Controlling self-assembly of diphenylalanine peptides at high pH using heterocyclic capping groups

Using small angle neutron scattering (SANS), it is shown that the existence of pre-assembled structures at high pH for a capped diphenylalanine hydrogel is controlled by the selection of N-terminal heterocyclic capping group, namely indole or carbazole. At high pH, changing from a somewhat hydrophilic indole capping group to a more hydrophobic carbazole capping group results in a shift from a high proportion of monomers to self-assembled fibers or wormlike micelles. The presence of these different self-assembled structures at high pH is confirmed through NMR and circular dichroism spectroscopy, scanning probe microscopy and cryogenic transmission electron microscopy.

• Publication year

  2017

• Venue

  Scientific Reports

• Publication date

  2017-03-08

• Fields of study

  Medicine, Materials Science, Chemistry

• Identifiers
  DOI 10.1038/srep43947PMID 28272523PMCID 5341053
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• A peptide hydrogel derived from a fragment of human cardiac troponin C.

  2016cited by this paper
• A Peptide-Based Mechano-sensitive, Proteolytically Stable Hydrogel with Remarkable Antibacterial Properties.

  2016cited by this paper
• A Capped Dipeptide Which Simultaneously Exhibits Gelation and Crystallization Behavior.

  2016cited by this paper
• Linking micellar structures to hydrogelation for salt-triggered dipeptide gelators.

  2016cited by this paper
• Fmoc-modified amino acids and short peptides: simple bio-inspired building blocks for the fabrication of functional materials.

  2016cited by this paper
• Effect of heterocyclic capping groups on the self-assembly of a dipeptide hydrogel.

  2016cited by this paper
• Injectable peptide hydrogels for controlled-release of opioids

  2016cited by this paper
• Peptide Self-Assembly for Nanomaterials: The Old New Kid on the Block

  2015cited by this paper
• Biocompatible fluorescent supramolecular nanofibrous hydrogel for long-term cell tracking and tumor imaging applications

  2015cited by this paper
• Time-dependent gel to gel transformation of a peptide based supramolecular gelator.

  2015cited by this paper
• Spatially resolved multicomponent gels

  2015cited by this paper
• Rational design of a hexapeptide hydrogelator for controlled-release drug delivery.

  2015cited by this paper
• Solvent Controlled Structural Transition of KI4K Self-Assemblies: from Nanotubes to Nanofibrils.

  2015cited by this paper
• Peptide self-assembly for nanomaterials: the old new kid on the block.

  2015cited by this paper
• Biocompatible small peptide super-hydrogelators bearing carbazole functionalities.

  2015cited by this paper
• Self-assembly of short peptides to form hydrogels: design of building blocks, physical properties and technological applications.

  2014cited by this paper
• Intramolecular interactions of a phenyl/perfluorophenyl pair in the formation of supramolecular nanofibers and hydrogels.

  2014cited by this paper
• The physical properties of supramolecular peptide assemblies: from building block association to technological applications.

  2014cited by this paper
• Self-assembling peptide/thermoresponsive polymer composite hydrogels: effect of peptide-polymer interactions on hydrogel properties.

  2014cited by this paper
• Exceptionally strong hydrogels through self-assembly of an indole-capped dipeptide.

  2014cited by this paper
• The past, present, and future of molecular gels. What is the status of the field, and where is it going?

  2014cited by this paper
• Small angle neutron scattering (SANS) studies on the structural evolution of pyromellitamide self-assembled gels.

  2014cited by this paper
• Cell death versus cell survival instructed by supramolecular cohesion of nanostructures

  2014cited by this paper
• Rational design of injectable hexapeptide hydrogelators for controlled-release drug delivery

  2014cited by this paper
• Insights into low molecular mass organic gelators: a focus on drug delivery and tissue engineering applications.

  2014cited by this paper
• The influence of the kinetics of self-assembly on the properties of dipeptide hydrogels.

  2013cited by this paper
• Salt-induced hydrogels from functionalised-dipeptides

  2013cited by this paper
• Tuning the self-assembly of short peptides via sequence variations.

  2013cited by this paper
• Chemically programmed self-sorting of gelator networks

  2013cited by this paper
• Using small angle scattering (SAS) to structurally characterise peptide and protein self-assembled materials.

  2011cited by this paper
• Salt-induced hydrogelation of functionalised-dipeptides at high pH.

  2011cited by this paper
• Self-assembly of fibronectin mimetic peptide-amphiphile nanofibers.

  2010cited by this paper
• A new method for maintaining homogeneity during liquid–hydrogel transitions using low molecular weight hydrogelators

  2009cited by this paper
• Fast dynamics of semiflexible chain networks of self-assembled peptides.

  2009cited by this paper
• Dependence of Self-Assembled Peptide Hydrogel Network Structure on Local Fibril Nanostructure.

  2009cited by this paper
• De novo design of strand-swapped beta-hairpin hydrogels.

  2008cited by this paper

• RAFT Synthesis of Photo Cross‐Linkable Tyrosine‐Containing Copolymers With Self‐Assembling and Thermoresponsive Properties

  2025cites this paper
• Self-sorting and co-assembly control in multicomponent supramolecular hydrogels with dual monomer and polymer statistical distribution

  2025cites this paper
• Self-Sorting in Multicomponent Supramolecular Gels Using Different Assembly Triggers and Calcium Ion-Induced Diffusion Patterning

  2024cites this paper
• Atomic structures of naphthalene dipeptide micelles unravel mechanisms of assembly and gelation

  2024cites this paper
• Applications of microscopy and small angle scattering techniques for the characterisation of supramolecular gels

  2024cites this paper
• Advancing Synthetic Hydrogels through Nature‐Inspired Materials Chemistry

  2024cites this paper
• Differently N-Capped Analogues of Fmoc-FF.

  2023cites this paper
• RAFT-synthesis and self-assembly-induced emission of pendant diphenylalanine-tetraphenylethylene copolymers.

  2023cites this paper
• Mechanistic Insights into Hyaluronic Acid Induced Peptide Nanofiber Organization in Supramolecular Hydrogels.

  2023cites this paper
• Self-assembly of thyminyl l-tryptophanamide (TrpT) building blocks for the potential development of drug delivery nanosystems

  2023cites this paper
• Development and Characterization of Nanoscale Gel-Core Liposomes Using a Short Self-Assembled Peptide Hydrogel: Implications for Drug Delivery

  2023cites this paper
• Localized Enzyme-Assisted Self-Assembly of low molecular weight hydrogelators. Mechanism, applications and perspectives.

  2022cites this paper
• Self-Assembly and Gelation Study of Dipeptide Isomers with Norvaline and Phenylalanine

  2022cites this paper
• Peptide‐based hydrogels as delivery systems for doxorubicin

  2021cites this paper
• Varying the hydrophobic spacer to influence multicomponent gelation.

  2021cites this paper
• Synthesis and organogelating behaviour of urea- and Fmoc-containing diphenylalanine based hexaamide

  2021cites this paper
• Self‐Assembly of Unprotected Dipeptides into Hydrogels: Water‐Channels Make the Difference

  2021cites this paper
• Peptide Aggregation Induced Immunogenic Rupture (PAIIR)

  2021cites this paper
• Peptides as 3D Printable Feedstocks: Design Strategies and Emerging Applications

  2021cites this paper
• C-amidation of substituted β 3 oligoamides yields novel supramolecular assembly motif

  2021cites this paper
• Cosolvents Restrain Self-Assembly of a Fibroin-Like Peptide on Graphite.

  2021cites this paper
• The Role of Fiber Agglomeration in Formation of Perylene-Based Fiber Networks

  2020cites this paper
• Beyond Fmoc: a review of aromatic peptide capping groups.

  2020cites this paper
• Using Small-Angle Scattering and Contrast Matching to Understand Molecular Packing in Low Molecular Weight Gels

  2020cites this paper
• Self-Assembling, Ultrashort Peptides Gels as Antimicrobial Agents.

  2020cites this paper
• Programmable enzymatic oxidation of tyrosine-lysine tetrapeptides.

  2020cites this paper
• Using Rheo-Small-Angle Neutron Scattering to Understand How Functionalised Dipeptides Form Gels

  2020cites this paper
• The basics of small-angle neutron scattering (SANS for new users of structural biology)

  2020cites this paper
• Ultra-low molecular weight photoswitchable hydrogelators.

  2020cites this paper
• Protein-induced low molecular weight hydrogelator self-assembly through a self-sustaining process

  2019cites this paper
• Synthesis and Hierarchical Self‐Assembly of Diphenylalanine‐Based Homopolymer and Copolymers By RAFT Polymerization

  2019cites this paper
• Self-assembly of PEGylated diphenylalanines into photoluminescent fibrillary aggregates.

  2019cites this paper
• The Kinetics, Thermodynamics and Mechanisms of Short Aromatic Peptide Self-Assembly.

  2019cites this paper
• Probing the self-assembled structures and pKa of hydrogels using electrochemical methods.

  2019cites this paper
• The aromaticity of the phenyl ring imparts thermal stability to a supramolecular hydrogel obtained from low molecular mass compound

  2019cites this paper
• Using chirality to influence supramolecular gelation

  2019cites this paper
• Modulating amyloid fibrillation in a minimalist model peptide by intermolecular disulfide chemical reduction.

  2019cites this paper
• Controlling the Assembly and Properties of Low-Molecular-Weight Hydrogelators.

  2019cites this paper
• Hierarchically Compartmentalized Supramolecular Gels through Multilevel Self-Sorting

  2018cites this paper
• Controlled Tuning of the Properties in Optoelectronic Self-Sorted Gels.

  2018cites this paper
• Hydrogelation Kinetics Measured in a Microfluidic Device with in Situ X-ray and Fluorescence Detection.

  2018cites this paper
• Morphology Diversity of L-Phenylalanine-Based Short Peptide Supramolecular Aggregates and Hydrogels

  2018cites this paper
• The role of aromatic side chains on the supramolecular hydrogelation of naphthalimide/dipeptide conjugates

  2018cites this paper
• Alkene-Azide 1,3-Dipolar Cycloaddition as a Trigger for Ultrashort Peptide Hydrogel Dissolution.

  2018cites this paper
• Drying Affects the Fiber Network in Low Molecular Weight Hydrogels

  2017cites this paper
• Thermodynamics of Polypeptide Supramolecular Assembly in the Short-Chain Limit.

  2017cites this paper
• Tuning hydrogels through metal-based gelation triggers.

  2017cites this paper
• Self-sorted Oligophenylvinylene and Perylene Bisimide Hydrogels

  2017cites this paper