Colloid Polym Sci (ISSN: 0303-402x), 2008 Dec; 286(14-15): 1643-1652.
Impact Factor: 1.736
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Accardo A, Tesauro D, Del Pozzo L, Mangiapia G, Paduano L, Morelli G
* Micelles by self-assembling peptide-conjugate amphiphile: Synthesis and structural characterization (410 views)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2008 Sep; 14(8): 903-910.
Impact Factor: 1.654
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D'Andrea LD, Testa I, Panico M, Di Stasi R, Carac C, Tarallo L, Arra C, Barbieri A, Romanelli A, Aloj L
* In vivo and in vitro characterization of CCK8 bearing a histidine-based chelator labeled with Tc-99m-tricarbonyl (424 views)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 2008; 90(5): 707-712.
Impact Factor: 2.823
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Vaccaro M, Accardo A, D'Errico G, Schillen K, Radulescu A, Tesauro D, Morelli G, Paduano L
* Peptides and gd complexes containing colloidal assemblies as tumor-specific contrast agents in MRI: Physicochemical characterization (399 views)
Biophysical Journal (ISSN: 0006-3495, 1542-0086), 2007 Sep; 93(5): 1736-1746.
Impact Factor: 4.627
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Cuzzocrea S, Genovese T, Failla M, Vecchio G, Fruciano M, Mazzon E, Di Paola R, Muià C, La Rosa C, Crimi N, Rizzarelli E, Vancheri C
* Protective effect of orally administered carnosine on bleomycin-induced lung injury (721 views)
Am J Physiol Lung Cell Mol Physiol (ISSN: 1040-0605), 2007 May; 292(5): L1095-L1095.
Impact Factor: 4.214
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Accardo A, Tesauro D, Morelli G, Gianolio E, Aime S, Vaccaro M, Mangiapia G, Paduano L, Schillén K
* High-relaxivity supramolecular aggregates containing peptides and Gd complexes as contrast agents in MRI (433 views)
J Biol Inorg Chem (ISSN: 0949-8257, 1432-1327electronic, 0949-8257print), 2007 Feb; 12(2): 267-276.
Impact Factor: 3.325
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De Luca S, Morelli G
* Synthesis and characterization of a sulfated and a non-sulfated cyclic CCK8 analogue functionalized with a chelating group for metal labelling (395 views)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2004 May; 10(5): 265-273.
Impact Factor: 1.652
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Mansi R, Tesauro D, De Capua A, Fattorusso R, Carac C, Aloj L, Benedetti E, Morelli G
* Peptide-chelating agent conjugate for selective targeting of somatostatin receptor type 1: Synthesis and characterization (472 views)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 2004; 76(6): 527-534.
Impact Factor: 2.863
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21 Records (18 excluding Abstracts).
Total impact factor: 68.253 (55.596 excluding Abstracts).
Total 5 year impact factor: 69.62 (56.442 excluding Abstracts).
Total impact factor: 68.253 (55.596 excluding Abstracts).
Total 5 year impact factor: 69.62 (56.442 excluding Abstracts).
325 views. Last view on Monday 29 May 2023, 20:52:28
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