Trifluoromethyl-functionalized poly(lactic acid): a fluoropolyester designed for blood contact applications

Khalifehzadeh, Razieh; Ratner, Buddy D.

doi:10.1039/c9bm00353c

Cited by 11 publications

(6 citation statements)

References 64 publications

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“…The results obtained in the current study were consistent with the literature. 61,62 In the case of dHTzmodified glass samples (C6), the contact angle was observed at 61°, which was consistent with the expected value since dHTz moiety with pyridyl substituents has higher hydrogen-bonding capacity compared to the precursor, carboxylic acid group. When Concanavalin A was grafted to the dHTz-modified surfaces via photo-IEDDA reaction (C5), the contact angle decreased to 56°due to the hydrophilic nature of the protein.…”

Section: ■ Results and Discussionmentioning

confidence: 93%

Light-Induced Inverse Electron Demand Diels–Alder Reaction as an Approach for Grafting Macromolecules to Glass Surfaces

Özbek

Kahveci

2021

ACS Appl. Polym. Mater.

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This study aims to develop a grafting technique for glass surfaces by light-induced inverse electron demand Diels−Alder (photo-IEDDA) reaction. The approach depends on the in situ formation of tetrazine molecule in the reaction medium and a subsequent IEDDA reaction of tetrazine moieties with transcyclooctene groups. First, light-induced formation of a tetrazine derivative from a precursor, 6-(6-(pyridin-2-yl)-1,4-dihydro-1,2,4,5-tetrazin-3-yl)pyridin-3-amine (PPA-dHTz), in the presence of a photosensitizer under visible light irradiation was evaluated by nuclear magnetic resonance (NMR) spectroscopy. For grafting glass surfaces, dihydrotetrazine (dHTz) end-functionalized poly(N-isopropylacrylamide) (PNIPAAm-dHTz) and poly(DL-lactide) (PLA-dHTz) were prepared by reversible addition-fragmentation chain-transfer (RAFT) polymerization and ringopening polymerization (ROP), respectively, and postpolymerization functionalization with a dihydrotetrazine molecule (PPA-dHTz). However, glass surfaces were decorated with trans-cyclooctenol (TCO) groups by functionalization with 3-aminopropyltriethoxysilane, succinic anhydride, and TCO successively. Then, photo-IEDDA was performed between the dHTz end-functionalized polymers and TCO-decorated glass surface in the presence of methylene blue and under visible light irradiation. To extend the applicability of the approach, grafting TCO-functionalized protein, namely, Concanavalin A-TCO, to dHTz-modified glass surface was achieved as well. In this case, glass surfaces were functionalized with PPA-dHTz. The successful polymer and protein grafting to glass surfaces were shown with X-ray photoelectron spectroscopy, contact angle measurement, scanning electron microscopy, atomic force microscopy, and Fourier transform infrared (FT-IR) spectroscopy.

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Section: ■ Results and Discussionmentioning

confidence: 93%

Light-Induced Inverse Electron Demand Diels–Alder Reaction as an Approach for Grafting Macromolecules to Glass Surfaces

Özbek

Kahveci

2021

ACS Appl. Polym. Mater.

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“…2,3 Consequently, fluorinated polyesters have shown great potential in textiles, antifouling coatings, optical waveguide devices, biomedical devices, etc. 2,[4][5][6][7][8][9][10][11][12][13][14][15] Nevertheless, studies on fluorinated polyesters were few compared to other fluoropolymers, because of the difficulty in synthesis. 3 Polycondensation is the most common strategy to prepare fluorinated polyesters.…”

Section: Introductionmentioning

confidence: 99%

“…1 The installation of fluorine atoms may endow the polyester with excellent thermal and surface properties, such as low surface energy, good hydropho-bicity and oleophobicity, high thermal stability, and solvent resistance due to the large bond energy of C-F and the small radius of the fluorine atom. 2,3 Consequently, fluorinated polyesters have shown great potential in textiles, antifouling coatings, optical waveguide devices, biomedical devices, etc. 2,[4][5][6][7][8][9][10][11][12][13][14][15] Nevertheless, studies on fluorinated polyesters were few compared to other fluoropolymers, because of the difficulty in synthesis.…”

Section: Introductionmentioning

confidence: 99%

Preparation of fluorinated polyesters by reversible addition–fragmentation chain transfer step-growth polymerization

Mei,

Lei,

et al. 2024

Polym. Chem.

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“…Among the iodine labeling methods, , the iodine monochloride (ICl) method, initially published by McFarlane for protein determination and quantification, is versatile and has been extensively used in different biomaterials studies. − The labeling reaction is conducted under mild conditions, with a minimal effect on the activity of the protein target. Studies also suggest that this method shows a higher labeling efficiency and a more controllable conjugation ratio compared to other iodine labeling methods like chloramine T, iodogen, and enzymatic methods. , …”

Section: Introductionmentioning

confidence: 99%

A Radiolabeling Method for Precise Quantification of Polymers

et al. 2022

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Radiolabeling a protein, molecule, or polymer can provide accurate and precise quantification in biochemistry, biomaterials, pharmacology, and drug delivery research. Herein, we describe a method to 125I label two different polymers for precise quantification in different applications. The surfaces of model contact lenses were modified with phenylboronic acid to bind and release the natural polymer, hyaluronic acid (HA); HA uptake and release were quantified by radiolabeling. In the second example, the in vivo distribution of a mucoadhesive micelle composed of the block copolymer of poly(lactide)-b-poly(methacrylic acid-co-acrylamidophenylboronic acid) was investigated. The presence of phenyl boronic acid groups (PBA), which bind to mucosal surfaces, was proposed to improve the retention of the micelle. 125I labeling of polymers was examined for quantification of microgram amounts of HA present on a contact lens or to evaluate the enhanced retention of PBA micelles on mucosal surfaces in vivo. The introduction of phenol groups onto the polymers allowed for the labeling. HA was modified with phenol groups through a coupling reaction of its carboxylic acid with hydroxybenzylamine. Phenol functional block copolymer micelles with and without PBA were synthesized by including N-(4-hydroxyphenethyl)acrylamide during polymerization. The phenol groups of HA and the block copolymers were labeled with 125I using a modified ICl labeling method. 125I labeling enabled quantification of HA loading and release including the effect of varying amounts of PBA on the contact lens surfaces. Micelles made from 125I-labeled block copolymers with and without PBA were administered intranasally to Brown Norway rats. The animals were sacrificed either immediately after or 4 h after their last nasal instillation, and the nasopharyngeal tissues were removed and quantified. Radioactivity measurements demonstrated that the presence of the PBA mucosal binding groups led to approximately four times higher retention. The HA and block copolymer 125I labeling presented in this article demonstrates the utility of the method for quantification and tracking of microgram quantities of polymers in diverse applications.

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Trifluoromethyl-functionalized poly(lactic acid): a fluoropolyester designed for blood contact applications

Abstract: Fluorinated polymers are strong candidates for development of new cardiovascular medical devices, due to their lower thrombogenicity as compared to other polymers used for cardiovascular implants.

Cited by 11 publications

References 64 publications

Light-Induced Inverse Electron Demand Diels–Alder Reaction as an Approach for Grafting Macromolecules to Glass Surfaces

Light-Induced Inverse Electron Demand Diels–Alder Reaction as an Approach for Grafting Macromolecules to Glass Surfaces

Preparation of fluorinated polyesters by reversible addition–fragmentation chain transfer step-growth polymerization

A Radiolabeling Method for Precise Quantification of Polymers

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