A cyclic CCK8 analogue selective for the cholecystokinin type A receptor: design, synthesis, NMR structure and binding measurements (472 views)
Chembiochem (ISSN: 1439-7633, 1439-4227, 1439-7633electronic), 2003 Nov 7; 4(11): 1176-1187.
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Paper type: Journal Article, Research Support, Non-U. S. Gov'T,
Impact factor: 3.992, 5-year impact factor: 3.307
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-0344875561&partnerID=40&md5=e794bb44603ee52f7e685fb17ff9a655
Keywords: Binding Studies, Cck Analogues, Conformation Analysis, Cyclic Peptides, Ligand Design, Cholecystokinin A Receptor, Cholecystokinin Derivative, Cyclopeptide, Dodecylphosphorylcholine, Methionine, Tryptophan, Water, Amino Terminal Sequence, Aqueous Solution, Article, Carboxy Terminal Sequence, Dissociation Constant, Fluorescence Spectroscopy, Human, Human Cell, Micelle, Nuclear Magnetic Resonance Spectroscopy, Priority Journal, Receptor Binding, Spatial Orientation, Cultured, Drug Design, Models, Molecular, Molecular Structure, Peptide Fragments, Protein Binding, Protein Conformation, Chemical Synthesis, Chemistry, Pharmacology, Metabolism,
Affiliations:
*** IBB - CNR ***
CIRPeB, Ist. Biostrutture/Bioimmagini CNR, Via Mezzocannone, 6/8, 80134 Napoli, Italy
Dipto. di Biochimica e Biofisica, Seconda Università di Napoli, Via Costantinopoli, 16, 80138 Napoli, Italy
Bioindustry Park del Canavese, Via Ribes, 5, 10010 Colleretto Giacosa (TO), Italy
Centro Interuniversitario per la Ricerca sui Peptidi Bioattivi (CIRPeB), & Istituto di Biostrutture e Bioimmagini del CNR, Via Mezzocannone 6/8, 80134 Naples, Italy.,
References:
Not available.
Chembiochem (ISSN: 1439-7633, 1439-4227, 1439-7633electronic), 2003 Nov 7; 4(11): 1176-1187.
Export to BibTeX Export to EndNote
Paper type: Journal Article, Research Support, Non-U. S. Gov'T,
Impact factor: 3.992, 5-year impact factor: 3.307
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-0344875561&partnerID=40&md5=e794bb44603ee52f7e685fb17ff9a655
Keywords: Binding Studies, Cck Analogues, Conformation Analysis, Cyclic Peptides, Ligand Design, Cholecystokinin A Receptor, Cholecystokinin Derivative, Cyclopeptide, Dodecylphosphorylcholine, Methionine, Tryptophan, Water, Amino Terminal Sequence, Aqueous Solution, Article, Carboxy Terminal Sequence, Dissociation Constant, Fluorescence Spectroscopy, Human, Human Cell, Micelle, Nuclear Magnetic Resonance Spectroscopy, Priority Journal, Receptor Binding, Spatial Orientation, Cultured, Drug Design, Models, Molecular, Molecular Structure, Peptide Fragments, Protein Binding, Protein Conformation, Chemical Synthesis, Chemistry, Pharmacology, Metabolism,
Affiliations:
*** IBB - CNR ***
CIRPeB, Ist. Biostrutture/Bioimmagini CNR, Via Mezzocannone, 6/8, 80134 Napoli, Italy
Dipto. di Biochimica e Biofisica, Seconda Università di Napoli, Via Costantinopoli, 16, 80138 Napoli, Italy
Bioindustry Park del Canavese, Via Ribes, 5, 10010 Colleretto Giacosa (TO), Italy
Centro Interuniversitario per la Ricerca sui Peptidi Bioattivi (CIRPeB), & Istituto di Biostrutture e Bioimmagini del CNR, Via Mezzocannone 6/8, 80134 Naples, Italy.,
References:
Not available.
A cyclic CCK8 analogue selective for the cholecystokinin type A receptor: design, synthesis, NMR structure and binding measurements
A cyclic CCK8 analogue, cyclo(29,34)[Dpr(29),Lys(34)]-CCK8 (Dpr=L-2,3-diaminopropionic acid), has been designed on the basis of the NMR structure of the bimolecular complex between the N-terminal fragment of the CCK(A) receptor and its natural ligand CCK8. The conformational features of cyclo(29,34)[Dpr(29),Lys(34)]-CCK8 have been determined by NMR spectroscopy in aqueous solution and in water containing DPC-d(38) micelles (DPC=dodecylphosphocholine). The structure of the cyclic peptide in aqueous solution is found to be in a relaxed conformation, with the backbone and Dpr29 side chain atoms making a planar ring and the N-terminal tripeptide extending approximately along the plane of this ring. In DPC/water, the cyclic peptide adopts a "boat-shaped" conformation, which is more compact than that found in aqueous solution. The cyclic constraint between the Dpr29 side chain and the CCK8 carboxyl terminus (Lys34) introduces a restriction in the backbone conformational freedom. However, the interaction of cyclo(29,34)[Dpr(29),Lys(34)]-CCK8 with the micelles still plays an important role in the stabilisation of the bioactive conformation. A careful comparison of the NMR structure of the cyclic peptide in a DPC micelle aqueous solution with the structure of the rationally designed model underlines that the turn-like conformation in the Trp30-Met31 region is preserved, such that the Trp30 and Met31 side chains can adopt the proper spatial orientation to interact with the CCK(A) receptor. The binding properties of cyclo(29,34)[Dpr(29),Lys(34)]-CCK8 to the N-terminal receptor fragment have been investigated by fluorescence spectroscopy in a micellar environment. Estimates of the apparent dissociation constant, K(d), were in the range of 70-150 nM, with a mean value of 120+/-27 nM. Preliminary nuclear medicine studies on cell lines transfected with the CCK(A) receptor indicate that the sulfated-Tyr derivative of cyclo(29,34)[Dpr(29),Lys(34)]-CCK8 displaces the natural ligand with an IC(50) value of 15 microM.
A cyclic CCK8 analogue, cyclo(29,34)[Dpr(29),Lys(34)]-CCK8 (Dpr=L-2,3-diaminopropionic acid), has been designed on the basis of the NMR structure of the bimolecular complex between the N-terminal fragment of the CCK(A) receptor and its natural ligand CCK8. The conformational features of cyclo(29,34)[Dpr(29),Lys(34)]-CCK8 have been determined by NMR spectroscopy in aqueous solution and in water containing DPC-d(38) micelles (DPC=dodecylphosphocholine). The structure of the cyclic peptide in aqueous solution is found to be in a relaxed conformation, with the backbone and Dpr29 side chain atoms making a planar ring and the N-terminal tripeptide extending approximately along the plane of this ring. In DPC/water, the cyclic peptide adopts a "boat-shaped" conformation, which is more compact than that found in aqueous solution. The cyclic constraint between the Dpr29 side chain and the CCK8 carboxyl terminus (Lys34) introduces a restriction in the backbone conformational freedom. However, the interaction of cyclo(29,34)[Dpr(29),Lys(34)]-CCK8 with the micelles still plays an important role in the stabilisation of the bioactive conformation. A careful comparison of the NMR structure of the cyclic peptide in a DPC micelle aqueous solution with the structure of the rationally designed model underlines that the turn-like conformation in the Trp30-Met31 region is preserved, such that the Trp30 and Met31 side chains can adopt the proper spatial orientation to interact with the CCK(A) receptor. The binding properties of cyclo(29,34)[Dpr(29),Lys(34)]-CCK8 to the N-terminal receptor fragment have been investigated by fluorescence spectroscopy in a micellar environment. Estimates of the apparent dissociation constant, K(d), were in the range of 70-150 nM, with a mean value of 120+/-27 nM. Preliminary nuclear medicine studies on cell lines transfected with the CCK(A) receptor indicate that the sulfated-Tyr derivative of cyclo(29,34)[Dpr(29),Lys(34)]-CCK8 displaces the natural ligand with an IC(50) value of 15 microM.
A cyclic CCK8 analogue selective for the cholecystokinin type A receptor: design, synthesis, NMR structure and binding measurements
A cyclic CCK8 analogue selective for the cholecystokinin type A receptor: design, synthesis, NMR structure and binding measurements
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Impact Factor: 1.807
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De Luca S, De Capua A, Saviano M, Della Moglie R, Aloj L, Tarallo L, Pedone C, Morelli G
* Synthesis and biological evaluation of cyclic and branched peptide analogues as ligands for cholecystokinin type 1 receptor (425 views)
Bioorg Med Chem (ISSN: 0968-0896, 1464-3391, 1464-3391electronic), 2007 Sep 1; 15(17): 5845-5853.
Impact Factor: 2.662
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Roviello GN, Musumeci D, Moccia M, Castiglione M, Sapio R, Valente M, Bucci EM, Perretta G, Pedone C
* Dabpna: Design, Synthesis And Nucleic Acids Binding Studies (437 views)
Nucleosides Nucleotides Nucleic Acids (ISSN: 1525-7770), 2007; 26(10-12): 1307-1310.
Impact Factor: 0.723
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De Capua A, Goodman M, Amino Y, Saviano M, Benedetti E
* Conformation analysis of aspartame-based sweeteners by NMR spectroscopy, molecular dynamics simulations, and X-ray diffraction studies (680 views)
Chembiochem (ISSN: 1439-4227, 1439-7633, 1439-7633electronic), 2006 Feb; 7(2): 377-387.
Impact Factor: 4.1
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Benedetti E, Pedone C
* Cyclolinopeptide A: inhibitor, immunosuppressor or other? (578 views)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2005 May; 11(5): 268-272.
Impact Factor: 1.803
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Falcigno L, Oliva R, D'Auria G, Maletta M, Dettin M, Pasquato A, Di Bello C, Paolillo L
* Structural investigation of the HIV-1 envelope glycoprotein gp160 cleavage site 3: Role of site-specific mutations (438 views)
Chembiochem (ISSN: 1439-4227, 1439-7633, 1439-7633electronic), 2004 Dec 3; 5(12): 1653-1661.
Impact Factor: 3.474
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Saviano M, Improta R, Benedetti E, Carrozzini B, Cascarano GL, Didierjean C, Toniolo C, Crisma M
* Benzophenone photophore flexibility and proximity: Molecular and crystal-state structure of a Bpa-containing trichogin dodecapeptide analogue (388 views)
Chembiochem (ISSN: 1439-4227, 1439-7633, 1439-7633electronic), 2004 Apr 2; 5(4): 541-544.
Impact Factor: 3.474
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Oliva R, Falcigno L, D'Auria G, Dettin M, Scarinci C, Pasquato A, Di Bello C, Paolillo L
* Structural investigation of the HIV-1 envelope glycoprotein gp160 cleavage site (382 views)
Chembiochem (ISSN: 1439-4227, 1439-7633, 1439-7633electronic), 2003 Sep 4; 4(8): 727-733.
Impact Factor: 3.992
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Oliva R, Falcigno L, D'Auria G, Dettin M, Scarinci C, Pasquato A, Di Bello C, Paolillo L
* Structural investigation of the HIV-1 envelope glycoprotein gp160 cleavage site, 2: relevance of an N-terminal helix (361 views)
Chembiochem (ISSN: 1439-4227, 1439-7633, 1439-7633electronic), 2003 Aug 4; 4(8): 727-733.
Impact Factor: 2.92
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Wiesehan K, Buder K, Linke RP, Patt S, Stoldt M, Unger E, Schmitt B, Bucci E, Willbold D
* Selection of D-amino-acid peptides that bind to Alzheimer's disease amyloid peptide Aβ1-42 by mirror image phage display (755 views)
Chembiochem (ISSN: 1439-4227, 1439-7633, 1439-7633electronic), 2003; 4(8): 748-753.
Impact Factor: 3.992
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Oliva R, Leone M, Falcigno L, D'Auria G, Dettin M, Scarinci C, Di Bello C, Paolillo L
* Structural investigation of the HIV-1 envelope glycoprotein gp160 cleavage site (512 views)
Chemistry (ISSN: 0947-6539, 1521-3765, 1521-3765electronic), 2002 Mar 15; 8(6): 1467-1473.
Impact Factor: 4.238
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Formaggio F, Bonchio M, Crisma M, Peggion C, Mezzato S, Polese A, Barazza A, Antonello S, Maran F, Broxterman QB, Kaptein B, Kamphuis J, Vitale RM, Saviano M, Benedetti E, Toniolo C
* Nitroxyl peptides as catalysts of enantioselective oxidations (499 views)
Chemistry (ISSN: 0947-6539, 1521-3765, 1521-3765electronic), 2002; 8(1): [d]84-93.
Impact Factor: 4.238
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Zanotti G, Saviano M, Saviano G, Tancredi T, Rossi F, Pedone C, Benedetti E
Structure of cyclic peptides: the crystal and solution conformation of cyclo(Phe-Phe-Aib-Leu-Pro) (738 views)
Journal Of Peptide Research (ISSN: 1397-002x), 1998 Jun; 51(6): 460-466.
Impact Factor: 1.125
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D'Andrea LD, Mazzeo M, Isernia C, Rossi F, Saviano M, Gallo P, Paolillo L, Pedone C
Solution conformational preferences of a peptidic analogue of a natural macrolide (382 views)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 1997; 42(3): 349-361.
Impact Factor: 2.425
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Lombardi A, Saviano M, Nastri F, Maglio O, Mazzeo M, Pedone C, Isernia C, Pavone V
Unusual conformational preferences of β-alanine containing cyclic peptides. VII (456 views)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 1996 Jun; 38(6): 683-691.
Impact Factor: 2.425
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Lombardi A, D'Auria G, Saviano M, Maglio O, Nastri F, Quartara L, Pedone C, Pavone V
Bicyclic Peptides As Type I/Type Ii Beta-Turn Scaffolds (518 views)
Biopolym Pept Sci Sect, 1996; 40(5): 505-518.
Impact Factor: 0
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Pavone V, Lombardi A, Saviano M, Nastri F, Fattorusso R, Maglio O, Isernia C, Paolillo L, Pedone C
β-alanine containing cyclic peptides with turned structure: The 'pseudo type II β-turn. ' VI (464 views)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 1994 Nov; 34(11): 1517-1526.
Impact Factor: 2.425
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33 Records (33 excluding Abstracts).
Total impact factor: 95.096 (95.096 excluding Abstracts).
Total 5 year impact factor: 94.183 (94.183 excluding Abstracts).
Total impact factor: 95.096 (95.096 excluding Abstracts).
Total 5 year impact factor: 94.183 (94.183 excluding Abstracts).
472 views. Last view on Tuesday 28 February 2023, 5:03:38
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