✦ LIBER ✦

[3H]-labelling of hydroxyethyl groups – synthesis of s-2-hydroxy [2-3H] ethyl) glutathione and of [3H]-melphalan

✍ Scribed by M. Verny; C. Nicolas

Publisher: John Wiley and Sons
Year: 1988
Tongue: French
Weight: 291 KB
Volume: 25
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580250905

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✦ Synopsis

m e easy prepamtion of 2-bromo E I -~H I ethanol allows the tritium labelling of molecules bearing S-or N-hydroxyethyl groups. Thus S-0-hydroxy [2- HI ethyl) glutathione and [3HfMelphalan were qmthesised with specific mdioactivities of around 10 mCi/mmol (370 MBq/mmol). These values could be theoretically mised to 10 .Ci/mmol (370 GBq/mmol), according to the specific activity of the labelling precursor, sodium ?HI borohydride.

K ~u o r d s :

2-Hydraxy C2-3Hl ethyl groups

S-(2-hydmxy 12-3Hl ethyl) glutathione ?HI Melphahn

INTRODUCnON

The study of two oncostatics, namely

2-Chloroethanol was identified in plasma and after oxidation into 2-chloroacetaldehyde, appeared to be elfminoted mainly as four sulphur containing metabolites (1,2). Two intermediates in this metabolic scheme could be S-(2-chloroethyl) glutathione and S-(2-hydmxyethyl) glutathione (3), the latter being expected to exhibit high concentmtions in thymus and pancreas.

In order to study the metabolism and Modisposttion of RFNCU and RPNCU, it WQS useful to synthesize the s u p p e d intermediates as labelled species. The S-alkylation of glutathione by the means of ethylene oxide (available as the [ CJlabelled reagent), according to the method described by Johnson (41, failed to @w the expected results. Thus, following the methods of Z i h and Weinstein (5) and Nachtomi (6), we attempted to use bornoathano1 as the alkylating reagent (Scheme 11, on the assumption that the ?HJlabelled compound could be easily obtained, by the reduction of ethyl bromwcetate WIth a trttiated hydride : Unit 71, led to the proposal of a biotmnsformation scheme in animals (I).

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