The interactions at the bio-interfaces are major triggers regulating a wide variety of physiological actions such as adhesion, signaling, and substance transportation. Therefore, understanding the molecular mechanisms underlying the contact is one of the central subjects in biological science. For bioengineering, regulation of the bio-interfaces is one effective approach, and chemistry can contribute to the development of bottom-up methodologies for bio-interface manipulation. In this Feature Article, our recent studies about the development of supramolecular materials mimicking the contact events at the bio-interfaces were highlighted. ECM is a fundamental tissue at the cellular interface constructed by networks of fibrous proteins, which regulates a variety of cellular activities. Reconstruction of ECM has been demonstrated by self-assembling peptides. Conjugation of the peptides with proteins allows for displaying N-cadherin and VEGF onto the supramolecular nanofibres. By combining the dynamic properties of the self-assembling peptides with displaying N-cadherin and sustained-releasing VEGF, the protein-peptide conjugated materials enable neuronal migration and regeneration of injured neural tissue. The dynamic properties of the self-assembling peptides can be effectively controlled by point mutations such as amino acid replacement in the main chain and structural modification by redox in the side chain. The phospholipid bilayer is the main component of the cell membrane. The morphology and deformation of the phospholipid bilayer relate directly to the dynamic interfacial functions. Stabilization of the phospholipid nanosheet structure has been demonstrated by synthetic surfactant bearing metal-chelating, selfassembling peptides. The stabilized bicelle is functional for extended blood circulation. By using photo-responsive synthetic surfactant showing mechanical opening/closing motion, endocytosis-like outside-in membrane deformation is triggered. The outside-in deformation allows for efficient encapsulation of micrometer-size substances such as phage viruses into the liposomes and protects them from external environments. The encapsulated viruses can be delivered to multiple organs in a living body via blood administration. These supramolecular approaches to mimicking and controlling biointerfaces present powerful ways to develop unprecedented regenerative medicines and drug delivery systems. The materials science to reconstruct biomimetic interfaces with a dynamic nature is still in its infancy and is expected to make significant progress in the future toward biomedical applications. (n) Time-course profiles over 15 min of the fluorescence intensity in the blood vessels of unencapsulated M13 phagesCy5 (dashed line) and M13 phagesCy5 encapsulated into GUVDOPC/AzoMEx-pAsp (solid line). Plaque assays of homogenized samples of (o) spleen, (p) liver, (q) kidney, (r) heart, (s) lung, and (t) brain 15 min after injection of 100 μL of GUVDOPC/AzoMEx-pAsp encapsulating M13 phages. The samples of spleen and liver are diluted 10-fold before the plaque assay. Insets: photographs of the corresponding organs. Representative spots of M13 phage-infected E. coli in (o-t) are indicated by blue circles.