Anthranilic acid based CCK1 receptor antagonists and CCK-8 have a common step in their "receptor desmodynamic processes" (439 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2006 Apr 20; 49(8): 2456-2462.
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Paper type: Journal Article,
Impact factor: 5.115, 5-year impact factor: 5.504
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-33646076226&partnerID=40&md5=88e47eb1a452d41d261243c3a72c427d
Keywords: 3 Phenyl [2 (cinnamoylamino)benzoylamino]propionic Acid, [2 [(1h Indole 2 Carbonyl)amino]benzoylamino] 3 Phenylpropionic Acid, [2 [(1h Indole 2 Carbonyl)amino]benzoylamino]propionic Acid, [2 [(2 Acetylaminocinnamoyl)amino]benzoylamino] 3 Phenylpropionic Acid, Anthranilic Acid Derivative, Cholecystokinin A Receptor, Cholecystokinin A Receptor Antagonist, Cholecystokinin Octapeptide, Cholecystokinin Receptor Blocking Agent, Loxiglumide, Unclassified Drug, Vl 0395, Amino Terminal Sequence, Article, Drug Structure, Fluorescence Spectroscopy, Molecular Interaction, Nuclear Magnetic Resonance, Protein Conformation, Receptor Binding, Animals, Competitive, Biological Assay, Humans, Ligands, Magnetic Resonance Spectroscopy, Models, Molecular Structure, Pancreas, Proglumide, Sincalide, Spectrometry, Structure-Activity Relationship, 3 Phenyl [2 (cinnamoylamino) Benzoylamino] Propionic Acid, [2 [(1h Indole 2 Carbonyl) Amino] Benzoylamino] 3 Phenylpropionic Acid, [2 [(1h Indole 2 Carbonyl) Amino] Benzoylamino] Propionic Acid, [2 [(2 Acetylaminocinnamoyl) Amino] Benzoylamino] 3 Phenylpropionic Acid,
Affiliations:
*** IBB - CNR ***
Interuniversity Research Center on Bioactive Peptides (CIRPeB), University of Naples Federico II, Institute of Biostructures and Bioimaging of CNR, Via Mezzocannone, 16, I-80134 Naples, Italy
Department of Pharmaceutical Sciences, University of Trieste, P.le Europa 1, 34127 Trieste, Italy
Institute of Physical Chemistry, NCSR Demokritos Ag. Paraskevi, 15310 Athens, Greece
References:
Wank, S.A., Cholecystokinin receptors (1995) Am. J. Physiol., 269, pp. 628-64
Herranz, R., Cholecystokinn antagonists: Pharmacological and terapeutic potential (2003) Med. Res. Rev., 23, pp. 559-605
De Tullio, P., Delarge, J., Piroette, B., Recent advances in the chemistry of cholecystokinin receptor ligands (agonists and antagonists) (1999) Curr. Med. Chem., 6, pp. 433-455
Varnavas, A., Lassiani, L., Valenta, V., Berti, F., Mennuni, L., Makovec, F., Anthranilic acid derivatives: A new class of non-peptide CCK1 receptor antagonists (2003) Bioorg. Med. Chem., 11, pp. 741-751
Kennedy, K., Gigoux, V., Escrieut, C., Maigret, B., Martinez, J., Moroder, L., Fréhel, 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
Pellegrini, M., Mierke, D.F., Molecular complex of cholecystokinin-8 and N-terminus of the cholecystokinin a receptor by NMR spectroscopy (1999) Biochemistry, 38, pp. 14775-14783
Gigoux, V., Maigret, B., Escrieut, C., Silvente-Poirot, S., Bouisson, M., Fehrentz, J.-A., Moroder, L., Fourmy, D., Arginine 197 of the cholecystokinin-A receptor binding site interacts with the sulfate of the peptide agonist cholecystokinin (1999) Protein Sci., 8, pp. 2347-2354
Archer-Lahlou, E., Tikhonova, I., Escrieut, C., Dufresne, M., Seva, C., Pradayrol, L., Moroder, L., Fourmy, D., Modeled structure of a G-protein-coupled receptor: The cholecystokinin-1 receptor (2005) J. Med. Chem., 48, pp. 180-191
Martín-Martínez, M., Marty, A., Jourdan, M., Escrieut, C., Archer, E., González-Muñiz, R., García-López, M.T., Fourmy, D., Combination of molecular modeling, site-directed mutagenesis, and SAR studies to delineate the binding site of pyridopyrimidine antagonists on the human CCK1 receptor (2005) J. Med. Chem., 48, pp. 4842-4850
Giragossian, C., Sugg, E.E., Szewczyk, J.R., Mierke, D.F., Intermolecular interactions between peptidic and nonpeptidic agonists and the third extracellular loop of the cholecystokinin 1 receptor (2003) J. Med. Chem., 46, pp. 3476-3482
Giragossian, C., Mierke, D.F., Intermolecular interactions between cholecystokinin-8 and the third extracellular Loop of the cholecystokinin a receptor (2001) Biochemistry, 40, pp. 3804-3809
Ragone, R., De Luca, S., Tesauro, D., Pedone, C., Morelli, G., Fluorescence studies on the binding between 1 and 47 fragment of cholecystokinin receptor CCK(A)-R(1-47) and nonsulfated cholecystokinin octapeptide. CCK8 (2001) Biopolymers, 56, pp. 47-53
Aloj, L., Caracò, C., Panico, M.R., Zannetti, A., Del Vecchio, S., Tesauro, D., De Luca, S., Salvatore, M., In vitro and in vivo evaluation of 111In-DTPAGlu-G-CCK8 for cholecystokinin-B receptor imaging (2004) J. Nucl. Med., 45, pp. 485-494
Revel, L., Makovec, F., Castaner, J., Dexloxiglumide. CCK1 (CCKA) receptor antagonist, Treatment of irritable bowel syndrome (1999) Drugs Eur., 24, pp. 725-728
Meyer, E.A., Castellano, R.K., Diederich, F., Interactions with aromatic rings in chemical and biological recognition (2003) Angew. Chem., Int. Ed., 42, pp. 1210-1250
Kim, E., Paliwal, S., Wilcox, C.S., Measurements of molecular electrostatic field effects in edge-to-face aromatic interactions and CH-π interactions with implications for protein folding and molecular recognition (1998) J. Am. Chem. Soc., 120, pp. 11192-11193
Farmer, P.S., Ariëns, E.J., Speculations on the design of nonpeptidic peptidomimetics (1982) Trends Pharmacol. Sci., 5, pp. 362-365
Pace, C.N., Vajados, F., Fee, L., Grinsley, G., Gray, T., How to measure and predict the molar absorption coefficient of a protein (1995) Protein Sci., 4, pp. 2411-2423
De Luca, S., Sanseverino, M., Zocchi, I., Pedone, C., Morelli, G., Ragone, R., Receptor fragment approach to the binding between CCK8 peptide and cholecystokinin receptors: A fluorescence study on type B receptor fragment CCK(B)-R (352-379) (2005) Biopolymers, 77, pp. 205-211
Hagler, A.T., Dauber, P., Lifson, S., Consistent force field studies of intermolecular forces in hydrogen-bonded crystals. 3. The C=O ⋯ H-O hydrogen bond and the analysis of the energetics and packing of carboxylic acids (1979) J. Am. Chem. Soc., 101, pp. 5131-5141
Hagler, A.T., Lifson, S., Dauber, P., Consistent force field studies of intermolecular forces in hydrogen-bonded crystals. 2. A benchmark for the objective comparison of alternative force fields (1979) J. Am. Chem. Soc., 101, pp. 5122-5130
Hagler, A.T., Stern, P.S., Sharon, R., Becker, J.M., Naider, F., Computer simulation of the conformational properties of oligopeptides. Comparison of theoretical methods and analysis of experimental results (1979) J. Am. Chem. Soc., 101, pp. 6842-6852
Wank, S. A., Cholecystokinin receptors (1995) Am. J. Physiol., 269, pp. 628-64
Mart n-Mart nez, M., Marty, A., Jourdan, M., Escrieut, C., Archer, E., Gonz lez-Mu iz, R., Garc a-L pez, M. T., Fourmy, D., Combination of molecular modeling, site-directed mutagenesis, and SAR studies to delineate the binding site of pyridopyrimidine antagonists on the human CCK1 receptor (2005) J. Med. Chem., 48, pp. 4842-4850
Aloj, L., Carac, C., Panico, M. R., Zannetti, A., Del Vecchio, S., Tesauro, D., De Luca, S., Salvatore, M., In vitro and in vivo evaluation of 111In-DTPAGlu-G-CCK8 for cholecystokinin-B receptor imaging (2004) J. Nucl. Med., 45, pp. 485-494
Meyer, E. A., Castellano, R. K., Diederich, F., Interactions with aromatic rings in chemical and biological recognition (2003) Angew. Chem., Int. Ed., 42, pp. 1210-1250
Farmer, P. S., Ari ns, E. J., Speculations on the design of nonpeptidic peptidomimetics (1982) Trends Pharmacol. Sci., 5, pp. 362-365
Pace, C. N., Vajados, F., Fee, L., Grinsley, G., Gray, T., How to measure and predict the molar absorption coefficient of a protein (1995) Protein Sci., 4, pp. 2411-2423
Hagler, A. T., Dauber, P., Lifson, S., Consistent force field studies of intermolecular forces in hydrogen-bonded crystals. 3. The C=O H-O hydrogen bond and the analysis of the energetics and packing of carboxylic acids (1979) J. Am. Chem. Soc., 101, pp. 5131-5141
Hagler, A. T., Lifson, S., Dauber, P., Consistent force field studies of intermolecular forces in hydrogen-bonded crystals. 2. A benchmark for the objective comparison of alternative force fields (1979) J. Am. Chem. Soc., 101, pp. 5122-5130
Hagler, A. T., Stern, P. S., Sharon, R., Becker, J. M., Naider, F., Computer simulation of the conformational properties of oligopeptides. Comparison of theoretical methods and analysis of experimental results (1979) J. Am. Chem. Soc., 101, pp. 6842-6852
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2006 Apr 20; 49(8): 2456-2462.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 5.115, 5-year impact factor: 5.504
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-33646076226&partnerID=40&md5=88e47eb1a452d41d261243c3a72c427d
Keywords: 3 Phenyl [2 (cinnamoylamino)benzoylamino]propionic Acid, [2 [(1h Indole 2 Carbonyl)amino]benzoylamino] 3 Phenylpropionic Acid, [2 [(1h Indole 2 Carbonyl)amino]benzoylamino]propionic Acid, [2 [(2 Acetylaminocinnamoyl)amino]benzoylamino] 3 Phenylpropionic Acid, Anthranilic Acid Derivative, Cholecystokinin A Receptor, Cholecystokinin A Receptor Antagonist, Cholecystokinin Octapeptide, Cholecystokinin Receptor Blocking Agent, Loxiglumide, Unclassified Drug, Vl 0395, Amino Terminal Sequence, Article, Drug Structure, Fluorescence Spectroscopy, Molecular Interaction, Nuclear Magnetic Resonance, Protein Conformation, Receptor Binding, Animals, Competitive, Biological Assay, Humans, Ligands, Magnetic Resonance Spectroscopy, Models, Molecular Structure, Pancreas, Proglumide, Sincalide, Spectrometry, Structure-Activity Relationship, 3 Phenyl [2 (cinnamoylamino) Benzoylamino] Propionic Acid, [2 [(1h Indole 2 Carbonyl) Amino] Benzoylamino] 3 Phenylpropionic Acid, [2 [(1h Indole 2 Carbonyl) Amino] Benzoylamino] Propionic Acid, [2 [(2 Acetylaminocinnamoyl) Amino] Benzoylamino] 3 Phenylpropionic Acid,
Affiliations:
*** IBB - CNR ***
Interuniversity Research Center on Bioactive Peptides (CIRPeB), University of Naples Federico II, Institute of Biostructures and Bioimaging of CNR, Via Mezzocannone, 16, I-80134 Naples, Italy
Department of Pharmaceutical Sciences, University of Trieste, P.le Europa 1, 34127 Trieste, Italy
Institute of Physical Chemistry, NCSR Demokritos Ag. Paraskevi, 15310 Athens, Greece
References:
Wank, S.A., Cholecystokinin receptors (1995) Am. J. Physiol., 269, pp. 628-64
Herranz, R., Cholecystokinn antagonists: Pharmacological and terapeutic potential (2003) Med. Res. Rev., 23, pp. 559-605
De Tullio, P., Delarge, J., Piroette, B., Recent advances in the chemistry of cholecystokinin receptor ligands (agonists and antagonists) (1999) Curr. Med. Chem., 6, pp. 433-455
Varnavas, A., Lassiani, L., Valenta, V., Berti, F., Mennuni, L., Makovec, F., Anthranilic acid derivatives: A new class of non-peptide CCK1 receptor antagonists (2003) Bioorg. Med. Chem., 11, pp. 741-751
Kennedy, K., Gigoux, V., Escrieut, C., Maigret, B., Martinez, J., Moroder, L., Fréhel, 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
Pellegrini, M., Mierke, D.F., Molecular complex of cholecystokinin-8 and N-terminus of the cholecystokinin a receptor by NMR spectroscopy (1999) Biochemistry, 38, pp. 14775-14783
Gigoux, V., Maigret, B., Escrieut, C., Silvente-Poirot, S., Bouisson, M., Fehrentz, J.-A., Moroder, L., Fourmy, D., Arginine 197 of the cholecystokinin-A receptor binding site interacts with the sulfate of the peptide agonist cholecystokinin (1999) Protein Sci., 8, pp. 2347-2354
Archer-Lahlou, E., Tikhonova, I., Escrieut, C., Dufresne, M., Seva, C., Pradayrol, L., Moroder, L., Fourmy, D., Modeled structure of a G-protein-coupled receptor: The cholecystokinin-1 receptor (2005) J. Med. Chem., 48, pp. 180-191
Martín-Martínez, M., Marty, A., Jourdan, M., Escrieut, C., Archer, E., González-Muñiz, R., García-López, M.T., Fourmy, D., Combination of molecular modeling, site-directed mutagenesis, and SAR studies to delineate the binding site of pyridopyrimidine antagonists on the human CCK1 receptor (2005) J. Med. Chem., 48, pp. 4842-4850
Giragossian, C., Sugg, E.E., Szewczyk, J.R., Mierke, D.F., Intermolecular interactions between peptidic and nonpeptidic agonists and the third extracellular loop of the cholecystokinin 1 receptor (2003) J. Med. Chem., 46, pp. 3476-3482
Giragossian, C., Mierke, D.F., Intermolecular interactions between cholecystokinin-8 and the third extracellular Loop of the cholecystokinin a receptor (2001) Biochemistry, 40, pp. 3804-3809
Ragone, R., De Luca, S., Tesauro, D., Pedone, C., Morelli, G., Fluorescence studies on the binding between 1 and 47 fragment of cholecystokinin receptor CCK(A)-R(1-47) and nonsulfated cholecystokinin octapeptide. CCK8 (2001) Biopolymers, 56, pp. 47-53
Aloj, L., Caracò, C., Panico, M.R., Zannetti, A., Del Vecchio, S., Tesauro, D., De Luca, S., Salvatore, M., In vitro and in vivo evaluation of 111In-DTPAGlu-G-CCK8 for cholecystokinin-B receptor imaging (2004) J. Nucl. Med., 45, pp. 485-494
Revel, L., Makovec, F., Castaner, J., Dexloxiglumide. CCK1 (CCKA) receptor antagonist, Treatment of irritable bowel syndrome (1999) Drugs Eur., 24, pp. 725-728
Meyer, E.A., Castellano, R.K., Diederich, F., Interactions with aromatic rings in chemical and biological recognition (2003) Angew. Chem., Int. Ed., 42, pp. 1210-1250
Kim, E., Paliwal, S., Wilcox, C.S., Measurements of molecular electrostatic field effects in edge-to-face aromatic interactions and CH-π interactions with implications for protein folding and molecular recognition (1998) J. Am. Chem. Soc., 120, pp. 11192-11193
Farmer, P.S., Ariëns, E.J., Speculations on the design of nonpeptidic peptidomimetics (1982) Trends Pharmacol. Sci., 5, pp. 362-365
Pace, C.N., Vajados, F., Fee, L., Grinsley, G., Gray, T., How to measure and predict the molar absorption coefficient of a protein (1995) Protein Sci., 4, pp. 2411-2423
De Luca, S., Sanseverino, M., Zocchi, I., Pedone, C., Morelli, G., Ragone, R., Receptor fragment approach to the binding between CCK8 peptide and cholecystokinin receptors: A fluorescence study on type B receptor fragment CCK(B)-R (352-379) (2005) Biopolymers, 77, pp. 205-211
Hagler, A.T., Dauber, P., Lifson, S., Consistent force field studies of intermolecular forces in hydrogen-bonded crystals. 3. The C=O ⋯ H-O hydrogen bond and the analysis of the energetics and packing of carboxylic acids (1979) J. Am. Chem. Soc., 101, pp. 5131-5141
Hagler, A.T., Lifson, S., Dauber, P., Consistent force field studies of intermolecular forces in hydrogen-bonded crystals. 2. A benchmark for the objective comparison of alternative force fields (1979) J. Am. Chem. Soc., 101, pp. 5122-5130
Hagler, A.T., Stern, P.S., Sharon, R., Becker, J.M., Naider, F., Computer simulation of the conformational properties of oligopeptides. Comparison of theoretical methods and analysis of experimental results (1979) J. Am. Chem. Soc., 101, pp. 6842-6852
Wank, S. A., Cholecystokinin receptors (1995) Am. J. Physiol., 269, pp. 628-64
Mart n-Mart nez, M., Marty, A., Jourdan, M., Escrieut, C., Archer, E., Gonz lez-Mu iz, R., Garc a-L pez, M. T., Fourmy, D., Combination of molecular modeling, site-directed mutagenesis, and SAR studies to delineate the binding site of pyridopyrimidine antagonists on the human CCK1 receptor (2005) J. Med. Chem., 48, pp. 4842-4850
Aloj, L., Carac, C., Panico, M. R., Zannetti, A., Del Vecchio, S., Tesauro, D., De Luca, S., Salvatore, M., In vitro and in vivo evaluation of 111In-DTPAGlu-G-CCK8 for cholecystokinin-B receptor imaging (2004) J. Nucl. Med., 45, pp. 485-494
Meyer, E. A., Castellano, R. K., Diederich, F., Interactions with aromatic rings in chemical and biological recognition (2003) Angew. Chem., Int. Ed., 42, pp. 1210-1250
Farmer, P. S., Ari ns, E. J., Speculations on the design of nonpeptidic peptidomimetics (1982) Trends Pharmacol. Sci., 5, pp. 362-365
Pace, C. N., Vajados, F., Fee, L., Grinsley, G., Gray, T., How to measure and predict the molar absorption coefficient of a protein (1995) Protein Sci., 4, pp. 2411-2423
Hagler, A. T., Dauber, P., Lifson, S., Consistent force field studies of intermolecular forces in hydrogen-bonded crystals. 3. The C=O H-O hydrogen bond and the analysis of the energetics and packing of carboxylic acids (1979) J. Am. Chem. Soc., 101, pp. 5131-5141
Hagler, A. T., Lifson, S., Dauber, P., Consistent force field studies of intermolecular forces in hydrogen-bonded crystals. 2. A benchmark for the objective comparison of alternative force fields (1979) J. Am. Chem. Soc., 101, pp. 5122-5130
Hagler, A. T., Stern, P. S., Sharon, R., Becker, J. M., Naider, F., Computer simulation of the conformational properties of oligopeptides. Comparison of theoretical methods and analysis of experimental results (1979) J. Am. Chem. Soc., 101, pp. 6842-6852
Anthranilic acid based CCK1 receptor antagonists and CCK-8 have a common step in their "receptor desmodynamic processes"
The interaction between the 1-47 N-terminus of the CCK1-R and the anthranilic acid based antagonists has been investigated by fluorescence spectroscopy. These antagonists interact with W39 of the N-terminal domain of the CCK1-R like that of the endogenous ligand CCK-8. This specific interaction was not found in other nonpeptide ligands of the CCK1-R. Conformational studies, using NMR and energy minimization procedures, have allowed formulation of a new hypothesis on the CCK1-R binding mode of the anthranilic antagonists. © 2006 American Chemical Society.
The interaction between the 1-47 N-terminus of the CCK1-R and the anthranilic acid based antagonists has been investigated by fluorescence spectroscopy. These antagonists interact with W39 of the N-terminal domain of the CCK1-R like that of the endogenous ligand CCK-8. This specific interaction was not found in other nonpeptide ligands of the CCK1-R. Conformational studies, using NMR and energy minimization procedures, have allowed formulation of a new hypothesis on the CCK1-R binding mode of the anthranilic antagonists. © 2006 American Chemical Society.
Anthranilic acid based CCK1 receptor antagonists and CCK-8 have a common step in their "receptor desmodynamic processes"
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