Photo-responsive reversible micelles based on azobenzene-modified poly(carbonate)s via azide–alkyne click chemistry

Ding, Hongyan; Li, Yefei; Niu, Yile; Li, Ling; He, Jian; Liu, Xiangyu; Xia, Xinnian; Lu, Yanbing; Xiong, Yan; Xu, Weijian

doi:10.1039/c4ra07345b

Cited by 38 publications

(29 citation statements)

References 43 publications

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“…1,8‐Diazabicyclo[5.4.0] undec‐7‐ene (DBU) and 2‐chloro‐ N , N ‐diethylethylamine hydrochloride were bought from Energy Chemical. 4‐(4‐Azidebutyloxy)−4'‐trifluoromethoxy‐azobenzene (Azo‐N 3 ) was prepared as reported previously . All other reagents and solvents were purchased from Sinopharm Chemical Reagent, China and used as received.…”

Section: Methodsmentioning

confidence: 99%

“…However, limited reports regarding the synthesis of light‐responsive poly(carbonate)s based on Azo have been explored. We have previously developed a type of photo‐induced reversible poly(carbonate)s PMPC‐Azo by covalent binding of the Azo photochromic moieties to the main chain . But polymeric nanoparticles just dealing with response to single stimulus were not sufficient enough to meet the need of triggering drug release in tumor tissues exactly.…”

Section: Introductionmentioning

confidence: 99%

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Light and pH dual‐sensitive biodegradable polymeric nanoparticles for controlled release of cargos

Xia

Zeng

Ding

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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In this article, a light and pH dual‐sensitive block copolymer PEG‐b‐poly(MPC‐Azo/DEA) was facilely prepared for the first time by azide‐alkyne click chemistry between amphiphilic block copolymer bearing pendant alkynyl group poly(ethylene glycol)‐poly(5‐methyl‐5‐propargylxycarbonyl‐1,3‐dioxane‐2‐one) (PEG‐b‐poly(MPC)) and two azide‐containing compounds azobenzene derivative (Azo‐N3) and 2‐azido‐1‐ethyl‐diethylamine (DEA‐N3). Light response of the polymeric nanoparticles benefits from the azobenzene segments and pH responsiveness is attributed to DEA moieties. The prepared copolymer could self‐assemble into spherical micelle particles. The morphological changes of these particles in response to dual stimuli were investigated by UV/vis spectroscopy, dynamic light scattering (DLS), and transmission electron microscopy (TEM). Nile Red (NR) was utilized as probe, and fluorescence spectroscopy was served as an evidence for the enhanced release of cargos from polymeric nanoparticles under combined stimulation. Anticancer drug, DOX was loaded into the nanoparticles and the loaded‐DOX could be released from these nanoparticles under dual stimuli. MTT assays further demonstrated that PEG‐b‐poly(MPC) and PEG‐b‐poly(MPC‐Azo/DEA) were of biocompatibility and low toxicity against HepG2 cells as well as SMCC‐7721 cells. More importantly, the prepared DOX‐loaded nanoparticles exhibited good anticancer ability for the two cells. The synthesized light and pH dual‐sensitive biodegradable polymeric nanoparticles were expected to be platforms for precisely controlled release of encapsulated molecules. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 1773–1783

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Light and pH dual‐sensitive biodegradable polymeric nanoparticles for controlled release of cargos

Xia

Zeng

Ding

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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“…By exploiting ring‐opening polymerization (ROP) and alkyne–azide click reaction, Lu et al reported a nanoscale polymer micelle based on PEO‐modified amphiphilic polycarbonate with AZO side chains (PTMC‐azo) for drug delivery ( Figure a) . The polymer micelles were formed by mixing copolymer within aqueous solution, allowed hydrophobic drugs (NR as the model drug) in the hydrophobic core.…”

Section: Uv/vis Light Controlled Drug Delivery Systemsmentioning

confidence: 99%

“…UV–vis spectra of the PTMC‐azo micelles upon irradiation with b) 365 nm UV light for the drug release and with c) 450 nm visible light for the drug re‐encapsulation. Reproduced with permission . Copyright 2014, Royal Society of Chemistry.…”

Section: Uv/vis Light Controlled Drug Delivery Systemsmentioning

confidence: 99%

Remote Light‐Responsive Nanocarriers for Controlled Drug Delivery: Advances and Perspectives

Zhao

Wang

et al. 2019

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Engineering of smart photoactivated nanomaterials for targeted drug delivery systems (DDS) has recently attracted considerable research interest as light enables precise and accurate controlled release of drug molecules in specific diseased cells and/or tissues in a highly spatial and temporal manner. In general, the development of appropriate light‐triggered DDS relies on processes of photolysis, photoisomerization, photo‐cross‐linking/un‐cross‐linking, and photoreduction, which are normally sensitive to ultraviolet (UV) or visible (Vis) light irradiation. Considering the issues of poor tissue penetration and high phototoxicity of these high‐energy photons of UV/Vis light, recently nanocarriers have been developed based on light‐response to low‐energy photon irradiation, in particular for the light wavelengths located in the near infrared (NIR) range. NIR light‐triggered drug release systems are normally achieved by using two‐photon absorption and photon upconversion processes. Herein, recent advances of light‐responsive nanoplatforms for controlled drug release are reviewed, covering the mechanism of light responsive small molecules and polymers, UV and Vis light responsive nanocarriers, and NIR light responsive nanocarriers. NIR‐light triggered drug delivery by two‐photon excitation and upconversion luminescence strategies is also included. In addition, the challenges and future perspectives for the development of light triggered DDS are highlighted.

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“…Wang et al [20,21], and Jochum and Theato [22] used this reversible polarity shift to fabricate micellar systems that could be disrupted and reformed by controlling UV and visible light illumination. Hu et al [23] demonstrated encapsulation of the model drug Nile Red and the photoresponsive release and re-encapsulation behaviors of amphiphilic azobenzene-modified copolymers with low cell cytotoxicity. There are several other reports on synthesis and function of photoresponsive amphiphilic polymers that are based on the isomerization of azobenzene [24][25][26][27][28].…”

Section: Introductionmentioning

confidence: 98%

Photocontrolled micellar aggregation of amphiphilic DNA-azobenzene conjugates

Lamas

Rastogi

et al. 2015

Colloids and Surfaces B: Biointerfaces

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Photo-responsive reversible micelles based on azobenzene-modified poly(carbonate)s via azide–alkyne click chemistry

Abstract: We provide a convenient method to construct photo-responsive poly(carbonate)s via ring-opening polymerization of cyclic carbonates followed by azide–alkyne click chemistry.

Cited by 38 publications

References 43 publications

Light and pH dual‐sensitive biodegradable polymeric nanoparticles for controlled release of cargos

Light and pH dual‐sensitive biodegradable polymeric nanoparticles for controlled release of cargos

Remote Light‐Responsive Nanocarriers for Controlled Drug Delivery: Advances and Perspectives

Photocontrolled micellar aggregation of amphiphilic DNA-azobenzene conjugates

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