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The Synthesis and Radiolabeling of 2-Nitroimidazole Derivatives of Cyclam and Their Preclinical Evaluation as Positive Markers of Tumor Hypoxia

¹ Department of Radiation Oncology, Fox Chase Cancer Center, Philadelphia, Pennsylvania
² The Institute for Cancer Research, Fox Chase Cancer Center, Philadelphia, Pennsylvania

View larger version (10K): [in a new window]   FIGURE 1. (A–D) Structural components of azomycin-cyclam compounds.

View larger version (24K): [in a new window]   FIGURE 2. 13C-NMR spectra of FC-327 (A) and FC-334 (B).

View larger version (17K): [in a new window]   FIGURE 3. Uptake of 64Cu-FC-327 into DU-145 prostate cancer cells at various times as function of O2 concentration in gas phase. Crosses indicate radioactive background that adhered to filters. Lines are linear regressions through early time points, before saturation. • = air; =1% O2; = 0.3% O2; = 0.1% O2; = nitrogen.

View larger version (19K): [in a new window]   FIGURE 4. Linear binding rates (Fig. 3) of various hypoxia markers to DU-145 cells as function of O2 concentration in gas phase, normalized to their binding rate in air. + = 64Cu-cyclam; = 64Cu-CuCl2; = 67Cu-FC-316; • = 64Cu-ATSM; = 64Cu-FC-327; = 64Cu-FC-334.

View larger version (15K): [in a new window]   FIGURE 5. (A) Specific activity (%ID/g*) ± SE (n = 5) of 64Cu-FC-334 in liver (), kidney (), EMT-6 tumor (), blood (), and muscle () at various times after intravenous administration to EMT-6 tumor-bearing SCID mice. (B) Specific activity (%ID/g*) ± SE (n = 5) of 99mTc-HL-91 in liver (), kidney (), EMT-6 tumor (), blood (), and muscle () at various times after intravenous administration to tumor-bearing SCID mice.

View larger version (128K): [in a new window]   FIGURE 6. Planar images of R3327-AT tumor-bearing rats (3 per group) 24 h after administration of 123I-ß-D-IAZGP (A) and 5–6 h after administration of 99mTc-FC-325 (B), 99mTc-HL-91 (C), and 67Cu-FC-316 (D). Images in panels A and B were acquired at x1.42 zoom, and images in panels C and D were acquired at x1.33 zoom.