A Light-Responsive Self-Assembly Formed by a Cationic Azobenzene Derivative and SDS as a Drug Delivery System

Geng, Shengyong; Wang, Yuzhu; Wang, Liping; Kouyama, Tsutomu; Gotoh, Toshiyuki; Wada, Satoshi; Wang, Jin‐Ye

doi:10.1038/srep39202

Cited by 59 publications

(40 citation statements)

References 69 publications

(89 reference statements)

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“…Although this method is less specific than the covalent approach, the relatively weak non‐covalent interactions still allow for driving affinity to various bio‐interfaces, while ensuring full reversibility and much lower invasiveness. For instance, the ability of amphiphilic azobenzenes to intercalate spontaneously in model artificial membranes and micelles has been used to guide their internalization into these systems, mostly to study intrinsic membrane properties,15,31 to build up photoresponsive cargos for drug delivery applications,32,33 or to provide novel antibacterial systems 25. Very recently a new amphiphilic azobenzene molecule named ZIAPIN2 has been introduced.…”

Section: Figurementioning

confidence: 99%

Membrane Environment Enables Ultrafast Isomerization of Amphiphilic Azobenzene

et al. 2020

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The non‐covalent affinity of photoresponsive molecules to biotargets represents an attractive tool for achieving effective cell photo‐stimulation. Here, an amphiphilic azobenzene that preferentially dwells within the plasma membrane is studied. In particular, its isomerization dynamics in different media is investigated. It is found that in molecular aggregates formed in water, the isomerization reaction is hindered, while radiative deactivation is favored. However, once protected by a lipid shell, the photochromic molecule reacquires its ultrafast photoisomerization capacity. This behavior is explained considering collective excited states that may form in aggregates, locking the conformational dynamics and redistributing the oscillator strength. By applying the pump probe technique in different media, an isomerization time in the order of 10 ps is identified and the deactivation in the aggregate in water is also characterized. Finally, it is demonstrated that the reversible modulation of membrane potential of HEK293 cells via illumination with visible light can be indeed related to the recovered trans→cis photoreaction in lipid membrane. These data fully account for the recently reported experiments in neurons, showing that the amphiphilic azobenzenes, once partitioned in the cell membrane, are effective light actuators for the modification of the electrical state of the membrane.

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Section: Figurementioning

confidence: 99%

Membrane Environment Enables Ultrafast Isomerization of Amphiphilic Azobenzene

et al. 2020

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“…Their numerous technological and bio-related applications emerge due to the UV/Vis light-induced reversible trans-cis-trans isomerization. They can be employed as containers with photosensitive lock for delivery and release of drugs into cells [ 16 ], in biofilms, photoresponsive DNA thermotropic liquid crystals [ 17 ], for photoregulated antibacterial activity, and biological photocontrol [ 17 , 18 , 19 , 20 ]. The light-controlled reversible DNA packaging is well studied when using azobenzene-containing surfactants [ 1 , 5 , 11 , 21 , 22 , 23 ].…”

Section: Introductionmentioning

confidence: 99%

DNA Interaction with Head-to-Tail Associates of Cationic Surfactants Prevents Formation of Compact Particles

et al. 2018

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Cationic azobenzene-containing surfactants are capable of condensing DNA in solution with formation of nanosized particles that can be employed in gene delivery. The ratio of surfactant/DNA concentration and solution ionic strength determines the result of DNA-surfactant interaction: Complexes with a micelle-like surfactant associates on DNA, which induces DNA shrinkage, DNA precipitation or DNA condensation with the emergence of nanosized particles. UV and fluorescence spectroscopy, low gradient viscometry and flow birefringence methods were employed to investigate DNA-surfactant and surfactant-surfactant interaction at different NaCl concentrations, [NaCl]. It was observed that [NaCl] (or the Debye screening radius) determines the surfactant-surfactant interaction in solutions without DNA. Monomers, micelles and non-micellar associates of azobenzene-containing surfactants with head-to-tail orientation of molecules were distinguished due to the features of their absorption spectra. The novel data enabled us to conclude that exactly the type of associates (together with the concentration of components) determines the result of DNA-surfactant interaction. Predomination of head-to-tail associates at 0.01 M < [NaCl] < 0.5 M induces DNA aggregation and in some cases DNA precipitation. High NaCl concentration (higher than 0.8 M) prevents electrostatic attraction of surfactants to DNA phosphates for complex formation. DAPI dye luminescence in solutions with DNA-surfactant complexes shows that surfactant tails overlap the DNA minor groove. The addition of di- and trivalent metal ions before and after the surfactant binding to DNA indicate that the bound surfactant molecules are located on DNA in islets.

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“…Among the external stimuli, light has attracted special attention due to ease of production, noninvasive nature, controllable intensity, and spatially confined application for finely controlled durations [15–19]. Thus, light has been utilized in an abundance of applications for intelligent targeted delivery systems that can provide control of treatment processes and allow for transport and release of drugs at disease sites [20–22].…”

Section: Introductionmentioning

confidence: 99%

Photo-controlled release of paclitaxel and model drugs from RNA pyramids

Zhang

et al. 2018

Nano Res.

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Stimuli-responsive release of drugs from a nanocarrier in spatial-, temporal-, and dosage-controlled fashions is of great interest in the pharmaceutical industry. Paclitaxel is one of the most effective and popular chemotherapeutic drugs against a number of cancers such as metastatic or nonmetastatic breast cancer, non–small cell lung cancer, refractory ovarian cancer, AIDS-related Kaposi’s sarcoma, and head and neck cancers. Here, by taking the advantage of RNA nanotechnology in biomedical and material science, we developed a three-dimensional pyramid-shaped RNA nanocage for a photocontrolled release of cargo, using paclitaxel as a model drug. The light-triggered release of paclitaxel or fluorophore Cy5 was achieved by incorporation of photocleavable spacers into the RNA nanoparticles. Upon irradiation with ultraviolet light, cargos were rapidly released (within 5 min). In vitro treatment of breast cancer cells with the RNA nanoparticles harboring photocleavable paclitaxel showed higher cytotoxicity as compared to RNA nanoparticles without the photocleavable spacer. The methodology provides proof of concept for the application of the light-triggered controlled release of drugs from RNA nanocages.

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A Light-Responsive Self-Assembly Formed by a Cationic Azobenzene Derivative and SDS as a Drug Delivery System

Cited by 59 publications

References 69 publications

Membrane Environment Enables Ultrafast Isomerization of Amphiphilic Azobenzene

Membrane Environment Enables Ultrafast Isomerization of Amphiphilic Azobenzene

DNA Interaction with Head-to-Tail Associates of Cationic Surfactants Prevents Formation of Compact Particles

Photo-controlled release of paclitaxel and model drugs from RNA pyramids

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