title: Synthesis and application of visible light sensitive azobenzene.
abstract: Methods for regulating peptide conformation by non-harmful light stimuli can be useful for remotely controlling cellular functions in vitro. Here, we synthesized a series of p-heteroatom-substituted azobenzenes and studied their photoisomerization properties. The trans-isomer of p-sulfur-substituted azobenzene was effectively isomerized by visible light irradiation and the cis-isomer was thermally stable at physiological temperature. We developed a novel visible light sensitive amino acid (AZO), via p-sulfur-substituted azobenzene, and utilized it as a photosensitive modulator of the SV40 nuclear localization signal (NLS). The cellular uptake of the AZO-NLS conjugate was controlled by visible light irradiation. Our technology can be utilized for regulating not only the cellular uptake, but also the function of peptides within cells by non-harmful visible light irradiation.
authors: Department of Organic Fine Chemicals, The Institute of Scientific and Industrial Research, Osaka University, 8-1, Mihogaoka, Ibaraki, Osaka 567-0047, Japan. kunihiro@sanken.osaka-u.ac.jp
authors: Shinjiro
authors: S
authors: Sawada
authors: Nobuo
authors: N
authors: Kato
authors: Kunihiro
authors: K
authors: Kaihatsu
mesh_terms: D000596:Amino Acids / Q000008:administration & dosage / Q000737:chemistry / Q000528:radiation effects; D001391:Azo Compounds / Q000008:administration & dosage / Q000737:chemistry / Q000528:radiation effects*; D006367:HeLa Cells; D006801:Humans; D007536:Isomerism; D008027:Light; D019913:Nuclear Localization Signals / Q000008:administration & dosage / Q000737:chemistry / Q000528:radiation effects*
chemical_list: D000596:Amino Acids; D001391:Azo Compounds; D019913:Nuclear Localization Signals; C009850:azobenzene