A Nitronaphthalimide Probe for Fluorescence Imaging of Hypoxia in Cancer Cells

Kumari, Rashmi and Vasumathy, R and Sunil, Dhanya and Ningthoujam, Raghumani S and Pandey, Badri Narain and Kulkarni, Suresh D and Thivaharan, Varadavenkatesan and Venkatachalam, Ganesh and Kumar, Anil N V (2021) A Nitronaphthalimide Probe for Fluorescence Imaging of Hypoxia in Cancer Cells. Journal of Fluorescence. pp. 1665-1673. ISSN 1053-0509

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Abstract

The bioreductive enzymes typically upregulated in hypoxic tumor cells can be targeted for developing diagnostic and drug delivery applications. In this study, a new fuorescent probe 4−(6−nitro−1,3−dioxo−1H−benzo[de]isoquinolin−2(3H)−yl) benzaldehyde (NIB) based on a nitronaphthalimide skeleton that could respond to nitroreductase (NTR) overexpressed in hypoxic tumors is designed and its application in imaging tumor hypoxia is demonstrated. The docking studies revealed favourable interactions of NIB with the binding pocket of NTR-Escherichia coli. NIB, which is synthesized through a sim�ple and single step imidation of 4−nitro−1,8−naphthalic anhydride displayed excellent reducible capacity under hypoxic conditions as evidenced from cyclic voltammetry investigations. The fuorescence measurements confrmed the formation of identcal products (NIB-red) during chemical as well as NTR−aided enzymatic reduction in the presence of NADH. The potential fuorescence imaging of hypoxia based on NTR-mediated reduction of NIB is confrmed using in-vitro cell culture experiments using human breast cancer (MCF−7) cells, which displayed a signifcant change in the fuorescence colour and intensity at low NIB concentration within a short incubation period in hypoxic conditions.

Item Type: Article
Uncontrolled Keywords: Docking · Fluorescence · Hypoxia · Molecular probe · Nitronaphthalimide · Nitroreductase
Subjects: Engineering > MIT Manipal > Chemistry
Depositing User: MIT Library
Date Deposited: 23 Mar 2022 09:03
Last Modified: 23 Mar 2022 09:03
URI: http://eprints.manipal.edu/id/eprint/158425

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