14817-57-3Relevant academic research and scientific papers
Synthesis, guest-binding, and reduction-responsive degradation properties of water-soluble cyclophanes having disulfide moieties
Hayashida, Osamu,Ichimura, Kazuaki,Sato, Daisuke,Yasunaga, Terutaka
, p. 5463 - 5469 (2013)
Water-soluble cationic cyclophane having diphenyl disulfide moieties (1a) was synthesized as a reduction-responsive degradable host. The stoichiometry for the complex of 1a with anionic fluorescence guests, such as 4,4′-bis(1-anilinonaphthalene-8-sulfonate) (Bis-ANS) and 4-(1-pyrene)-butanoic acid (PBA), was confirmed to be 1:1 host:guest by a Job plot. The binding constants (K) of 1a toward Bis-ANS and PBA were evaluated to be 6.7 × 103 and 4.5 × 104 M-1, respectively, as confirmed by fluorescence spectroscopy. Reduction of disulfide bonds of 1a by dithiothreitol gave its reduced form having poor guest-binding affinity that led to release of the entrapped guest molecules to the bulk aqueous phase. Meanwhile, anionic cyclophane 1b, which was derived from 1a by a reaction with succinic anhydride, binds cationic anticancer drugs, such as daunorubicin hydrochloride (DNR) and doxorubicin hydrochloride (DOX), with a K of 2.1 × 103 and 7.5 × 102 M-1, respectively. A similar reduction-responsive guest release feature was observed when DNR and DOX were employed as a guest for complexation with 1b.
