A pH-Responsive Glycyrrhetinic-Acid-Modified Small-Molecule Conjugate for NIR Imaging of Hepatocellular Carcinoma (HCC)

Hardev Singh; Ja Yun Lim; Amit Sharma; Dae Wui Yoon; Ji Hyeon Kim; Zhigang Yang; Junle Qu; Jinkwan Kim; Seung Gwan Lee; Jong Seung Kim

doi:10.1002/cbic.201800619

A pH-Responsive Glycyrrhetinic-Acid-Modified Small-Molecule Conjugate for NIR Imaging of Hepatocellular Carcinoma (HCC)

Hardev Singh, Ja Yun Lim, Amit Sharma, Dae Wui Yoon, Ji Hyeon Kim, Zhigang Yang, Junle Qu, Jinkwan Kim, Seung Gwan Lee, Jong Seung Kim

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

14 Citations (Scopus)

Abstract

We report a glycyrrhetinic-acid (GA)-decorated small-molecule conjugate for pH-triggered near-infrared (NIR) fluorescence imaging of hepatocellular carcinoma (HCC). Our in vitro studies demonstrated that the conjugate, referred to as NIR-GA, was efficiently taken up by liver cancer cell lines such as HepG2 and Huh7 through an endocytic pathway mediated by GA receptors. As suggested by co-localization studies, NIR-GA mainly localized in the lysosome, where the acidic pH results in the activation of the fluorescent dye through H ⁺ -triggered spirolactam ring opening to give strong fluorescence in the NIR region.

Original language	English
Pages (from-to)	614-620
Number of pages	7
Journal	ChemBioChem
Volume	20
Issue number	4
DOIs	https://doi.org/10.1002/cbic.201800619
Publication status	Published - 2019 Feb 15

Keywords

fluorescent probes
glycyrrhetinic acid
hepatocellular carcinoma
imaging agents
natural products

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/cbic.201800619

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title = "A pH-Responsive Glycyrrhetinic-Acid-Modified Small-Molecule Conjugate for NIR Imaging of Hepatocellular Carcinoma (HCC)",

abstract = " We report a glycyrrhetinic-acid (GA)-decorated small-molecule conjugate for pH-triggered near-infrared (NIR) fluorescence imaging of hepatocellular carcinoma (HCC). Our in vitro studies demonstrated that the conjugate, referred to as NIR-GA, was efficiently taken up by liver cancer cell lines such as HepG2 and Huh7 through an endocytic pathway mediated by GA receptors. As suggested by co-localization studies, NIR-GA mainly localized in the lysosome, where the acidic pH results in the activation of the fluorescent dye through H + -triggered spirolactam ring opening to give strong fluorescence in the NIR region.",

keywords = "fluorescent probes, glycyrrhetinic acid, hepatocellular carcinoma, imaging agents, natural products",

author = "Hardev Singh and Lim, {Ja Yun} and Amit Sharma and Yoon, {Dae Wui} and Kim, {Ji Hyeon} and Zhigang Yang and Junle Qu and Jinkwan Kim and Lee, {Seung Gwan} and Kim, {Jong Seung}",

note = "Funding Information: This work was supported by the National Research Foundation of Korea (CRI 2018R1A3B1052702, JSK). Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2019",

month = feb,

day = "15",

doi = "10.1002/cbic.201800619",

language = "English",

volume = "20",

pages = "614--620",

journal = "ChemBioChem",

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AU - Singh, Hardev

AU - Lim, Ja Yun

AU - Sharma, Amit

AU - Yoon, Dae Wui

AU - Kim, Ji Hyeon

AU - Yang, Zhigang

AU - Qu, Junle

AU - Kim, Jinkwan

AU - Lee, Seung Gwan

AU - Kim, Jong Seung

PY - 2019/2/15

Y1 - 2019/2/15

N2 - We report a glycyrrhetinic-acid (GA)-decorated small-molecule conjugate for pH-triggered near-infrared (NIR) fluorescence imaging of hepatocellular carcinoma (HCC). Our in vitro studies demonstrated that the conjugate, referred to as NIR-GA, was efficiently taken up by liver cancer cell lines such as HepG2 and Huh7 through an endocytic pathway mediated by GA receptors. As suggested by co-localization studies, NIR-GA mainly localized in the lysosome, where the acidic pH results in the activation of the fluorescent dye through H + -triggered spirolactam ring opening to give strong fluorescence in the NIR region.

AB - We report a glycyrrhetinic-acid (GA)-decorated small-molecule conjugate for pH-triggered near-infrared (NIR) fluorescence imaging of hepatocellular carcinoma (HCC). Our in vitro studies demonstrated that the conjugate, referred to as NIR-GA, was efficiently taken up by liver cancer cell lines such as HepG2 and Huh7 through an endocytic pathway mediated by GA receptors. As suggested by co-localization studies, NIR-GA mainly localized in the lysosome, where the acidic pH results in the activation of the fluorescent dye through H + -triggered spirolactam ring opening to give strong fluorescence in the NIR region.

KW - fluorescent probes

KW - glycyrrhetinic acid

KW - hepatocellular carcinoma

KW - imaging agents

KW - natural products

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U2 - 10.1002/cbic.201800619

DO - 10.1002/cbic.201800619

M3 - Article

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AN - SCOPUS:85060337974

SN - 1439-4227

VL - 20

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EP - 620

JO - ChemBioChem

JF - ChemBioChem

IS - 4

ER -

A pH-Responsive Glycyrrhetinic-Acid-Modified Small-Molecule Conjugate for NIR Imaging of Hepatocellular Carcinoma (HCC)

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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