Synthesis of Intelligent Bioactive Peptides and Their Application to Controlling Cellular Function

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The purpose of this study is to design, synthesize and characterize the photoresponsible nonnatural bioactive peptides. RGD (Arg-Gly-Asp) peptides and bradykinin analogues in which a photoisomerizable nonnatural amino acid, L-p-(phenylazo)phenylalanine (azoAla) was incorporated were designed and synthesized by solid phase synthesis. Reversible photoisomerization of the azoAla side chain in the peptides by alternative irradiation of UV and visible light was demonstrated by spectroscopic measurement. HPLC analysis indicated that the trans to cis isomerization of the azoAla side chain by UV irradiation induced the large decrease of hydrophobicity of the peptides. Finally it was clearly demonstrated that the cyclic RGD-azoAla peptide and the azoAka8-bradykinin analogue showed different bioactivity for the target cells at the trans state and the cis state.