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CYP450 Enzymes Effect Oxygen-Dependent Reduction of Azide-Based Fluorogenic Dyes
Liam J O'Connor1, Ishna N Mistry2, Sarah L Collins3
1Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, U.K.; CRUK/MRC Oxford Institute for Radiation Oncology, Department of Oncology, University of Oxford, Old Road Campus Research Building, Oxford, OX3 7DQ, U.K.
ACS Central Science
|February 3, 2017
Summary
Azide-based dyes can now detect low oxygen levels (hypoxia) in cancer cells. This discovery offers a new method for imaging hypoxia and has implications for drug development.
Area of Science:
- Organic Chemistry
- Chemical Biology
- Biomedical Imaging
Background:
- Azide-containing compounds are versatile in synthesis and chemical biology.
- Current applications include click chemistry and hydrogen sulfide detection.
- Probes for quantifying oxygen tension are crucial in biological research.
Purpose of the Study:
- To explore a novel application of azide-containing compounds as fluorogenic probes.
- To investigate the potential of azide dyes for detecting depleted oxygen levels (hypoxia).
- To elucidate the mechanism of azide reduction in biological systems.
Main Methods:
- Development of azide-based fluorogenic probes.
- Testing probe performance in various human cancer cell lines.
- Investigating the role of cytochrome P450 enzymes and hydrogen sulfide in probe reduction.
Main Results:
- Azide-based dyes were successfully employed to image hypoxia in cancer cells.
- Probe reduction was found to be dependent on oxygen levels and mediated by cytochrome P450 enzymes.
- Hydrogen sulfide was not a significant factor in the reduction process.
Conclusions:
- Azide functionality can serve as a novel bioreductive group for prodrugs and dyes.
- A new mechanism for cellular azide reduction has been identified.
- This finding impacts the application of click chemistry in hypoxic environments.
