Facile approach to prepare pH and redox-responsive nanogels via Diels-Alder click reaction

Le, Cuong Minh Quoc; Cao, Xuan Thang; Tu, Trang T.K.; Gal, Y-S.; Lim, Kwon Taek

doi:10.3144/expresspolymlett.2018.59

Cited by 16 publications

(9 citation statements)

References 46 publications

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“…Therefore, the design and implementation of these functionalities can provide another crosslinking/de-crosslinking platform orthogonal to pH or redox-responsive linkers. This technology has been used for both drug and protein delivery via hydrogels crosslinked via the Diels–Alder reaction. − However, there are few examples in the literature that explore the utility of Diels–Alder chemistry as it relates specifically to polymer functionalization in gene delivery. Brust and coworkers successfully attached DNA to silica-coated gold nanoparticles via the Diels–Alder reaction by attaching a maleimide group to the end of a siloxane and reacting this to one of two different dienes linked to the phosphate group of an oligonucleotide (synthesized directly from a modified phosphoramidite and subjected to an automated DNA synthesis) .…”

Section: Engineering Multifunctional Polyplexes Through Chemical Modi...mentioning

confidence: 99%

Polymeric Delivery of Therapeutic Nucleic Acids

et al. 2021

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The advent of genome editing has transformed the therapeutic landscape for several debilitating diseases, and the clinical outlook for gene therapeutics has never been more promising. The therapeutic potential of nucleic acids has been limited by a reliance on engineered viral vectors for delivery. Chemically defined polymers can remediate technological, regulatory, and clinical challenges associated with viral modes of gene delivery. Because of their scalability, versatility, and exquisite tunability, polymers are ideal biomaterial platforms for delivering nucleic acid payloads efficiently while minimizing immune response and cellular toxicity. While polymeric gene delivery has progressed significantly in the past four decades, clinical translation of polymeric vehicles faces several formidable challenges. The aim of our Account is to illustrate diverse concepts in designing polymeric vectors towards meeting therapeutic goals of in vivo and ex vivo gene therapy. Here, we highlight several classes of polymers employed in gene delivery and summarize the recent work on understanding the contributions of chemical and architectural design parameters. We touch upon characterization methods used to visualize and understand events transpiring at the interfaces between polymer, nucleic acids, and the physiological environment. We conclude that interdisciplinary approaches and methodologies motivated by fundamental questions are key to designing high-performing polymeric vehicles for gene therapy.

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Section: Engineering Multifunctional Polyplexes Through Chemical Modi...mentioning

confidence: 99%

Polymeric Delivery of Therapeutic Nucleic Acids

et al. 2021

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“…The molecular weight of PSMA can be manipulated precisely by a controlled radical polymerization of readily available monomers and furthermore, its maleic anhydride moieties enable various functionalities in the copolymer backbones by subsequent ring-opening reactions, which open the possibility for its use in large-scale applications. Recently, our group reported on the PSMA based nanogels via Diels-Alder click reaction [30] and grafted PSMA onto multi-walled carbon nanotubes for pHresponsive release of DOX [31]. Inspired by successful click reactions of PSMA derivatives [29,30,32,33], here, we attempted to produce click-cross-linked hydrogels at fast gelation under physiological conditions.…”

mentioning

confidence: 99%

“…Recently, our group reported on the PSMA based nanogels via Diels-Alder click reaction [30] and grafted PSMA onto multi-walled carbon nanotubes for pHresponsive release of DOX [31]. Inspired by successful click reactions of PSMA derivatives [29,30,32,33], here, we attempted to produce click-cross-linked hydrogels at fast gelation under physiological conditions. To the best of our knowledge, there has been no published study related to the formation of click-cross-linked PSMA hydrogels.…”

mentioning

confidence: 99%

Click-cross-linked, doxorubicin-loaded hydrogels based on poly(styrene-alt-maleic anhydride)

Anugrah¹,

Patil²,

Li³

et al. 2020

Express Polym. Lett.

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A hydrogel is a cross-linked three-dimensional product of macromolecular hydrophilic networks. Due to their unique properties, hydrogels have been extensively studied for tissue engineering, especially, they have excellent biocompatibility and the capability to be the type of drug delivery system [1, 2]. The high water content provides them with properties similar to natural extracellular matrixes. The risk of the drug denaturation and aggregation due to exposure to an organic solvent can be minimized by hydrogels. The internal network makes hydrogels have solid-like properties. Hydrogel networks may be physical gels or chemical gels. Physical gels form through physical interactions, while chemical gels are held together by covalent bonds. Chemical gel methods for making the internal network have made significant progress so far. Click chemistry, one of the methods, provided hydrogels with moderately high mechanical properties [3-6] and was also useful in biomedical engineering [7-12]. The emerging studies in click chemistry have generated 'metal-free' reactions. One example of interesting metal-free click chemistry is the inverse 248

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“…[137] In a similar approach, Lim and co-workers used redox-responsive dithio-containing bismaleimides as crosslinking agent via DA reaction, to prepare redox-responsive core-crosslinked micelles for doxorubicin loading. [139,140] In subsequent studies, the authors furthermore introduced a diselenide containing bismaleimide crosslinker to obtain a sensitive crosslinking agent in the presence of a reductive-oxidative medium. [141,142] In general, the DA reaction is highly efficient, however at room temperature the DA reaction only exhibit a very low reaction rate.…”

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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Facile approach to prepare pH and redox-responsive nanogels via Diels-Alder click reaction

Cited by 16 publications

References 46 publications

Polymeric Delivery of Therapeutic Nucleic Acids

Polymeric Delivery of Therapeutic Nucleic Acids

Click-cross-linked, doxorubicin-loaded hydrogels based on poly(styrene-alt-maleic anhydride)

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

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