ISSN Print 2500–1094
ISSN Online 2542–1204
BIOMEDICAL JOURNAL OF PIROGOV UNIVERSITY (MOSCOW, RUSSIA)
METHOD
Synthesis of 13С- and 14С-labeled linoleic acids for use in diagnostic breath tests for hepatobiliary system disorders
About authors
1 Russian State University of Physical Education, Sport, Youth and Tourism, Moscow, Russia
2 Skryabin Moscow State Academy of Veterinary Medicine and Biotechnology, Moscow
3 Vavilov Institute of General Genetics, Russian Academy of Sciences, Moscow, Russia
4 I. M. Sechenov First Moscow State Medical University, Moscow, Russia
5 Blokhin National Medical Research Center of Oncology, Moscow, Russia
6 Plekhanov Russian University of Economics, Moscow, Russia
Correspondence should be addressed: Yaroslav Y. Tynio
Sirenevyi bulvar, 4, Moscow, 105122; ur.liam@oinytyy
About paper
Author contribution: Tynio YY conceived and supervised the study; Morozova GV synthesized the final product by carboxylation of the Grignard reagent with 13С and 14С dioxides, did preparative calculations; Biryukova YuK conducted NMR-analysis of the final product; Sivokhin DA analyzed the literature and wrote the manuscript; Pozdniakova NV analyzed the literature; Zylkova MV measured the radioactivity of carbon atoms in the reagents, intermediate and final products; Bogdanova ES analyzed the NMR spectra of the final products; Smirnova MS determined the melting point of the final products; Shevelev AB provided reagents and instrumentation and revised the manuscript.
Received: 2020-03-31
Accepted: 2020-04-15
Published online: 2020-04-25
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At present, there is a need for a simple, noninvasive, highly specific and sensitive diagnostic test for hepatobiliary system disorders. Compounds labeled with carbon isotopes are widely used in various diagnostic breath tests; they are safe and can reliably detect a metabolic disorder or enzyme deficiency. The aim of this study was to synthesize 13С- and 14С-labeled linoleic acids suitable for use in hepatobiliary breath tests in terms of purity. In the synthesis of 13С-labeled linoleic acid, the chemical yield for 1-bromo-8,11-heptadecadien was 86.4% and the chemical yield for barium carbonate-13С, 96.0%. In the synthesis of 14С-labeled linoleic acid, the chemical yield for 1-bromo-8,11-heptadecadien was 87.39%; for barium carbonate-14С it was 97.1%. The specific radioactivity of 14С-labeled linoleic acids was 45.36 ± 0.02 mCi/g. The radiochemical yield of the reaction was 96.0%. The proposed method is suitable for batch production.
Keywords: breath test, linoleic acid, 13С, 14С, hepatobiliary system, liver disease