Hydrogen Bonded Multilayer Films Based on Poly(2‐oxazoline)s and Tannic Acid

Sundaramurthy, Anandhakumar; Vergaelen, Maarten; Maji, Samarendra; Auzély‐Velty, Rachel; Zhang, Zhiyue; Geest, Bruno G. De; Hoogenboom, Richard

doi:10.1002/adhm.201400377

Cited by 48 publications

(55 citation statements)

References 41 publications

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“…Additionally, the lower critical solution temperature (LCST) of hydrophilic POx can be tailored over a broad temperature range by means of the molar mass and composition adjustment, which is frequently required by diverse applications areas . Recently, POx and TA were also used to construct various multilayers …”

Section: Introductionmentioning

confidence: 99%

Thermoresponsive polymeric nanoparticles based on poly(2‐oxazoline)s and tannic acid

Wang

et al. 2018

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

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Hydrogen bonding is widely present and plays a significant role in material science and supramolecular chemistry. This work reports a straightforward strategy for the preparation of polymeric nanoparticles from neutral poly(2‐oxazoline)s (POx) and tannic acid (TA) driven by their intermolecular hydrogen bonding. Dynamic light scattering (DLS) and scanning electron microscope (SEM) measurements showed that POx bearing different substituents, that is, methyl, ethyl and n‐propyl in the 2‐position all could assemble with TA into stable nanoparticles in water or ethanol. The diameter of the assembled nanoparticles could be manipulated by varying parameters such as molecular weight of POx, concentration and ratio of POx, and TA. Interestingly, POx/TA nanoparticles exhibited upper critical solution temperature (UCST)‐type thermoresponsive properties in ethanol or water depending on the molecular weight and substituent in the 2‐position of POx. Increasing or decreasing the temperature at the transition point resulted in the reversible transformation between assembled nanoparticles and disassembled poly(2‐n‐propyl‐2‐oxazoline) (PnPrOx) and TA. In view of the tailored size of the stable nanoparticles and the biocompatibilities of POx and TA, the prepared thermoresponsive nanoparticles are promising candidates as carriers for medicine toward related biomedical applications. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 1520–1527

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Section: Introductionmentioning

confidence: 99%

Thermoresponsive polymeric nanoparticles based on poly(2‐oxazoline)s and tannic acid

Wang

et al. 2018

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

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“…De Geest and Hoogenboom and their co‐workers demonstrated the LbL deposition of poly( n ‐propyl oxazoline) and TA at temperatures below or above the LCST of poly( n ‐propyl oxazoline) and found that the growth mechanism differs depending on the assembly temperature . In another study, the same researchers presented a detailed investigation of the thermodynamics of the multilayer assembly of poly(2‐alkyl‐2‐oxazoline)s and TA . Caruso and co‐workers prepared low‐fouling LbL capsules using either linear or brush‐like poly(2‐oxazoline)s and poly(methacrylic acid) (PMA) .…”

Section: Introductionmentioning

confidence: 99%

pH- and temperature-induced release of doxorubicin from multilayers of poly(2-isopropyl-2-oxazoline) and tannic acid

et al. 2017

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We present a simple strategy to prepare doxorubicin (DOX) containing hydrogen-bonded films of poly(2-isopropyl-2-oxazoline) (PIPOX) and tannic acid (TA) which release DOX in acidic conditions while releasing a minimal amount of DOX at physiological pH. Water soluble complexes of TA and DOX (TA − DOX) were prepared prior to film construction. PIPOX and TA − DOX were deposited at the surface at pH 6.5 using the layer-by-layer (LbL) technique. We found that multilayers released a minimal amount of DOX at physiological pH due to further ionization of TA with increasing pH and enhanced electrostatic interactions between TA and DOX. In contrast, pH-induced release of DOX was observed in moderately acidic conditions due to protonation of TA as the acidity increased and electrostatic interactions between TA and DOX decreased. Moreover, we found that raising the temperature from 25 ∘ C to 37.5 ∘ C increased the amount of DOX released from the surface. This can be rationalized with the conformational changes within the multilayers correlated with the lower critical solution temperature behaviour of PIPOX and increased kinetic energy of DOX molecules. Considering the acidic nature of tumour tissues and important biological properties of PIPOX and TA, these multilayers are promising for pH-and temperature-triggered release of DOX from surfaces.

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“…1,2 It consists of a center glucose molecule with all five hydroxyl moieties esterified with two gallic acid (3,4,5-trihydroxybenzoic acid) molecules. The trihydroxylphenyl groups play an important role in binding a variety of substrates through chemical and physical interactions, [3][4][5][6][7][8][9][10][11][12][13] which are similar to the adhesion mechanism of 3,4-dihydroxyphenylalanine (DOPA)-enriched adhesive proteins of blue mussels. 14 TA can be deposited onto various organic and inorganic substrates because of its inherent affinity towards surfaces.…”

Section: Introductionmentioning

confidence: 99%

Thiol Reactive Maleimido-Containing Tannic Acid for the Bioinspired Surface Anchoring and Post-Functionalization of Antifouling Coatings

Pranantyo

Neoh

et al. 2016

ACS Sustainable Chem. Eng.

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Inspired by tea stains, a new surface anchor, maleimido-containing tannic acid (TAMA), was developed to introduce the maleimido functionality onto the stainless steel (SS) surfaces. The feasibility of maleimido groups to serve as anchoring sites for surface functionalization via Michael addition was explored in a model experiment using thiol-containing 1H,1H,2H,2H-perfluorodecanethiol. The surface conjugation efficiency of TAMA with the thiol-containing compounds via Michael addition was also compared to that of the surface with tannic acid (TA) only. Water-soluble thiolated carboxymethyl chitosan (CMCSSH) was then grafted on the SS surface pre-anchored with TAMA via solution immersion and spin coating.The deposition of CMCSSH was characterized by contact angle measurement, surface zeta potential, and X-ray photoelectron spectroscopy (XPS). The antifouling efficacy of the CMCSSH coatings was evaluated by protein adsorption and bacterial adhesion. The cytotoxic effect of the CMCSSH coatings on mammalian cells was evaluated using the standard 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay with 3T3 fibroblasts.

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Hydrogen Bonded Multilayer Films Based on Poly(2‐oxazoline)s and Tannic Acid

Cited by 48 publications

References 41 publications

Thermoresponsive polymeric nanoparticles based on poly(2‐oxazoline)s and tannic acid

Thermoresponsive polymeric nanoparticles based on poly(2‐oxazoline)s and tannic acid

pH- and temperature-induced release of doxorubicin from multilayers of poly(2-isopropyl-2-oxazoline) and tannic acid

Thiol Reactive Maleimido-Containing Tannic Acid for the Bioinspired Surface Anchoring and Post-Functionalization of Antifouling Coatings

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