Synthesis of cyclic amphiphilic homopolymers and their potential application as polymeric micelles

Laurent, Boyd A.; Grayson, Scott M.

doi:10.1039/c1py00378j

Cited by 41 publications

(58 citation statements)

References 49 publications

(57 reference statements)

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“…25–27 Cyclization was confirmed by a shift toward longer retention times on GPC relative to the linear precursor and by the disappearance of the characteristic azide signal (2100 cm −1 ) from the Fourier transform-infrared (FT-IR) spectrum (Figure S1). …”

Section: Resultsmentioning

confidence: 98%

Sunflower Polymers for Folate-Mediated Drug Delivery

Wang¹,

Wei

Tan³

et al. 2015

Biomacromolecules

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Polymeric delivery vehicles can improve the safety and efficacy of chemotherapy drugs by facilitating preferential tumor delivery. Polymer-drug conjugates are especially attractive carriers because additional formulation steps are not required during manufacturing, and drug release profiles can be altered based on linker choice. For clinical translation, these vehicles should also be reproducibly and controllably synthesized. Recently, we reported the development of a class of materials called “sunflower polymers,” synthesized by controlled radical polymerization of hydrophilic “petals” from a cyclic multimacroinitiator “core.” This synthesis strategy afforded control over the size of the polymer nanostructures based on their petal polymerization time. In this work, we demonstrate that particle size can be further tuned by varying the degree of polymerization of the cyclic core in addition to that of the petals. Additionally, we investigate the application of these materials for tumor-targeted drug delivery. We demonstrate that folate-targeted, doxorubicin-conjugated sunflower polymers undergo receptor-mediated uptake into cancer cells and pH-triggered drug release leading to cytotoxicity. These materials are attractive as drug carriers due to their discrete and small size, shielded drug cargo that can be triggered for release, and relative ease of synthesis.

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Section: Resultsmentioning

confidence: 98%

Sunflower Polymers for Folate-Mediated Drug Delivery

Wang¹,

Wei

Tan³

et al. 2015

Biomacromolecules

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“…This amplification via self-assembly of a cyclic amphiphile18 was expected to be expandable to salt stability, which has been hinted by archaea that reside in hypersaline environments19. Amphiphiles that form a salt-resistant micelle are applicable not only in detergents used in hard water but also in food and pharmacological processing operations that involve buffer conditions2021.…”

mentioning

confidence: 99%

Tuneable enhancement of the salt and thermal stability of polymeric micelles by cyclized amphiphiles

2013

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Cyclic molecules provide better stability for their aggregates. Typically in nature, the unique cyclic cell membrane lipids allow thermophilic archaea to inhabit extreme conditions. By mimicking the biological design, the robustness of self-assembled synthetic nanostructures is expected to be improved. Here we report topology effects by cyclized polymeric amphiphiles against their linear counterparts, demonstrating a drastic enhancement in the thermal, as well as salt stability of self-assembled micelles. Furthermore, through coassembly of the linear and cyclic amphiphiles, the stability was successfully tuned for a wide range of temperatures and salt concentrations. The enhanced thermal/salt stability was exploited in a halogen exchange reaction to stimulate the catalytic activity. The mechanism for the enhancement was also investigated. These topology effects by the cyclic amphiphiles offer unprecedented opportunities in polymer materials design unattainable by traditional means.

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“…In order to encourage the formation of cyclic polymer via intramolecular coupling relative to oligomer formation via intermolecular coupling, the cyclization was carried out under high dilution [15,[31][32][33]. These dilution conditions were achieved by adding a degassed solution of the 25 ml of linear precursor 3 as a 0.18 mM solution in DMF at a rate of 2 ml/h into a 100 ml catalyst solution (CuBr (0.316 g, 2.2 mmol) and PMDETA (0.422 g, 2.4 mmol) in DMF) using a continuous addition.…”

Section: High Purity Cyclic Polystyrene Unimermentioning

confidence: 99%