Natural dissipative assembly (DSA) often exhibit energy‐driven shifts in natural functions. However, creating man‐made DSA that can mimic such biological activities transformation remains relatively rare. Herein, we introduce a cytomembrane‐like dissipative assembly system based on chiral supramolecules. This system employs benzoyl cysteine in an out of equilibrium manner, enabling the shifts in biofunctions while minimizing material use. Specifically, aroyl‐cystine derivatives primarily assemble into stable M‐helix nanofibers under equilibrium conditions. These nanofibers enhance fibroblast adhesion and proliferation through stereospecific interactions with chiral cellular membranes. Upon the addition of chemical fuels, these functional nanofibers temporarily transform into non‐equilibrium nanospheres, facilitating efficient drug delivery. Subsequently, these nanospheres revert to their original nanofiber state, effectively recycling the drug. The programmable function‐shifting ability of this DSA establishes it as a novel, fuel‐driven drug delivery vehicle. And the bioactive DSA not only addresses a gap in synthetic DSAs within biological applications but also sets the stage for innovative designs of 'living' materials.