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Furusho, Yoshio,Sanno, Ryoko,Oku, Tomoya,Takata, Toshikazu Korean Chemical Society 2004 Bulletin of the Korean Chemical Society Vol.25 No.11
Several [2]- and [3]rotaxanes bearing some functional groups on their wheel components and spacers with different lengths between two ammonium centers on their dumbbell components were prepared in good yields from dibenzo-24-crown-8-ether derivatives and dumbbell-shaped bis(sec-ammonium salt)s having a centrally located disulfide linkage, by utilizing the reversible thiol-disulfide interchange reaction. The shuttling behaviors of the [2]rotaxanes were investigated by $^1H$ NMR by use of the spin polarization transfer-selective inversion recovery technique. It was found that the change in spacer length in the axle resulted in a drastic change in shuttling rate of the [2]rotaxanes, although the introduction of the functional groups to the wheels did not affect the shuttling behavior at all.
Yoshihiko Fujita,Masahiko Kimura,Hiroki Sato,Toshikazu Takata,Nobufumi Ono,Kazuto Nishio 대한약학회 2016 Archives of Pharmacal Research Vol.39 No.6
Rotaxanes comprise a class of interlocked moleculescontaining a wheel threaded onto an axle with blockinggroups on the ends to keep thewheel fromsliding off.Here,weshow that [2][bis(2-(3,5-dimethylphenylcarbonyloxy)ethyl)ammoniumtrifluoromethanesulfonate]-[dibenzo-24-crown-8]rotaxane (TRO-A0001), a rotaxane compound, exerted agrowth inhibitory effect on several human cancer cell lines.AnMTT assay revealed an IC50 of 14-830 nMfor TRO-A0001 inthese cells. Neither the wheel nor the axle part alone inhibitedtumor cell growth, suggesting that the complete rotaxanemolecule with its unique ‘‘intramolecular mobility’’ is requiredto inhibit cell growth. Annexin-V/PI staining provided evidenceof the induction of apoptosis, which was further confirmedby the observation of poly (ADP-ribose) polymerasecleavage. Furthermore, a cell cycle analysis using flowcytometry showed that TRO-A0001 treatment resulted in G1arrest in glioblastoma T98G and melanoma G361 cells. Animmunoblot analysis revealed that in both cell lines, TROA0001treatment caused the induction of p21/Cip1, therebydown-regulating Cdks 2, 4 and 6 and reducing Cyclins D1 andE. The results presented in this study demonstrate cytotoxicityof the rotaxane compound and its potential as a lead compoundfor the development of a chemotherapeutic agent againstcancer.