Biomolecular Densely Grafted Brush Polymers: Oligonucleotides, Oligosaccharides and Oligopeptides

Choi, Wonmin; Sun, Hao; Battistella, Claudia; Berger, Or; Vratsanos, Maria; Wang, Max; Gianneschi, Nathan C.

doi:10.1002/ange.202005379

Cited by 4 publications

(2 citation statements)

References 114 publications

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“…ATRP shows low cross-reactivity with biomolecules and biological functional groups and maintains a low concentration of radicals in the system. As a result, ATRP and other RDRP methods have been widely employed in the preparation of polymer biohybrids from proteins, peptides, nucleic acids, and carbohydrates (22,(43)(44)(45). More recently, polymer functionalization of membrane enclosed systems like cells and liposomes have also been reported (46)(47)(48).…”

Section: Discussionmentioning

confidence: 99%

Engineering exosome polymer hybrids by atom transfer radical polymerization

Lathwal

Yerneni

Boye

et al. 2020

Proc. Natl. Acad. Sci. U.S.A.

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Exosomes are emerging as ideal drug delivery vehicles due to their biological origin and ability to transfer cargo between cells. However, rapid clearance of exogenous exosomes from the circulation as well as aggregation of exosomes and shedding of surface proteins during storage limit their clinical translation. Here, we demonstrate highly controlled and reversible functionalization of exosome surfaces with well-defined polymers that modulate the exosome’s physiochemical and pharmacokinetic properties. Using cholesterol-modified DNA tethers and complementary DNA block copolymers, exosome surfaces were engineered with different biocompatible polymers. Additionally, polymers were directly grafted from the exosome surface using biocompatible photo-mediated atom transfer radical polymerization (ATRP). These exosome polymer hybrids (EPHs) exhibited enhanced stability under various storage conditions and in the presence of proteolytic enzymes. Tuning of the polymer length and surface loading allowed precise control over exosome surface interactions, cellular uptake, and preserved bioactivity. EPHs show fourfold higher blood circulation time without altering tissue distribution profiles. Our results highlight the potential of precise nanoengineering of exosomes toward developing advanced drug and therapeutic delivery systems using modern ATRP methods.

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Section: Discussionmentioning

confidence: 99%

Engineering exosome polymer hybrids by atom transfer radical polymerization

Lathwal

Yerneni

Boye

et al. 2020

Proc. Natl. Acad. Sci. U.S.A.

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“…In recent years, ring-opening metathesis polymerization (ROMP), which generates well-defined polymers with diverse structure and function, [5][6][7][8][9] has been further explored in the context of generating polymers with degradable backbones. 10 Given the excellent functional group tolerance, monomers with a variety of degradable linkages, such as acetal/ketal, [11][12][13] carbonate, 14 oxazinone, 15 enol ether, 16 silyl ether, 17 phosphoester, 18 and phosphoramidate, 19 have been successfully polymerized via ROMP.…”

Section: Introductionmentioning

confidence: 99%

Inflammation-Responsive Micellar Nanoparticles from Degradable Polyphosphoramidates for Targeted Delivery to Myocardial Infarction

Liang

Sullivan

Carrow

et al. 2022

Preprint

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Nanoparticles that undergo a localized morphology change to target areas of inflammation have been previously developed but are limited by their lack of biodegradability. In this paper, we describe a low ring strain cyclic olefin monomer, 1,3-dimethyl-2-phenoxy-1,3,4,7-tetrahydro-1,3,2-diazaphosphepine 2-oxide (MePTDO), that rapidly polymerizes via ring-opening metathesis polymerization (ROMP) at room temperature to generate well-defined degradable polyphosphoramidates with high monomer conversion (>84%). Efficient MePTDO copolymerizations with norbornene-based monomers are demonstrated, including a norbornenyl monomer functionalized with a peptide substrate for inflammation-associated matrix metalloproteinases (MMPs). The resulting amphiphilic peptide brush copolymers self-assembled in aqueous solution to generate micellar nanoparticles (30 nm in diameter) which exhibit excellent cyto- and hemocompatibility and undergo MMP-induced assembly into micron scale aggregates. As MMPs are upregulated in the heart post-myocardial infarction (MI), the MMP-responsive micelles were applied to target and accumulate in the infarcted heart following intravenous administration in a rat model of MI. These particles displayed a distinct biodistribution and clearance pattern in comparison to non-degradable analogues. Specifically, accumulation at the site of MI, competed with elimination predominantly through the kidney rather than the liver. Together, these results suggest this as a promising new biodegradable platform for inflammation targeted delivery.

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Construction of Highly Ordered Glyco‐Inside Nano‐Assemblies through RAFT Dispersion Polymerization of Galactose‐Decorated Monomer

et al. 2021

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Glyco‐assemblies derived from amphiphilic sugar‐decorated block copolymers (ASBCs) have emerged prominently due to their wide application, for example, in biomedicine and as drug carriers. However, to efficiently construct these glyco‐assemblies is still a challenge. Herein, we report an efficient technology for the synthesis of glyco‐inside nano‐assemblies by utilizing RAFT polymerization of a galactose‐decorated methacrylate for polymerization‐induced self‐assembly (PISA). Using this approach, a series of highly ordered glyco‐inside nano‐assemblies containing intermediate morphologies were fabricated by adjusting the length of the hydrophobic glycoblock and the polymerization solids content. A specific morphology of complex vesicles was captured during the PISA process and the formation mechanism is explained by the morphology of its precursor and intermediate. Thus, this method establishes a powerful route to fabricate glyco‐assemblies with tunable morphologies and variable sizes, which is significant to enable the large‐scale fabrication and wide application of glyco‐assemblies.

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Biomolecular Densely Grafted Brush Polymers: Oligonucleotides, Oligosaccharides and Oligopeptides

Cited by 4 publications

References 114 publications

Engineering exosome polymer hybrids by atom transfer radical polymerization

Engineering exosome polymer hybrids by atom transfer radical polymerization

Inflammation-Responsive Micellar Nanoparticles from Degradable Polyphosphoramidates for Targeted Delivery to Myocardial Infarction

Construction of Highly Ordered Glyco‐Inside Nano‐Assemblies through RAFT Dispersion Polymerization of Galactose‐Decorated Monomer

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