Photo and redox dual-stimuli-responsive β-cyclodextrin-ferrocene supramolecules for drug delivery

• Published in: Journal of macromolecular science. Part A, Pure and applied chemistry Pure and applied chemistry, 2021-01, Vol.58 (1), p.8-21
• Main Authors: Yin-Ku, Lin, Shiu-Wei, Wang, Ren-Shen, Lee
• Format: Article
• Language: English
• Subjects: Cyclodextrins; Doxorubicin; Entrapment; ferrocene; host-guest supramolecules; Hydrogen peroxide; Micelles; micellization; Nanoparticles; Photo/redox responsive; Stimuli; Supramolecular compounds; Toxicity; Ultraviolet radiation; β-cyclodextrin
• ISSN: 1060-1325; 1520-5738
• DOI: 10.1080/10601325.2020.1814158

Amphiphilic photo and redox dual-stimuli-cleavable β-cyclodextrin-ferrocene supramolecules were synthesized through noncovalent interactions of ferrocene (Fc) and β-cyclodextrin (β-CD) born by 5-hydroxy-2-nitrobenzyl alcohol (ONB), a photodegradable linker between the β-CD and poly(4-substituted-ɛ-caprolactone) (PXCL n ) chain. The terminal host-guest MPEG-Fc/β-CD-ONB-PXCL n complex can formed micelles in the aqueous phase. The critical micelle concentration ranged from 3.16 to 11.50 mg L −1 . The drug-loading content and drug entrapment efficiency of the complex were lower than those of the parent β-CD. When exposed to ultraviolet irradiation and hydrogen peroxide, complex micelles could dissociate and efficiently release the loaded drug. Nanoparticles exhibited almost no toxicity at concentrations up to 1000 μg mL −1 . The uptake of doxorubicin-incorporated micelles by HeLa cells was faster than that of free doxorubicin within the first 5 min. DOX-loaded MPEG 45 -Fc/β-CD-ONB-PMCL 23 micelles effectively inhibited the proliferation of HeLa cells with a half maximal inhibitory concentration (IC 50 ) of 3.8 µg mL −1 .