Cellular Localisation of Antitumoral 6-Alkyl Thymoquinones Revealed by an Alkyne-Azide Click Reaction and the Streptavidin-Biotin System

被引：10

作者：

Effenberger-Neidnicht, Katharina ^{[1
]}

Breyer, Sandra ^{[1
]}

Mahal, Katharina ^{[1
]}

Diestel, Randi ^{[2
]}

Sasse, Florenz ^{[2
]}

Schobert, Rainer ^{[1
]}

机构：

[1] Univ Bayreuth, Organ Chem Lab, D-95440 Bayreuth, Germany

[2] Helmholtz Ctr Infect Res HZI, Dept Biol Chem, D-38124 Braunschweig, Germany

来源：

CHEMBIOCHEM | 2011年 / 12卷 / 08期

关键词：

alkynes; biotin; click chemistry; fluorescent probes; thymoquinone; CANCER; ACTIVATION; CHEMISTRY; PEPTIDES; GROWTH;

D O I：

10.1002/cbic.201000762

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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 PtK2 potoroo kidney cells, and in adjoining regions that were stained with an anti-body specific for the Golgi apparatus. In contrast, a biotin-labelled 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.

引用

页码：1237 / 1241

页数：5