Dinitro Derivative of Naphthalimide as a Fluorescent Probe for Tumor Hypoxia Imaging

Fluorescence imaging of tumor hypoxia can potentially offer insights in grading a progressing malignancy, which might subsequently result in metastasis and treatment resistance. Elevated levels of nitroreductase (NTR) have been perceived in hypoxic malignant tumors, and this typical feature was expl...

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Bibliographic Details
Published in:Polycyclic aromatic compounds 2023-01, Vol.43 (1), p.54-63
Main Authors: Kumari, Rashmi, R., Vasumathy, Sunil, Dhanya, N. V., Anil Kumar, Ningthoujam, Raghumani Singh, Pandey, Badri Narain, D. Kulkarni, Suresh, Varadavenkatesan, Thivaharan, Venkatachalam, Ganesh
Format: Article
Language:English
Subjects:
Adenine
Cell culture
Chemical reduction
Electrochemistry
Fluorescence
Fluorescent indicators
Fluorescent probe
Hypoxia
Imaging
Malignancy
Metastases
NAD
naphthalimide
Nicotinamide
Nicotinamide adenine dinucleotide
Nitroreductase
Tumors
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Summary:Fluorescence imaging of tumor hypoxia can potentially offer insights in grading a progressing malignancy, which might subsequently result in metastasis and treatment resistance. Elevated levels of nitroreductase (NTR) have been perceived in hypoxic malignant tumors, and this typical feature was exploited to develop a NTR-targeted probe NNQA to sense hypoxia in vitro through fluorescence imaging. The probe synthesized through imidation of 4-bromo-5-nitro-1,8-naphthalic anhydride and subsequent Suzuki coupling with 4-formylphenylboronic acid displayed a weak blue fluorescence. Electrochemical reduction studies revealed good reducible capacity of probe NNQA. The NTR mediated reduction of NNQA in presence of nicotinamide adenine dinucleotide formed the reduction product with intense green emission. Endogenous NTR-mediated transformation of blue emitting molecular probe NNQA to intensely green fluorescent reduction product was evident in the in vitro cell culture experiments.
ISSN:1040-6638
1563-5333
DOI:10.1080/10406638.2021.2009525