123622-48-0Relevant articles and documents
Cyclopentapeptide derivatives and uses thereof
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Page/Page column 58; 56; 59, (2016/04/20)
The present invention, among others, relates to a compound having a structure according to formula (I) or a pharmaceutically acceptable salt thereof, wherein Xaa1 to Xaa4 are independently of each other, an optionally N-alkylated nat
MODIFIED CYCLOPENTAPEPTIDES AND USES THEREOF
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Page/Page column 70, (2016/03/04)
The present invention, among others, relates to a compound having a structure according to formula (I) or a pharmaceutically acceptable salt thereof, wherein Xaa1 are the iodo- substituted or methyl-substituted amino acids D- and L-Tyr, iodo-substituted or methyl- substituted D- and L- homotyrosine, iodo-substituted or methyl-substituted D- and L-Phe, iodo-substituted or methyl-substituted D- and L- p-OH-phenylglycine, and iodo-substituted or methyl-substituted D- or L- Trp, Xaa2 to Xaa4 are independently of each other, an optionally N-alkylated natural or unnatural amino acid, R is H or methyl, L is a linker moiety, Ar is a spacer comprising an aromatic moiety, and D comprises, preferably is i) a combination of an organic complexation agent and a radioactive or a detectable label; or ii) a radioactive or a detectable label, an organic complexation agent or an active substance, said active substance particularly being selected from cytotoxic agents, lipids, sugars, sugar conjugates, sugar derivatives, proteins and combinations thereof.
Conversion of a non-selective adenosine receptor antagonist into A 3-selective high affinity fluorescent probes using peptide-based linkers
Vernall, Andrea J.,Stoddart, Leigh A.,Briddon, Stephen J.,Ng, Hui Wen,Laughton, Charles A.,Doughty, Stephen W.,Hill, Stephen J.,Kellam, Barrie
supporting information, p. 5673 - 5682 (2013/09/12)
Advances in fluorescence-based imaging technologies have helped propel the study of real-time biological readouts and analysis across many different areas. In particular the use of fluorescent ligands as chemical tools to study proteins such as G protein-coupled receptors (GPCRs) has received ongoing interest. Methods to improve the efficient chemical synthesis of fluorescent ligands remain of paramount importance to ensure this area of bioanalysis continues to advance. Here we report conversion of the non-selective GPCR adenosine receptor antagonist Xanthine Amine Congener into higher affinity and more receptor subtype-selective fluorescent antagonists. This was achieved through insertion and optimisation of a dipeptide linker between the adenosine receptor pharmacophore and the fluorophore. Fluorescent probe 27 containing BODIPY 630/650 (pKD = 9.12 ± 0.05 [hA3AR]), and BODIPY FL-containing 28 (pKD = 7.96 ± 0.09 [hA3AR]) demonstrated clear, displaceable membrane binding using fluorescent confocal microscopy. From in silico analysis of the docked ligand-receptor complexes of 27, we suggest regions of molecular interaction that could account for the observed selectivity of these peptide-linker based fluorescent conjugates. This general approach of converting a non-selective ligand to a selective biological tool could be applied to other ligands of interest.
Basic techniques of working on a solid phase: From ABC of the peptide synthesis to libraries of non-natural amino acids
Babaev,Ermolat'ev
experimental part, p. 2572 - 2589 (2011/04/15)
Libraries of hardly available amino acids bearing a heteroaromatic ring (2-pyrimidyl, substituted 2-pyridyl or 2-thiazolyl) at the amino group were prepared using solid-phase synthesis on various resins. The synthesized compounds are structurally similar to some known antidiabetic drugs. The paper combines features of a review (elementary introduction to the solid-phase synthesis methodology and technique for beginners and selected methods from peptide chemistry) and step-by-step experimental protocols (tested by the authors) useful as a methodic tool. The presented protocols (immobilization and modification of amino acids, placing and removal of common protective groups) require no sophisticated equipment and may be useful as pictorial introductory tasks for students education. Pleiades Publishing, Ltd., 2010.
Syntheses and transglutaminase-catalyzed incorporation of novel spin-labeled primary amines into proteins
Narasimhan, Chakravarthy,Lai, Ching-San,Joseph, Joy
, p. 50 - 58 (2007/10/03)
A series of spin-labeled primary amine derivatives, namely, 2,2,6,6-tetramethyl-piperidinyl-oxyl-4-amidoalkylamines with varying alkyl chain lengths, have been synthesized. The spin-labeled primary amine-with a tetramethylene or a pentamethylene chain covalently modifies human plasma fibronectin with a stoichiometry of 0.97-to-1.0 (probe-to-subunit) in the presence of coagulation factor XIIIa. The labels with two or one methylene chain also similarly modify fibronectin, but with a stoichiometry of only about 0.3-0.4 per subunit. The spin-labeled primary amine with a trimethylene chain does not label fibronectin. The labeling site appears to be the glutamine-3 residue at the amino-terminal region of fibronectin. Electron spin resonance studies show that the bound labels are partially immobilized with an effective rotational correlation time of 0.4-0.6 ns. The spin-labeled primary amine with tetramethylene chain also is shown to covalently incorporate into bee venom melittin in the presence of guinea-pig liver transglutaminase. The syntheses of the various spin-labeled primary amines and their applications in the study of structure and dynamics of different proteins and peptides are discussed. The observations from this study suggest that these spin-labeled primary amines have potentially wide application as structural probes.
Novel arginine, glycine, aspartic acid derivatives as platelet-aggregation inhibitors
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, (2008/06/13)
Disclosed are novel amino acid derivatives of the formula: STR1 wherein X is H, amidino or STR2 Y is H, amino or STR3 Z is STR4 OR1 or a naturally occurring L-amino acid, bounded to the carbon atom at the α-amino position; R is alkyl, aryl or aralkyl; R1 and R2 are independently H, alkyl, aryl, aralkyl or allyl; m is 1 through 5; n is 0 through 4; and pharmaceutically acceptable salts thereof, that inhibit platelet aggregation and thrombus formation in mammalian blood.
Site-specific incorporation of non-natural residues into peptides: Effect of residue structure on suppression and translation efficiencies
Bain,Wacker, Dean A.,Kuo, Eric E.,Chamberlin, A. Richard
, p. 2389 - 2400 (2007/10/02)
A systematic survey of the structural requirements for biosynthetic incorporation of non-natural residues into a polypeptide is presented. Relative translation efficiencies for a series of 12 semi-synthetic acylated suppressor tRNAs ranged from 0 to 91% depending on the structure of the residue incorporated.
Rapid Continous Peptide Synthesis via FMOC Amino Acid Chloride Coupling and 4-(Aminomethyl)piperidine Deblocking
Beyermann, Michael,Bienert, Michael,Niedrich, Hartmut,Carpino, Louis A.,Sadat-Aalaee, Dean
, p. 721 - 728 (2007/10/02)
The recently described FMOC/4-AMP technique for rapid continous solution synthesis of peptides involving coupling by crystalline FMOC amino acid chlorides and deblocking via 4-(aminomethyl)piperidine (4-AMP) has been extended to the synthesis of a varied
