Synthesis and Application of Visible Light Sensitive Azobenzene

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

Journal Name: Current Pharmaceutical Biotechnology

Volume 13 , Issue 14 , 2012

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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.

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

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Article Details

Year: 2012
Page: [2642 - 2648]
Pages: 7
DOI: 10.2174/138920101314151120122912
Price: $58

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