Open Access Open Access  Restricted Access Subscription Access

HETEROCYCLIC ANALOGS OF 5,12-NAPHTHACENEQUINONE 16*. SYNTHESIS AND PROPERTIES OF NEW DNA LIGANDS BASED ON 4,11-DIAMINOANTHRA[2,3-b]THIOPHENE-5,10-DIONE

Дарья B. Андреева, Александр С. Тихомиров, Любовь Г. Деженкова, Дмитрий Н. Калюжный, Ольга К. Мамаева, Светлана Е. Соловьева, Юрий Б. Синькевич, Андрей Е. Щекотихин
Cover Image

Abstract


A divergent route for the synthesis of new derivatives of 4,11-diaminoanthra[2,3-b]thiophene-5,10-dione was developed based on the
introduction of cyclic amines to the terminal positions of 4,11-aminoalkyl groups. Modification of the side chains of anthra[2,3-b]thiophene-5,10-dione increases the affinity of ligands to DNA duplex and decreases the affinity to G-quadruplexes. An analysis of the structure–activity relationship showed that 2-(piperidin-1-yl)ethylamine is the most promising side chain fragment for the development of new double-stranded DNA ligands. The ability of new ligands to bind to DNA duplex correlates with inhibition of tumor cell growth,
which indicates the prospects for a further search for new antitumor compounds or chemical probes for duplex-forming nucleic acid sequences among 4,11-diaminoanthra[2,3-b]thiophene-5,10-diones.

Keywords


anthra[2,3-b]thiophene-5,10-diones; nucleic acids; antitumor properties; G-quadruplexes; nucleophilic substitution.

Full Text: PDF (Russian) Supplementary File(s): None


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv