Micellar nanoparticles with tuneable morphologies through interactions between nucleobase-containing synthetic polymers in aqueous solution

Hua, Zan; Pitto-Barry, Anaïs; Kang, Yan; Kirby, Nigel; Wilks, Thomas R.; O’Reilly, Rachel K.

doi:10.1039/c6py00716c

Cited by 40 publications

(68 citation statements)

References 68 publications

(89 reference statements)

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“…Inspired by this selective recognition, synthetic chemists have widely utilized complementary H-bonding interactions to achieve templated polymerization/synthesis, [1][2][3][4][5][6] fabricate DNA-like supramolecular aggregates, 7 and tune nanostructure morphologies and functionalities. [8][9][10][11][12] Thymine, one of the natural nucleobases, can undergo photodimerization under UV irradiation to generate a cyclobutane pyrimidine, 13,14 and this has been exploited by various groups, for example in the fabrication of adhesive materials 15 and the formation of core-crosslinked polymer nanoparticles. 16 Photodimerization is an attractive crosslinking method as it is non-toxic, tunable, controllable remotely and does not yield any byproducts.…”

Section: Introductionmentioning

confidence: 99%

Entrapment and Rigidification of Adenine by a Photo-Cross-Linked Thymine Network Leads to Fluorescent Polymer Nanoparticles

et al. 2018

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Photocrosslinking of nucleobase-containing polymer micelles was observed to result in fluorescent polymer nanoparticles. By varying the micelle assembly conditions, it was possible to probe the origins of this behavior. A number of factors were investigated including the effect of omitting one of the nucleobases, blocking hydrogen-bonding interactions, detaching the nucleobase from the polymer backbone and changing the degree of core crosslinking. Spectroscopic investigations were also carried out to further characterize the fluorescent nanoparticles. These data revealed that no new small molecule fluorophores were created during crosslinking and that a dense, hydrogen-bonded network of photodimerized thymine with entrapped adenine was required for fluorescence to arise. We conclude that rigidification and immobilization of adenine in this way leads to the enhancement of an already extant fluorescence pathway, and suggests that synergistic covalent and supramolecular entrapment of profluorophores may provide a general strategy for the production of novel fluorescent polymer nanoparticles.

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Section: Introductionmentioning

confidence: 99%

Entrapment and Rigidification of Adenine by a Photo-Cross-Linked Thymine Network Leads to Fluorescent Polymer Nanoparticles

et al. 2018

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“…CNAs are a recently reported synthetic analogs of DNA that are produced by photoinitiated thiolene chemistry . While synthetic polymers have been used to incorporate nucleobases for building assemblies and new materials, CNAs present a new class of nucleobase polymers that have the potential to be made with sequence control through thiol‐click reactions. As compared to other synthetic DNA systems such as peptide nucleic acids, CNA monomer units can be synthesized at scale and both the monomer and oligomers have mutual solvent compatibility with other synthetic polymers such as PEG and PLGA.…”

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confidence: 99%

Synthesis and Assembly of Click‐Nucleic‐Acid‐Containing PEG–PLGA Nanoparticles for DNA Delivery

et al. 2017

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Co-delivery of both chemotherapy drugs and siRNA from a single delivery vehicle can have a significant impact on cancer therapy due to the potential for overcoming issues such as drug resistance. However, the inherent chemical differences between charged nucleic acids and hydrophobic drugs have hindered entrapment of both components within a single carrier. While poly(ethylene glycol)-block-poly(lactic-co-glycolic acid) (PEG-PLGA) copolymers have been used successfully for targeted delivery of chemotherapy drugs, loading of DNA or RNA has been poor. It is demonstrated that significant amounts of DNA can be encapsulated within PLGA-containing nanoparticles through the use of a new synthetic DNA analog, click nucleic acids (CNAs). First, triblock copolymers of PEG-CNA-PLGA are synthesized and then formulated into polymer nanoparticles from oil-in-water emulsions. The CNA-containing particles show high encapsulation of DNA complementary to the CNA sequence, whereas PEG-PLGA alone shows minimal DNA loading, and non-complementary DNA strands do not get encapsulated within the PEG-CNA-PLGA nanoparticles. Furthermore, the dye pyrene can be successfully co-loaded with DNA and lastly, a complex, larger DNA sequence that contains an overhang complementary to the CNA can also be encapsulated, demonstrating the potential utility of the CNA-containing particles as carriers for chemotherapy agents and gene silencers.

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“…and Supporting Information, Figs. S1–S3) . Each of the polymerizations were carried out for 2 h at 70 °C in a mixture of water and 1,4‐dioxane prior to analysis by 1 H NMR spectroscopy and size exclusion chromatography (SEC).…”

Section: Resultsmentioning

confidence: 99%

“…Polymerization of monomers that have been functionalized with one of the natural nucleobases (adenine, thymine, guanine, or cytosine) produces polymers with nucleobase‐containing side chains. Although less architecturally controlled and sequence specific than DNA, these synthetic analogues have been shown to undergo self‐assembly processes controlled by Watson‐Crick base pairing and can be prepared on a relatively large scale . Here, we examine the interactions of a new class of nucleobase‐functionalized poly(acrylamide) (PAAm) polymers with SWNTs, and their ability to form stable nanotube dispersions through π‐stacking of the nucleobases with the SWNT sidewall.…”

Section: Introductionmentioning

confidence: 99%

Dispersion of single‐walled carbon nanotubes using nucleobase‐containing poly(acrylamide) polymers

Fong

Hua

Wilks

et al. 2017

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

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Single-walled carbon nanotubes (SWNTs) possess extraordinary properties, but suffer from poor solubility and a lack of purity. Of the possible routes available to solubilize and purify nanotube samples, the use of noncovalent functionalization is ideal as carbon nanotube properties are not deleteriously affected. A multitude of different dispersants have been investigated thus far, but of particular interest is deoxyribonucleic acid (DNA), which has previously been demonstrated to effectively separate metallic and semiconducting carbon nanotubes. Here, we investigate the ability of synthetic nucleobase-containing poly(acrylamide) polymers to produce stable nanotube dispersions in organic solvents. Polymers bearing different nucleobase and backbone structures, as well as block copolymers with different block sequences were investigated. Polymer:SWNT mass ratios and solvent compositions were optimized for the nucleobase-functionalized polymers, and semiconducting and metallic SWNT populations were identified by a combination of UV-Vis-NIR absorption, Raman, and fluorescence spectroscopy. These results demonstrate the capacity for synthetic DNA analogues to disperse SWNTs in organic media.

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Micellar nanoparticles with tuneable morphologies through interactions between nucleobase-containing synthetic polymers in aqueous solution

Abstract: Herein, we report the preparation of nucleobase-containing synthetic amphiphilic diblock copolymers using RAFT polymerization.

Cited by 40 publications

References 68 publications

Entrapment and Rigidification of Adenine by a Photo-Cross-Linked Thymine Network Leads to Fluorescent Polymer Nanoparticles

Entrapment and Rigidification of Adenine by a Photo-Cross-Linked Thymine Network Leads to Fluorescent Polymer Nanoparticles

Synthesis and Assembly of Click‐Nucleic‐Acid‐Containing PEG–PLGA Nanoparticles for DNA Delivery

Dispersion of single‐walled carbon nanotubes using nucleobase‐containing poly(acrylamide) polymers

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