A fluorescent ESIPT-based benzimidazole platform for the ratiometric two-photon imaging of ONOO-: In vitro and ex vivo

Maria L. Odyniec; Sang Jun Park; Jordan E. Gardiner; Emily C. Webb; Adam C. Sedgwick; Juyoung Yoon; Steven D. Bull; Hwan Myung Kim; Tony D. James

doi:10.1039/d0sc02347g

A fluorescent ESIPT-based benzimidazole platform for the ratiometric two-photon imaging of ONOO^-: In vitro and ex vivo

Maria L. Odyniec, Sang Jun Park, Jordan E. Gardiner, Emily C. Webb, Adam C. Sedgwick, Juyoung Yoon, Steven D. Bull, Hwan Myung Kim, Tony D. James

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

47 Scopus citations

Abstract

In this work, we have developed an ESIPT-based benzimidazole platform (MO-E1 and MO-E2) for the two-photon cell imaging of ONOO- and a potential ONOO-activated theranostic scaffold (MO-E3). Each benzimidazole platform, MO-E1-3, were shown to rapidly detect ONOO- at micromolar concentrations (LoD = 0.28 μM, 6.53 μM and 0.81 μM respectively). The potential theranostic MO-E3 was shown to release the parent fluorophore and drug indomethacin in the presence of ONOO- but unfortunately did not perform well in vitro due to low solubility. Despite this, the parent scaffold MO-E2 demonstrated its effectiveness as a two-photon imaging tool for the ratiometric detection of endogenous ONOO- in RAW264.7 macrophages and rat hippocampus tissue. These results demonstrate the utility of this ESIPT benzimidazole-based platform for theranostic development and bioimaging applications.

Original language	English
Pages (from-to)	7329-7334
Number of pages	6
Journal	Chemical Science
Volume	11
Issue number	28
DOIs	https://doi.org/10.1039/d0sc02347g
State	Published - 28 Jun 2020

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry.

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10.1039/d0sc02347g

Cite this

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title = "A fluorescent ESIPT-based benzimidazole platform for the ratiometric two-photon imaging of ONOO-: In vitro and ex vivo",

abstract = "In this work, we have developed an ESIPT-based benzimidazole platform (MO-E1 and MO-E2) for the two-photon cell imaging of ONOO- and a potential ONOO-activated theranostic scaffold (MO-E3). Each benzimidazole platform, MO-E1-3, were shown to rapidly detect ONOO- at micromolar concentrations (LoD = 0.28 μM, 6.53 μM and 0.81 μM respectively). The potential theranostic MO-E3 was shown to release the parent fluorophore and drug indomethacin in the presence of ONOO- but unfortunately did not perform well in vitro due to low solubility. Despite this, the parent scaffold MO-E2 demonstrated its effectiveness as a two-photon imaging tool for the ratiometric detection of endogenous ONOO- in RAW264.7 macrophages and rat hippocampus tissue. These results demonstrate the utility of this ESIPT benzimidazole-based platform for theranostic development and bioimaging applications.",

author = "Odyniec, {Maria L.} and Park, {Sang Jun} and Gardiner, {Jordan E.} and Webb, {Emily C.} and Sedgwick, {Adam C.} and Juyoung Yoon and Bull, {Steven D.} and Kim, {Hwan Myung} and James, {Tony D.}",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2020",

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doi = "10.1039/d0sc02347g",

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T1 - A fluorescent ESIPT-based benzimidazole platform for the ratiometric two-photon imaging of ONOO-

T2 - In vitro and ex vivo

AU - Odyniec, Maria L.

AU - Park, Sang Jun

AU - Gardiner, Jordan E.

AU - Webb, Emily C.

AU - Sedgwick, Adam C.

AU - Yoon, Juyoung

AU - Bull, Steven D.

AU - Kim, Hwan Myung

AU - James, Tony D.

PY - 2020/6/28

Y1 - 2020/6/28

N2 - In this work, we have developed an ESIPT-based benzimidazole platform (MO-E1 and MO-E2) for the two-photon cell imaging of ONOO- and a potential ONOO-activated theranostic scaffold (MO-E3). Each benzimidazole platform, MO-E1-3, were shown to rapidly detect ONOO- at micromolar concentrations (LoD = 0.28 μM, 6.53 μM and 0.81 μM respectively). The potential theranostic MO-E3 was shown to release the parent fluorophore and drug indomethacin in the presence of ONOO- but unfortunately did not perform well in vitro due to low solubility. Despite this, the parent scaffold MO-E2 demonstrated its effectiveness as a two-photon imaging tool for the ratiometric detection of endogenous ONOO- in RAW264.7 macrophages and rat hippocampus tissue. These results demonstrate the utility of this ESIPT benzimidazole-based platform for theranostic development and bioimaging applications.

AB - In this work, we have developed an ESIPT-based benzimidazole platform (MO-E1 and MO-E2) for the two-photon cell imaging of ONOO- and a potential ONOO-activated theranostic scaffold (MO-E3). Each benzimidazole platform, MO-E1-3, were shown to rapidly detect ONOO- at micromolar concentrations (LoD = 0.28 μM, 6.53 μM and 0.81 μM respectively). The potential theranostic MO-E3 was shown to release the parent fluorophore and drug indomethacin in the presence of ONOO- but unfortunately did not perform well in vitro due to low solubility. Despite this, the parent scaffold MO-E2 demonstrated its effectiveness as a two-photon imaging tool for the ratiometric detection of endogenous ONOO- in RAW264.7 macrophages and rat hippocampus tissue. These results demonstrate the utility of this ESIPT benzimidazole-based platform for theranostic development and bioimaging applications.

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