Dynamic-covalent nanostructures prepared by Diels–Alder reactions of styrene-maleic anhydride-derived copolymers obtained by one-step cascade block copolymerization

Bapat, Abhijeet P.; Ray, Jacob G.; Savin, Daniel A.; Hoff, Emily A.; Patton, Derek L.; Sumerlin, Brent S.

doi:10.1039/c2py20351k

Cited by 103 publications

(96 citation statements)

References 88 publications

(15 reference statements)

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“…35 Oxime ligation was also utilized by Becker et al to prepare poly(ethylene glycol)-based hydrogels for three-dimensional patterning of peptides onto a hydrogel matrix by photoinitiated thiol-ene chemistry. 38 Inspired by our recent success with core-crosslinked star polymers, 38,39 we reasoned that the controlled exchange behavior of oxime bonds could be tuned to obtain self-repairable hydrogels having reversible sol-to-gel transition capabilities under suitable conditions. 38 Inspired by our recent success with core-crosslinked star polymers, 38,39 we reasoned that the controlled exchange behavior of oxime bonds could be tuned to obtain self-repairable hydrogels having reversible sol-to-gel transition capabilities under suitable conditions.…”

Section: Introductionmentioning

confidence: 99%

Self-healing hydrogels containing reversible oxime crosslinks

2015

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Self-healing oxime-functional hydrogels have been developed that undergo a reversible gel-to-sol transition via oxime exchange under acidic conditions. Keto-functional copolymers were prepared by conventional radical polymerization of N,N-dimethylacrylamide (DMA) and diacetone acrylamide (DAA). The resulting water soluble copolymers (P(DMA-stat-DAA)) were chemically crosslinked with difunctional alkoxyamines to obtain hydrogels via oxime formation. Gel-to-sol transitions were induced by the addition of excess monofunctional alkoxyamines to promote competitive oxime exchange under acidic conditions at 25 °C. The hydrogel could autonomously heal after it was damaged due to the dynamic nature of the oxime crosslinks. In addition to their chemo-responsive behavior, the P(DMA-stat-DAA) copolymers exhibit cloud points which vary with the DAA content in the copolymers. This thermo-responsive behavior of the P(DMA-stat-DAA) was utilized to form physical hydrogels above their cloud point. Therefore, these materials can either form dynamic-covalent or physically-crosslinked gels, both of which demonstrate reversible gelation behavior.

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Section: Introductionmentioning

confidence: 99%

Self-healing hydrogels containing reversible oxime crosslinks

2015

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“…reaction in non-selective solvent To obtain nanogels with suitable size for drug delivery, we systematically investigated the effect of the molecular weight and concentration of the polymer and crosslinker on the nanogel formation by the mean of GPC, as shown in Figure 5 [36]. The GPC analysis of nanogels from copolymers with different molecular weights of PEG-b-PSM1f, PEG-b-PSM2f, and PEG-b-PSM3f (Table 1) showed a new peak at the lower retention time, indicating the formation of crosslinked nanogels (Figure 5a).…”

Section: Nanogel Formation By Diels-aldermentioning

confidence: 99%

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

Le¹,

Cao²,

Tu³

et al. 2018

Express Polym. Lett.

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Abstract.A novel pH and redox responsive system of sub-100 nm nanogels was prepared by arm-first approach via DielsAlder click reaction. First, well-defined poly(ethylene glycol)-block-poly(styrene-alt-maleic anhydride) (PEG-b-PSM) was synthesized and subsequently functionalized with furfuryl amine, leading to the formation of the dual-functional block copolymer of PEG-b-PSMf. The furfuryl groups in the PSMf block were employed to incorporate a redox-responsive linkage and the carboxylic acid moieties generated through functionalization acted as a pH-responsive part. The Diels-Alder click reaction between a bismaleimide crosslinker and PEG-b-PSMf was conducted at 60°C, affording star-like nanogel structures. Doxorubicin, a model anticancer drug, was loaded into to the core of the nanogels primarily by the ionic interaction with carboxylates of core blocks and a highest drug loading capacity of 38.1% was obtained. Furthermore, the in vitro profile showed a low release percentage (11.2%) of DOX at PBS pH 7.4, whereas a burst release (62%) at pH 5.0 in the presence of 10 mM glutathione, indicating the effective pH and redox responsive characteristic of the PEG-b-PSMf nanogels.

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“…Various approaches have been investigated to stabilize copolymer micelles by employing covalent [13] or reducible linkages. [14] Moreover, both the Mirkin group [15] and the Rouge group [16] recently reported cross-linking methods for stabilizing DLMs, but they required long preparation times and additional cross-linkers. Thus, the challenge of constructing simple but specific and stable DLMs still remains.…”

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confidence: 99%

Cross‐Linked Aptamer–Lipid Micelles for Excellent Stability and Specificity in Target‐Cell Recognition

Figg

Wang

et al. 2018

Angew Chem Int Ed

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The specific binding ability of DNA-lipid micelles (DLMs) can be increased by the introduction of an aptamer. However, supramolecular micellar structures based on self-assemblies of amphiphilic DLMs are expected to demonstrate low stability when interacting with cell membranes under certain conditions, which could lead to a reduction in selectivity for targeting cancer cells. We herein report a straightforward cross-linking strategy that relies on a methacrylamide branch to link aptamer and lipid segments. By an efficient photoinduced polymerization process, covalently linked aptamer-lipid units help stabilize the micelle structure and enhance aptamer probe stability, further improving the targeting ability of the resulting nanoassembly. Besides the development of a facile cross-linking method, this study clarifies the relationship between aptamer-lipid concentration and the corresponding binding ability.

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Dynamic-covalent nanostructures prepared by Diels–Alder reactions of styrene-maleic anhydride-derived copolymers obtained by one-step cascade block copolymerization

Cited by 103 publications

References 88 publications

Self-healing hydrogels containing reversible oxime crosslinks

Self-healing hydrogels containing reversible oxime crosslinks

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

Cross‐Linked Aptamer–Lipid Micelles for Excellent Stability and Specificity in Target‐Cell Recognition

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