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Microrheological characterization of covalent adaptable hydrogel degradation in response to temporal pH changes that mimic the gastrointestinal tract.

ABSTRACT: Covalent adaptable hydrogels (CAHs) reversibly adapt their structure in response to external stimuli, emerging as a new platform for biological applications. Due to the unique and complex nature of these materials, a characterization technique is needed to measure the rheology of these CAHs in biological processes. μ²rheology, microrheology in a microfluidic device, is a technique that can fully characterize real-time CAH degradation in a changing environment, such as the pH environment of the GI tract. This characterization will enable design and tailoring of these materials for controlled and targeted oral drug delivery. Using μ²rheology, we can exchange the fluid environment without sample loss and measure the change in CAH rheological properties. We show degradation kinetics and material property evolution are independent of degradation history. However, the initial cross-link density at each pH exchange can be decreased by degradation history which decreases the time for the CAH to degrade to the gel-sol transition. These results indicate that CAH degradation can be tuned by changing the initial material properties by varying polymer concentration and ratio of functional groups. We also show that μ²rheology will enable the design of new dynamic materials for targeted drug delivery by enabling these materials to be characterized and tailored in vitro.

SUBMITTER: Wu N

PROVIDER: S-EPMC7365765 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Microrheological characterization of covalent adaptable hydrogels for applications in oral delivery.

Project description:The feasibility of a covalent adaptable hydrogel (CAH) as an oral delivery platform is explored using μ2rheology, microrheology in a microfluidic device. CAH degradation is initiated by physiologically relevant pHs, including incubation at a single pH and consecutively at different pHs. At a single pH, we determine CAH degradation can be tuned by changing the pH, which can be exploited for controlled release. We calculate the critical relaxation exponent, which defines the gel-sol transition and is independent of the degradation pH. We mimic the changing pH environment through part of the gastrointestinal tract (pH 4.3 to 7.4 or pH 7.4 to 4.3) in our microfluidic device. We determine that dynamic material property evolution is consistent with degradation at a single pH. However, the time scale of degradation is reduced by the history of degradation. These investigations inform the design of this material as a new vehicle for targeted delivery.

| S-EPMC6677256 | biostudies-literature

Recyclable Organocatalyzed Poly(Thiourethane) Covalent Adaptable Networks.

Project description:A new type of tetraphenylborate salts derived from highly basic and nucleophilic amines, namely 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU) and triazabicyclodecene (TBD), was applied to the preparation of networked poly(thiourethane)s (PTUs), which showed a vitrimer-like behavior, with higher stress-relaxation rates than PTUs prepared by using dibutyl thin dilaurate (DBTDL) as the catalyst. The use of these salts, which release the amines when heated, instead of the pure amines, allows the formulation to be easily manipulated to prepare any type of samples. The materials prepared from stoichiometric mixtures of hexamethylene diisocyanate (HDI), trithiol (S3) and with a 10% of molar excess of isocyanate or thiol were characterized by FTIR, thermomechanical analysis, thermogravimetry, stress-relaxation tests and tensile tests, thus obtaining a complete thermal and mechanical characterization of the materials. The recycled materials obtained by grinding the original PTUs and hot-pressing the small pieces in the optimized time and temperature conditions were fully characterized by mechanical, thermomechanical and FTIR studies. This allowed us to confirm their recyclability, without appreciable changes in the network structure and performance. From several observations, the dissociative interchange trans-thiocarbamoylation mechanism was evidenced as the main responsible of the topological rearrangements at high temperature, resulting in a vitrimeric-like behavior.

| S-EPMC7761908 | biostudies-literature

Structure-Reactivity-Property Relationships in Covalent Adaptable Networks.

Project description:Polymer networks built out of dynamic covalent bonds offer the potential to translate the control and tunability of chemical reactions to macroscopic physical properties. Under conditions at which these reactions occur, the topology of covalent adaptable networks (CANs) can rearrange, meaning that they can flow, self-heal, be remolded, and respond to stimuli. Materials with these properties are necessary to fields ranging from sustainability to tissue engineering; thus the conditions and time scale of network rearrangement must be compatible with the intended use. The mechanical properties of CANs are based on the thermodynamics and kinetics of their constituent bonds. Therefore, strategies are needed that connect the molecular and macroscopic worlds. In this Perspective, we analyze structure-reactivity-property relationships for several classes of CANs, illustrating both general design principles and the predictive potential of linear free energy relationships (LFERs) applied to CANs. We discuss opportunities in the field to develop quantitative structure-reactivity-property relationships and open challenges.

| S-EPMC9812368 | biostudies-literature

Recyclable Covalent Adaptable Polystyrene Networks Using Boronates and TetraAzaADamantanes

Project description: Not available

| S-EPMC11250031 | biostudies-literature

Covalent adaptable networks using boronate linkages by incorporating TetraAzaADamantanes

Project description:Boronic esters prepared by condensation of boronic acids and diols have been widely used as dynamic covalent bonds in the synthesis of both discrete assemblies and polymer networks. In this study we investigate the potential of a new dynamic-covalent motif, derived from TetraAzaADamantanes (TAADs), with their adamantane-like triol structure, in boronic ester-based covalent adaptable networks (CANs). The TetraAzaADamantane-boronic ester linkage has recently been reported as a more hydrolytically stable boronic ester variant, while still having a dynamic pH response: small-molecule studies found little exchange at neutral pH, while fast exchange occurred at pH 3.8. In this work, bi- and trifunctional TetraAzaADamantane linkers were synthesised and crosslinked with boronic acids to form rubber-like materials, with a Young’s modulus of 1.75 MPa. The dynamic nature of the TetraAzaADamantane networks was confirmed by stress relaxation experiments, revealing Arrhenius-like behaviour, with a corresponding activation energy of 142 ± 10 kJ/mol. Increasing the crosslinking density of the material from 10% to 33% resulted in reduced relaxation times, as is consistent with a higher degree of crosslinking within the dynamic networks. In contrast to the reported accelerating effect of acid addition to small-molecule TetraAzaADamantane complexes, within the polymer network the addition of acid increased relaxation times, suggesting unanticipated interactions between the acid and the polymer that cannot occur in the corresponding small-molecules analogues. The obtained boronate-TetraAzaADamantane materials were thermally stable up to 150°C. This thermal stability, in combination with the intrinsically dynamic bonds inside the polymer network, allowed these materials to be reprocessed and healed after damage by hot-pressing.

| S-EPMC9995436 | biostudies-literature

Probing the Solubility of Imine-Based Covalent Adaptable Networks

Project description: Not available

| S-EPMC10788871 | biostudies-literature

A magnetic solder for assembling bulk covalent adaptable network blocks.

Project description:Covalent adaptable networks (CANs) represent a novel covalently cross-linked polymer that is capable of being reprocessed and recycled relying on reversible covalent bond structures and present exceptional opportunities in a wide range of prospective applications. However, it is genuinely difficult to fabricate bulk CAN blocks with solid-core geometries that possess complex shapes or multiple materials, which are crucial in cutting-edge fields such as soft robotics, flexible electronic devices and biomedical engineering. Here we report a welding technique to strategically construct complex and heterogeneous 3D CAN structures by utilizing a solder doped with magnetic nanoparticles. The solder is able to induce a bond exchange reaction at the interface between the to-be-welded pieces. Using this method, not only CAN bulks with the same materials can be welded to form complex geometries, distinctive bulks with different physical properties and chemical compositions can also be connected to fabricate multimaterial devices. Besides, this method can be used to repair damaged CAN materials and efficiently recycle scrap CAN materials, which can effectively save resources and protect the environment. The universality and robustness of this strategy is expected to promote CAN application in broader functional polymer fields.

| S-EPMC7473190 | biostudies-literature

Biofilm Formation and Virulence of Shigella flexneri Are Modulated by pH of Gastrointestinal Tract.

Project description:Shigella infection remains a public health problem in much of the world. Classic models of Shigella pathogenesis suggest that microfold epithelial cells in the small intestine are the preferred initial site of invasion. However, recent evidence supports an alternative model in which Shigella primarily infects a much wider range of epithelial cells that reside primarily in the colon. Here, we investigated whether the luminal pH difference between the small intestine and the colon could provide evidence in support of either model of Shigella flexneri pathogenesis. Because virulence factors culminating in cellular invasion are linked to biofilms in S. flexneri, we examined the effect of pH on the ability of S. flexneri to form and maintain adherent biofilms induced by deoxycholate. We showed that a basic pH (as expected in the small intestine) inhibited formation of biofilms and dispersed preassembled mature biofilms, while an acidic pH (similar to the colonic environment) did not permit either of these effects. To further elucidate this phenomenon at the molecular level, we probed the transcriptomes of biofilms and S. flexneri grown under different pH conditions. We identified specific amino acid (cysteine and arginine) metabolic pathways that were enriched in the bacteria that formed the biofilms but decreased when the pH increased. We then utilized a type III secretion system reporter strain to show that increasing pH reduced deoxycholate-induced virulence of S. flexneri in a dose-dependent manner. Taken together, these experiments support a model in which Shigella infection is favored in the colon because of the local pH differences in these organs.

| S-EPMC8519285 | biostudies-literature

Proteomes of gastrointestinal tract organoids

Project description:Examination of differential susceptibility of the gastric, small intestine and colon epithelium to SARS-CoV-2 infection Data used in the manuscript "SARS-CoV-2 tropism to intestinal but not gastric epithelial cells is defined by limited ACE2 expression" (Pauzuolis M, Fatykhova D, Zühlke B, Schwecke T, Neyazi M, Samperio-Ventayol P, Aguilar C, Döckel S, Ralser M, Hocke A, Schlegel N, Krempl C, Bartfeld S

2024-03-20 | PXD044789 | Pride

Covalent Adaptable Networks with Tailorable Material Properties Based on Divanillin Polyimines.

Project description:Covalent adaptable networks (CANs) are being developed as future replacements for thermosets as they can retain the high mechanical and chemical robustness inherent to thermosets but also integrate the possibility of reprocessing after material use. Here, covalent adaptable polyimine-based networks were designed with methoxy and allyloxy-substituted divanillin as a core component together with long flexible aliphatic fatty acid-based amines and a short rigid chain triamine, yielding CANs with a high renewable content. The designed series of CANs with reversible imine functionality allowed for fast stress relaxation and tailorability of the thermomechanical properties, as a result of the ratio between long flexible and short rigid amines, with tensile strength (σb) ranging 1.07-18.7 MPa and glass transition temperatures ranging 16-61 °C. The CANs were subsequently successfully reprocessed up to three times without determinantal structure alterations and retained mechanical performance. The CANs were also successfully chemically recycled under acidic conditions, where the starting divanillin monomer was recovered and utilized for the synthesis of a recycled CAN with similar thermal and mechanical properties. This promising class of thermosets bearing sustainable dynamic functionalities opens a window of opportunity for the progressive replacement of fossil-based thermosets.

| S-EPMC11005045 | biostudies-literature

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