A guanosine-based 2-formylphenylborate ester hydrogel with high selectivity to K<sup>+</sup> ions

Qiao, Hongwei; Bai, Jiakun; Zhang, Sichun; Li, Chao

doi:10.1039/d0ra05254j

Cited by 18 publications

(26 citation statements)

References 35 publications

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“…Only sol−gel or assembly solution with weak circular dichroism (CD) signals was observed when the concentration of 1 (determined by G) was lower than 30 mM (Figures S2A and S4A). Similar to the guanosine 2formylphenylborate assembly reported by our previous work, 30 the current system showed extreme selectivity to K + ions than to other alkali cations. No self-supporting hydrogel was obtained in the presence of Li + , Na + , Rb + , or Cs + because it was unsuitable to fit inside the G 4 cavities and resulted in the formation of a strong hydrogel (Figure 2A).…”

Section: ■ Results and Discussionsupporting

confidence: 85%

Guanosine Borate Hydrogel and Self-Assembled Nanostructures Capable of Enantioselective Aldol Reaction in Water

et al. 2022

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A guanosine-based hydrogel formed by the self-assembly of guanosine and 4-((l-prolinamide)methyl)phenylboronic acid was constructed. The G quartets were selectively stabilized by K+ ions to form a self-supporting transparent hydrogel. These guanosine-derived assemblies were used to catalyze the aldol reaction in water without any additives, affording desirable conversion and enantioselectivity of the product. The controlled assays of small-molecule components indicated that the stable assemblies were the definite species that achieved high enantioselective catalysis. The current catalytic system can be readily recovered by simple extraction and still acquired good performance of the reaction after four cycles.

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Section: ■ Results and Discussionsupporting

confidence: 85%

Guanosine Borate Hydrogel and Self-Assembled Nanostructures Capable of Enantioselective Aldol Reaction in Water

et al. 2022

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“…The transparent drug-loaded hydrogel can be formed when the amount of rutin was not more than 0.4 equiv (Figure S1D). In addition, the selectivity of the current system for K + ions is significantly higher than other alkali cations , and Li + , Na + , Rb + , or Cs + systems did not afford self-supporting hydrogels (Figure S2), which was similar to guanosine 2-formylphenylbotate assembly in our previous report. , …”

Section: Results and Discussionsupporting

confidence: 56%

“…In addition, the selectivity of the current system for K + ions is significantly higher than other alkali cations 26,27 and Li + , Na + , Rb + , or Cs + systems did not afford self-supporting hydrogels (Figure S2), which was similar to guanosine 2-formylphenylbotate assembly in our previous report. 28,29 Structural Information of the Rutin-Loaded Hydrogel. The 1 H and 11 B NMR experiments were performed to investigate the substances in solution and indirectly determine the structural information of the gel-phase composition, as shown in Figure 2.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Rutin-Loaded Stimuli-Responsive Hydrogel for Anti-Inflammation

Wang

Guo

et al. 2022

ACS Appl. Mater. Interfaces

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An active flavonoid compound rutin was incorporated into a guanosine phenylborate hydrogel (GBR) by a stimuli-responsive borate ester linkage for the treatment of inflammatory bowel disease (IBD). The components and morphology of the drug delivery system were characterized by NMR, UV–vis spectroscopy, and AFM. Rheological measurements revealed the required injectability and self-healing ability, which contributed to its application in rectal administration. The cell assays proved the excellent compatibility and safety of the system, and a possible pathway to form multicellular aggregates. In vitro drug-release studies showed that the hydrogel exhibited good stability in physiological medium, and the drug was almost completely released (more than 90 wt % after 24 h of incubation) in acidic pH and excessive ROS-containing medium, realizing the dual-responsive release of pH/ROS. In vivo activities of the GBR hydrogel showed higher therapeutic efficacy than free rutin in a colitis mice model, and it could significantly inhibit overexpressed inflammatory cytokines, including TNF-α and IL-6. Degradation studies of the hydrogel provided further evidence for the safety of its in vivo application. The work provided a simple strategy to prepare a G-quadruplex drug carrier, which was expected to achieve multi-drug delivery.

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“…A gradual increase in the intensity of the peak around δ = 9 ppm with an increase in temperature is observed. This result suggests that the boronate ester bonds between G and 4-FPBA are the key component of the self-assembled G4NP hydrogel . The imino-boronate ester bonds are crucial for the formation of the G4NP hydrogel.…”

Section: Resultsmentioning

confidence: 80%

Nucleopeptide-Coupled Injectable Bioconjugated Guanosine-Quadruplex Hydrogel with Inherent Antibacterial Activity

Ghosh

Bhowmik

et al. 2023

ACS Appl. Bio Mater.

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The multicomponent reaction-directed self-assembled hydrogels offer the opportunities to fabricate materials with ubiquitous properties which sometimes are not possible to generate from single components. Therefore, multicomponent-derived hydrogels have enormous applications in biomedical fields, and the number of such systems is increasing day by day. Herein, the multicomponent self-assembly techniques have been employed to develop a biomimetic low-molecular-weight G-quadruplex hydrogel under physiological conditions. The bioconjugation of guanosine, 4-formylphenylboronic acid, and cytosine-functionalized nucleopeptide (NP) is important to generate the multicomponent self-assembled dynamic imino-boronate ester-mediated bioconjugated G-quadruplex hydrogels. Using thioflavin T fluorescence assay, powder X-ray diffraction, and circular dichroism spectroscopic techniques, we confirm the existence of a G-quartet-like structure as the key parameter for the formation of nanofibrillar hydrogels. The multicomponent self-assembled G-quadruplex hydrogel possesses excellent inherent antibacterial activity against a broad range of bacterial species. The in vitro cytocompatibility of the synthesized hydrogel was evaluated on MCF-7 and HEK 293T cell lines to study the biocompatibility of the hydrogel. The proposed injectable, biocompatible, and NP-coupled G-quadruplex hydrogel with inherent antibacterial efficiency holds promising importance to prevent localized bacterial infections.

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A guanosine-based 2-formylphenylborate ester hydrogel with high selectivity to K⁺ ions

Abstract: A new self-assembling system prepared from guanosine and 2-formylbenzeneboronic acid showed a high selectivity to potassium ions and has a fluorescent enhancement effect on berberine, which can be used for serum potassium detection.

Cited by 18 publications

References 35 publications

Guanosine Borate Hydrogel and Self-Assembled Nanostructures Capable of Enantioselective Aldol Reaction in Water

Guanosine Borate Hydrogel and Self-Assembled Nanostructures Capable of Enantioselective Aldol Reaction in Water

Rutin-Loaded Stimuli-Responsive Hydrogel for Anti-Inflammation

Nucleopeptide-Coupled Injectable Bioconjugated Guanosine-Quadruplex Hydrogel with Inherent Antibacterial Activity

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A guanosine-based 2-formylphenylborate ester hydrogel with high selectivity to K+ ions

Abstract: A new self-assembling system prepared from guanosine and 2-formylbenzeneboronic acid showed a high selectivity to potassium ions and has a fluorescent enhancement effect on berberine, which can be used for serum potassium detection.

Cited by 18 publications

References 35 publications

Guanosine Borate Hydrogel and Self-Assembled Nanostructures Capable of Enantioselective Aldol Reaction in Water

Guanosine Borate Hydrogel and Self-Assembled Nanostructures Capable of Enantioselective Aldol Reaction in Water

Rutin-Loaded Stimuli-Responsive Hydrogel for Anti-Inflammation

Nucleopeptide-Coupled Injectable Bioconjugated Guanosine-Quadruplex Hydrogel with Inherent Antibacterial Activity

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A guanosine-based 2-formylphenylborate ester hydrogel with high selectivity to K⁺ ions