Functional sugar-based polymers and nanostructures comprised of degradable poly(<scp>d</scp>-glucose carbonate)s

Su, Lu; Khan, Sarosh; Fan, Jingwei; Lin, Yen‐Nan; Wang, Hai; Gustafson, Tiffany P.; Zhang, Fuwu; Wooley, Karen L.

doi:10.1039/c6py01978a

Cited by 57 publications

(74 citation statements)

References 29 publications

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“…The surface charge densities were characterized by zeta ( ζ )‐potential measurements in nanopure water. Nanostructures formed from B1 and B2 were slightly negatively charged, with ζ ‐potentials of about −10 mV, a common phenomenon observed for neutral polymer assemblies . Interestingly, the nanostructures assembled from B3 showed bimodal distributions centered at about 50 and 150 nm by DLS (Supporting Information Fig.…”

Section: Resultsmentioning

confidence: 99%

Syntheses of triblock bottlebrush polymers through sequential ROMPs: Expanding the functionalities of molecular brushes

Heo

Lin

et al. 2017

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

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Well‐defined triblock bottlebrush copolymers, composed of a hydrophilic and stealth graft segment, a hydrophobic and self‐assembly‐driving segment, and a protected amine‐containing segment which could serve as a functional segment after deprotection, were synthesized through sequential ring‐opening metathesis polymerizations of corresponding norbornene‐terminated macromonomers. Aqueous solution‐state assembly behaviors were studied before and after deprotection of the functional segments.

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Section: Resultsmentioning

confidence: 99%

Syntheses of triblock bottlebrush polymers through sequential ROMPs: Expanding the functionalities of molecular brushes

Heo

Lin

et al. 2017

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

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“…Amphiphilic block copolymer PEG‐ b ‐PMPC could be used to construct redox‐responsive, core‐crosslinked micelles via click reaction with the addition of bis‐(azidoethyl) disulfide . Other alkyne‐containing cyclic carbonate monomers such as 5‐methyl‐5‐propargyl‐1,3‐dioxan‐2‐one, 5,5‐di(propargyl)‐1,3‐dioxan‐2‐one, and methyl‐2‐ O ‐ethyloxycarbonyl‐3‐ O ‐propargyloxycarbonyl‐4,6‐ O ‐carbonyl‐α‐ d ‐glucopyranoside were also reported for the preparation of reduction‐sensitive polymeric prodrug, tumor‐targeting polymeric nanocarriers, and functional sugar‐based polymers, respectively. These alkyne‐containing cyclic carbonate monomers are capable of improving the property of aliphatic polycarbonates such as on‐demand drug release, high intracellular doxorubicin accumulation at cancer cells, and low cytotoxicity.…”

Section: Click Chemistry In the Synthesis Of Functional Aliphatic Polmentioning

confidence: 99%

Click Chemistry in Functional Aliphatic Polycarbonates

Dai

Zhang

Xia

2017

Macromol. Rapid Commun.

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Click chemistry, one of the most important methods in conjugation, plays an extremely significant role in the synthesis of functional aliphatic polycarbonates, which are a group of biodegradable polymers containing carbonate bonds in their main chains. To date, more than 75 articles have been reported on the topic of click chemistry in functional aliphatic polycarbonates. However, these efforts have not yet been highlighted. Six categories of click reactions (alkyne-azide reaction, thiol-ene reaction, Michael addition, epoxy-amine/thiol reaction, Diels-Alder reaction, and imine formation) that have been afforded for further post-polymerization modification of polycarbonates are reviewed. Through this review, a comprehensive understanding of functional aliphatic polycarbonates aims to afford insight on the design of polycarbonates for further post-polymerization modification via click chemistry and the expectation of the practical application.

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“…Each of the steps was technically challenging. Other naturally occurring building blocks have been employed, but the conversions into polymerizable monomers also suffered similar challenges …”

Section: Figurementioning

confidence: 99%

Complete Depolymerization and Repolymerization of a Sugar Poly(orthoester)

Maiti

Thompson

et al. 2017

ChemSusChem

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The capability of a polymer to depolymerize, regenerating its original monomer for further polymerization, is very attractive in terms of sustainability. Recently discovered sugar poly(orthoesters) are an important class of glycopolymer. The high sensitivity of the backbone orthoester linkage toward acidolysis provides a valuable model to study the depolymerization. Herein, a sugar poly(orthoester) is shown to be completely depolymerized under acidic conditions. Interestingly, instead of the original monomer, the depolymerization gave a stable cyclic product (1,6-anhydro glucopyranose) in most cases, which was kinetically and thermodynamically favored. However, this pathway could be inhibited by chemically deactivating a key intermediate and thus favoring the formation of the original monomer. Efficient repolymerizaton of the regenerated monomer is also demonstrated.

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Functional sugar-based polymers and nanostructures comprised of degradable poly(d-glucose carbonate)s

Abstract: This paper presents the synthesis and aqueous solution-state assembly of functional degradable poly(d-glucose carbonate)s, derived from renewable sources, with practical utility in biomedical applications.

Cited by 57 publications

References 29 publications

Syntheses of triblock bottlebrush polymers through sequential ROMPs: Expanding the functionalities of molecular brushes

Syntheses of triblock bottlebrush polymers through sequential ROMPs: Expanding the functionalities of molecular brushes

Click Chemistry in Functional Aliphatic Polycarbonates

Complete Depolymerization and Repolymerization of a Sugar Poly(orthoester)

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