Construction of coumarin-based cross-linked micelles with pH responsive hydrazone bond and tumor targeting moiety

Long, Yubo; Gu, Wenxing; Pang, Chengcai; Ma, Jianbiao; Gao, Hui

doi:10.1039/c5tb02729b

Cited by 41 publications

(21 citation statements)

References 40 publications

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“…Additionally, as analysed in the previous section, coumarin-based fluorescent probes in controlled delivery processes with polyurethanes have been reported. Then, photo-responsive polyurethane micellar drug delivery systems have also been studied [103]. Based on previous work developing light cross-linkable and pH de-cross-linkable drug nanocarriers by attaching 7-((4-15 oxopentyl)oxy)-4-methylcoumarin to poly(ethylene-glycol)-poly(hydrazine)aspartamide block polymer [104], active polyurethane micelles were synthesised.…”

Section: Controlled Drug Deliverymentioning

confidence: 99%

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Coumarins into Polyurethanes for Smart and Functional Materials

et al. 2020

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Polyurethanes are of undoubted interest for the scientific community and the industry. Their outstanding versatility from tailor-made structures turns them into major polymers for use in a wide range of different applications. As with other polymers, new, emerging molecules and monomers with specific attributes can provide new functions and capabilities to polyurethanes. Natural and synthetic coumarin and its derivatives are characterised by interesting biological, photophysical and photochemical properties. Then, the polyurethanes can exploit those features of many coumarins which are present in their composition to achieve new functions and performances. This article reviews the developments in the proper use of the special properties of coumarins in polyurethanes to produce functional and smart materials that can be suitable for new specific applications.

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Section: Controlled Drug Deliverymentioning

confidence: 99%

“…Schematic structure of polyurethane functionalised with a photo-crosslinkable coumarin derivative and folic acid. Reproduced from[103] with permission from the Royal Society of Chemistry.…”

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confidence: 99%

Coumarins into Polyurethanes for Smart and Functional Materials

et al. 2020

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“…Due to limitations of SCL micelles as carriers, core cross‐linked (CCL) micelles, and/or interlayer cross‐linked (ILCL) micelles have been reported to be promising materials as stable drug or organic–inorganic material carriers . Cross‐linked micelles (CLMs) have been reported from various functional monomers with radical polymerization, photodimerization, and other reactions . Most common method is the usage of a cross‐linker agent such as azide or alkyne (click chemistry), 1,2‐bis(2‐iodoethoxy)‐ethane, divinyl sulfone, diamine, dialdehyde, and dicarboxylic acid to react with the functional groups in the polymer chain such as halogen, epoxy, hydroxyl, isocyanate, carboxyl, and amine.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Cross‐Linked Micelles from Glycidyl Methacrylate Based Block Copolymers and Their Usages as Nanoreactors in the Preparation of Gold Nanoparticles

Koçak

Solmaz

Dikmen

et al. 2017

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

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This study reports the synthesis of poly(ethylene glycol)methyl ether‐block‐poly(glycidyl methacrylate) (MPEG‐b‐PGMA) diblock, and poly(ethylene glycol)methyl ether‐block‐poly(glycidyl methacrylate)‐block‐poly(methyl methacrylate) (MPEG‐b‐PGMA‐b‐PMMA) triblock copolymers via atom transfer radical polymerization and their self‐assembly behaviors in aqueous media by using acetone as cosolvent. These block copolymers formed near monodisperse core–shell micelles having cross‐linkable cores. Two types of cross‐linked micelles, namely spherical MPEG‐b‐PGMA core cross‐linked (CCL) micelles and MPEG‐b‐PGMA‐b‐PMMA interlayer cross‐linked (ILCL) micelles, were also successfully prepared from these block copolymers by using various bifunctional cross‐linkers such as hexamethylenediamine (HMDA), ethylenediamine (EDA), and 2‐aminoethanethiol (AET). Cross‐linking was successfully carried out via ring‐opening reactions of epoxy residues of hydrophobic‐cores with primary amine or thiol groups of bifunctional cross‐linkers. Finally, these cross‐linked micelles were successfully used as nanoreactors in the synthesis of gold nanoparticles (AuNPs) in aqueous media. Both CCL and ILCL micelles were found to be good stabilizers for AuNPs in aqueous media. Both CCL‐ and ILCL‐stabilized AuNP dispersions were stable for a long time without any size changes and flocculation at room temperature. These cross‐linked stabilized AuNPs exhibited good catalytic activities in the reduction of p‐nitrophenol. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 514–526.

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“…These micellar formulations improve upon the inherent poor water solubility of anticancer drugs . In addition to increasing soluble concentrations, these micellar formulations also provide therapeutic benefits, including prolonged in vivo circulation time, designable versatility via decorating functionalities, tunable drug release profiles, stimuli‐responsive release properties, targeting ability, improved drug bioavailability, and enhanced drug accumulation in tumor tissues via the enhanced permeability and retention (EPR) effect . More importantly, degradable ester, amide, and anhydride bonds can be incorporated into amphiphilic copolymer precursors, thereby conferring biodegradability to the resultant micellar carriers .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Polylactide‐Based Core–Shell Interface Cross‐Linked Micelles for Anticancer Drug Delivery

Chen

Lin

Hsia

et al. 2016

Macromolecular Bioscience

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Well-defined poly(ethylene glycol)-b-allyl functional polylactide-b-polylactides (PEG-APLA-PLAs) are synthesized through sequential ring-opening polymerization. PEG-APLA-PLAs that have amphiphilic properties and reactive allyl side chains on their intermediate blocks are successfully transferred to core-shell interface cross-linked micelles (ICMs) by micellization and UV-initiated irradiation. ICMs have demonstrated enhanced colloidal stability in physiological-mimicking media. Hydrophobic molecules such as Nile Red or doxorubicin (Dox) are readily loaded into ICMs; the resulting drug-ICM formulations possess slow and sustained drug release profiles under physiological-mimicking conditions. ICMs exhibit negligible cytotoxicity in human uterine sarcoma cancer cells by using biodegradable aliphatic polyester as the hydrophobic segments. Relative to free Dox, Dox-loaded ICMs show a reduced cytotoxicity due to the late intracellular release of Dox from ICMs. Overall, ICMs represent a new type of biodegradable cross-linked micelle and can be employed as a promising platform for delivering a broad variety of hydrophobic drugs.

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Construction of coumarin-based cross-linked micelles with pH responsive hydrazone bond and tumor targeting moiety

Abstract: Responsive cross-linked micelles (x-micelles) based on polyurethane with photo-responsive coumarin derivatives and pH-responsive hydrazone groups were synthesized.

Cited by 41 publications

References 40 publications

Coumarins into Polyurethanes for Smart and Functional Materials

Coumarins into Polyurethanes for Smart and Functional Materials

Preparation of Cross‐Linked Micelles from Glycidyl Methacrylate Based Block Copolymers and Their Usages as Nanoreactors in the Preparation of Gold Nanoparticles

Synthesis of Polylactide‐Based Core–Shell Interface Cross‐Linked Micelles for Anticancer Drug Delivery

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