16:00 - 18:00
Room: San Francisco
Poster session
Preparation and chemo-sensitizing activity of nitrogen-containing ecdysteroid derivatives: 6-oximes, oxime ethers, and a lactam
Vágvölgyi Máté 1, Martins Ana 2, Kulmány Ágnes 3, Zupkó István 3, Tóth Gábor 1, 4, Hunyadi Attila 1, 5
1 Institute of Pharmacognosy, University of Szeged, Szeged, Hungary
2 Department of Medical Microbiology and Immunobiology, Faculty of Medicine, University of Szeged, Szeged, Hungary
3 Department of Pharmacodynamics and Biopharmacy, University of Szeged, Szeged, Hungary
4 Department of Inorganic and Analytical Chemistry, NMR Group, Budapest University of Technology and Economics, Budapest, Hungary
5 Interdisciplinary Centre for Natural Products, University of Szeged, Szeged, Hungary

Ecdysteroids are a group of natural hydroxysteroids, widespread in plants and invertebrates, exerting a broad spectrum of biological functions. These nontoxic compounds are commonly valued for their beneficial, non-hormonal bioactivities also in mammals including humans. Recent studies of our group revealed that less polar ecdysteroids can strongly sensitize various cancer cell lines, including multi-drug resistant (MDR) and drug susceptible ones, to chemotherapeutics. [1-3] Oxime functionalities can increase the antitumor activity of certain steroids; [4] however, no related studies on ecdysteroid oximes have been performed.

Here we report the synthesis and bioactivity testing of a set of nitrogen-containing ecdysteroid derivatives. By optimizing previously published methodology [5], 14 compounds including 12 new derivatives (oximes, oxime ethers and a lactam) were prepared from the semi-synthetic modification of 20-hydroxyecdysone 2,3;20,22-diacetonide.

All compounds were tested for their antiproliferative activity against various cancer cells followed by determination of the chemo-sensitizing potential towards doxorubicin on a P-glycoprotein (Pgp) transfected MDR cancer cell line and on its sensitive counterpart. Moderate to strong anti-proliferative activities were observed. Each compound could considerably sensitize the studied cancer cell lines, with a noticeable selectivity towards the MDR one. The most promising results were obtained for a new ecdysteroid lactam, which showed remarkably strong chemo-sensitizing potential without interfering with the efflux function of Pgp.


This work was supported by the NKFIH, Hungary (K119770), the EU-funded Hungarian grant EFOP-3.6.1-16-2016-00008, and GINOP-2.3.2-15-2016-00012. A.H. acknowledges the János Bolyai fellowship of the Hungarian Academy of Sciences and the Kálmán Szász Prize.


[1] Martins A et al. J Med Chem 2012; 55 : 5034-5043.

[2] Martins A et al. Biomed Res Int , 2015; 895360.

[3] Cui JG et al. Steroids 2009; 74 : 62-72 and 2009; 74 : 989-995.

[4] Galyautdinov IV et al. Russ J Org Chem 2006; 42 : 1333-1339.

[5] Shafikov RV Russ J Org Chem 2009; 45 : 1456-1463.

Mo-Poster Session 1-PO-98:
Poster Session 1
Attila Hunyadi
Presentation type:
Poster presentation
San Francisco
Monday, 4th September, 2017
16:00 - 18:00
Session times:
16:00 - 18:00