Unique post-functionalization method for ROMP polymers based on Triazolinedione Alder-ene chemistry

Zhao, Yuming; Chen, Jiqiang; Zhu, Wen; Zhang, Ke

doi:10.1016/j.polymer.2015.07.050

Cited by 22 publications

(12 citation statements)

References 41 publications

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“…Preorganization of charge on the nanoparticle surface was considered to be a key factor in enabling direct cytosolic delivery. , We hypothesized that the “semiarthritic” backbone of poly(oxanorbornene)imide (PONI) polymers could replicate key functional aspects of the nanoparticle delivery systems and provide similar self-assembly and delivery capabilities while allowing for greater flexibility of design. , We report here the direct cytosolic delivery of three E-tagged proteins across a wide range of working formulations using rationally designed cationic guanidinium-functionalized PONI homopolymers (Figure ). These polymers self-assemble with E-tagged proteins to form discrete polymer–protein nanocomposites (PPNCs) that are stable under serum-containing conditions.…”

Section: Introductionmentioning

confidence: 99%

Direct Cytosolic Delivery of Proteins through Coengineering of Proteins and Polymeric Delivery Vehicles

et al. 2020

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Nanocarrier-mediated protein delivery is a promising strategy for fundamental research and therapeutic applications. However, the efficacy of the current platforms for delivery into cells is limited by endosomal entrapment of delivered protein cargo with concomitantly inefficient access to the cytosol and other organelles, including the nucleus. We report here a robust, versatile polymeric–protein nanocomposite (PPNC) platform capable of efficient (≥90%) delivery of proteins to the cytosol. We synthesized a library of guanidinium-functionalized poly(oxanorborneneimide) (PONI) homopolymers with varying molecular weights to stabilize and deliver engineered proteins featuring terminal oligoglutamate “E-tags”. The polymers were screened for cytosolic delivery efficiency using imaging flow cytometry with cytosolic delivery validated using confocal microscopy and activity of the delivered proteins demonstrated through functional assays. These studies indicate that the PPNC platform provides highly effective and tunable cytosolic delivery over a wide range of formulations, making them robust agents for therapeutic protein delivery.

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Section: Introductionmentioning

confidence: 99%

Direct Cytosolic Delivery of Proteins through Coengineering of Proteins and Polymeric Delivery Vehicles

et al. 2020

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“…Post-polymerization is an effective way to modify polymers with varied structures and improved properties. As for c -[ PBNP 10 -( b - PTNP x ) 2 - b - PBNP 10 ], it has the unsaturated PNBE backbone and could be easily modified by triazolinedione (TAD)-based Alder-ene chemistry 41 . Taking c -[ PBNP 10 -(( b - PTNP 160 ) 2 - b - PBNP ) 10 ] as an example, its post-polymerization modification was conducted to make it be transformed into the bulky POSS moiety-contained c -[ PBNP 10 -(( b - PTNP 160 ) 2 - b - PBNP ) 10 ]- POSS (Supplementary Fig.…”

Section: Resultsmentioning

confidence: 99%

Blocking-cyclization technique for precise synthesis of cyclic polymers with regulated topology

Chen

Zhang

et al. 2018

Nat Commun

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Ring-closure and ring-expansion techniques are the two routes for extensive synthesis of cyclic polymers. Here, we report an alternative blocking-cyclization technique referred to as the third route to prepare cyclic polymers with regulated ring size and ring number by ring-opening metathesis polymerization of di- and monofunctional monomers in a one-pot process, where the polymer intermediates bearing two single-stranded blocks are efficiently cyclized by the cyclizing unit of propagated ladderphane to generate corresponding mono-, bis-, and tricyclic polymers, and the well-defined ladderphane structure plays a crucial role in forming the cyclic topology. Monocyclic polymer is further modified via Alder-ene reaction and the cyclic molecular topology is clearly demonstrated. The diversity features of cyclic polymers are comprehensively revealed. This strategy has broken through the limitations of previous two cyclizing routes, and indeed opens a facile and popular way to various cyclic polymers by commercial Grubbs catalyst and conventional metathesis polymerization.

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“…Postpolymerization was an effective way to modify the structure and properties of polymers, and the block copolymers with the unsaturated PNBE backbone and conjugated PA backbone were easily modified by Diels–Alder and Alder–ene reactions based on TAD molecules. , …”

Section: Resultsmentioning

confidence: 99%

“…1,2,4-Triazoline-3,5-dione (TAD) as a polar molecule has a high dipole moment and can effectively react with many different functional aryl and unsaturated aliphatic groups in seconds under mild conditions without the requirement of catalysts, irradiation, or other external stimulus. , The Diels–Alder and Alder–ene reactions based on TAD as one of the versatile click chemistry molecules have attracted more and more attention from engineering practice and academic field. − Despite the large number of reports on the modification of different nanostructures previously by using click chemistry, , the TAD-based click reaction is rarely used to modify self-assemblies, especially all-polymeric nanostructures. It is well-known that the conjugated dienes and enes are widely used for efficient postfunctionalization by virtue of the TAD click reaction. − For example, when the TAD molecule was reacted with the double bonds on the PNBE backbone, the glass transition temperature, molecular polarity, and mechanical properties of polymers were optimized, which drastically improve the dielectric properties and application potential of PNBE film in energy storage devices. Herein, the random copolymer based on the 1,6-heptadiyne-polymerized PA derivative containing conjugated backbone with five-membered rings and different pendants was synthesized by MCP, and also the block copolymer containing unsaturated PNBE backbone and conjugated PA backbone with five-membered rings was synthesized by tandem ROMP-MCP, which were then modified by TAD chemistry.…”

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Tandem Metathesis Polymerization-Induced Self-Assembly to Nanostructured Block Copolymer and the Controlled Triazolinedione Modification for Enhancing Dielectric Properties

et al. 2018

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The efficient and versatile click chemistry based on 1,2,4-triazoline-3,5-dione (TAD) was used as one of the most potential postfunctionalizing pathways to specially design polymer nanostructure for dielectric materials. The block copolymer was synthesized by tandem ring-opening metathesis polymerization and metathesis cyclopolymerization and self-assembled into the core− shell nanostructure in the selective solvent, which could be modified by TAD in a controlled manner by tuning the TAD feeding amount, enabling the Alder−ene reaction of TAD with the double bonds to occur first on the polynorbornene backbone in the shell and then the cascade Alder−ene and Diels−Alder reactions on the polyacetylene backbone bearing five-membered rings in the core. The modified block copolymers incorporating varied amount of urazole moieties exhibited enhanced dielectric constant from 16.2 to 20.3 and lowered dielectric loss from 0.031 to 0.013 to 0.009, which provides a new idea of the selective postfunctionalization of nanostructures in solution for regulating the polymer structure and properties.

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Unique post-functionalization method for ROMP polymers based on Triazolinedione Alder-ene chemistry

Cited by 22 publications

References 41 publications

Direct Cytosolic Delivery of Proteins through Coengineering of Proteins and Polymeric Delivery Vehicles

Direct Cytosolic Delivery of Proteins through Coengineering of Proteins and Polymeric Delivery Vehicles

Blocking-cyclization technique for precise synthesis of cyclic polymers with regulated topology

Tandem Metathesis Polymerization-Induced Self-Assembly to Nanostructured Block Copolymer and the Controlled Triazolinedione Modification for Enhancing Dielectric Properties

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