A carboxylesterase-selective ratiometric fluorescent two-photon probe and its application to hepatocytes and liver tissues

Chemical Science
Sang Jun ParkHwan Myung Kim

Abstract

Carboxylesterases (CEs) are widely distributed enzymes in the human body that catalyze hydrolysis of various endogenous and exogenous substrates. They are directly linked to hepatic drug metabolisms and steatosis, and their regulations are important issues in pharmacological and clinical applications. In this work, we have developed an emission ratiometric two-photon probe (SE1) for quantitatively detecting CE in situ. This probe is based on a translation of intramolecular charge transfer character upon reaction with CE. It shows a sensitive blue-to-yellow emission change in response to human CE activity, easy loading into cells, insensitivity to pH and other metabolites including ROS and RNS, high photostability, and low cytotoxicity. Using live hepatocytes and liver tissues, we found that ratiometric two-photon microscopic imaging with SE1 is an effective tool for monitoring CE activities at the subcellular level in live tissues. This probe will find useful applications in biomedical research, including studies of hepatic steatosis and drug developments.

References

May 23, 1998·Annual Review of Pharmacology and Toxicology·T Satoh, M Hosokawa
Jan 29, 2002·Archives of Biochemistry and Biophysics·Marko GolicnikJure Stojan
Jun 8, 2002·Advanced Drug Delivery Reviews·Francesco M VeroneseMauro Sergi
Jul 23, 2004·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Toshiki TabataTsuyoshi Yokoi
Feb 11, 2005·Journal of the American Chemical Society·Sunil S ChandranRonald T Raines
Mar 8, 2005·Drug Discovery Today·Matthew R Redinbo, Philip M Potter
Nov 22, 2005·Nature Methods·Fritjof Helmchen, Winfried Denk
Jun 17, 2006·Pharmaceutical Research·Jeffery J PrusakiewiczRichard Voorman
Aug 22, 2006·Chemico-biological Interactions·Tetsuo Satoh, Masakiyo Hosokawa
Feb 29, 2008·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Masakiyo Hosokawa
Mar 14, 2008·Journal of the American Chemical Society·Duangkhae SrikunChristopher J Chang
Jun 11, 2008·Optics Express·Nikolay S MakarovAleksander Rebane
Apr 2, 2009·Accounts of Chemical Research·Hwan Myung Kim, Bong Rae Cho
Sep 24, 2010·Journal of Molecular Modeling·Daniel HasenpuschWalter Langel
Mar 12, 2011·Chemical Science·Luke D LavisRonald T Raines
May 5, 2011·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Jie WangChristopher J Patten
Nov 17, 2011·Journal of Clinical Laboratory Analysis·Abdolkarim MahroozMohammad Nouri
Jan 25, 2012·Journal of Applied Toxicology : JAT·Wanida SukketsiriSomsong Lawanprasert
Jul 19, 2012·Hepatology : Official Journal of the American Association for the Study of Liver Diseases·Ariel D QuirogaRichard Lehner
Feb 20, 2013·Accounts of Chemical Research·Lin YuanSasa Zhu
Nov 19, 2013·Journal of the American Chemical Society·Hyung Joong KimHwan Myung Kim
Jun 6, 2014·ACS Medicinal Chemistry Letters·Wataru HakamataToshiyuki Nishio
Jan 8, 2015·Chemical Communications : Chem Comm·Avik R SarkarHwan Myung Kim
May 6, 2015·Chemical Reviews·Hwan Myung Kim, Bong Rae Cho
Jan 1, 2016·Chemical Science·Avik Ranjan SarkarHwan Myung Kim

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Citations

Aug 25, 2018·Chemical Society Reviews·Hong-Wen LiuWeihong Tan
Apr 4, 2020·Organic & Biomolecular Chemistry·Jong Min AnDokyoung Kim
Apr 20, 2017·Chemical Communications : Chem Comm·Jiangli FanXiaojun Peng
Mar 21, 2018·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Jianguo WangBen Zhong Tang
Feb 26, 2021·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Xin-Yue ZhangCheng-Peng Sun
Jun 28, 2021·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Yu Zhu YangHong Qun Luo
Nov 3, 2020·Journal of Pharmaceutical Analysis·Hao Zhu, Itaru Hamachi

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Methods Mentioned

BETA
Fluorescence
immunoprecipitation
fluorescence microscopy

Software Mentioned

AutoQuant X2
MetaMorph
OriginPro

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