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Tritiation of azido‐labeled diiodo cabazitaxel (Jevtana) and docetaxel (Taxotere) derivatives to generate 3 H‐photoaffinity probes
Author(s) -
Jones Seth,
Weck Remo,
Burhop Annina,
Atzrodt Jens,
Derdau Volker
Publication year - 2018
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/jlcr.3675
Subject(s) - chemistry , azide , docetaxel , aryl , moiety , radiochemistry , combinatorial chemistry , halogenation , photoaffinity labeling , stereochemistry , organic chemistry , alkyl , biochemistry , binding site , medicine , surgery , chemotherapy
Radiolabelled azidophenyl analogues can make powerful photoaffinity probes for the identification of molecular targets. We describe our efforts to prepare tritiated azidophenyl analogues of the taxols cabazitaxel and docetaxel. Late‐stage tritiation by isotope exchange with diiodo precursors resulted in reduction of the azide moiety, which could only be overcome by addition of high excess of a sacrificial azide. Iodine‐deuterium exchange experiments on a model system established that deiodination with concomitant azide reduction is a general problem when performing such isotope‐exchange reactions on azide‐containing aryl iodides.