Redox-responsive comparison of diselenide micelles with disulfide micelles

Zhang, Longshuai; Liu, Yuancheng; Zhang, Kui; Chen, Yuanwei; Luο, Xingguang

doi:10.1007/s00396-018-4457-x

Cited by 36 publications

(26 citation statements)

References 30 publications

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“…In the presence of H 2 O 2 , diselenide/disulfide bonds were oxidized to hydrophilic selenoxide/sulfoxide or selenone/sulfone, which could facilitate the hydrolysis of the adjacent ester bond and the release of DTX from the prodrugs. [ 12,17 ] To confirm the release mechanism, we investigated the molecular weights of intermediates after incubating prodrug nanoassemblies in release medium containing 10 × 10 −3 m H 2 O 2 . The molecular weights of the monoxides of DSeSeD and DSSD were appeared in the presence of H 2 O 2 , confirming the formation of selenoxide and sulfoxide (Figures S6 and S7, Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

Probing the Superiority of Diselenium Bond on Docetaxel Dimeric Prodrug Nanoassemblies: Small Roles Taking Big Responsibilities

Zuo

Sun

Yang

et al. 2020

Small

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The current state of chemotherapy is far from satisfaction, restricted by the inefficient drug delivery and the off‐target toxicity. Prodrug nanoassemblies are emerging as efficient platforms for chemotherapy. Herein, three docetaxel dimeric prodrugs are designed using diselenide bond, disulfide bond, or dicarbide bond as linkages. Interestingly, diselenide bond‐bridged dimeric prodrug can self‐assemble into stable nanoparticles with impressive high drug loading (≈70%, w/w). Compared with disulfide bond and dicarbide bond, diselenide bond greatly facilitates the self‐assembly of dimeric prodrug, and then improves the colloidal stability, blood circulation time, and antitumor efficacy of prodrug nanoassemblies. Furthermore, the redox‐sensitive diselenide bond can specifically respond to the overexpressed reactive oxygen species and glutathione in tumor cells, leading to tumor‐specific drug release. Therefore, diselenide bond bridged prodrug nanoassemblies exhibit discriminating cytotoxicity between tumor cells and normal cells, significantly alleviating the systemic toxicity of docetaxel. The present work gains in‐depth insight into the impact of diselenide bond on the dimeric prodrug nanoassemblies, and provides promising strategies for the rational design of the high efficiency–low toxicity chemotherapeutical nanomedicines.

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Section: Resultsmentioning

confidence: 99%

Probing the Superiority of Diselenium Bond on Docetaxel Dimeric Prodrug Nanoassemblies: Small Roles Taking Big Responsibilities

Zuo

Sun

Yang

et al. 2020

Small

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“…Thus, dynamic S-S and Se-Se bonds containing crosslinking agents are ideal to maintain the in vivo stability of PMs and achieve controlled release of payloads in the milieu of cancer tissue. The lower Se-Se bond energy, larger atomic size, and weak electronegativity of selenium endowed Se-Se bonds with a more dynamic nature and higher redox responsiveness than S-S bonds [30,31]. Moreover, the induction of diselenide metathesis reactions in the presence of visible light or mild heat (<100 • C) as compared to disulfide exchange reactions that demand catalysts and/or harmful UV irradiation [32], inspired researchers to engineer Se-Se bonds containing shell or core crosslinked micelles (CCMs).…”

Section: Introductionmentioning

confidence: 99%

Fabrication of Core Crosslinked Polymeric Micelles as Nanocarriers for Doxorubicin Delivery: Self-Assembly, In Situ Diselenide Metathesis and Redox-Responsive Drug Release

et al. 2020

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Polymeric micelles (PMs) have been used to improve the poor aqueous solubility, slow absorption and non-selective biodistribution of chemotherapeutic agents (CAs), albeit, they suffer from disassembly and premature release of payloads in the bloodstream. To alleviate the thermodynamic instability of PMs, different core crosslinking approaches were employed. Herein, we synthesized the poly(ethylene oxide)-b-poly((2-aminoethyl)diselanyl)ethyl l-aspartamide)-b-polycaprolactone (mPEG-P(LA-DSeDEA)-PCL) copolymer which self-assembled into monodispersed nanoscale, 156.57 ± 4.42 nm, core crosslinked micelles (CCMs) through visible light-induced diselenide metathesis reaction between the pendant selenocystamine moieties. The CCMs demonstrated desirable doxorubicin (DOX)-loading content (7.31%) and encapsulation efficiency (42.73%). Both blank and DOX-loaded CCMs (DOX@CCMs) established appreciable colloidal stability in the presence of bovine serum albumin (BSA). The DOX@CCMs showed redox-responsive drug releasing behavior when treated with 5 and 10 mM reduced glutathione (GSH) and 0.1% H2O2. Unlike the DOX-loaded non-crosslinked micelles (DOX@NCMs) which exhibited initial burst release, DOX@CCMs demonstrated a sustained release profile in vitro where 71.7% of the encapsulated DOX was released within 72 h. In addition, the in vitro fluorescent microscope images and flow cytometry analysis confirmed the efficient cellular internalization of DOX@CCMs. The in vitro cytotoxicity test on HaCaT, MDCK, and HeLa cell lines reiterated the cytocompatibility (≥82% cell viability) of the mPEG-P(LA-DSeDEA)-PCL copolymer and DOX@CCMs selectively inhibit the viabilities of 48.85% of HeLa cells as compared to 15.75% of HaCaT and 7.85% of MDCK cells at a maximum dose of 10 µg/mL. Overall, all these appealing attributes make CCMs desirable as nanocarriers for the delivery and controlled release of DOX in tumor cells.

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“…In an ideal system, disulfide bond scission will prompt anticancer drug release from the drug delivery system substrate only within the cancer cell. The concentration of GSH in cancer cells ranges between 2–10 mM, which is 100-1,000 times greater than in non-cancer cells [ 80 ].…”

Section: Reaction Types and Applicationsmentioning

confidence: 99%

Thiol- and Disulfide-Based Stimulus-Responsive Soft Materials and Self-Assembling Systems

Beaupre

Weiss

2021

Molecules

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Redox-responsive comparison of diselenide micelles with disulfide micelles

Cited by 36 publications

References 30 publications

Probing the Superiority of Diselenium Bond on Docetaxel Dimeric Prodrug Nanoassemblies: Small Roles Taking Big Responsibilities

Probing the Superiority of Diselenium Bond on Docetaxel Dimeric Prodrug Nanoassemblies: Small Roles Taking Big Responsibilities

Fabrication of Core Crosslinked Polymeric Micelles as Nanocarriers for Doxorubicin Delivery: Self-Assembly, In Situ Diselenide Metathesis and Redox-Responsive Drug Release

Thiol- and Disulfide-Based Stimulus-Responsive Soft Materials and Self-Assembling Systems

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