Diselenide Core Cross-Linked Micelles of Poly(Ethylene Oxide)-b-Poly(Glycidyl Methacrylate) Prepared through Alkyne-Azide Click Chemistry as a Near-Infrared Controlled Drug Delivery System

Siboro, Sonita A.P.; Salma, Sabrina Aufar; Kim, Hyeung‐Rak; Jeong, Yeon Tae; Gal, Yeong‐Soon; Lim, Kwon Taek

doi:10.3390/ma13122846

Cited by 12 publications

(4 citation statements)

References 32 publications

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“…However, due to the fluidity similar to that of biofilms, liposomes are easily affected by temperature changes in vivo , resulting in membrane permeability changes and drug leakage. Micelle has a unique cored-shell structure, but compared with other common types of nanomaterials, the drug loading of micelle is usually less, which may make it difficult to exert the expected therapeutic effect of UA ( Siboro et al, 2020 ). Nanocrystals is pure drug nano preparation with a very perfect drug loading capacity, and is easy to scale up production.…”

Section: Current Situation and Future Prospects Of Ua Nanoformulationsmentioning

confidence: 99%

Nanoformulations of Ursolic Acid: A Modern Natural Anticancer Molecule

et al. 2021

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Background: Ursolic acid (UA) is a natural pentacyclic triterpene derived from fruit, herb, and other plants. UA can act on molecular targets of various signaling pathways, inhibit the growth of cancer cells, promote cycle stagnation, and induce apoptosis, thereby exerting anticancer activity. However, its poor water-solubility, low intestinal mucosal absorption, and low bioavailability restrict its clinical application. In order to overcome these deficiencies, nanotechnology, has been applied to the pharmacological study of UA.Objective: In this review, we focused on the absorption, distribution, and elimination pharmacokinetics of UA in vivo, as well as on the research progress in various UA nanoformulations, in the hope of providing reference information for the research on the anticancer activity of UA.Methods: Relevant research articles on Pubmed and Web of Science in recent years were searched selectively by using the keywords and subheadings, and were summarized systematically.Key finding: The improvement of the antitumor ability of the UA nanoformulations is mainly due to the improvement of the bioavailability and the enhancement of the targeting ability of the UA molecules. UA nanoformulations can even be combined with computational imaging technology for monitoring or diagnosis.Conclusion: Currently, a variety of UA nanoformulations, such as micelles, liposomes, and nanoparticles, which can increase the solubility and bioactivity of UA, while promoting the accumulation of UA in tumor tissues, have been prepared. Although the research of UA in the nanofield has made great progress, there is still a long way to go before the clinical application of UA nanoformulations.

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Section: Current Situation and Future Prospects Of Ua Nanoformulationsmentioning

confidence: 99%

Nanoformulations of Ursolic Acid: A Modern Natural Anticancer Molecule

et al. 2021

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“…These results validated the role of diselenide bonds in the shell of the micelles, whose cleavage could be controlled by the NIR exposure. The diselenide bond is cleaved by the ROS produced from ICG during NIR exposure, which disrupts the micellar structure to enhance the DOX release [41,56]. The lower release without NIR exposure under similar conditions resulted from the compactness of the SCL structure because the crosslinked micellar coronas act as a diffusion barrier for the drug [20].…”

Section: Nir-responsive In Vitro Dox Releasementioning

confidence: 99%

Near-Infrared Light-Responsive Shell-Crosslinked Micelles of Poly(d,l-lactide)-b-poly((furfuryl methacrylate)-co-(N-acryloylmorpholine)) Prepared by Diels–Alder Reaction for the Triggered Release of Doxorubicin

et al. 2021

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In the present study, we developed near-infrared (NIR)-responsive shell-crosslinked (SCL) micelles using the Diels–Alder (DA) click reaction between an amphiphilic copolymer poly(d,l-lactide)20-b-poly((furfuryl methacrylate)10-co-(N-acryloylmorpholine)78) (PLA20-b-P(FMA10-co-NAM78)) and a diselenide-containing crosslinker, bis(maleimidoethyl) 3,3′-diselanediyldipropionoate (BMEDSeDP). The PLA20-b-P(FMA10-co-NAM78) copolymer was synthesized by RAFT polymerization of FMA and NAM using a PLA20-macro-chain transfer agent (PLA20-CTA). The DA reaction between BMEDSeDP and the furfuryl moieties in the copolymeric micelles in water resulted in the formation of SCL micelles. The SCL micelles were analyzed by 1H-NMR, FE-SEM, and DLS. An anticancer drug, doxorubicin (DOX), and an NIR sensitizer, indocyanine green (ICG), were effectively incorporated into the SCL micelles during the crosslinking reaction. The DOX/ICG-loaded SCL micelles showed pH- and NIR-responsive drug release, where burst release was observed under NIR laser irradiation. The in vitro cytotoxicity analysis demonstrated that the SCL was not cytotoxic against normal HFF-1 cells, while DOX/ICG-loaded SCL micelles exhibited significant antitumor activity toward HeLa cells. Thus, the SCL micelles of PLA20-b-P(FMA10-co-NAM78) can be used as a potential delivery vehicle for the controlled drug release in cancer therapy.

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“…Core-cross-linked (CCL) micelles, on the other hand, have gained a lot of attention in the drug delivery field recently because of the many benefits they offer over conventional polymeric micelles, including improved colloidal stability, biocompatibility, drug-loading, stimuli control, and prolonged drug release [11][12][13]. The most common techniques for generating CCL micelles include radical polymerization, disulfide bridges, photo crosslinking, bifunctional cross-linkers, and the Diels-Alder (DA) reaction [14][15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%

Redox-Responsive Comparison of Diselenide and Disulfide Core-Cross-Linked Micelles for Drug Delivery Application

Yadav

Ramesh²,

Obireddy

et al. 2023

Pharmaceutics

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In this study, diselenide (Se–Se) and disulfide (S–S) redox-responsive core-cross-linked (CCL) micelles were synthesized using poly(ethylene oxide)2k-b-poly(furfuryl methacrylate)1.5k (PEO2k-b-PFMA1.5k), and their redox sensitivity was compared. A single electron transfer-living radical polymerization technique was used to prepare PEO2k-b-PFMA1.5k from FMA monomers and PEO2k-Br initiators. An anti-cancer drug, doxorubicin (DOX), was incorporated into PFMA hydrophobic parts of the polymeric micelles, which were then cross-linked with maleimide cross-linkers, 1,6-bis(maleimide) hexane, dithiobis(maleimido) ethane and diselenobis(maleimido) ethane via Diels–Alder reaction. Under physiological conditions, the structural stability of both S–S and Se–Se CCL micelles was maintained; however, treatments with 10 mM GSH induced redox-responsive de-cross-linking of S–S and Se–Se bonds. In contrast, the S–S bond was intact in the presence of 100 mM H2O2, while the Se–Se bond underwent de-crosslinking upon the treatment. DLS studies revealed that the size and PDI of (PEO2k-b-PFMA1.5k-Se)2 micelles varied more significantly in response to changes in the redox environment than (PEO2k-b-PFMA1.5k-S)2 micelles. In vitro release studies showed that the developed micelles had a lower drug release rate at pH 7.4, whereas a higher release was observed at pH 5.0 (tumor environment). The micelles were non-toxic against HEK-293 normal cells, which revealed that they could be safe for use. Nevertheless, DOX-loaded S–S/Se–Se CCL micelles exhibited potent cytotoxicity against BT-20 cancer cells. Based on these results, the (PEO2k-b-PFMA1.5k-Se)2 micelles can be more sensitive drug carriers than (PEO2k-b-PFMA1.5k-S)2 micelles.

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Diselenide Core Cross-Linked Micelles of Poly(Ethylene Oxide)-b-Poly(Glycidyl Methacrylate) Prepared through Alkyne-Azide Click Chemistry as a Near-Infrared Controlled Drug Delivery System

Cited by 12 publications

References 32 publications

Nanoformulations of Ursolic Acid: A Modern Natural Anticancer Molecule

Nanoformulations of Ursolic Acid: A Modern Natural Anticancer Molecule

Near-Infrared Light-Responsive Shell-Crosslinked Micelles of Poly(d,l-lactide)-b-poly((furfuryl methacrylate)-co-(N-acryloylmorpholine)) Prepared by Diels–Alder Reaction for the Triggered Release of Doxorubicin

Redox-Responsive Comparison of Diselenide and Disulfide Core-Cross-Linked Micelles for Drug Delivery Application

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