Conformational Analysis of the C-Terminal Gly-Leu-Met-NH2 Tripeptide of Substance P Bound to the NK-1 Receptor

Sumner, 1990, Conformational analysis of the tachykinins in solution: substance P and physalaemin, J. Biomol. Struct. Dyn., 8, 687, 10.1080/07391102.1990.10507836 Grdadolnik, 1994, Comparison of the conformation of active and nonactive backbone cyclic analogs of substance P as a tool to elucidate features of the bioactive conformation: NMR and molecular dynamics in DMSO and water, J. Med. Chem., 37, 2145, 10.1021/jm00040a005 Young, 1994, NMR and molecular modeling investigations of the neuropeptide substance P in the presence of 15 mM sodium dodecyl sulfate micelles, Biopolymers, 34, 1449, 10.1002/bip.360341102 Keire, 1998, The orientation and dynamics of substance P in lipid environments, Protein Sci., 7, 2438, 10.1002/pro.5560071122 Cowsik, 1997, Lipid-induced conformation of substance P, J. Biomol. Struct. Dyn., 15, 27, 10.1080/07391102.1997.10508942 Wymore, 1999, Molecular dynamics study of substance P peptides in a biphasic membrane mimic, Biophys. J., 76, 1199, 10.1016/S0006-3495(99)77284-X Wymore, 1999, Molecular dynamics study of substance P peptides partitioned in a sodium dodecylsulfate micelle, Biophys. J., 76, 1213, 10.1016/S0006-3495(99)77285-1 Lee, 1999, Comparison of the structures of beta amyloid peptide (25–35) and substance P in trifluoroethanol/water solution, J. Biomol. Struct. Dyn., 17, 381, 10.1080/07391102.1999.10508369 Qi, 2000, CD, 1H NMR and molecular modeling studies of the interaction of Ca2+ with substance P and Ala7-substance P in a nonpolar solvent, J. Pept. Sci., 6, 57, 10.1002/(SICI)1099-1387(200002)6:2<57::AID-PSC245>3.0.CO;2-M Auge, 2000, Characterization of substance P-membrane interaction by transferred nuclear Overhauser effect, Biopolymers, 54, 297, 10.1002/1097-0282(20001015)54:5<297::AID-BIP10>3.0.CO;2-9 Schwyzer, 1986, Membrane structure of Substance P: prediction of preferred conformation, orientation and accumulation of substance P on lipid membranes, Helv. Chim. Acta, 69, 1789, 10.1002/hlca.19860690802 Schwyzer, 1987, Membrane-assisted molecular mechanism of neurokinin receptor subtype selection, EMBO J., 6, 2255, 10.1002/j.1460-2075.1987.tb02498.x Chassaing, 1986, Preferential conformation of substance P in solution, Eur. J. Biochem., 154, 77, 10.1111/j.1432-1033.1986.tb09361.x Ploux, 1987, Interaction of tachykinins with their receptors studied with cyclic analogs of substance P and neurokinin B, Proc. Natl. Acad. Sci. USA, 84, 8095, 10.1073/pnas.84.22.8095 Convert, 1988, Analysis of tachykinin-binding site interactions using NMR and energy calculation data of potent cyclic analogs of substance P, Biochim. Biophys. Acta, 954, 287, 10.1016/0167-4838(88)90084-2 Lavielle, 1988, Analysis of tachykinin binding site interactions using constrained analogs of tachykinins, Biochem. Pharmacol., 37, 41, 10.1016/0006-2952(88)90753-8 Sagan, 1999, Further delineation of the two binding sites (R*(n)) associated with tachykinin neurokinin-1 receptors using [3-prolinomethionine(11)]SP analogs, J. Biol. Chem., 274, 23770, 10.1074/jbc.274.34.23770 Quancard, 2003, Characterization of the bioactive conformation of the C-terminal tripeptide Gly-Leu-Met-NH2 of substance P using [3-prolinoleucine10]SP analogues, Eur. J. Biochem., 270, 2869, 10.1046/j.1432-1033.2003.03665.x Sagan, 1997, High affinity binding of [3H]propionyl-[Met(O2)11]substance P(7–11), a tritiated septide-like peptide, in Chinese hamster ovary cells expressing human neurokinin-1 receptors and in rat submandibular glands, Mol. Pharmacol., 52, 120, 10.1124/mol.52.1.120 Sagan, 1996, Tachykinin peptides affect differently the second messenger pathways after binding to CHO-expressed human NK-1 receptors, J. Pharmacol. Exp. Ther., 276, 1039 Chalmers, 1995, Pro-D-NMe-amino acid and D-Pro-NMe-amino acid: simple, efficient reverse turn constraints, J. Am. Chem. Soc., 117, 5927, 10.1021/ja00127a004 Laskowski, 1993, Procheck: a program to check the stereochemical quality of protein structures, J. Appl. Crystallogr., 26, 283, 10.1107/S0021889892009944 MacArthur, 1991, Influence of proline residues on protein conformation, J. Mol. Biol., 218, 397, 10.1016/0022-2836(91)90721-H Josien, 1994, Design and synthesis of side-chain conformationally restricted phenylalanines and their use for structure-activity studies on tachykinin NK-1 receptor, J. Med. Chem., 37, 1586, 10.1021/jm00037a009 Sagan, 2003, Structural and biological effects of a beta2- or beta3-amino acid insertion in a peptide, Eur. J. Biochem., 270, 939, 10.1046/j.1432-1033.2003.03456.x Cavelier, 2004, Biological activity of silylated amino acid containing substance P analogues, J. Pept. Res., 63, 290, 10.1111/j.1399-3011.2004.00145.x Lavielle, 1993, Importance of the leucine side-chain to the spasmogenic activity and binding of substance P analogues, J. Pept. Protein Res., 42, 270, 10.1111/j.1399-3011.1993.tb00142.x Williams, 2003, How can enzymes be so efficient?, Chem. Commun., 16, 1973, 10.1039/b305544m Williams, 2004, Order changes within receptor systems upon ligand binding: receptor tightening/oligomerisation and the interpretation of binding parameters, J. Mol. Biol., 340, 373, 10.1016/j.jmb.2004.04.056 Hunter, 2003, Cooperativity, partially bound states, and enthalpy-entropy compensation, Chem. Biol., 10, 1023, 10.1016/j.chembiol.2003.10.009 Clackson, 1995, A hot spot of binding energy in a hormone-receptor interface, Science, 267, 383, 10.1126/science.7529940 Kenakin, 2004, Principles: receptor theory in pharmacology, Trends Pharmacol. Sci., 25, 186, 10.1016/j.tips.2004.02.012 Gether, 1998, G protein-coupled receptors: II. Mechanism of agonist activation, J. Biol. Chem., 273, 17979, 10.1074/jbc.273.29.17979 Ghanouni, 2001, Functionally different agonists induce distinct conformations in the G protein coupling domain of the β2 adrenergic receptor, J. Biol. Chem., 276, 24433, 10.1074/jbc.C100162200 Ghanouni, 2001, Agonist-induced conformational changes in the G-protein-coupling domain of the beta2 adrenergic receptor, Proc. Natl. Acad. Sci. USA, 98, 5997, 10.1073/pnas.101126198 Swaminath, 2004, Sequential binding of agonists to the β2 adrenoceptor: kinetic evidence for intermediate conformational states, J. Biol. Chem., 279, 686, 10.1074/jbc.M310888200 Peleg, 2001, Single-molecule spectroscopy of the β2 adrenergic receptor: observation of conformational substates in a membrane protein, Proc. Natl. Acad. Sci. USA, 98, 8469, 10.1073/pnas.151239698 Vollmer, 1999, Subcellular compartmentalization of activation and desensitization of responses mediated by NK2 neurokinin receptors, J. Biol. Chem., 274, 37915, 10.1074/jbc.274.53.37915 Palanche, 2001, The neurokinin A receptor activates calcium and cAMP responses through distinct conformational states, J. Biol. Chem., 276, 34853, 10.1074/jbc.M104363200 Lecat, 2002, Mutations in the extracellular amino-terminal domain of the NK2 neurokinin receptor abolish cAMP signaling but preserve intracellular calcium responses, J. Biol. Chem., 277, 42034, 10.1074/jbc.M203606200 Kim, 2003, The two NK-1 binding sites are distinguished by one radiolabelled substance P analogue, Biochem. Biophys. Res. Commun., 306, 725, 10.1016/S0006-291X(03)01063-5 Ward, 1990, Potent and highly selective neurokinin antagonists, J. Med. Chem., 33, 1848, 10.1021/jm00169a003 Lavielle, 1994, Highly potent substance P antagonists substituted with β-phenyl- or β-benzyl-proline at position 10, Eur. J. Pharmacol., 258, 273, 10.1016/0014-2999(94)90491-X Poulos, 1994, Synthesis and biological activity of NK1 tachykinin antagonists not containing D-residues, Neuropeptides, 26, 55, 10.1016/0143-4179(94)90093-0 Karagiannis, 1993, Synthesis of a potent antagonist of substance P by replacing the CH2SCH3 and the α-carboxamide groups of the methionine at [Orn6]-SP(6–11) by benzyl ester groups, Int. J. Pept. Protein Res., 42, 565, 10.1111/j.1399-3011.1993.tb00365.x Sachon, 2002, Analogues of substance P modified at the C-terminus which are both agonist and antagonist of the NK-1 receptor depending on the second messenger pathway, J. Pept. Res., 59, 232, 10.1034/j.1399-3011.2002.01977.x Karoyan, 1997, Asymmetric synthesis of (2S,3S)- and (2S,3R)-3-prolinomethionines: 3-methylsulfonylmethyl-pyrrolidine-2-carboxylic acids, Tetrahedron Asymmetry, 8, 2025, 10.1016/S0957-4166(97)00203-6 Karoyan, 2003, Amino-zinc-enolate carbometalation reactions: application to ring closure of terminally substituted olefin for the asymmetric synthesis of cis- and trans-3-prolinoleucine, J. Org. Chem., 68, 2256, 10.1021/jo026535n