Preparation of alkyne-labeled 2-nitroimidazoles for identification of tumor hypoxia by Raman spectroscopy.

Abstract

Hypoxia is a characteristic feature of solid tumors. Herein, we have developed novel hypoxia-sensitive probes (IM-ACs) for Raman spectroscopic analysis, consisting of nitroimidazole as a hypoxia-targeting unit and acetylene group as the signal-emitting unit. Among IM-ACs synthesized in this study, IM-AC possessing a diacetylene group (IM-AC 3), showed suitable properties as a hypoxia indicator. When administered to A549 cells, we observed a strong signal of IM-AC 3 around 2200cm-1 in the Raman spectra from hypoxic cells. Ex vivo experiments suggest that IM-AC 3 remained in hypoxic tumor tissue and emitted a strong signal.

• Authors: Ryohsuke Kurihara, Yuta Ikemura, Kazuhito Tanabe
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 26 Issue 20 Pg. 4892-4894 (10 15 2016) ISSN: 1464-3405 [Electronic] England
• PMID: 27646700 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2016 Elsevier Ltd. All rights reserved.

Chemical References

• Alkynes
• Molecular Probes
• Nitroimidazoles

Topics

• A549 Cells
• Alkynes (chemistry)
• Cell Hypoxia
• Humans
• Lung Neoplasms (pathology)
• Molecular Probes
• Nitroimidazoles (chemistry)
• Spectrum Analysis, Raman (methods)