Synthesis of Thiophene-Based LCOs

The detailed synthesis of p-FTAA, p-FTAM and p-FTAA are shown in the supplementary material and in scheme 1. Briefly, all of the LCO were synthesized by iodination of a trimeric thiophene precursor (1) (15 (link)). The iodinated trimer (2) was further converted to pentamers by addition of 2-thiopheneboronic acid or 5-(dihydroxyboryl)-2-thiophenecarboxylic through Suzuki coupling (3, p-FTAM (5)). The methyl group was removed by NaOH to achieve p-HTAA (4) and p-FTAA (6). p-HTAA and p-FTAA was converted to its corresponding sodium salt by dissolving it in H₂O and equimolar amounts of sodium hydroxide, relative the number of carboxylic acids.

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Åslund A., Sigurdson C.J., Klingstedt T., Grathwohl S., Bolmont T., Dickstein D.L., Glimsdal E., Prokop S., Lindgren M., Konradsson P., Holtzman D.M., Hof P.R., Heppner F.L., Gandy S., Jucker M., Aguzzi A., Hammarström P, & Nilsson K.P. (2009). Novel pentameric thiophene derivatives for in vitro and in vivo optical imaging of a plethora of protein aggregates in cerebral amyloidoses. ACS chemical biology, 4(8), 673-684.

Publication 2009

Acid Carboxylic acids Iodination P ftaa Salt Sodium Sodium hydroxide Synthesis Thiophene

Corresponding Organization :

Other organizations : Linköping University, University Hospital of Zurich, Hertie Institute for Clinical Brain Research, Icahn School of Medicine at Mount Sinai, Norwegian University of Science and Technology, Charité - Universitätsmedizin Berlin, Washington University in St. Louis

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Variable analysis

independent variables

Iodination of a trimeric thiophene precursor (**1**)
Addition of 2-thiopheneboronic acid or 5-(dihydroxyboryl)-2-thiophenecarboxylic through Suzuki coupling (**3**, p-FTAM (**5**))
Removal of the methyl group by NaOH to achieve p-HTAA (**4**) and p-FTAA (**6**)
Conversion of p-HTAA and p-FTAA to their corresponding sodium salts by dissolving in H2O and adding equimolar amounts of sodium hydroxide, relative to the number of carboxylic acids

dependent variables

Synthesis of p-FTAA, p-FTAM, and p-FTAA

control variables

Not explicitly mentioned

positive controls

Not specified

negative controls

Not specified

Annotations

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