Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Development of a Hypoxia-Selective Near-Infrared Fluorescent Probe for Non-invasive Tumor Imaging
Bahaa Gamal Mohamed YoussifKensuke OkudaTetsuya KadonosonoOla Ibrahim Abdel Razek SalemAlaa Arafat Mohamed HayallahMostafa Ahmed HusseinShinae Kizaka-KondohHideko Nagasawa
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2012 Volume 60 Issue 3 Pages 402-407


A near-infrared fluorochrome, GPU-311, was designed, synthesized and evaluated for its application in non-invasive imaging of tumor hypoxia. Efficient synthesis was achieved by nucleophilic substitution and click chemistry ring using the bifunctional tetraethylene glycol linker 2 containing thiol and azide groups for the conjugation of the propargylated nitroimidazole 1 and the heptamethine cyanine dye 3 bearing a 2-chloro-1-cyclohexenyl ring. GPU-311 exhibited long excitation and emission wavelength (Ex/Em=785/802 nm) and a decent quantum yield (0.05). The water solubility and hydrophilicity of GPU-311 increased. After in vitro treatment of SUIT-2/HRE-Luc pancreatic cancer cells with GPU-311, a higher level of fluorescence was observed selectively in hypoxia than in normoxia. However, in vivo fluorescence imaging of a mouse xenograft model after GPU-311 administration revealed inadequate accumulation of GPU-311 in tumors due to its rapid elimination through the liver.

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© 2012 The Pharmaceutical Society of Japan
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