Synthesis, biological activity, and conformational analysis of [pGlu6,N-MePhe8,Aib9] substance P (6-11): a selective agonist for the NK-3 receptor.

Abstract:

:A highly potent and selective agonist to the tachykinin NK-3 receptor, [pGlu6,N-MePhe8,Aib9] substance P (6-11) (I), was synthesized via the solid phase method. The ED50 of I was 4 nM in the guinea pig ileum in the absence of atropine (NK-1+NK-3 receptors) and this agonist was 5000-fold less potent in the presence of atropine (NK-1 receptor). The analogue was virtually inactive in the rat vas deferens (NK-2 receptor). A detailed analysis of the solution conformation of this analogue in DMSO-d6 and in a DMSO-d6/H2O cryomixture was carried out by a combination of 1H-nmr 2D techniques (DQF-COSY, TOCSY, NOESY and ROESY) and model building based on empirical energy calculations. Peptide I exists as a mixture of isomers containing cis and trans Phe-N-MePhe peptide bonds. The main isomer, containing a cis Phe-N-MePhe peptide bond, shows a preferred folded conformation characterized by a type VI beta-turn with Phe and N-MePhe in the i + 1 and i + 2 positions. The turn is followed by a helical segment extending to the C-terminal. This conformation is compared to previously reported conformations of other selective tachykinin agonists and may be a promising lead for the design of novel NK-3 agonists with additional conformational constraints.

journal_name

Biopolymers

journal_title

Biopolymers

authors

Tallon M,Ron D,Halle D,Amodeo P,Saviano G,Temussi PA,Selinger Z,Naider F,Chorev M

doi

10.1002/bip.360330607

subject

Has Abstract

pub_date

1993-06-01 00:00:00

pages

915-26

issue

6

eissn

0006-3525

issn

1097-0282

journal_volume

33

pub_type

杂志文章
  • Biasing a Monte Carlo chain growth method with Ramachandran's plot: application to twenty-L-alanine.

    abstract::In this paper, we explore the possibility of using experimental observations in the Monte Carlo chain growth method that we have previously developed. In this method, the macromolecule (peptide, protein, nuclei acid, etc.) is grown atom-by-atom (or residue-by-residue, etc.) and partial chains are replicated according ...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360331210

    authors: Bascle J,Garel T,Orland H,Velikson B

    更新日期:1993-12-01 00:00:00

  • Deletion of a single amino acid changes the folding of an apamin hybrid sequence peptide to that of endothelin.

    abstract::The solution conformations of a hybrid sequence peptide related to the bee venom peptide apamin have been determined using two-dimensional 1H-nmr. Apamin is an 18 amino acid peptide containing a C-terminal helix that is stabilized by two disulfide bonds. The deletion of one residue (K4) of the N-terminal "scaffold" re...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/(SICI)1097-0282(19970405)41:4<451::AID-BIP

    authors: Volkman BF,Wemmer DE

    更新日期:1997-04-05 00:00:00

  • Characterization of hyaluronic acid and synovial fluid in stagnation point elongational flow.

    abstract::Hyaluronic acid (HA) is an important biomacromolecule, which fulfils a number of vital physiological functions (especially in the joint synovial fluid) and also has consumer and pharmaceutical applications. HA solution properties have already been quite thoroughly characterized in response to steady shear flows but ar...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.22357

    authors: Haward SJ

    更新日期:2014-03-01 00:00:00

  • The legacies of Langmuir, Ising, and Pauling: ligand binding and the helix-coil transition.

    abstract::Multiple, independent sites or domains behave, on chemical change, in a manner predicted by Langmuir. Distortions of this behavior have been attributed to interactions between the domains, which vary with the progress of the changes occurring at the sites or domains. The two main models for nearest neighbor interactio...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/(SICI)1097-0282(199905)49:6<425::AID-BIP1>

    authors: Saroff HA,Kiefer JE

    更新日期:1999-05-01 00:00:00

  • FTIR study on heat-induced and pressure-assisted cold-induced changes in structure of bovine alpha-lactalbumin: stabilizing role of calcium ion.

    abstract::The second derivative FTIR study of heat-induced and pressure-assisted cold-induced changes in the secondary structure of bovine alpha-lactalbumin was carried out for native holoprotein and calcium ion depleted apoprotein. The secondary structure and compactness of alpha-lactalbumin were examined in a temperature rang...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/1097-0282(2001)62:1<29::AID-BIP50>3.0.CO;2

    authors: Dzwolak W,Kato M,Shimizu A,Taniguchi Y

    更新日期:2001-01-01 00:00:00

  • Determination of isokinetic ratios necessary for equimolar incorporation of carboxylic acids in the solid-phase synthesis of mixture-based combinatorial libraries.

    abstract::The methods used to study the relative reaction rates of 45 different aliphatic and aromatic carboxylic acids when coupled to resin-bound amino acid amides is described. Competition experiments involving the coupling of incoming carboxylic acids to resin-bound amino acid amides were performed. The relative composition...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.10206

    authors: Acharya AN,Ostresh JM,Houghten RA

    更新日期:2002-10-05 00:00:00

  • Does the anesthetic 2,2,2-trifluoroethanol interact with bovine serum albumin by direct binding or by solvent-mediated effects? A calorimetric and spectroscopic investigation.

    abstract::Thermal unfolding of bovine serum albumin (BSA) has been studied in the presence of 2,2,2-trifluoroethanol (TFE) using high-sensitivity microdifferential scanning calorimetry. Quantitative thermodynamic parameters accompanying the thermal transitions have been evaluated. TFE is observed to be a stabilizer or a destabi...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20262

    authors: Banerjee T,Kishore N

    更新日期:2005-06-05 00:00:00

  • Development of a model for the delta-opioid receptor pharmacophore. 4. Residue 3 dehydrophenylalanine analogues of Tyr-c[D-Cys-Phe-D-Pen]OH (JOM-13) confirm required gauche orientation of aromatic side chain.

    abstract::We have previously proposed a model for the delta-opioid receptor binding conformation of the high affinity tetrapeptide Tyr-c[D-Cys-Phe-D-Pen]OH (JOM-13) based on experimental and theoretical conformational analysis of this peptide and a correlation of conformational preferences of further conformationally restricted...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/(sici)1097-0282(199609)39:3<287::aid-bip2>

    authors: Mosberg HI,Dua RK,Pogozheva ID,Lomize AL

    更新日期:1996-09-01 00:00:00

  • Kinetic analysis of the hydrodynamic transition accompanying protein folding using size exclusion chromatography. 2. Comparison of spectral and chromatographic kinetic analyses.

    abstract::The kinetics of the hydrodynamic volume change associated with the unfolding and refolding of a globular protein can be observed using high performance size exclusion chromatography. Chromatographic profiles that evidence such dynamics can be simulated using equations in which chromatographic partitioning and the conf...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360330113

    authors: Shalongo W,Jagannadham M,Stellwagen E

    更新日期:1993-01-01 00:00:00

  • Chiral interaction in Gly-capped N-terminal motif of 3(10)-helix and domino-type induction in helix sense.

    abstract::Chiral interaction of helical peptide with chiral molecule, and concomitant induction in its helix sense have been demonstrated in optically inactive nonapeptide (1) possessing Gly at its N-terminus: H-Gly-(Delta(Z)Phe-Aib)(4)-OCH(3) (1: Delta(Z)Phe = Z-dehydrophenylalanine; Aib = alpha-aminoisobutyric acid). Spectros...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20557

    authors: Ousaka N,Inai Y,Okabe T

    更新日期:2006-11-01 00:00:00

  • VCD spectroscopic and molecular dynamics analysis of the Trp-cage miniprotein TC5b.

    abstract::TC5b is a 20 residue polypeptide notable for its compact tertiary structure, a rarity for a short peptide. This structure is due to the "Trp-cage" motif, an association of aromatic, Pro, and Gly residues. The structure of TC5b has been fully characterized by NMR and electronic circular dichroism (ECD) studies, but has...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20709

    authors: Copps J,Murphy RF,Lovas S

    更新日期:2007-01-01 00:00:00

  • Role of water molecules in the crystal structure of Gly-L-Ala-L-Phe: a possible sequence preference for nucleation of alpha-helix?

    abstract::The synthetic peptide Gly-L-Ala-L-Phe (C14H19N3O4.2H2O; GAF) crystallizes in the monoclinic space group P2I1), with a = 5.879(1), b = 7.966(1), c = 17.754(2) A, beta = 95.14(2) degrees, Dx = 1.321 g cm-3, and Z = 2. The crystal structure was solved by direct methods using the program SHELXS-86 and refined to an R valu...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360280707

    authors: Ramasubbu N,Parthasarathy R

    更新日期:1989-07-01 00:00:00

  • The X-ray structure of the monoclinic crystal form of [D-Hyi2, L-Hyi4] meso-valinomycin.

    abstract::The conformation and intermolecular association of [D-Hyi2, L-Hyi4] meso-valinomycin [cyclo[-D-Val-D-Hyi-L-Val-L-Hyi-(D-Val-L-Hyi-L-Val-D-+ ++Hyi)2-], C60H102N6O18] in a crystal form obtained from ethanol solution has been determined by x-ray crystallography. Two depsipeptides and one ethanol molecule per asymmetric u...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/(SICI)1097-0282(199711)42:6<645::AID-BIP3>

    authors: Pletnev VZ,Ivanov VT,Langs DA,Burkhart BM,Duax WL

    更新日期:1997-11-01 00:00:00

  • Evidence for a strong selenium-aromatic interaction derived from crystallographic data and ab initio quantum chemical calculations.

    abstract::Increasing attention is being paid to the role of selenium, both as an essential component required for the activity of many enzymes and in the context of selenium-based pharmaceutical agents. A wide range of therapeutics that include selenium are on the market and under development, such as antihypertensive, anticanc...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20592

    authors: Hartman I,Raia CA,Zauhar RJ

    更新日期:2006-12-15 00:00:00

  • An estimate of the nearest neighbor base-pair content of 5S RNA using CD and absorption spectroscopy.

    abstract::We analyzed the CD and uv absorption spectra of 5S RNA from Escherichia coli using the method developed in the preceding paper. The analysis of spectra of 5S RNA at 20 degrees C in 0.1M NaClO4, 2.5 mM Na+ (phosphate), pH 7.0, and 0.5 mM MgSO4 gave 7 +/- 3.6 A.U base pairs, 25 +/- 3.6 G.C base pairs, and 7.5 +/- 3.6 G....

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360310404

    authors: Johnson KH,Gray DM

    更新日期:1991-03-01 00:00:00

  • Revisiting "reverse hydrophobic effect": applicable only to coil mutations at the surface.

    abstract::In a seminal paper, Pakula and Sauer (Nature, 1990, 344, 363-364) demonstrated that the increase in side-chain hydrophobicity has a reverse relationship with protein stability. We have addressed this problem with several examples of mutants that span at different locations in protein structure based on secondary struc...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.21187

    authors: Gromiha MM

    更新日期:2009-07-01 00:00:00

  • Spectroscopic studies of interaction of chlorobenzylidine with DNA.

    abstract::Electronic absorbance and fluorescence titrations are used to probe the interaction of chlorobenzylidine with DNA. The binding of chlorobenzylidine to DNA results in hypochromism, a small shift to a longer wavelength in the absorption spectra, and emission quenching in the fluorescence spectra. These spectral characte...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.10001

    authors: Zhong W,Yu JS,Huang W,Ni K,Liang Y

    更新日期:2001-01-01 00:00:00

  • Selective agonists for receptors of substance P and related neurokinins.

    abstract::Neurokinins and their receptors are a complex system consisting of at least three endogenous agents--substance P (SP), neurokinin A (NKA), and neurokinin B (NKB)--and their corresponding receptor types, respectively, NK-1, NK-2, and NK-3. Investigations on receptors have been made using sensitive and fairly selective ...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360280111

    authors: Regoli D,Dion S,Rhaleb NE,Rouissi N,Tousignant C,Jukic D,D'Orleans-Juste P,Drapeau G

    更新日期:1989-01-01 00:00:00

  • Rapid communication: Computational simulation and analysis of a candidate for the design of a novel silk-based biopolymer.

    abstract::This work theoretically investigates the mechanical properties of a novel silk-derived biopolymer as polymerized in silico from sericin and elastin-like monomers. Molecular Dynamics simulations and Steered Molecular Dynamics were the principal computational methods used, the latter of which applies an external force o...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.22494

    authors: Golas EI,Czaplewski C

    更新日期:2014-09-01 00:00:00

  • Structural investigation of helices II, III, and IV of B. megaterium 5S ribosomal RNA by molecular dynamics calculations.

    abstract::The structures of the helices II-III region and the helix IV region of B. megaterium 5S rRNA have been examined by means of energy minimization and molecular dynamics calculations. Calculated distances between neighboring hydrogen-bonded imino protons in helices II, III, and IV were between 3.5 and 4.5 A. The overall ...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360320915

    authors: Kim JH,Marshall AG

    更新日期:1992-09-01 00:00:00

  • Synthesis and characterization of ester-based prodrugs of glucagon-like peptide 1.

    abstract::Peptides represent a rich natural source of potential medicines with one notable pharmaceutical limitation being their relatively short duration of action. A particularly good example of this phenomenon is glucagon-like peptide 1 (GLP), a hormone of appreciable interest for the treatment of type II diabetes. In the na...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.21418

    authors: De A,DiMarchi RD

    更新日期:2010-01-01 00:00:00

  • Electrospun tecophilic/gelatin nanofibers with potential for small diameter blood vessel tissue engineering.

    abstract::Tissue engineering techniques particularly using electrospun scaffolds have been intensively used in recent years for the development of small diameter vascular grafts. However, the development of a completely successful scaffold that fulfills multiple requirements to guarantee complete vascular regeneration remains c...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.22524

    authors: Vatankhah E,Prabhakaran MP,Semnani D,Razavi S,Morshed M,Ramakrishna S

    更新日期:2014-12-01 00:00:00

  • Homo- and heteropolymer self-assembly of recombinant trichocytic keratins.

    abstract::In the past two decades, keratin biomaterials have shown impressive results as scaffolds for tissue engineering, wound healing, and nerve regeneration. In addition to its intrinsic biocompatibility, keratin interacts with specific cell receptors eliciting beneficial biochemical cues. However, during extraction from na...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.23037

    authors: Parker RN,Roth KL,Kim C,McCord JP,Van Dyke ME,Grove TZ

    更新日期:2017-10-01 00:00:00

  • The sensitivity of conformational free energies of the alanine dipeptide to atomic site charges.

    abstract::Different atomic point charge sets are obtained for the alpha R and C7,eq conformations of the alanine dipeptide by fitting the charges of each conformation to the respective ab initio electrostatic potential surfaces both individually and simultaneously, in both the united atom and the all-atom representations. Using...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/(SICI)1097-0282(199701)41:1<73::AID-BIP7>3

    authors: Resat H,Maye PV,Mezei M

    更新日期:1997-01-01 00:00:00

  • Biological activity of peptide-conjugated polyion complex matrices consisting of alginate and chitosan.

    abstract::Peptide-conjugated polysaccharide matrices using bioactive laminin-derived peptides are useful biomaterials for tissue and cell engineering. Here, we demonstrate an easy handling preparation method for peptide-polysaccharide matrices using polyion complex with both alginate and chitosan. First, aldehyde-alginate was s...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.22983

    authors: Fujimori C,Kumai J,Nakamura K,Gu Y,Katagiri F,Hozumi K,Kikkawa Y,Nomizu M

    更新日期:2017-01-01 00:00:00

  • Water-mediated contacts in the trp-repressor operator complex recognition process.

    abstract::Water-mediated contacts are known as an important recognition tool in trp-repressor operator systems. One of these contacts involves two conserved base pairs (G(6).C(-6) and A(5). T(-5)) and three amino acids (Lys 72, Ile 79, and Ala 80). To investigate the nature of these contacts, we analyzed the X-ray structure (PD...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20023

    authors: Wibowo FR,Rauch C,Trieb M,Wellenzohn B,Liedl KR

    更新日期:2004-04-15 00:00:00

  • Comparison of monovalent and divalent ion distributions around a DNA duplex with molecular dynamics simulation and a Poisson-Boltzmann approach.

    abstract::The ion atmosphere created by monovalent (Na(+) ) or divalent (Mg(2+) ) cations surrounding a B-form DNA duplex were examined using atomistic molecular dynamics (MD) simulations and the nonlinear Poisson-Boltzmann (PB) equation. The ion distributions predicted by the two methods were compared using plots of radial and...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.22461

    authors: Robbins TJ,Ziebarth JD,Wang Y

    更新日期:2014-08-01 00:00:00

  • Study of tumor cell invasion by Fourier transform infrared microspectroscopy.

    abstract::Lung cancer is usually fatal once it becomes metastatic. However, in order to develop metastases, a tumor usually invades the basal membrane and enters the vascular or lymphatic system. In this study, a three-dimensional artificial membrane using collagen type I, one of the main components of basal membranes, was esta...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20297

    authors: Yang Y,Sulé-Suso J,Sockalingum GD,Kegelaer G,Manfait M,El Haj AJ

    更新日期:2005-08-15 00:00:00

  • External reversible control of recognition behavior of alpha-peptide ribonucleic acid (alpha-PRNA) through anti-syn orientational switching of the nucleobase induced by borate esterification of the cis-2',3'-diol.

    abstract::A novel nucleic acid model using peptide ribonucleic acid (PRNA), which contains 5'-amino-5'-deoxypyrimidine ribonucleoside as a recognition site for nucleic acids, has been designed, synthesized and applied to the external reversible control of recognition behavior of the complementary polynucleotide through the orie...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.10563

    authors: Wada T,Sato H,Inoue Y

    更新日期:2004-01-01 00:00:00

  • Orphan PTMs: Rare, yet functionally important modifications of cysteine.

    abstract::The enhanced nucleophilicity and redox sensitivity of the thiol group renders cysteine residues susceptible to numerous electrophilic and oxidative post-translational modifications to form disulfides, sulfenic acids, nitrosothiols, and lipid-modified species. Outside of these well-characterized modifications of cystei...

    journal_title:Biopolymers

    pub_type: 杂志文章,评审

    doi:10.1002/bip.22252

    authors: Shannon DA,Weerapana E

    更新日期:2014-02-01 00:00:00