Chemiluminescent Probe for the In Vitro and In Vivo Imaging of Cancers Over-Expressing NQO1

Subin Son, Miae Won, Ori Green, Nir Hananya, Amit Sharma, Yukyoung Jeon, Jong Hwan Kwak, Jonathan L. Sessler, Doron Shabat, Jong Seung Kim

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Activatable (turn-on) probes that permit the rapid, sensitive, selective, and accurate identification of cancer-associated biomarkers can help drive advances in cancer research. Herein, a NAD(P)H:quinone oxidoreductase-1 (NQO1)-specific chemiluminescent probe 1 is reported that allows the differentiation between cancer subtypes. Probe 1 incorporates an NQO1-specific trimethyl-locked quinone trigger moiety covalently tethered to a phenoxy-dioxetane moiety through a para-aminobenzyl alcohol linker. Bio-reduction of the quinone to the corresponding hydroquinone results in a chemiluminescent signal. As inferred from a combination of in vitro cell culture analyses and in vivo mice studies, the probe is safe, cell permeable, and capable of producing a “turn-on” luminescence response in an NQO1-positive A549 lung cancer model. On this basis, probe 1 can be used to identify cancerous cells and tissues characterized by elevated NQO1 levels.

Original languageEnglish
JournalAngewandte Chemie - International Edition
DOIs
Publication statusAccepted/In press - 2019 Jan 1

Fingerprint

Imaging techniques
Biomarkers
Cell culture
NAD
Luminescence
Oxidoreductases
Alcohols
Tissue
benzoquinone

Keywords

  • chemiluminescence
  • in vivo imaging
  • molecular probe
  • NQO1

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Chemiluminescent Probe for the In Vitro and In Vivo Imaging of Cancers Over-Expressing NQO1. / Son, Subin; Won, Miae; Green, Ori; Hananya, Nir; Sharma, Amit; Jeon, Yukyoung; Kwak, Jong Hwan; Sessler, Jonathan L.; Shabat, Doron; Kim, Jong Seung.

In: Angewandte Chemie - International Edition, 01.01.2019.

Research output: Contribution to journalArticle

Son, Subin ; Won, Miae ; Green, Ori ; Hananya, Nir ; Sharma, Amit ; Jeon, Yukyoung ; Kwak, Jong Hwan ; Sessler, Jonathan L. ; Shabat, Doron ; Kim, Jong Seung. / Chemiluminescent Probe for the In Vitro and In Vivo Imaging of Cancers Over-Expressing NQO1. In: Angewandte Chemie - International Edition. 2019.
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