Development of a hypoxia-selective near-infrared fluorescent probe for non-invasive tumor imaging

Bahaa Gamal Mohamed Youssif, Kensuke Okuda, Tetsuya Kadonosono, Ola Ibrahim Abdel Razek Salem, Alaa Arafat Mohamed Hayallah, Mostafa Abdulaal, Shinae Kizaka-Kondoh, Hideko Nagasawa

Research output: Contribution to journalJournal articlepeer-review

21 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)402-407
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume60
Issue number3
DOIs
StatePublished - Mar 2012
Externally publishedYes

Keywords

  • 2-Nitroimidazole
  • In vivo imaging
  • Near-infrared fluorescence
  • Tumor hypoxia

Fingerprint

Dive into the research topics of 'Development of a hypoxia-selective near-infrared fluorescent probe for non-invasive tumor imaging'. Together they form a unique fingerprint.

Cite this