Synthesis and biological studies of iodinated (127/125I) derivatives of rhodamine 123

Abstract

Rhodamine 123, a mitochondrial stain that preferentially accumulates in certain cancer cells, has been reduced and iodinated by using NaI in the presence of N-chlorosuccinimide. The various mono-, di-, and triiodo derivatives have been isolated and characterized. These nonfluorescent compounds are taken up by mammalian cells, become fluorescent within the cytoplasm (presumably following oxidation), and show the same pattern of localization as the parent compound. Iodination with no-carrier-added Na125I yields the same mixture of compounds. All 125I derivatives accumulate preferentially in PC3 adenocarcinoma cells compared with V79 lung fibroblasts, with the differential being greatest for the monoiodo compound, followed by the di- and triiodo derivatives.

ROS Production and Scavenging under Anoxia and Re-Oxygenation in Arabidopsis Cells: A Balance between Redox Signaling and Impairment

“…H 2 O 2 accumulation was then investigated by using 1,2,3-dihydrorhodamine (DHR), a probe which in the presence of H 2 O 2 is oxidized to its fluorescent form R123 (Hensley et al, 2003). While DHR passively diffuses across plasma membrane, the charged fluorescent rhodamine-123 cannot cross being trapped in cellular compartments (Kinsey et al, 1987; Henderson and Chappell, 1993). Confocal images ( Figure 2 ) show that, in normoxic conditions (T0), only few Arabidopsis cells displayed green fluorescence, due to the basal metabolism.…”

[125I/127I/131I]Iodorhodamine: Synthesis, Cellular Localization, and Biodistribution in Athymic Mice Bearing Human Tumor Xenografts and Comparison with [99mTc]Hexakis(2-methoxyisobutylisonitrile)

“…11 In searching for a nonhalogenated oxidizing agent for radioiodination, we selected peracetic acid. The parameters of radiolabeling including the buffer and its strength and pH, time, and temperature were optimized, and 125 I/ 131 I-Rh 123 (6b) was obtained in 40-45% yield (Scheme 1).…”

Effects ofHyperkinetic, a β Subunit ofShakerVoltage-Dependent K+Channels, on the Oxidation State of Presynaptic Nerve Terminals

“…In this study, we examined the cellular oxidation state in Drosophila Hk mutants by using dihydrorhodamine-123 (DHR), a fluorescent probe sensitive to oxidation (Kinsey et al, 1987). DHR is a non-fluorescent and uncharged derivative of a fluorescent dye, rhodamine-123.…”