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Photo-enhanced Aqueous Solubilization of an Azo-compound.

ABSTRACT: We previously showed that disruption of intermolecular interactions, e.g., by lowering the molecular planarity and/or introducing bent structures, improves the aqueous solubility of compounds, and based upon that work, we hypothesized that azobenzene trans-to-cis photoswitching could also be utilized to enhance the aqueous solubility of compounds. Here, we demonstrate that UV/visible light irradiation can reversibly switch the aqueous solubilization of an anti-cancer candidate drug, a low-molecular-weight kinase inhibitor bearing an azobenzene moiety. The increase of solubilization associated with UV-induced trans-to-cis conversion may have clinical relevance, because the time-scale of thermal cis-to-trans reversion at 37?°C is longer than that of oral absorption.

SUBMITTER: Ishikawa M

PROVIDER: S-EPMC5537305 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

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Photo-enhanced Aqueous Solubilization of an Azo-compound.

Ishikawa Minoru M Ohzono Takuya T Yamaguchi Takao T Norikane Yasuo Y

Scientific reports 20170731 1

We previously showed that disruption of intermolecular interactions, e.g., by lowering the molecular planarity and/or introducing bent structures, improves the aqueous solubility of compounds, and based upon that work, we hypothesized that azobenzene trans-to-cis photoswitching could also be utilized to enhance the aqueous solubility of compounds. Here, we demonstrate that UV/visible light irradiation can reversibly switch the aqueous solubilization of an anti-cancer candidate drug, a low-molecu ...[more]

PMID: 28761073

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