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 b...

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Autores principales:	Minoru Ishikawa, Takuya Ohzono, Takao Yamaguchi, Yasuo Norikane
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2017
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/820b08ff43c74866ae4d972646d76f4e
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spelling	oai:doaj.org-article:820b08ff43c74866ae4d972646d76f4e2021-12-02T11:53:00ZPhoto-enhanced Aqueous Solubilization of an Azo-compound10.1038/s41598-017-06947-w2045-2322https://doaj.org/article/820b08ff43c74866ae4d972646d76f4e2017-07-01T00:00:00Zhttps://doi.org/10.1038/s41598-017-06947-whttps://doaj.org/toc/2045-2322Abstract 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.Minoru IshikawaTakuya OhzonoTakao YamaguchiYasuo NorikaneNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 7, Iss 1, Pp 1-6 (2017)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Minoru Ishikawa Takuya Ohzono Takao Yamaguchi Yasuo Norikane Photo-enhanced Aqueous Solubilization of an Azo-compound
description	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.
format	article
author	Minoru Ishikawa Takuya Ohzono Takao Yamaguchi Yasuo Norikane
author_facet	Minoru Ishikawa Takuya Ohzono Takao Yamaguchi Yasuo Norikane
author_sort	Minoru Ishikawa
title	Photo-enhanced Aqueous Solubilization of an Azo-compound
title_short	Photo-enhanced Aqueous Solubilization of an Azo-compound
title_full	Photo-enhanced Aqueous Solubilization of an Azo-compound
title_fullStr	Photo-enhanced Aqueous Solubilization of an Azo-compound
title_full_unstemmed	Photo-enhanced Aqueous Solubilization of an Azo-compound
title_sort	photo-enhanced aqueous solubilization of an azo-compound
publisher	Nature Portfolio
publishDate	2017
url	https://doaj.org/article/820b08ff43c74866ae4d972646d76f4e
work_keys_str_mv	AT minoruishikawa photoenhancedaqueoussolubilizationofanazocompound AT takuyaohzono photoenhancedaqueoussolubilizationofanazocompound AT takaoyamaguchi photoenhancedaqueoussolubilizationofanazocompound AT yasuonorikane photoenhancedaqueoussolubilizationofanazocompound
_version_	1718394936046387200

Photo-enhanced Aqueous Solubilization of an Azo-compound

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