Synthesis of new poly(ethylene glycol)-block-poly(ester sulfide) dendrimers

Fury, Jonathan; Altenhofer, Erich; Sedaghat‐Herati, Reza

doi:10.1016/j.tetlet.2009.04.138

Cited by 3 publications

(1 citation statement)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thiol-ene photochemistry has been proved to be efficient for free radical addition of thiol with ethenyl group in the presence of a photo initiator. Sedaghat-Herati and co-workers synthesised lineardendritic copolymers of methoxy-poly(ethylene glycol) (MPEG) and poly(ester-sulfide) (PES) dendron via acrylation by acryloyl chloride and thiol-ene addition with thioglycerol (Fury et al, 2009). However the thiol-ene reaction was completed via an ionic mechanism (Michael addition).…”

Section: Introductionmentioning

confidence: 99%

Preparation of core-crosslinked linear-dendritic copolymer micelles with enhanced stability and their application for drug solubilisation

Zhou

Forbes

D’Emanuele

2017

International Journal of Pharmaceutics

View full text Add to dashboard Cite

In this study we explore the preparation of core-crosslinked micelles of linear-dendritic methoxy-poly(ethylene glycol) (MPEG)-co-poly(ester-sulfide) (PES) polymers to improve the stability of such polymeric micelle systems against premature disintegration and drug release. A series of MPEG-PES copolymers were synthesised via stepwise reactions of acetylation and thiol-ene photoreaction. Surface tension measurement showed that the copolymers with ethenyl surface groups could self-associate in dilute aqueous solutions to form micelles. Crosslinking within the micelle cores in the presence of dithioerythritol (DTT) linker was initiated under UV radiation. The formation of core-crosslinked micelles was confirmed by HPLC in combination with charged aerosol detection (CAD). The copolymers were found to readily hydrolyse under acidic conditions due to the ester-containing dendrons. Drug solubilisation capacities of the micellar solutions were determined using griseofulvin as a poorly water-soluble model drug. The solubility of griseofulvin showed a 10-fold enhancement in 1% w/v micelle solution and increased with the concentration of the copolymers. Drug release studies indicated that a more sustained release of griseofulvin was achieved for the core-crosslinked micelles compared to the non-crosslinked micelles, attributable to greater stability of the crosslinked core structure. The findings of this study present a new pathway towards developing biodegradable polymeric nanocarriers.

show abstract

Section: Introductionmentioning

confidence: 99%

Preparation of core-crosslinked linear-dendritic copolymer micelles with enhanced stability and their application for drug solubilisation

Zhou

Forbes

D’Emanuele

2017

International Journal of Pharmaceutics

View full text Add to dashboard Cite

show abstract

Thiol‐ene/yne Chemistry for the Synthesis of Branched and Star‐shaped Macromolecules

Jennings

Son

2013

Thiol‐X Chemistries in Polymer and Materials Science

View full text Add to dashboard Cite

The advances and discoveries that have been made in the synthesis of dendrimers and other hyper‐branched materials by employing the anionic thiol‐ene or thiol‐Michael reaction, as well as the free‐radical thiol‐ene and thiol‐yne reactions, are discussed. The characterization methods and potential applications of the resulting materials are also mentioned. The initial examples presented involve using the thiol‐Michael reaction for the convergent synthesis of star polymers, divergent synthesis of dendritic molecules, and dendronizing linear polymers. The free‐radical thiol‐ene and free‐ radical thiol‐yne reactions are discussed next, specifically using these “click” reactions for the divergent synthesis of dendritic molecules and for the syntheses of hyperbranched polymers. Finally, examples of using the thiol‐Michael reaction and the free‐radical thiol‐yne reactions in sequence for the preparation of hyper‐branched materials are conveyed.

show abstract

Synthesis and Self-Assembly of New Poly(ethylene glycol)-block-poly(ester-sulfide) Dendrimers

Fury

Robison

Sedaghat‐Herati

2013

Journal of Macromolecular Science, Part A

View full text Add to dashboard Cite

Synthesis of new poly(ethylene glycol)-block-poly(ester sulfide) dendrimers

Cited by 3 publications

References 19 publications

Preparation of core-crosslinked linear-dendritic copolymer micelles with enhanced stability and their application for drug solubilisation

Preparation of core-crosslinked linear-dendritic copolymer micelles with enhanced stability and their application for drug solubilisation

Thiol‐ene/yne Chemistry for the Synthesis of Branched and Star‐shaped Macromolecules

Synthesis and Self-Assembly of New Poly(ethylene glycol)-block-poly(ester-sulfide) Dendrimers

Contact Info

Product

Resources

About