Synthesis and Application of Visible Light Sensitive Azobenzene

Title:Synthesis and Application of Visible Light Sensitive Azobenzene

Volume: 13 Issue: 14

Author(s): Shinjiro Sawada, Nobuo Kato and Kunihiro Kaihatsu

Affiliation:

Keywords: Cellular uptake, nuclear localization signal, photoisomerization, p-sulfur-substituted azobenzene, visible light sensitive amino acid, regulating peptide, non-harmful light stimuli, p-heteroatom-substituted azobenzenes, isomerized, cis-isomer, cellular uptake, peptides, cells, non-harmful visible light irradiation

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.

Cite this article as:

Sawada Shinjiro, Kato Nobuo and Kaihatsu Kunihiro, Synthesis and Application of Visible Light Sensitive Azobenzene, Current Pharmaceutical Biotechnology 2012; 13 (14) . https://dx.doi.org/10.2174/138920101314151120122912