Synthesis of Self-assembling Cyclic Peptide-polymer Conjugates using Click Chemistry

2010 ◽  
Vol 63 (8) ◽  
pp. 1169 ◽  
Author(s):  
Robert Chapman ◽  
Katrina A. Jolliffe ◽  
Sébastien Perrier
Keyword(s):  
Click Chemistry ◽  
Self Assembly ◽  
Cyclic Peptide ◽  
Raft Polymerization ◽  
Cycloaddition Reaction ◽  
Polymer Chains ◽  
Dipolar Cycloaddition ◽  
Molecular Weights ◽  
Polymer Conjugates ◽  
Self Assembling

Self-assembling cyclic peptide-polymer conjugates were prepared by ‘clicking’ polymers (prepared by RAFT polymerization) to an azide functionalized d-alt-l cyclic octapeptide via the Huisgen 1,3-dipolar cycloaddition reaction. Due to the high graft density, the efficiency of the click chemistry conjugation reaction was found to be highly dependent on the size of the polymer. At relatively low molecular weights, as many as four polymer chains could be grafted to each 8 residue cyclic peptide ring. Evidence for the self assembly of the conjugates into peptide-polymer nanotubes was observed by TEM and IR.

scholarly journals Water vapor induced self-assembly of islands/honeycomb structure by secondary phase separation in polystyrene solution with bimodal molecular weight distribution

2021 ◽  
Author(s):  
Maciej Łojkowski ◽  
Adrian Chlanda ◽  
Emilia Choińska ◽  
Wojciech Swieszkowski
Keyword(s):  
Molecular Weight ◽  
Phase Separation ◽  
Molecular Weight Distribution ◽  
Weight Distribution ◽  
Self Assembly ◽  
Secondary Phase ◽  
Honeycomb Structure ◽  
Polymer Chains ◽  
Molecular Weights ◽  
Secondary Phase Separation

<p>The formation of complex structures in thin films is of interest in many fields. Segregation of polymer chains of different molecular weights is a well-known process. However, here, polystyrene with bimodal molecular weight distribution, but no additional chemical modification was used. It was proven that at certain conditions, the phase separation occurred between two fractions of bimodal polystyrene/methyl ethyl ketone solution. The films were prepared by spin-coating, and the segregation between polystyrene phases was investigated by force spectroscopy. Next, water vapour induced secondary phase separation was investigated. The introduction of moist airflow induced the self-assembly of the lower molecular weight into islands and the heavier fraction into a honeycomb. As a result, an easy, fast, and effective method of obtaining island/honeycomb morphologies was demonstrated. The possible mechanisms of the formation of such structures were discussed.</p>

Advances in click chemistry for silica-based material construction

RSC Advances ◽  
2016 ◽  
Vol 6 (26) ◽  
pp. 21979-22006 ◽  
Author(s):  
Ghodsi Mohammadi Ziarani ◽  
Zahra Hassanzadeh ◽  
Parisa Gholamzadeh ◽  
Shima Asadi ◽  
Alireza Badiei
Keyword(s):  
Click Chemistry ◽  
Organic Synthesis ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition

Click chemistry is undoubtedly the most powerful 1,3-dipolar cycloaddition reaction in organic synthesis.

scholarly journals The interplay between bi-modal molecular weight distribution in polystyrene and humidity induces self-assembly of biomimetic micropillars/honeycomb morphology in the thin polymer film

2021 ◽  
Author(s):  
Maciej Łojkowski ◽  
Adrian Chlanda ◽  
Emilia Choińska ◽  
Wojciech Swieszkowski
Keyword(s):  
Molecular Weight ◽  
Molecular Weight Distribution ◽  
Weight Distribution ◽  
Self Assembly ◽  
Phase Segregation ◽  
Polymer Chains ◽  
Thin Polymer Film ◽  
Chemical Compositions ◽  
Molecular Weights ◽  
The Right

<p>Segregation of polymer chains of different molecular weights is a well-known process. A traditional experimental approach of studying phase segregation in thin films composed of polymer blends with identical chemical compositions but different molecular weights was focused on functionalisation of chemical group or modification of end-group. In this study, however, a different approach was proposed. Polystyrene with bimodal molecular weight distribution, but no additional chemical modification was used. The films were prepared by spin-coating and the segregation between polystyrene phases was investigated by force spectroscopy. The solubility of bimodal polystyrene was explored. At the right molecular weight distribution and soluted in Methyl Ethyl Ketone, the phase segregation occurred. Introduction of moist airflow induced the separation of the lower molecular weight into micropillars and the heavier fraction self-organized into a honeycomb. As a result, an easy, fast, and effective method of obtaining micropillar/honeycomb morphologies was demonstrated. The mechanism of formation of such structures was explained. </p>

scholarly journals "Click" chemistry as a tool to create novel biomaterials: a short review

2017 ◽  
Vol 1 (1) ◽  
pp. 22-34
Author(s):  
Mariana Barbosa ◽  
Cristina Martins ◽  
Paula Gomes
Keyword(s):  
Click Chemistry ◽  
Biomedical Applications ◽  
Recent Literature ◽  
Click Reaction ◽  
Cycloaddition Reaction ◽  
Polymeric Materials ◽  
Short Review ◽  
Dipolar Cycloaddition ◽  
Functionalization Of Polymers ◽  
Grafting Modification

In recent years, there has been a growing demand for novel strategies for biomedical applications. Chitosan is a typical cationic amino-containing polysaccharide that has been widely used due to its unique properties. The grafting modification of chitosan has been explored as an interesting method to develop multifunctional novel chitosan hybrid materials for drug delivery, tissue engineering, and other biomedical applications. Recently, “click” chemistry has been introduced into the synthesis of polymeric materials with well-defined and complex chain architectures. The Huisgen’s 1,3-dipolar cycloaddition reaction between alkynes and azides yielding triazoles is the principal example of a “click” reaction. Bioconjugation, surface modification, and orthogonal functionalization of polymers were successfully performed through this chemoselective reaction. In recent literature interest has been shown in this cycloaddition for the modification of polysaccharides, however, only a few chitosan graft copolymers have been synthesized by this technique.

Utilization of click chemistry to study the effect of poly(ethylene)glycol molecular weight on the self-assembly of PEGylated gambogic acid nanoparticles for the treatment of rheumatoid arthritis

2020 ◽  
Vol 8 (16) ◽  
pp. 4626-4637 ◽  
Author(s):  
Anne Nguyen ◽  
Hidenori Ando ◽  
Roland Böttger ◽  
K. K. DurgaRao Viswanadham ◽  
Elham Rouhollahi ◽  
...  
Keyword(s):  
Rheumatoid Arthritis ◽  
Molecular Weight ◽  
Ethylene Glycol ◽  
Click Chemistry ◽  
Self Assembly ◽  
The Self ◽  
Gambogic Acid ◽  
Poly Ethylene Glycol ◽  
Molecular Weights ◽  
Poly Ethylene

Click chemistry was used to study the effect of varied PEG molecular weights on the self-assembly of PEG-gambogic acid (GA) conjugates into nanoparticles.

scholarly journals Synthesis of Poly(3-vinylpyridine)-Block-Polystyrene Diblock Copolymers via Surfactant-Free RAFT Emulsion Polymerization

Materials ◽  
2019 ◽  
Vol 12 (19) ◽  
pp. 3145 ◽  
Author(s):  
Katharina Nieswandt ◽  
Prokopios Georgopanos ◽  
Clarissa Abetz ◽  
Volkan Filiz ◽  
Volker Abetz
Keyword(s):  
Emulsion Polymerization ◽  
Self Assembly ◽  
Diblock Copolymers ◽  
Chain Transfer ◽  
Raft Polymerization ◽  
Free Water ◽  
Monomer Conversion ◽  
Molecular Weights ◽  
Reversible Addition

In this work, we present a novel synthetic route to diblock copolymers based on styrene and 3-vinylpyridine monomers. Surfactant-free water-based reversible addition–fragmentation chain transfer (RAFT) emulsion polymerization of styrene in the presence of the macroRAFT agent poly(3-vinylpyridine) (P3VP) is used to synthesize diblock copolymers with molecular weights of around 60 kDa. The proposed mechanism for the poly(3-vinylpyridine)-block-poly(styrene) (P3VP-b-PS) synthesis is the polymerization-induced self-assembly (PISA) which involves the in situ formation of well-defined micellar nanoscale objects consisting of a PS core and a stabilizing P3VP macroRAFT agent corona. The presented approach shows a well-controlled RAFT polymerization, allowing for the synthesis of diblock copolymers with high monomer conversion. The obtained diblock copolymers display microphase-separated structures according to their composition.

PolyPEGylation of Protein using Semitelechelic and Mid-functional Poly(PEGMA)s synthesized by RAFT polymerization

2011 ◽  
Vol 64 (12) ◽  
pp. 1602 ◽  
Author(s):  
Yingkai Liu ◽  
Mei Li ◽  
Dengxu Wang ◽  
Jinshui Yao ◽  
Jianxing Shen ◽  
...  
Keyword(s):  
Steric Hindrance ◽  
Chain Transfer ◽  
Raft Polymerization ◽  
Polymer Chains ◽  
High Yield ◽  
Protein Surface ◽  
Molecular Weights ◽  
Pharmaceutical Protein ◽  
Reversible Addition ◽  
Poly Ethylene

A series of well defined semitelechelic and mid-functionalized poly(poly(ethylene glycol) methyl ether methacrylate)s (poly(PEGMA)s) were synthesized through reversible addition-fragmentation chain transfer (RAFT) polymerization using thiazolidine-2-thione-functionalized chain transfer agents (CTAs). The thiazolidine-2-thione group was located either at the end or in the middle of polymer chains depending on the different structural CTAs. All polymers were fully analyzed by 1H NMR spectroscopy and GPC, confirming their well-defined structures, such as predesigned molecular weights, narrow polydispersity indices, and high yield chain-end or chain-middle functionalization. The thiazolidine-2-thione functionality located at the end of or at the middle of the polymer chains can react with amine residues on protein surfaces, forming protein-polymer conjugates via amide linkages. The bioactivity of protein conjugates were subsequently tested using micrococcus lysodeikticus cell as substitute. The protein conjugations from the mid-functionalized polymer remained much more protein bioactivity comparing to their semitelechelic counterpart with similar molecular weights, indicating the steric hindrance of the mid-functionalized poly(PEGMA)s lead to the better selective conjugation to protein. The number of polymer chains on the protein surface was additionally evaluated by TNBS analysis, exhibiting that there are less mid-functionalized poly(PEGMA)s linked on the protein surface than the semitelechelic polymers, also supporting the hypothesis that the steric hindrance from branch-structural polymers results in the better reaction selectivity. This synthetic methodology is suitable for universal proteins, seeking a balance between the protein bioactivity and the protein protection by the covalent linkage with polymer, and exhibits promising potential for pharmaceutical protein conjugation.

scholarly journals Exploiting the Interplay Between Bi-Modal Molecular Weight Distribution in Polystyrene and Humidity to Induce Self-Assembly of Biomimetic Micropillars/honeycomb Morphology in Thin Polymer Film

2021 ◽  
Author(s):  
Maciej Łojkowski ◽  
Adrian Chlanda ◽  
Emilia Choińska ◽  
Wojciech Swieszkowski
Keyword(s):  
Molecular Weight ◽  
Molecular Weight Distribution ◽  
Weight Distribution ◽  
Self Assembly ◽  
Spin Coating ◽  
Phase Segregation ◽  
Polymer Chains ◽  
Thin Polymer Film ◽  
Chemical Compositions ◽  
Molecular Weights

<p>Segregation of polymer chains of different molecular weights is a well-known process. For many years, it was assumed that this process occurs over long-time intervals. On the contrary, solvent evaporation during spin-coating is very fast. A traditional experimental approach of studying phase segregation of thin films composed of polymer blends with identical chemical compositions but different molecular weights, was focused on functionalization of chemical group or modification of end-group. In this study however, a different approach was proposed, in which polystyrene with a bimodal molecular weight distribution but no additional chemical modification was implemented in order to examine and analyze its phase segregation. By doing this, we have presented an easy, fast, effective and fully controlled method of obtaining biomimetic micropillar/honeycomb morphologies. In addition, the evaporation rate during spin-coating and the viscosity of a solution with a bimodal molecular weight distribution was described.</p>

scholarly journals Systematic study of the structural parameters affecting the self-assembly of cyclic peptide–poly(ethylene glycol) conjugates

Soft Matter ◽  
2018 ◽  
Vol 14 (30) ◽  
pp. 6320-6326 ◽  
Author(s):  
Edward D. H. Mansfield ◽  
Matthias Hartlieb ◽  
Sylvain Catrouillet ◽  
Julia Y. Rho ◽  
Sophie C. Larnaudie ◽  
...  
Keyword(s):  
Amino Acids ◽  
Self Assembly ◽  
Cyclic Peptides ◽  
Cyclic Peptide ◽  
Hydrophobic Interactions ◽  
Structural Parameters ◽  
The Self ◽  
Poly Ethylene Glycol ◽  
Self Assembling ◽  
Poly Ethylene

Self-assembling cyclic peptides (CP) consisting of amino acids with alternating d- and l-chirality form nanotubes by hydrogen bonding, hydrophobic interactions, and π–π stacking in solution.

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