Synthesis and antinociceptive activity of peptides related to interleukin-1 beta 193-195 Lys-Pro-Thr.

Abstract:

:To obtain information about the structure-activity relationships of analgesic peptides, we modified the previously reported tripeptide, H-Lys-Pro-Thr-OH (C). The proline part in C was replaced with various analogues of unconventional amino acids [(3aS, 7aS)-octahydroindole-2-carboxylic acid (Oic), (S,S,S,)-2-azabiciclo [3.3.0]octane-3-carboxylic acid (Aoc), D-Aoc, and (2S, 4R)-hydroxyproline (Hyp)] with varying lipophilic, steric, and conformational properties, and alternatively with Lys and Orn in the lysine part. Moreover, the threonine part was changed to various natural amino acids (Ser, Thr, Val, Leu). All the compound were screened in vivo for their analgesic effects in mouse writhing test. Compound 24 (H-Orn-Hyp-Val-OH), the most active compound within the series, showed an ED50 value of 10 mg/kg, which is comparable with the ED50 values exhibited by indometacin (4.1 mg/kg) and the dipeptide H-Lys-D-Pro-OH (6.9 mg/kg), both used as reference drugs.

journal_name

Biopolymers

journal_title

Biopolymers

authors

Caliendo G,Greco G,Grieco P,Perissutti E,Santagada V,Ialenti A,Maffia P,Albrizio S,Santini A

doi

10.1002/(sici)1097-0282(1996)40:5<479::aid-bip5>3.

subject

Has Abstract

pub_date

1996-01-01 00:00:00

pages

479-84

issue

5

eissn

0006-3525

issn

1097-0282

pii

10.1002/(SICI)1097-0282(1996)40:5<479::AID-BIP5>3.

journal_volume

40

pub_type

杂志文章
  • Kinetics of the helix/coil transition of the collagen-like peptide (Pro-Hyp-Gly)10.

    abstract::This article measures the rates of folding and unfolding of the collagen-like peptide (Pro-Hyp-Gly)(10) over overlapping concentration and temperature ranges. The data allow calculation of the orders of the folding and the unfolding reactions, the effective Arrhenius activation energies, and numerical solution of the ...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20787

    authors: Miles CA

    更新日期:2007-09-01 00:00:00

  • A dipeptide-based superhydrogel: Removal of toxic dyes and heavy metal ions from waste water.

    abstract::A short peptide-based molecule has been found to form a strong hydrogel at phosphate buffer solution of pH 7.46. The hydrogel has been characterized thoroughly using various techniques including field emission scanning electron microscopy (FE-SEM), wide angle powder X-ray diffraction (PXRD), and rheological analysis. ...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.22915

    authors: Nandi N,Baral A,Basu K,Roy S,Banerjee A

    更新日期:2017-01-01 00:00:00

  • Intermolecular Overhauser effects in fluoroalcohol solutions of cyclo-alanylglycine.

    abstract::Interactions between the diketopiperazine cyclo-alanylglycine and four fluorinated alcohols in water-fluoroalcohol mixtures were examined by (1)H[(19)F] intermolecular nuclear Overhauser effects (NOE) experiments. The alcohols studied were trifluoroethanol, hexafluoroacetone trihydrate, 1,1,1,3,3,3-hexafluoroisopropan...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.10176

    authors: Strickler MA,Gerig JT

    更新日期:2002-08-15 00:00:00

  • Amylose chain behavior in an interacting context. III. Complete occupancy of the AMY2 barley alpha-amylase cleft and comparison with biochemical data.

    abstract::In the first two papers of this series, the tools necessary to evaluate substrate ring deformations were developed, and then the modeling of short amylose fragments (maltotriose and maltopentaose) inside the catalytic site of barley alpha-amylase was performed. In this third paper, this docking has been extended to th...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/(SICI)1097-0282(199912)50:7<751::AID-BIP8>

    authors: André G,Buléon A,Haser R,Tran V

    更新日期:1999-12-01 00:00:00

  • FTIR microspectroscopy study of composition fluctuations in extruded amylopectin-gelatin blends.

    abstract::The spatial variation in the composition of nonexpanded biopolymer blends prepared by extrusion of mixtures of gelatin with either native or pregelatinized waxy maize starch was studied using a 30-microm aperture FTIR microspectroscopy technique. The ratio of the areas of the "saccharide" bands (953-1180 cm(-1)) and t...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.1015

    authors: Mousia Z,Farhat IA,Pearson M,Chesters MA,Mitchell JR

    更新日期:2001-01-01 00:00:00

  • Quantitative characterization of specific genomic promoters using agarose gel electrophoresis.

    abstract::Over the past decade a large number of studies have focused attention on the role of nucleosomes as negative and positive regulators of specific nuclear functions. Due to the lack of an analytical method to determine the higher order conformation of the nucleosomal arrays that encompass specific genetic loci (e.g., pr...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.10322

    authors: Georgel PT,Hansen JC

    更新日期:2003-04-01 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

  • Solvent reorganization contribution to the transfer thermodynamics of small nonpolar molecules.

    abstract::The experimental thermodynamic data for the dissolution of five simple hydrocarbon molecules in water were combined with the solute-solvent interaction energy from a computer simulation study to yield data on the enthalpy change of solvent reorganization. Similar data were generated for dissolving these same solute mo...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360310809

    authors: Lee B

    更新日期:1991-07-01 00:00:00

  • Review: Progresses in understanding N-ethylmaleimide sensitive factor (NSF) mediated disassembly of SNARE complexes.

    abstract::N-ethylmaleimide sensitive factor (NSF) is a key protein of intracellular membrane traffic. NSF is a highly conserved protein belonging to the ATPases associated with other activities (AAA+ proteins). AAA+ share common domains and all transduce ATP hydrolysis into major conformational movements that are used to carry ...

    journal_title:Biopolymers

    pub_type: 杂志文章,评审

    doi:10.1002/bip.22854

    authors: Ryu JK,Jahn R,Yoon TY

    更新日期:2016-08-01 00:00:00

  • Solvent interactions with the Trp-cage peptide in 35% ethanol-water.

    abstract::Intermolecular NOE experiments have been used to explore interactions of water and ethanol molecules in 35% ethanol/65% water (v/v) with the peptide Trp-cage at temperatures from 5 to 25 degrees C. Magnetic dipole-dipole cross-relaxation terms sigma(HH) (NOE) and sigma(HH) (ROE) for interaction of solvent components w...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.21028

    authors: Neuman RC Jr,Gerig JT

    更新日期:2008-10-01 00:00:00

  • Breaking non-native hydrophobic clusters is the rate-limiting step in the folding of an alanine-based peptide.

    abstract::The formation mechanism of an alanine-based peptide has been studied by all-atom molecular dynamics simulations with a recently developed all-atom point-charge force field and the Generalize Born continuum solvent model at an effective salt concentration of 0.2M. Thirty-two simulations were conducted. Each simulation ...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.10216

    authors: Chowdhury S,Zhang W,Wu C,Xiong G,Duan Y

    更新日期:2003-01-01 00:00:00

  • Chemical structure and chain conformation of the water-insoluble glucan isolated from Pleurotus tuber-regium.

    abstract::A water-insoluble polysaccharide (TM8) was isolated from sclerotium of Pleurotus tuber-regium by extraction with 0.5M NaOH aqueous solutions at 120 degrees C. Its chemical structure was confirmed by infrared, high performance liquid chromatography, gas chromatography, and (13)C NMR in dimethylsulfoxide (DMSO) to be co...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/1097-0282(200111)59:6<457::AID-BIP1050>3.0

    authors: Zhang L,Zhang M,Dong J,Guo J,Song Y,Cheung PC

    更新日期:2001-11-01 00:00:00

  • Synthesis and characterization of the sweet protein brazzein.

    abstract::The sweet protein brazzein isolated from the fruit of the African plant, Pentadiplandra brazzeana Baillon is 2000-500 times sweeter than sucrose and consists of 54 amino acid residues with four intramolecular disulfide bonds. Brazzein was prepared by the fluoren-9-yl-methoxycarbonyl solid-phase method, and was identic...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/(sici)1097-0282(199607)39:1<95::aid-bip10>

    authors: Izawa H,Ota M,Kohmura M,Ariyoshi Y

    更新日期:1996-07-01 00:00:00

  • Conformational and binding properties of chicken liver basic fatty acid binding protein in solution.

    abstract::The conformation of basic fatty acid binding protein from chicken liver and the binding properties of the apo protein toward 11-dansylamino-undecanoic acid were investigated by CD and fluorescence spectroscopy. In one set of experiments the binding process was followed by the appearance of induced optical activity in ...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360340707

    authors: Schievano E,Quarzago D,Spadon P,Monaco HL,Zanotti G,Peggion E

    更新日期:1994-07-01 00:00:00

  • Use of surface enhanced infrared absorption spectroscopy (SEIRA) to probe the functionality of a protein monolayer.

    abstract::We present a novel infrared method to investigate the functionality of a protein monolayer tethered to a metal substrate. The approach employs Surface Enhanced Infrared Absorption Spectroscopy (SEIRAS), which renders high surface sensitivity by enhancing the signal of the adsorbed protein by up to approximately 2 orde...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20501

    authors: Ataka K,Heberle J

    更新日期:2006-07-01 00:00:00

  • The serine palmitoyltransferase from Sphingomonas wittichii RW1: An interesting link to an unusual acyl carrier protein.

    abstract::Serine palmitoyltransferase (SPT) catalyses the first step in the de novo biosynthesis of sphingolipids (SLs). It uses a decarboxylative Claisen-like condensation reaction to couple L-serine with palmitoyl-CoA to generate a long-chain base product, 3-ketodihydrosphingosine. SLs are produced by mammals, plants, yeast, ...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.21482

    authors: Raman MC,Johnson KA,Clarke DJ,Naismith JH,Campopiano DJ

    更新日期:2010-09-01 00:00:00

  • Vibrational studies of the disulfide group in proteins. VI. General correlations of SS and CS stretch frequencies with disulfide bridge geometry.

    abstract::Normal mode calculations have been done on a range of disulfide bridge conformations in order to determine how the SS stretch and CS stretch frequencies depend on structure. In addition to varying the C alpha C beta SS and NC alpha C beta S dihedral angles, we have varied the phi, psi of the adjoining peptide groups s...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360320813

    authors: Qian W,Krimm S

    更新日期:1992-08-01 00:00:00

  • Enhanced deoxyribozyme-catalyzed RNA ligation in the presence of organic cosolvents.

    abstract::Deoxyribozyme and aptamer selections are typically conducted in aqueous buffer solutions. Using nonaqueous cosolvents in selection experiments will help expand the activity of deoxyribozymes with non-oligonucleotide substrates and will allow identification of new aptamers for nonprotein targets. We undertook in vitro ...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.22191

    authors: Behera AK,Schlund KJ,Mason AJ,Alila KO,Han M,Grout RL,Baum DA

    更新日期:2013-06-01 00:00:00

  • Small-angle x-ray scattering studies of metastable intermediates of beta-lactoglobulin isolated after heat-induced aggregation.

    abstract::Small-angle x-ray scattering was used for studying intermediate species, isolated after heat-induced aggregation of the A variant of bovine beta-lactoglobulin. The intermediates were separated in two fractions, the heated metastable dimer and heated metastable oligomers larger than the dimer. The pair distance distrib...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.10497

    authors: Carrotta R,Arleth L,Pedersen JS,Bauer R

    更新日期:2003-10-01 00:00:00

  • Fluorescence enhancement of fluorophores tethered to different sized silver colloids deposited on glass substrate.

    abstract::We studied fluorescence enhancements of fluorescein tethered to silver colloids of different size. Thiolated 23-mer oligonucleotide (ss DNA-SH) was bound selectively to silver colloids deposited on 3-aminopropyltriethoxysilane (APS)-treated quartz slides. Fluorescein-labeled complementary oligonucleotide (ss Fl-DNA) w...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20179

    authors: Lukomska J,Malicka J,Gryczynski I,Leonenko Z,Lakowicz JR

    更新日期:2005-01-01 00:00:00

  • Internal dynamics of linear and superhelical DNA as studied by photon correlation spectroscopy.

    abstract::Photon correlation spectroscopy has been used to study the translational (D0) and internal dynamics of monodisperse linear and polydisperse superhelical plasmid-DNAs. Scattering vector dependent correlation functions were measured and analyzed with the inverse Laplace transform CONTIN written by S. Provencher. For sca...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360310702

    authors: Seils J,Dorfmüller T

    更新日期:1991-06-01 00:00:00

  • Self-assembly of amphipathic β-sheet peptides: insights and applications.

    abstract::Amphipathic peptides composed of alternating polar and nonpolar residues have a strong tendency to self-assemble into one-dimensional, amyloid-like fibril structures. Fibrils derived from peptides of general (XZXZ)(n) sequence in which X is hydrophobic and Z is hydrophilic adopt a putative β-sheet bilayer. The bilayer...

    journal_title:Biopolymers

    pub_type: 杂志文章,评审

    doi:10.1002/bip.22058

    authors: Bowerman CJ,Nilsson BL

    更新日期:2012-01-01 00:00:00

  • New results concerning the behavior of cellulose acetate in solutions and films by means of CD measurements.

    abstract::Cellulose acetate (DS = 2.45) was extensively investigated by Circular Dichroism (CD) in acetonitrile and dioxane. We found great differences between the CD spectra of a 1 wt % acetonitrile solution and the corresponding dioxane solution of cellulose acetate (CA) indicating that the macromolecules exist in those solut...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/(SICI)1097-0282(199908)50:2<163::AID-BIP5>

    authors: Meissner D,Einfeldt J,Schareina T

    更新日期:1999-08-01 00:00:00

  • Solution structure of nocistatin, a new peptide analgesic.

    abstract::Nocistatin, a new heptadecapeptide encoded in the bPNP-3 gene, has a powerful biological activity connected with the mechanisms of pain transmission. It does not bind to the opioid receptors but to another brain receptor with high affinity. In order to substantiate these novel biological data with a structural basis, ...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/(SICI)1097-0282(200003)53:3<257::AID-BIP5>

    authors: Crescenzi O,Guerrini R,Picone D,Salvadori S,Tancredi T,Temussi PA

    更新日期:2000-03-01 00:00:00

  • Peptides in membranes: helicity and hydrophobicity.

    abstract::Synthetic model membrane-interactive peptides--both of natural and designed sequence--have become convenient and systematic tools for determination of how the membrane-spanning segments within integral membrane proteins confer protein structure and biology. Conformational studies on these peptides demonstrate that the...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360370503

    authors: Deber CM,Li SC

    更新日期:1995-01-01 00:00:00

  • Resolution of Trp near UV CD spectra of calmodulin-domain peptide complexes into the 1La and 1Lb component spectra.

    abstract::Near uv CD spectra of Trp residues in proteins frequently show a complex line shape deriving from the overlap of 1La and 1Lb electronic transitions. This study presents an original empirical method of resolving these components, based on the near uv CD spectra of well-defined complexes of calmodulin domains with targe...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/(SICI)1097-0282(199806)45:7<493::AID-BIP3>

    authors: Barth A,Martin SR,Bayley PM

    更新日期:1998-06-01 00:00:00

  • Conformational analysis of peptide T and of its C-pentapeptide fragment.

    abstract::The synthetic peptide of sequence H-Ala-Ser-Thr-Thr-Thr-Asn-Tyr-Thr-OH, termed peptide T, a competitor of the Human Immunodeficiency Virus in the binding to human T cells, and its C-terminal pentapeptide fragment, were studied by 1H-nmr in DMSO solution to determine conformational preferences. The observation of nucle...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360280142

    authors: Motta A,Picone D,Temussi PA,Marastoni M,Tomatis R

    更新日期:1989-01-01 00:00:00

  • Studies of low molecular weight samples of glucuronans with various acetylation degree.

    abstract::Partially acetylated, high molecular weight glucuronans were produced by a Sinorhizobium meliloti mutant strain. Two native glucuronan samples with various degrees of acetylation were sonicated to obtain lower molecular weight samples and with low viscosity suitable for chemical modification and (13)C NMR experiments....

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.10134

    authors: Pau-Roblot C,Petit E,Sarazin C,Courtois J,Courtois B,Barbotin JN,Séguin JP

    更新日期:2002-06-01 00:00:00

  • Normal mode calculation of a netropsin-DNA complex: effect of structural deformation on vibrational spectrum.

    abstract::Calculations of the normal mode spectrum of a netropsin-DNA complex, an isolated DNA helix of the same sequence, and a free netropsin molecule were carried out and compared with observations. We find that the frequency of modes of the complex that are primarily vibrations localized to the helix are relatively unchange...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.360350611

    authors: Chen YZ,Prohofsky EW

    更新日期:1995-06-01 00:00:00

  • Structural and dynamic consequences of increasing repeats in a MUC1 peptide tumor antigen.

    abstract::MUC1 mucin is a large transmembrane glycoprotein whose extracelluler domain is composed of repeating units of a 20 amino acid sequence. In the cancer associated state, this protein expression becomes upregulated and underglycosylated. Previous studies, which show an enhanced binding of a 5-repeat over a 1-repeat MUC1 ...

    journal_title:Biopolymers

    pub_type: 杂志文章

    doi:10.1002/bip.20190

    authors: Schuman JT,Grinstead JS,Apostolopoulos V,Campbell AP

    更新日期:2005-02-05 00:00:00