Bioinspired core‐crosslinked micelles from thymine‐functionalized amphiphilic block copolymers: Hydrogen bonding and photo‐crosslinking study

Kaur, Gagan Deep; Chang, Shery L. Y.; Bell, Toby D. M.; Hearn, Milton Thomas William; Saito, Kei

doi:10.1002/pola.24853

Cited by 31 publications

(29 citation statements)

References 57 publications

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“…The copolymer's ability to transition from individual polymeric chains to a crosslinked network allows for the modification of the polymer's physical properties, such as elasticity, tensile strength, and solubility. These properties provide an exciting wide variety of practical applications for the copolymer including antibacterial-coated surfaces [9], hair care products [10], printed circuit boards and photo-imaging systems [11][12][13][14], as well as controlled release systems for pharmaceutical and agricultural use [15][16][17].…”

Section: A C C E P T E D Accepted Manuscriptmentioning

confidence: 99%

Evaluation of photo-induced crosslinking of thymine polymers using FT-IR spectroscopy and chemometric analysis

Bortolato

Thomas

Mcdonough

et al. 2012

Polymer

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Please cite this article as: Bortolato SA, Thomas KE, McDonough K, Gurney RW, Martino DM, Evaluation of photo-induced crosslinking of thymine polymers using FT-IR spectroscopy and chemometric analysis, Polymer (2012), doi: 10.1016/j.polymer.2012.09.007. This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT 2 ABSTRACTThe photo-induced immobilization of 4-vinylbenzyl thymine (VBT) and 4-vinylbenzyl triethyl ammonium chloride (VBA) copolymers has been investigated with the aid of grazing-angle specular-reflectance FT-IR spectroscopy. As irradiation time increases, changes in the structure of pendant thymine groups in the copolymer due to the crosslinking process result in shifts of the copolymer network's vibrational frequencies, as well as changes in numerous IR band intensities.In this work, chemometric methods have been applied to the FTIR data obtained while

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Section: A C C E P T E D Accepted Manuscriptmentioning

confidence: 99%

Evaluation of photo-induced crosslinking of thymine polymers using FT-IR spectroscopy and chemometric analysis

Bortolato

Thomas

Mcdonough

et al. 2012

Polymer

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“…These photosensitive molecules such as anthracene [146,147], thymine [148,149] and coumarin [60,70,150] have been widely employed as photo-crosslinkers to reversibly crosslink polymeric micelles and hydrogels. Zhao's group [65,151,152] first reported the use of coumarin moieties incorporated in the diblock copolymer to crosslink assembled micelles by photo-dimerization under irradiation at UV wavelength >300 nm [153].…”

Section: On-demand Drug Releasementioning

confidence: 99%

Reversibly Crosslinked Nanocarriers for on-demand Drug Delivery in Cancer Treatment

Shao

Huang

Shi

et al. 2012

Therapeutic Delivery

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Polymer micelles have proven to be one of the most versatile nanocarriers for anticancer drug delivery. However, the in vitro and in vivo stability of micelles remains a challenge due to the dynamic nature of these self-assembled systems, which leads to premature drug release and nonspecific biodistribution in vivo. Recently, reversibly crosslinked micelles have been developed to provide solutions to stabilize nanocarriers in blood circulation. Increased stability allows nanoparticles to accumulate at tumor sites efficiently via passive and/or active tumor targeting, while cleavage of the micelle crosslinkages, through internal or external stimuli, facilitates on-demand drug release. In this review, various crosslinking chemistries as well as the choices for reversible linkages in these nanocarriers will be introduced. Then, the development of reversibly crosslinked micelles for on-demand drug release in response to single or dual stimuli in the tumor microenvironment is discussed, for example, acidic pH, reducing microenvironment, enzymatic microenvironment, photoirradiation and the administration of competitive reagents postmicelle delivery.

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“…Therefore, the accuracy of the method depends upon the standards and samples having the same relationship between their hydrodynamic volume, charge, and molecular weight. This is especially true for charged copolymers systems [20].…”

Section: Gel Permeation Chromatographymentioning

confidence: 99%

“…Thus, VBT is often polymerized in different ratios with styrene derivative charged monomers, such as anionic vinyl phenyl sulfonate (VPS) salts [7] or cationic vinylbenzyl triethylammonium chloride (VBA) [8][9][10] which allows the copolymer to be soluble in water. Extending the knowledge achieved from the study of the natural phenomena related to thymine reactivity and intermolecular interactions has generated a diapason of potential applications [11][12][13][14] ranging from photoresist material [15,16] and organic-inorganic hybrid devices [2] to antibacterial coatings [17], drug delivery systems [3,[18][19][20], recyclable plastics [21], and biosensors [22,23]. On the other hand, the increasing attention given to the environmental and toxicological dilemmas linked to commercial materials situates the thymine-based polymeric systems as a Green Chemistry platform [24].…”

Section: Introductionmentioning

confidence: 99%

Isolation and Characterization of 1,3-Bis(vinylbenzyl)thymine: Copolymerization with Vinylbenzyl Thymine Ammonium Chloride

Chen

Martino³

et al. 2017

Journal of Polymers

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A novel bioinspired molecule, 1,3-bis(vinylbenzyl)thymine (bisVBT), was isolated as a by-product during the synthesis of 1-(4-vinylbenzyl)thymine (VBT) and analyzed with various techniques: NMR, IR, and Single-Crystal X-ray Diffraction. In addition to embodying all the desired characteristics of VBT (i.e., having the ability to undergo a 2 + 2 photodimerization reaction upon UV irradiation, a derivatization site, hydrogen bonding sites, and aromatic stacking ability) the bisVBT monomer has the added benefit of having two vinyl groups for cross-polymerization. Copolymerizing the bisVBT monomer with the charged monomer vinylbenzyl triethylammonium (VBA) chloride, different copolymers/terpolymers/cross-linked network were obtained, as it was shown by the absence of the vinyl resonance in the NMR spectra. Thermal Gravimetric Analysis (TGA) and Differential Scanning Calorimetry (DSC) showed an indication of materials with low degree of cross-linking. A Gel Permeation Chromatography (GPC) method was improved to better characterize the molecular weight distributions of the cationic structures. Preliminary qualitative cross-linking studies were performed on bisVBT-VBA copolymers, and a comparison with VBT-VBA copolymers is presented.

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Bioinspired core‐crosslinked micelles from thymine‐functionalized amphiphilic block copolymers: Hydrogen bonding and photo‐crosslinking study

Cited by 31 publications

References 57 publications

Evaluation of photo-induced crosslinking of thymine polymers using FT-IR spectroscopy and chemometric analysis

Evaluation of photo-induced crosslinking of thymine polymers using FT-IR spectroscopy and chemometric analysis

Reversibly Crosslinked Nanocarriers for on-demand Drug Delivery in Cancer Treatment

Isolation and Characterization of 1,3-Bis(vinylbenzyl)thymine: Copolymerization with Vinylbenzyl Thymine Ammonium Chloride

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