Effect of structural isomerism and polymer end group on the pH-stability of hydrogen-bonded multilayers

Erel, Irem; Schlaad, Helmut; Demirel, A. Levent

doi:10.1016/j.jcis.2011.05.033

Cited by 40 publications

(26 citation statements)

References 27 publications

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“…This can be due to the lower number of free phenolic hydroxyl groups remaining on TA upon hydrogen bonding to DOX during the complexation process, resulting in a decrease in the extent of association between PIPOX and TA at the surface. The first study on poly(oxazoline)‐containing LbL films was reported by one of us and showed that LbL films of PIPOX and TA could be grown in strongly acidic conditions and the multilayers showed response only in basic conditions . Different from that study, the present work investigated the construction of multilayers just below the physiological pH, with DOX being included within the multilayers during film assembly which could then be released in moderately acidic conditions.…”

Section: Resultsmentioning

confidence: 93%

“…The studies concerning multilayers of poly(2‐alkyl‐2‐oxazoline)s are limited. One of us showed the first example of LbL films of poly(2‐alkyl‐2‐oxazoline)s using PIPOX and tannic acid (TA) as building blocks and contrasted the pH stability of PNIPAM/TA and PIPOX/TA films . 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 .…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 93%

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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“…90 Hydrogen bonding assembled films are of particular interest because, unlike electrostatically assembled films, they can be designed to be charge neutral and responsive to biological triggers. 92,93 Furthermore, the interaction between functional POx and PMAA was exploited for the assembly of low-fouling degradable polymer capsules. poly(ethylene glycol), and poly(Nvinylpyrrolidone)) and donors (e.g.…”

Section: Hydrogel Poly(2-oxazoline) Capsules Via Templated Assemblymentioning

confidence: 99%

Covalently cross-linked poly(2-oxazoline) materials for biomedical applications – from hydrogels to self-assembled and templated structures

2015

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REVIEW This journal isCovalently cross-linked polymeric materials play an important role in life science. Hydrogels produced from multifunctional polymers can be utilized in numerous (bio)applications, such as drug delivery, tissue engineering and (bio)sensing. Also nano-/micro-scaled assemblies benefit from a covalent linkage for instance to prevent premature disassembly or to generate a passive tissue specifity when used as drug delivery agent. In both cases there is a need for biocompatible polymers with manifold (orthogonal) functionalization possibilities. By using the cationic ring-opening polymerization of 2-oxazolines it is possible to accomplish both tasks. In this review we summerize covalantly cross-linked structures consisting of poly(2-oxazoline)s including three dimensional scaffolds, micellar systems as well as multilayer capsules. We focus on the cross-linking chemistry and the impact of the addressed systems regarding biological application.

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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%

“…[30][31][32][33] Recently, POx and TA were also used to construct various multilayers. [34][35][36][37][38] Although pioneering strategies have gained success in the preparation of polymeric nanoparticles, the inefficient and tedious preparation techniques involved may limit their broad applications. Therefore, facile and efficient preparation strategy is demanded in view of the increasing significance of polymeric nanoparticles in diverse research fields.…”

mentioning

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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Effect of structural isomerism and polymer end group on the pH-stability of hydrogen-bonded multilayers

Cited by 40 publications

References 27 publications

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

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

Covalently cross-linked poly(2-oxazoline) materials for biomedical applications – from hydrogels to self-assembled and templated structures

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

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