Reversible photo-responsive vesicle based on the complexation between an azobenzene containing molecule and α-cyclodextrin

Liu, Jianjia; Liang, Yan; Wang, Jie; Li, Tao; Zhao, Hanqing; Li, Li; Lincoln, Stephen F.; Prud'homme, Robert Krafft; Guo, Xuhong

doi:10.1039/c5ra04597e

Cited by 9 publications

(11 citation statements)

References 53 publications

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“…For the initial solution, the cross-peaks highlighted by black squares are contributed to the dipolar interactions between the signals in the range of 3.34–3.24 ppm assigned to the protons of β-CD and the peaks at 4.20 and 4.78 ppm ascribed to Fc group, indicating that Fc is embedded in the cavity of β-CD and confirming the formation of the Fc@β-CD SAP . After oxidation of Fc by Fe 2 (SO 4 ) 3 , a weak cross signal of β-CD and a series peaks from 7.26 to 7.76 ppm of trans -Azo group can be seen, as shown in Figure B, indicating that most of trans -Azo groups have been included in the cavity of β-CDs to form Azo@β-CD SAP . The result can be interpreted as follows: β-CDs will dissociate from the Fc group of the Fc@β-CD SAP after Fc is converted into Fc + due to its cationic nature and then the majority of β-CDs will include with trans -Azo groups.…”

Section: Resultsmentioning

confidence: 77%

“…It is therefore interesting to study the inclusion interactions to form Azo@β-CD SAP. 38 The result can be interpreted as follows: β-CDs will dissociate from the Fc group of the Fc@β-CD SAP after Fc is converted into Fc + due to its cationic nature 39 and then the majority of β-CDs will include with trans-Azo groups. Theoretically, C 11 alkyl chain will be embedded in the cavity of β-CD to form inclusion complex of C 11 @β-CD SAP after Fc + C 11 trans-AzoPEG is further exposed to UV irradiation because both Fc + and cis-Azo groups cannot be included by β-CD.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Controlled Self-Assembly of Multiple-Responsive Superamphiphilc Polymers Based on Host–Guest Inclusions of a Modified PEG with β-Cyclodextrin

Kang

Chang

et al. 2018

Langmuir

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Superamphiphilic polymers (SAPs) constructed by host-guest inclusion can self-assemble into various nanostructures in solution, which can find applications in many fields such as nanodevices, drug delivery, and template synthesis. Herein, we report the controlled self-assembly of multiple-responsive SAP based on a selective host-guest inclusion of β-cyclodextrin (β-CD) with a modified poly(ethylene glycol) (PEG) (FcCAzoPEG) consisting of a ferrocene (Fc) end group, a C alkyl chain, an azobenzene (Azo) block, and a poly(ethylene glycol)methyl ether (PEG) chain. These SAPs can self-assemble into interesting nanostructures in water upon exposure to different stimuli because β-CD can be selectively included with different guests, such as Fc, Azo, and C alkyl chain, under different stimuli. The inclusion complex of Fc with β-CD (Fc@β-CD SAP) can form nanowire micelles in aqueous solution. The nanowire micelles can be transformed into spindle micelles with the addition of oxidant because the majority of β-CDs dissociated from the complex Fc@β-CD SAP due to a conversion of Fc to Fc and will preferentially include with Azo group to form another dominant inclusion complex (Azo@β-CD SAP). After UV irradiation, the spindle micelles can be further transformed into spherical micelles because most of β-CDs are excluded from the complex Azo@β-CD SAP due to a trans- to cis-Azo conversion and then form a dominant inclusion complex with C alkyl chains (C@β-CD SAP). This work not only demonstrates the selective host-guest inclusion of stimuli-responsive groups modified PEG with β-CD but also provides a useful approach for construction of diverse morphologies.

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Section: Resultsmentioning

confidence: 77%

Section: ■ Results and Discussionmentioning

confidence: 99%

Controlled Self-Assembly of Multiple-Responsive Superamphiphilc Polymers Based on Host–Guest Inclusions of a Modified PEG with β-Cyclodextrin

Kang

Chang

et al. 2018

Langmuir

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“…A rapid, time-sensitive, and site-sensitive response can be achieved without additives. In previous reports, the photoisomerizations of azobenzene [21][22][23][24][25][26] and stilbene derivatives [27][28][29] tethered to the surface of nanoparticles have been investigated. Based on the structural changes triggered by the light irradiation, the dispersion states were controlled.…”

Section: Introductionmentioning

confidence: 99%

Control of interparticle spacing in stable aggregates of gold nanoparticles by light irradiation

Tanaka

Naka

Miyoshi

et al. 2015

Polym J

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This study describes the modulation of interparticle distances in aggregates of gold nanoparticles by light irradiation. Stable aggregates of a series of imidazolium-presenting gold nanoparticles were obtained via a photo-responsive mono-carboxylate linker. In the first step, the mono-carboxylate linker attracted the gold nanoparticles to form water-dispersive aggregates of gold nanoparticles with hydrophobic surface properties. By irradiating the aggregates with ultraviolet, the photo-responsive linker was transformed, leading to the generation of another carboxyl group. As a result, the gold nanoparticles were tightly bound via the dicarboxylate linkers. These changes decreased the interparticle distances in the aggregates, as verified by microscopic observations, and can induce significant changes in their optical characteristics. To the best of our knowledge, this is the first example of a light-driven manipulation system for the distribution of nanoparticles in an aggregate. INTRODUCTIONThe physical properties of metal nanoparticles strongly depend on their assembled states. It is known that an assembly of gold nanoparticles has different light-absorption properties to that of single particles. 1,2 Based on this phenomenon, a wide variety of biomedical applications has been accomplished. 3,4 In addition, by manipulating the hybridization process involved in anchoring DNA to the surface of particles, cluster formation and morphology can be precisely controlled. 5-7 These manipulation methods for the nanoparticle assembly are versatile and can be used to construct biosensors with good response to stimuli. 8,9 Furthermore, additional functions have been derived from the specific distribution of nanoparticles in an assembly. For instance, a class of unique optical functional materials involving metamaterials has been manufactured with a well-ordered assembly of gold nanoparticles. 10-13 Therefore, precisely controlling the morphology and relative positions of nanoparticles in an assembly is critically important to obtain superior or unexpected functions. [14][15][16][17][18][19][20] Structural manipulation with light has various advantages. A rapid, time-sensitive, and site-sensitive response can be achieved without additives. In previous reports, the photoisomerizations of azobenzene 21-26 and stilbene derivatives 27-29 tethered to the surface of nanoparticles have been investigated. Based on the structural changes triggered by the light irradiation, the dispersion states were controlled. The aggregation/dispersion of gold nanoparticles can also be modulated reversibly by the photo-triggered dimerization of thymine and the splitting of the thymine dimer. 30 Although the formation of aggregates can be controlled with various methods, as mentioned here, modulating the morphology of the aggregates is less well established.

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“…13−15 Common noncovalent interactions include hydrogen bonding, 16 coordination interaction, 17,18 electrostatic interaction, 19,20 and host−guest interaction. 21−23 The inclusion complex between host and guest is regarded as one important type to form amphiphile polymers, which endow assemblies with responsive characteristics with respect to pH, 10 light, 24,25 and voltage. 26,27 Among these, voltage response has attracted a lot of attention in the context of controlled drug release systems because the electric potential is considered as a "green" method.…”

Section: Introductionmentioning

confidence: 99%

“…Common noncovalent interactions include hydrogen bonding, coordination interaction, , electrostatic interaction, , and host–guest interaction. − The inclusion complex between host and guest is regarded as one important type to form amphiphile polymers, which endow assemblies with responsive characteristics with respect to pH, light, , and voltage. , Among these, voltage response has attracted a lot of attention in the context of controlled drug release systems because the electric potential is considered as a “green” method. Moreover, voltage stimuli generated by microdevices can be applied in vivo , and parameters like the potential, current, and duration of electric trigger can be simply controlled by a suitable electrochemical workstation .…”

Section: Introductionmentioning

confidence: 99%

Redox-Controlled Voltage Responsive Micelles Assembled by Noncovalently Grafted Polymers for Controlled Drug Release

Yuan

Wang

et al. 2019

Macromolecules

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Voltage responsive micelles prepared from noncovalently grafted amphiphilic polymers were reported. The noncovalent amphiphilic polymers were prepared through the host–guest interaction between β-cyclodextrin (β-CD) grafted dextran (Dex-CD) and ferrocene (Fc) terminated poly(ε-caprolactone) (PCL-Fc). Because of the presence of Fc groups, the inclusion complex between Fc and β-CD can be reversibly controlled by an external stimulating voltage, leading to reversible formation and disassembly of the micelles. The occurrence of the inclusion complex between Fc and β-CD was confirmed by cyclic voltammetry (CV) and the 2D NOESY spectrum. Furthermore, meloxicam was selected as a model drug to test the controlled release performance of these voltage responsive micelles. It was found that the release rate and the final cumulative release amount of meloxicam can be effectively controlled by the external voltage, which may be of use in controlled drug delivery.

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Reversible photo-responsive vesicle based on the complexation between an azobenzene containing molecule and α-cyclodextrin

Abstract: Reversible spherical vesicles were constructed by the self-assembly of an amphiphilic molecule (Azo-Cl). With equimolar α-cyclodextrin (α-CD), the vesicles formation and destruction could be controlled by alternating UV-vis irradiation.

Cited by 9 publications

References 53 publications

Controlled Self-Assembly of Multiple-Responsive Superamphiphilc Polymers Based on Host–Guest Inclusions of a Modified PEG with β-Cyclodextrin

Controlled Self-Assembly of Multiple-Responsive Superamphiphilc Polymers Based on Host–Guest Inclusions of a Modified PEG with β-Cyclodextrin

Control of interparticle spacing in stable aggregates of gold nanoparticles by light irradiation

Redox-Controlled Voltage Responsive Micelles Assembled by Noncovalently Grafted Polymers for Controlled Drug Release

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