We report on new thermotropic liquid-crystalline oligo(amino acid) derivatives forming columnar structures. These are based on branched oligo(glutamic acid)s and 2-(3,4-dialkyloxyphenyl)ethyl moieties. An oligo(glutamic acid) derivative, alpha,gamma-bis(L-glutamoyl) L-glutamic acid tetra[2-(3,4-dioctadecyloxyphenyl)ethyl]ester, shows a hexagonal columnar phase, whilst a glutamic acid derivative, alpha,gamma-bis[2-(3,4-dioctadecyloxyphenyl)ethyl] L-glutamate, does not show a mesophase. Hydrogen bonds formed by the oligo(glutamic acid) moieties should contribute to the induction of the columnar liquid-crystalline properties. In addition, we have examined the effects of the molecular chirality of the oligo(glutamic acid) parts and the functionalisation at the focal position of the taper shaped molecules on the liquid-crystalline properties of the compounds.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/b416474a | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Synthesis and Evaluation of Radiogallium Labeled Bone-Imaging Probes Using Oligo-γ-Carboxy Glutamic Acid Peptides as Carriers to Bone.
Mol Pharm
May 2024
Department of Nuclear Medicine, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Takara-machi 13-1, Kanazawa, Ishikawa 920-8641, Japan.
Article Synopsis
- The study focused on the role of carboxy group density in the effectiveness of peptide-based radiopharmaceuticals for targeting bones.
- Higher carboxy group densities were identified in oligo-γ-carboxy glutamic acid peptides (Gla), which were compared to other peptides like oligo-glutamic acid (Glu) and oligo-aspartic acid (Asp).
- Results demonstrated that the Gla-based radiopharmaceutical showed enhanced bone affinity, accumulation, and better imaging capabilities, indicating their potential as superior agents for bone imaging.
Human serum albumin-imprinted polymers with high capacity and selectivity for abundant protein depletion.
Acta Biomater
May 2021
Key Laboratory of Functional Polymer Materials and State Key Laboratory of Medicinal Chemical Biology, Institute of Polymer Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China; School of Material Science and Engineering, Tiangong University, Tianjin 300387, China. Electronic address:
Depletion of human serum albumin (HSA), the most abundant protein in human plasma, from serum/plasma is a prerequisite before their proteomic analysis. Molecularly imprinted polymers (MIPs) using HSA as a template have been designed for this purpose, but suffer from a low sorption capacity and low selectivity. Here, a new HSA-imprinted polymer was synthesized using N-isopropylacrylamide (NIPAM) as the main monomer; acrylamide (AAm), methacrylic acid (MAA), and dimethylaminoethyl methacrylate (DMAEMA) as functional monomers; and oligoglutamic acid-based peptide crosslinker (PC) as a crosslinker at pH 5.
View Article and Find Full Text PDFUsing Disease-Associated Enzymes to Activate Antimicrobial Peptide Prodrugs.
Methods Mol Biol
February 2018
Department of Pharmaceutical and Medicinal Chemistry, Centre for Synthesis and Chemical Biology, Royal College of Surgeons in Ireland, 123 Stephen's Green, Dublin 2, Ireland.
Prodrugs of antimicrobial peptides can be generated by modifying their sequences at their N-termini with a linker and a negatively charged promoiety. These modifications can be selectively reversed by a disease-associated enzyme, thereby confining the activity of the peptide to pathologically affected body parts. A general method for the generation of prodrug candidates, based on a linker constituting the substrate of a disease-associated protease and an oligo-glutamic acid promoiety, as well as a protocol to validate the activation of the prodrug, are described herein.
View Article and Find Full Text PDFLight-Controlled Cellular Internalization and Cytotoxicity of Nucleic Acid-Binding Agents: Studies in Vitro and in Zebrafish Embryos.
Chembiochem
January 2016
Departamento de Química Orgánica, Centro Singular de Investigación en Química Biolóxica e Materiais, Moleculares (CIQUS), Universidade de Santiago de Compostela, Jenaro de la Fuente s/n, Campus Vida, 15782, Santiago de Compostela, Spain.
We synthesized octa-arginine conjugates of DNA-binding agents (bisbenzamidine, acridine and Thiazole Orange) and demonstrated that their DNA binding and cell internalization can be inhibited by appending a (negatively charged) oligoglutamic tail through a photolabile linker. UV irradiation released the parent conjugates, thus restoring cell internalization and biological activity. Assays with zebrafish embryos demonstrates the potential of this prodrug strategy for controlling in vivo cytotoxicity.
View Article and Find Full Text PDFBiomimetic vaterite formation at surfaces structurally templated by oligo(glutamic acid) peptides.
Chem Commun (Camb)
November 2015
Max Planck Institute for Polymer Research, Ackermannweg 10, D-55128 Mainz, Germany.
Previous studies have reported that the metastable vaterite phase of calcium carbonate can be stabilized in solution by acidic additives. Here we demonstrate that vaterite can also be stabilized directly at surfaces by engineered peptides. Our data show that the mineralisation occurs in a 'self-templating' process where calcium ions restructure the peptide backbone, which in turn allows for effective vaterite precipitation.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!