Polypeptide-Based Organogelators: Effects of Secondary Structure

Hermes, Florian; Otte, Katharina; Brandt, Jessica; Gräwert, Marlies; Börner, Hans G.; Schlaad, Helmut

doi:10.1021/ma201232a

Cited by 20 publications

(19 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The use of racemic poly(amino acid) blocks in amphiphilic copolymers has been shown to disrupt α-helical formation and increase the overall flexibility. − Indeed, the incorporation of approximately 10% of a structurally dissimilar residue such as proline, or a stereochemically dissimilar residue such as a d -amino acid, is enough to produce random coils. Hence, we began preparing copolymers with mixed stereochemistry poly(amino acid) blocks.…”

Section: Results and Discussionmentioning

confidence: 99%

Synthesis and Characterization of Micelle-Forming PEG-Poly(Amino Acid) Copolymers with Iron-Hydroxamate Cross-Linkable Blocks for Encapsulation and Release of Hydrophobic Drugs

et al. 2017

View full text Add to dashboard Cite

Described is the development of a polymeric micelle drug delivery platform that addresses the physical property limitations of many nanovectors. The system employs triblock copolymers comprised of a hydrophilic poly(ethylene glycol) (PEG) block, and two poly(amino acid) (PAA) blocks: a stabilizing cross-linking central block, and a hydrophobic drug encapsulation block. Detailed description of synthetic strategies and considerations found to be critical are discussed. Of note, it was determined that the purity of the α-amino acid-N-carboxyanhydrides (NCA) monomers and PEG macroinitiator are ultimately responsible for impurities that arise during the polymerization. Also, contrary to current beliefs in the field, the presence of water does not adversely affect the polymerization of NCAs. Furthermore, we describe the impact of poly(amino acid) conformational changes, through the incorporation of d-amino acids to form mixed stereochemistry PAA blocks, with regard to the physical and pharmacokinetic properties of the resulting micelles.

show abstract

Section: Results and Discussionmentioning

confidence: 99%

Synthesis and Characterization of Micelle-Forming PEG-Poly(Amino Acid) Copolymers with Iron-Hydroxamate Cross-Linkable Blocks for Encapsulation and Release of Hydrophobic Drugs

et al. 2017

View full text Add to dashboard Cite

show abstract

“…Schlaad et al [68], have recently studied the influence on the secondary structure of different predefined D/L stereosequences by considering three block copolymers with the same composition and constituted by poly(ethylene oxide) and monodisperse peptide segments of 18 (N ε -benzyloxycarbonyl)lysine (ZLys) units. Secondary structures (i.e., random coil, β-sheet or α-helix) of these bioconjugate samples were determined by 1 H NMR, FTIR and CD spectroscopies and evaluated according to their ability to gelate tetrahydrofuran at room temperature (using viscosimetry and scanning force microscopy).…”

Section: Supramolecular Organization Of Peptide-synthetic Polymer Hybmentioning

confidence: 99%

Hybrid Block Copolymers Constituted by Peptides and Synthetic Polymers: An Overview of Synthetic Approaches, Supramolecular Behavior and Potential Applications

Morell

Puiggalı́

2013

Polymers

View full text Add to dashboard Cite

Hybrid block copolymers based on peptides and synthetic polymers, displaying different types of topologies, offer new possibilities to integrate the properties and functions of biomacromolecules and synthetic polymers in a single hybrid material. This review provides a current status report of the field concerning peptide-synthetic polymer hybrids. The first section is focused on the different synthetic approaches that have been used within the last three years for the preparation of peptide-polymer hybrids having different topologies. In the last two sections, the attractive properties, displayed in solution or in the solid state, together with the potential applications of this type of macromolecules or supramolecular systems are highlighted.

show abstract

“…13 In many cases, however, the amide groups do not form intermolecular hydrogen bonds with the solvent, and gelation occurs via different interactions, such as aromatic 14 and heteroaromatic stacking interactions. 15 Such a supramolecular-induced structural order is particularly apparent in peptides and proteins that form α-helices, β-sheets, and βstrands, 16 but also occurs in non-peptide amides, particularly those with aromatic ring components that have the ability to participate in favorable π−π stacking interactions 17 in addition to the amide−amide interactions. 18 A second class of compounds with a high propensity for gelation are naphthalimide-containing compounds.…”

Section: ■ Introductionmentioning

confidence: 99%

Sonication-Induced, Solvent-Selective Gelation of a 1,8-Napthalimide-Conjugated Amide: Structural Insights and Pollutant Removal Applications

et al. 2021

View full text Add to dashboard Cite

Reported herein is the synthesis, characterization, and dye removal applications of a highly solvent-selective organogel-forming amide, compound 1, which contains a 1,8-naphthalmide moiety, flexible n-hexyl chain, and benzene ring. This compound displayed remarkable solvent selectivity, with gel formation occurring only in the presence of alkylated aromatic solvents. Detailed structural characterization of the gels, combined with notable theoretical insights, is invoked to explain the highly selective gelation properties of compound 1, as is a comparison to non-gel forming structural isomer 2, which contains the same structural elements in a different arrangement. Finally, the ability of the gel derived from compound 1 to act as a reusable material for the efficient removal of cationic organic dyes from contaminated aqueous environments is also reported, with up to 11 repeated uses of the gel still maintaining the ability to effectively remove Rhodamine B.

show abstract

Polypeptide-Based Organogelators: Effects of Secondary Structure

Cited by 20 publications

References 31 publications

Synthesis and Characterization of Micelle-Forming PEG-Poly(Amino Acid) Copolymers with Iron-Hydroxamate Cross-Linkable Blocks for Encapsulation and Release of Hydrophobic Drugs

Synthesis and Characterization of Micelle-Forming PEG-Poly(Amino Acid) Copolymers with Iron-Hydroxamate Cross-Linkable Blocks for Encapsulation and Release of Hydrophobic Drugs

Hybrid Block Copolymers Constituted by Peptides and Synthetic Polymers: An Overview of Synthetic Approaches, Supramolecular Behavior and Potential Applications

Sonication-Induced, Solvent-Selective Gelation of a 1,8-Napthalimide-Conjugated Amide: Structural Insights and Pollutant Removal Applications

Contact Info

Product

Resources

About