The Diels–Alder reaction: A powerful tool for the design of drug delivery systems and biomaterials

Gregoritza, Manuel; Brandl, Fabian

doi:10.1016/j.ejpb.2015.06.007

Cited by 186 publications

(125 citation statements)

References 185 publications

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“…A typical method for this purpose is using a bifunctional group reagent which can be reacted with pendant groups on the polymer chains . Recently, cross‐linked polymers based on click chemistry have gained much attention, which is wide in scope, gives very high yields, generates only inoffensive by‐product that could be removed by non‐chromatographic methods . More recently we have reported synthesis of nanogels and dual‐responsive CCL micelles by using azide‐alkyne cycloaddition click reaction …”

Section: Introductionmentioning

confidence: 99%

“…33 Recently, cross-linked polymers based on click chemistry have gained much attention, which is wide in scope, gives very high yields, generates only inoffensive byproduct that could be removed by non-chromatographic methods. [34][35][36][37][38] More recently we have reported synthesis of nanogels and dual-responsive CCL micelles by using azide-alkyne cycloaddition click reaction. 39,40 Click reaction includes several classes of chemical transformations such as copper-catalyzed alkyne-azide cycloaddition, thiol-ene click, Diels-Alder (DA) cycloaddition, nucleophilic substitution chemistry, and thiol-Michael additions.…”

Section: Introductionmentioning

confidence: 99%

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Redox‐responsive core cross‐linked micelles of poly(ethylene oxide)‐b‐poly(furfuryl methacrylate) by Diels‐Alder reaction for doxorubicin release

Thi

Cao

et al. 2016

J. Polym. Sci. Part A: Polym. Chem.

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Redox‐responsive core cross‐linked (CCL) micelles of poly(ethylene oxide)‐b‐poly(furfuryl methacrylate) (PEO‐b‐PFMA) block copolymers were prepared by the Diels‐Alder click‐type reaction. First, the PEO‐b‐PFMA amphiphilic block copolymer was synthesized by the reversible addition‐fragmentation chain transfer polymerization. The hydrophobic blocks of PFMA were employed to encapsulate the doxorubicin (DOX) drug, and they were cross‐linked using dithiobismaleimidoethane at 60 °C without any catalyst. Under physiological circumstance, the CCL micelles demonstrated the enhanced structural stability of the micelles, whereas dissociation of the micelles took place rapidly through the breaking of disulfide bonds in the cross‐linking linkages under reduction environment. The core‐cross‐linked micelles showed fine spherical distribution with hydrodynamic diameter of 68 ± 2.9 nm. The in vitro drug release profiles presented a slight release of DOX at pH 7.4, while a significant release of DOX was observed at pH 5.0 in the presence of 1,4‐dithiothreitol. MTT assays demonstrated that the block copolymer did not have any practically cytotoxicity against the normal HEK293 cell line while DOX‐loaded CCL micelles exhibited a high antitumor activity towards HepG2 cells. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 3741–3750

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Redox‐responsive core cross‐linked micelles of poly(ethylene oxide)‐b‐poly(furfuryl methacrylate) by Diels‐Alder reaction for doxorubicin release

Thi

Cao

et al. 2016

J. Polym. Sci. Part A: Polym. Chem.

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“…In general, the DA reaction is highly efficient, however at room temperature the DA reaction only exhibit a very low reaction rate . This can be an issue for example for in situ crosslinking of nano‐ and microgels.…”

Section: Click Chemistry For Functionalization Of Reactive Particlesmentioning

confidence: 99%

“…[141,142] In general, the DA reaction is highly efficient, however at room temperature the DA reaction only exhibit a very low reaction rate. [143] This can be an issue for example for in situ crosslinking of nano-and microgels. Increasing the temperature or the addition of a catalyst could increase the reaction rate but limiting the biological applications.…”

Section: Complete and Interior Functionalization Using Da Reactionmentioning

confidence: 99%

Reactive Precursor Particles as Synthetic Platform for the Generation of Functional Nanoparticles, Nanogels, and Microgels

Gruber

Navarro

Klinger

2019

Adv Materials Inter

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Precise control of the chemical functionality of polymer nanoparticles is a key requirement in tailoring their (dynamic) colloidal properties toward advanced applications. However, current synthetic techniques are still limited in the versatility of chemical design and preparation of such functional colloidal nanomaterials. Two major challenges remain: First, various particle preparation methods are restricted in their functional group tolerance, thus hindering certain combinations of polymer backbones with specific functional groups. Second, the preparation of particles with different functionalities requires the synthesis of different particle batches. But this often results in a simultaneous variation of colloidal features. As a result, the accurate determination of important structure–property relations is still hindered. To address these restrictions, postmodification of preformed reactive particles is gaining more attention. This technique has evolved from polymer synthesis, where postpolymerization functionalization enables the introduction of a plethora of functional groups without changing the degree of polymerization and the molecular weight distribution. Similarly, modifying precursor particles enables the introduction of functional groups into particles while reducing variations in colloidal features, e.g., particle size and size distribution. This powerful synthetic method complements established procedures for functionalization of particle surfaces, thereby enabling the facile preparation of (multi‐)functional particle libraries, which will allow precise investigations of structure–property relations.

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“…Hetero-Diels–Alder reactions are considered to be a powerful methodology widely explored for the synthesis of six-membered heterocycles [1–2] with numerous applications for the construction of complex molecules including naturally occurring products [3–4], drugs [5–6], agrochemicals [7], etc. In addition, asymmetric hetero-Diels–Alder reactions are of current interest [8–10].…”

Section: Introductionmentioning

confidence: 99%

First thia-Diels–Alder reactions of thiochalcones with 1,4-quinones

Mlostoń

Urbaniak

et al. 2018

Beilstein J. Org. Chem.

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Aryl and hetaryl thiochalcones react smoothly with 1,4-quinones in THF solution at 60 °C yielding the corresponding fused 4H-thiopyrans after spontaneous dehydrogenation of the initially formed [4 + 2] cycloadducts. In general, the yields of the isolated products were high. With 5-chloro-10-hydroxy-1,4-anthraquinone, the thia-Diels–Alder reaction occurred with complete regioselectivity. In the case of the reaction of vitamin K3 (menadione) with diphenylthiochalcone, the initial cycloadduct was isolated in 37% yield.

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The Diels–Alder reaction: A powerful tool for the design of drug delivery systems and biomaterials

Cited by 186 publications

References 185 publications

Redox‐responsive core cross‐linked micelles of poly(ethylene oxide)‐b‐poly(furfuryl methacrylate) by Diels‐Alder reaction for doxorubicin release

Redox‐responsive core cross‐linked micelles of poly(ethylene oxide)‐b‐poly(furfuryl methacrylate) by Diels‐Alder reaction for doxorubicin release

Reactive Precursor Particles as Synthetic Platform for the Generation of Functional Nanoparticles, Nanogels, and Microgels

First thia-Diels–Alder reactions of thiochalcones with 1,4-quinones

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