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Molecules 2012, 17(6), 6808-6820; doi:10.3390/molecules17066808
Article

Synthesis, Radiolabeling and Biological Evaluation of Propylene Amine Oxime Complexes Containing Nitrotriazoles as Hypoxia Markers

,  and *
Beijing National Laboratory for Molecular Sciences, Radiochemistry and Radiation Chemistry Key Laboratory of Fundamental Science, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
* Author to whom correspondence should be addressed.
Received: 10 May 2012 / Revised: 28 May 2012 / Accepted: 29 May 2012 / Published: 4 June 2012
(This article belongs to the Section Medicinal Chemistry)
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Abstract

Two propylene amine oxime (PnAO) complexes, 1, containing a 3-nitro-1,2,4-triazole and 2, containing two 3-nitro-1,2,4-triazoles, were synthesized and radiolabeled with 99mTc in high labeling yields. Cellular uptakes of 99mTc-1 and 99mTc-2 were tested using a S180 cells line. Under anoxic conditions, the cellular uptakes of 99mTc-1 and 99mTc-2 were 33.7 ± 0.2% and 35.0 ± 0.7% at 4 h, whereas the normoxic uptakes of the two complexes were 6.0 ± 1.6% and 4.6 ± 0.9%, respectively. Both 99mTc-1 and 99mTc-2 displayed significant anoxic/normoxic differentials. The cellular uptakes were highly dependent on oxygen and temperature. Biodistribution studies revealed that both 99mTc-1 and 99mTc-2 showed a selective localization in tumor and slow clearance from it. At 4 h, the tumor-to-muscle ratios (T/M) were 3.79 for 99mTc-1 and 4.58 for 99mTc-2. These results suggested that 99mTc-labeled PnAO complexes 99mTc-1 and 99mTc-2 might serve as novel hypoxia markers. By introducing a second nitrotriazole redox center, the hypoxic accumulation of the marker was slightly enhanced.
Keywords: nitrotriazole; technetium-99m; tumor; hypoxia marker; cellular accumulation nitrotriazole; technetium-99m; tumor; hypoxia marker; cellular accumulation
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Huang, H.; Mei, L.; Chu, T. Synthesis, Radiolabeling and Biological Evaluation of Propylene Amine Oxime Complexes Containing Nitrotriazoles as Hypoxia Markers. Molecules 2012, 17, 6808-6820.

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