New fluorine-18 labeled benzaldehydes as precursors in the synthesis of radiopharmaceuticals for positron emission tomography
- Authors: Orlovskaja V.V.1, Fedorova O.S.1,2, Studentsov E.P.3, Golovina A.A.3, Krasikova R.N.1,2
-
Affiliations:
- N. P. Bechtereva Institute of Human Brain, Russian Academy of Sciences
- Department of Chemistry, Saint Petersburg State University
- Saint Petersburg State Technological Institute (Technical University)
- Issue: Vol 65, No 2 (2016)
- Pages: 507-512
- Section: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/237217
- DOI: https://doi.org/10.1007/s11172-016-1330-2
- ID: 237217
Cite item
Abstract
4,5-Bis(butoxy)-2-nitrobenzaldehyde and 4,5-bis(tert-butoxycarbonyloxy)-2-nitrobenzaldehyde, as well as their fluorine-18 labeled derivatives (the half-life of F18 is T1/2 = 110 min) were synthesized for use as precursors in the synthesis of fluorine-18 labeled catecholamines and 6-[18F]fluoro-l-DOPA ((S)-3-[4,5-dihydroxy-2-[18F]fluorophenyl]-2-aminopropionic acid), important radiopharmaceutical agents (RPAs) for positron emission tomography. An advantageous feature of the newly obtained substituted nitrobenzaldehydes is the presence of labile protective groups which can be removed without using aggressive chemicals and severe conditions, which is of fundamental importance for automation of the RPA synthesis in modern synthesis apparatus. A high and stable radiofluorination yield achieved under the optimum fluorination conditions (Kryptofix 222 [K/K2.2.2.]+[18F–], DMF, 140 °C, 10 min) using 4,5-bis(butoxy)-2-nitrobenzaldehyde as a substrate (83±6%, the number of experiments was n = 15) makes this compound a precursor of choice for the radioactive synthesis.
About the authors
V. V. Orlovskaja
N. P. Bechtereva Institute of Human Brain, Russian Academy of Sciences
Email: raisa@ihb.spb.ru
Russian Federation, 9 ul. Akad. Pavlova, Saint Petersburg, 197376
O. S. Fedorova
N. P. Bechtereva Institute of Human Brain, Russian Academy of Sciences; Department of Chemistry, Saint Petersburg State University
Email: raisa@ihb.spb.ru
Russian Federation, 9 ul. Akad. Pavlova, Saint Petersburg, 197376; 7—9 Universitetskaya nab., Saint Petersburg, 199034
E. P. Studentsov
Saint Petersburg State Technological Institute (Technical University)
Email: raisa@ihb.spb.ru
Russian Federation, 26 Moskovskii prosp., Saint Petersburg, 190013
A. A. Golovina
Saint Petersburg State Technological Institute (Technical University)
Email: raisa@ihb.spb.ru
Russian Federation, 26 Moskovskii prosp., Saint Petersburg, 190013
R. N. Krasikova
N. P. Bechtereva Institute of Human Brain, Russian Academy of Sciences; Department of Chemistry, Saint Petersburg State University
Author for correspondence.
Email: raisa@ihb.spb.ru
Russian Federation, 9 ul. Akad. Pavlova, Saint Petersburg, 197376; 7—9 Universitetskaya nab., Saint Petersburg, 199034