A Novel Glucose/pH Responsive Low-Molecular-Weight Organogel of Easy Recycling

Zhou, Chaoyu; Gao, Wenxia; Yang, Kaiwen; Xu, Long; Ding, Jinchang; Chen, Jiuxi; Liu, Miaochang; Huang, Xiaobo; Wang, Shun; Wu, Haixia

doi:10.1021/la4033578

Cited by 48 publications

(21 citation statements)

References 52 publications

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“…Given that at emperature of 100 8Ci st he gel-tosol transition point of GO,t he 1 HNMR spectra suggest that weak p-p stacking exists in the gel state. [81,82] The signal assigned to the amide (NH) proton Hc experiencesaslight up-shield shift as the temperature was raised from 40 (d = 8.028 ppm) to 80 8C( d = 8.025 ppm). Additionally,t he signal pattern was furtherb roadened between 100 and 120 8Ca nd Hc was shifted upfieldt os ome extent,w hich indicatedd isruption of the hydrogen bondinga te levated temperatures.…”

Section: Resultsmentioning

confidence: 99%

Steric‐Structure‐Dependent Gel Formation, Hierarchical Structures, Rheological Behavior, and Surface Wettability

Cao

Zhao

et al. 2016

Chemistry An Asian Journal

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A series of bicholesteryl-based gelators with different central linker atoms C, N, and O (abbreviated to GC, GN, and GO, respectively) have been designed and synthesized. The self-assembly processes of these gelators were investigated by using gelation tests, field-emission scanning electron microscopy, field-emission transmission electron microscopy, UV/Vis absorption, IR spectroscopy, X-ray diffraction, rheology, and contact-angle experiments. The gelation ability, self-assembly morphology, rheological, and surface-wettability properties of these gelators strongly depend on the central linker atom of the gelator molecule. Specifically, GC and GN can form gels in three different solvents, whereas GO can only form a gel in N,N-dimethylformamide (DMF). Morphologies from nanofibers and nanosheets to nanospheres and nanotubes can be obtained with different central atoms. Gels of GC, GN, and GO formed in the same solvent (DMF) have different tolerances to external forces. All xerogels gave a hydrophobic surface with contact angles that ranged from 121 to 152°. Quantum-chemical calculations indicate that the GC, GN, and GO molecules have very different steric structures. The results demonstrate that the central linker atom can efficiently modulate the molecular steric structure and thus regulate the supramolecular self-assembly process and properties of gelators.

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Section: Resultsmentioning

confidence: 99%

Steric‐Structure‐Dependent Gel Formation, Hierarchical Structures, Rheological Behavior, and Surface Wettability

Cao

Zhao

et al. 2016

Chemistry An Asian Journal

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“…The good gelation capability was due to the chemical structure of gelators. The self-assembly of gelators was driven by the hydrophobic interaction as well as hydrogen bonding and π-π interaction within the gelators [34] as illustrated in Figure 2. The 1 H NMR spectra of gelators with different concentrations were used to explore the formation of hydrogen bonding and π-π interaction.…”

Section: Characteristics Of Gelsmentioning

confidence: 99%

In situ injection of phenylboronic acid based low molecular weight gels for efficient chemotherapy

et al. 2016

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Injectable low molecular weight gels (LMWGs) based on the derivatives of phenylboronic acid were prepared and used as substrates for efficient in situ chemotherapy. The gelators as well as LMWGs were characterized by (1)H NMR, UV-vis, FTIR, MS and SEM. Anticancer drug doxorubicin hydrochloride (DOX) was encapsulated in the gels. The rheological properties and rapid recovery capability of both blank and drug-loaded gels were tested. The LMWGs were non-toxic to both 3T3 fibroblasts and 4T1 breast cancer cells. The gels were formed rapidly after injected in vivo. The in vivo anticancer activities of DOX-loaded LMWGs were investigated in breast cancer bearing mice. The intratumoral injection of DOX loaded LMWGs with dose of 30 mg/kg revealed that the gels could coat around the tumor tissues to release DOX sustainingly and maintain effective DOX concentration for chemotherapy. The systemic toxicity of DOX was reduced significantly with the in situ administration of LMWGs formulations. The injectable LMWGs exhibited excellent therapeutic efficacy and low side effects in local chemotherapy.

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“…It was mainly ascribed to the small molecule of sialic acid, which had a special complexation ability with PBA below its p K a, resulting in this neutral pH‐sensitivity. In addition, a low‐molecular‐weight organogel (LMOG) was used to detect saccharides, which was highly reversible and sensitive to the surrounding environment changes. Under the driving forces of H‐bonding and π–π stacking interactions, PBA‐based LMOGs displayed a distinct sol‐gel phase transition and had a high sensitivity to glucose among seven tested saccharides.…”

Section: Biomolecule‐driven Recognition and Functionmentioning

confidence: 99%

Dynamic Biointerfaces: From Recognition to Function

Chang

Zhang

Qing

et al. 2014

Small

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The transformation of recognition signals into regulating macroscopic behaviors of biological entities (e.g., biomolecules and cells) is an extraordinarily challenging task in engineering interfacial properties of artificial materials. Recently, there has been extensive research for dynamic biointerfaces driven by biomimetic techniques. Weak interactions and chirality are two crucial routes that nature uses to achieve its functions, including protein folding, the DNA double helix, phospholipid membranes, photosystems, and shell and tooth growths. Learning from nature inspires us to design dynamic biointerfaces, which usually take advantage of highly selective weak interactions (e.g., synergetic chiral H-bonding interactions) to tailor their molecular assemblies on external stimuli. Biomolecules can induce the conformational transitions of dynamic biointerfaces, then drive a switching of surface characteristics (topographic structure, wettability, etc.), and eventually achieve macroscopic functions. The emerging progresses of dynamic biointerfaces are reviewed and its role from molecular recognitions to biological functions highlighted. Finally, a discussion is presented of the integration of dynamic biointerfaces with the basic biochemical processes, possibly solving the big challenges in life science.

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A Novel Glucose/pH Responsive Low-Molecular-Weight Organogel of Easy Recycling

Cited by 48 publications

References 52 publications

Steric‐Structure‐Dependent Gel Formation, Hierarchical Structures, Rheological Behavior, and Surface Wettability

Steric‐Structure‐Dependent Gel Formation, Hierarchical Structures, Rheological Behavior, and Surface Wettability

In situ injection of phenylboronic acid based low molecular weight gels for efficient chemotherapy

Dynamic Biointerfaces: From Recognition to Function

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