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• W2040683648 abstract "In our aim to develop LacZ reporter probes with a good retention in LacZ expressing cells, we report the synthesis and preliminary evaluation of two carbon-11 labeled β-galactosyl triazoles 1-(β-d-galactopyranosyl)-4-(p-[11C]methoxyphenyl)-1,2,3-triazole ([11C]-6) and 1-(β-d-galactopyranosyl)-4-(6-[11C]methoxynaphthyl)-1,2,3-triazole ([11C]-13). The precursors for the radiolabeling and the non-radioactive analogues (6 and 13) were synthesized using straightforward ‘click’ chemistry. In vitro incubation experiments of 6 with β-galactosidase in the presence of o-nitrophenyl β-d-galactopyranoside (ONPG) showed that the triazolic compound was an inhibitor of β-galactosidase activity. Radiolabeling of both precursors was performed using [11C]methyl iodide as alkylating agent at 70 °C in DMF in the presence of a small amount of base. The log P values were −0.1 and 1.4, respectively, for [11C]-6 and [11C]-13, the latter therefore being a good candidate for increased cellular uptake via passive diffusion. Biodistribution studies in normal mice showed a good clearance from blood for both tracers. [11C]-6 was mainly cleared via the renal pathway, while the more lipophilic [11C]-13 was excreted almost exclusively via the hepatobiliary system. Despite the lipophilicity of [11C]-13, no brain uptake was observed. Reversed phase HPLC analysis of murine plasma and urine revealed high in vivo stability for both tracers. In vitro evaluation in HEK-293T cells showed an increased cell uptake for the more lipophilic [11C]-13, however, there was no statistically higher uptake in LacZ expressing cells compared to control cells." @default.
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• W2040683648 date "2009-07-01" @default.
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• W2040683648 title "Synthesis and biological evaluation of 11C-labeled β-galactosyl triazoles as potential PET tracers for in vivo LacZ reporter gene imaging" @default.
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• W2040683648 doi "https://doi.org/10.1016/j.bmc.2009.05.056" @default.
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