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Synthesis of 14 C‐labelled phenethyl isothiocyanate and the cysteine conjugate S‐(N‐phenethylthiocarbamoyl)cysteine and use under physiological conditions
Author(s) -
Xu Ke,
Thornalley Paul J.
Publication year - 1999
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199911)42:11<1069::aid-jlcr262>3.0.co;2-c
Subject(s) - chemistry , cysteine , isothiocyanate , yield (engineering) , conjugate , phenethyl isothiocyanate , in vitro , allyl isothiocyanate , phenyl isothiocyanate , fluorescein isothiocyanate , biochemistry , enzyme , fluorescence , mathematical analysis , materials science , physics , mathematics , quantum mechanics , metallurgy
2‐Phenyl‐[1‐ 14 C]‐ethyl isothiocyanate and S‐(N‐phenyl‐[1‐ 14 C]‐ethylthiocarbamoyl)cysteine were synthesised from 2‐phenyl‐[1‐ 14 C]‐ethylamine. Phenylethylamine was reacted with thiophosgene to make phenethyl isothiocyanate (yield: 36%, based on phenylethylamine). Phenethyl isothiocyanate was converted to the cysteine conjugate S‐(N‐phenethylthiocarbamoyl)cysteine by reaction with cysteine and crystallisation (yield: 86%, based on phenethyl isothiocyanate). The compounds have been used to study the cellular and subcellular labelling of tumour cells during the induction of apoptosis in human tumour cells by phenethyl isothiocyanate and S‐(N‐phenethylthiocarbamoyl)cysteine in vitro . Copyright © 1999 John Wiley & Sons, Ltd.