3'-Hydroxyesorubicin. Synthesis and antitumor activity.

A key compound, a precursor of water-soluble cyclophane hexamer, was prepared via Williamson ether synthesis of tetraaza[6.1.6.1]paracyclophane derivatives bearing a bromoacetamide moiety with triphenylene-2,3,6,7,10,11-hexaol as a core. A cationic cyclophane hexamer (1) was obtained by removing the protecting groups from the precursor. Fluorescence titration experiments proved that cationic cyclophane hexamer 1 showed macrocyclic multivalency effects; i.e., 1:1 host/guest binding constants (K) of 1 with anionic guests, 6-anilinonaphthalene-2-sulfonate and 6-p-toluidinonaphthalene-2-sulfonate, were increased about 63- and 62-fold, respectively, relative to those of monomeric cyclophane. Similarly, anionic cyclophane hexamer 2, which was easily prepared from 1, showed macrocyclic multivalency effects in K values with cationic guests such as hydrochlorides of doxorubicin and daunorubicin as an anticancer drug.

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3'-Hydroxyesorubicin. Synthesis and antitumor activity.

Cited by 7 publications

References 6 publications

Interaction of doxorubicin and its derivatives with DNA: Elucidation by resonance Raman and surface-enhanced resonance Raman spectroscopy

Interaction of doxorubicin and its derivatives with DNA: Elucidation by resonance Raman and surface-enhanced resonance Raman spectroscopy

Design and tumor targeting of anthracyclines able to overcome multidrug resistance: A double-advantage approach

Synthesis of Water-Soluble Cyclophane Hexamers Having a Triphenylene Core and Their Enhanced Guest-Binding Behavior

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