Premium
Cellular Localisation of Antitumoral 6‐Alkyl Thymoquinones Revealed by an Alkyne–Azide Click Reaction and the Streptavidin–Biotin System
Author(s) -
EffenbergerNeidnicht Katharina,
Breyer Sandra,
Mahal Katharina,
Diestel Randi,
Sasse Florenz,
Schobert Rainer
Publication year - 2011
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201000762
Subject(s) - streptavidin , alkyne , click chemistry , biotin , azide , alkyl , chemistry , combinatorial chemistry , biochemistry , organic chemistry , catalysis
The subcellular distribution and accumulation of thymoquinone 1 , a natural anticancer agent, has hitherto been unknown. We prepared 6‐(dec‐9‐ynyl)thymoquinone 3 , an alkyne‐labelled derivative with anticancer activity similar to that of its parent compound 1 . Alkyne 3 was seen, after a Huisgen‐type click reaction with 3‐azido‐7‐hydroxycoumarin, to accumulate in distinct compartments of the nuclei of PtK 2 potoroo kidney cells, and in adjoining regions that were stained with an antibody specific for the Golgi apparatus. In contrast, a biotinlabelled thymoquinone 4 seemed to accumulate across the entire cell nucleus upon visualisation with streptavidin; but this was less easily traceable because of co‐staining of other structures such as mitochondria. In conclusion, for small drug‐like molecules, visualisation by alkyne–azide cycloaddition seems to be superior to conventional visualisation by the biotin–streptavidin system.