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

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

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
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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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MDPI and ACS Style

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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