Self-assembly of supra-amphiphile of azobenzene-galactopyranoside based on dynamic covalent bond and its dual responses

Wang, Tian-Nan; Yang, Guang; Wu, Libin; Chen, Guosong

doi:10.1016/j.cclet.2016.05.009

Cited by 7 publications

(4 citation statements)

References 21 publications

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“…Precursors 1,1,2,2-tetrakis(4-(4-bromobutoxy)phenyl)ethene (T2), (E)-1-(4-(4-bromobutoxy)phenyl)-2-phenyldiazene (A2), and CB [8] were synthesized according to literature procedures. [54][55][56][57][58]…”

Section: General Informationmentioning

confidence: 99%

Dual‐Stimuli Responsive 2D Supramolecular Organic Framework for the Detection of Azoreductase Activity

Zhang

Liang

Yang

2019

Chemistry A European J

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A 2D supramolecular organic framework (SOF) based on synthetic macrocycles has been constructed in water by a self‐assembly strategy. Two new organic monomers of this SOF, possessing viologen and azobenzene functional groups, form a stimuli‐responsive host–guest system upon cooperatively binding with cucurbit[8]uril rings. The reversible formation and dissociation of 2D SOF can be realized by the isomerization of azobenzene under ultraviolet and visible light. The light‐responsive property of the SOF is highly reversible and stable for up to four cycles. Moreover, azoreductase produced by Escherichia coli can reduce the N=N double bond of azobenzene entities, resulting in fluorescence recovery of the system. As an excellent and effective fluorescent probe, the SOF can detect azoreductase activity for real‐time monitoring of the growth process of Escherichia coli. The dual‐stimuli responsive 2D SOF is envisioned to drive the development of responsive devices with complex functions.

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Section: General Informationmentioning

confidence: 99%

Dual‐Stimuli Responsive 2D Supramolecular Organic Framework for the Detection of Azoreductase Activity

Zhang

Liang

Yang

2019

Chemistry A European J

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“…773 A supramolecular amphiphile with a Gal headgroup and a distal azobenzene group has demonstrated photoswitchable properties. 774…”

Section: Chemical Reviewsmentioning

confidence: 99%

“…Maltose-based azobenzene-containing glycolipids were designed as photosenstitive supramolecular gelators . A supramolecular amphiphile with a Gal headgroup and a distal azobenzene group has demonstrated photoswitchable properties …”

Section: Labeled Glycolipid Analoguesmentioning

confidence: 99%

Synthetic Strategies for Modified Glycosphingolipids and Their Design as Probes

et al. 2018

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The plasma membrane of cells contains a diverse array of lipids that provide important structural and biological features. Glycolipids are typically a minor component of the cell membrane and consist primarily of glycosphingolipids (GSLs). GSLs in vertebrates contain a multifarious assortment of glycan headgroups, which can be important to biological functions based on lipid-lipid and lipid-protein interactions. The design of probes to study these complex targets requires advanced synthetic methodologies. In this Review, we will discuss recent advances in chemical and chemoenzymatic synthesis of GSLs in conjunction with the use of these approaches to design new probes. Examples using either chemical or enzymatic semisynthesis methods starting from isolated GSLs will also be reviewed. Focusing primarily on vertebrate glycolipids, we will highlight examples of radionuclide, fluorophore, photoresponsive, and bioorthogonal tagged GSL probes.

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“…Molecular photoswitches are potent tools for manipulating and studying biological systems. − Among the photochromic molecules, azobenzenes are extensively employed due to their remarkable capacity to undergo substantial alterations in geometry and polarity upon photoswitching. − Moreover, these molecules can be cleaved within hypoxic environments, rendering them highly promising contenders for photoswitching in combination with photodynamic and chemotherapeutic treatments. − While molecular photoswitches offer the capability of switching, supramolecular assembly expands upon this concept by facilitating the creation of larger, structurally diverse assemblies. Self-assembled supramolecular nanomaterials of amphiphilic molecules have found extensive applications in nanotechnology and biomedical engineering due to their unique properties, including sensors, batteries, catalysts, and drug delivery. − This integration can lead to synergistic effects and the emergence of new functionalities, combining the advantages of molecular photoswitching with the structural diversity and functionality of supramolecular assemblies.…”

mentioning

confidence: 99%

Well-Defined Oligo(azobenzene-graft-mannose): Photostimuli Supramolecular Self-Assembly and Immune Effect Regulation

Guo,

Wang,

et al. 2024

ACS Macro Lett.

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The immune system can recognize and respond to pathogens of various shapes. Synthetic materials that can change their shape have the potential to be used in vaccines and immune regulation. The ability of supramolecular assemblies to undergo reversible transformations in response to environmental stimuli allows for dynamic changes in their shapes and functionalities. A meticulously designed oligo(azobenzene-graf t-mannose) was synthesized using a stepwise iterative method and "click" chemistry. This involved integrating hydrophobic and photoresponsive azobenzene units with hydrophilic and bioactive mannose units. The resulting oligomer, with its precise structure, displayed versatile assembly morphologies and chiralities that were responsive to light. These varying assembly morphologies demonstrated distinct capabilities in terms of inhibiting the proliferation of cancer cells and stimulating the maturation of dendritic cells. These discoveries contribute to the theoretical comprehension and advancement of photoswitchable bioactive materials.

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Self-assembly of supra-amphiphile of azobenzene-galactopyranoside based on dynamic covalent bond and its dual responses

Cited by 7 publications

References 21 publications

Dual‐Stimuli Responsive 2D Supramolecular Organic Framework for the Detection of Azoreductase Activity

Dual‐Stimuli Responsive 2D Supramolecular Organic Framework for the Detection of Azoreductase Activity

Synthetic Strategies for Modified Glycosphingolipids and Their Design as Probes

Well-Defined Oligo(azobenzene-graft-mannose): Photostimuli Supramolecular Self-Assembly and Immune Effect Regulation

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