Chemiluminescent Probe for the In Vitro and In Vivo Imaging of Cancers Over-Expressing NQO1.
A549 Cells
Animals
Benzoquinones
/ chemistry
Biomarkers, Tumor
/ chemistry
Fluorescent Dyes
/ chemistry
Humans
Luminescent Measurements
Lung Neoplasms
/ diagnostic imaging
Mice
Molecular Structure
NAD(P)H Dehydrogenase (Quinone)
/ chemistry
Neoplasms, Experimental
/ diagnostic imaging
Optical Imaging
Tumor Cells, Cultured
NQO1
chemiluminescence
in vivo imaging
molecular probe
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
04 02 2019
04 02 2019
Historique:
received:
14
11
2018
revised:
17
12
2018
pubmed:
19
12
2018
medline:
19
8
2020
entrez:
19
12
2018
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 30561862
doi: 10.1002/anie.201813032
doi:
Substances chimiques
Benzoquinones
0
Biomarkers, Tumor
0
Fluorescent Dyes
0
quinone
3T006GV98U
NAD(P)H Dehydrogenase (Quinone)
EC 1.6.5.2
NQO1 protein, human
EC 1.6.5.2
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
1739-1743Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.