TY - JOUR
T1 - An improved method for the synthesis of radiolabeled McN5652 via thioester precursors
AU - Suehiro, Makiko
AU - Musachio, John L.
AU - Dannals, Robert F.
AU - Mathews, William B.
AU - Ravert, Hayden T.
AU - Scheffel, Ursula
AU - Wagner, Henry N.
PY - 1995/5
Y1 - 1995/5
N2 - An improved procedure that facilitates routine production and increases the radiochemical yield of [11C]McN5652 (trans - 1,2,3,5,6,10b-hexahydro-6-[4-([11C]methylthio)-phenyl]pyrrolo-[2,1-a]-isoquinoline) is presented. Specifically, thiol acetate, butyrate, and benzoate derivatives of McN5652 were prepared as the precursors for the [11C]McN5652 synthesis. These thioesters offer greater stability than the previously used thiol precursor (desmethyl McN5652) and enable a single batch of material to be used for multiple radiolabelings. Hydrolysis of the thioester functionality (tetrabutylammonium hydroxide, 10 min) unmasked the free thiol which, without purification, was reacted with [11C]iodomethane in DMF at 40-45 °C for 1 min. The average decay-corrected radiochemical yield for [11C]McN5652 was 26% with an average specific activity of 2290mCi/μmol (end of synthesis). This facile radiolabeling method, utilizing the butyrate thioester of McN5652, was also employed in the preparation of [3H](+)- and (-)McN5652 [trans-1,2,3,5,6S (or 6R),10bR, (or 10bS)-hexahydro-6-[4-([3H]methylthio)phenyl] pyrrolo-[2,1,a]-iso-quinoline] from [3H]iodomethane.
AB - An improved procedure that facilitates routine production and increases the radiochemical yield of [11C]McN5652 (trans - 1,2,3,5,6,10b-hexahydro-6-[4-([11C]methylthio)-phenyl]pyrrolo-[2,1-a]-isoquinoline) is presented. Specifically, thiol acetate, butyrate, and benzoate derivatives of McN5652 were prepared as the precursors for the [11C]McN5652 synthesis. These thioesters offer greater stability than the previously used thiol precursor (desmethyl McN5652) and enable a single batch of material to be used for multiple radiolabelings. Hydrolysis of the thioester functionality (tetrabutylammonium hydroxide, 10 min) unmasked the free thiol which, without purification, was reacted with [11C]iodomethane in DMF at 40-45 °C for 1 min. The average decay-corrected radiochemical yield for [11C]McN5652 was 26% with an average specific activity of 2290mCi/μmol (end of synthesis). This facile radiolabeling method, utilizing the butyrate thioester of McN5652, was also employed in the preparation of [3H](+)- and (-)McN5652 [trans-1,2,3,5,6S (or 6R),10bR, (or 10bS)-hexahydro-6-[4-([3H]methylthio)phenyl] pyrrolo-[2,1,a]-iso-quinoline] from [3H]iodomethane.
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U2 - 10.1016/0969-8051(94)00114-Y
DO - 10.1016/0969-8051(94)00114-Y
M3 - Article
C2 - 7550033
AN - SCOPUS:0029063893
SN - 0969-8051
VL - 22
SP - 543
EP - 545
JO - Nuclear Medicine and Biology
JF - Nuclear Medicine and Biology
IS - 4
ER -