We have developed steroid cyclophanes which are unique hosts with a cyclic core of a 1,6,20,25-tetraaza[6.1.6.1]paracyclophane connected to four steroid moieties through a flexible L-lysine spacer. The polarity of the cavity interior can be dynamically controlled by mixing artificial lipids, resulting in a change in fluorescence of the bound probe [6-(p-toluidino)naphthalene-2-sulfonate, TNS]. Dynamic light scattering and circular dichroism measurements revealed that the assembling structures of the mixtures of the steroid cyclophane and the lipid were altered depending on the mixing ratio. Electrostatic interaction and self-aggregation of the steroid cyclophanes would influence their mixing state. A fluorescence maximum of TNS bound to the steroid cyclophane cavity biphasically changed between 433 and 409 nm. This observation can be explained by a hydrophilic-hydrophobic cavity conversion. This system provides lipid-dependent photo-signal modulation as a novel type of information conversion.