New acetylenic derivatives of betulin and betulone, synthesis and cytotoxic activity

Ewa Bębenek; Monika Kadela-Tomanek; Elwira Chrobak; Joanna Wietrzyk; Joanna Sadowska; Stanisław Boryczka

doi:10.1007/s00044-016-1713-9

New acetylenic derivatives of betulin and betulone, synthesis and cytotoxic activity

Med Chem Res. 2017;26(1):1-8. doi: 10.1007/s00044-016-1713-9. Epub 2016 Sep 1.

Authors

Ewa Bębenek¹, Monika Kadela-Tomanek¹, Elwira Chrobak¹, Joanna Wietrzyk², Joanna Sadowska², Stanisław Boryczka¹

Affiliations

¹ Department of Organic Chemistry, Medical University of Silesia in Katowice, School of Pharmacy with the Division of Laboratory Medicine in Sosnowiec, 4 Jagiellońska Str., Sosnowiec, 41-200 Poland.
² Department of Experimental Oncology, Polish Academy of Sciences, Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, 12 R. Weigla Str., Wrocław, 53-114 Poland.

Abstract

Betulin 1 and its semisynthetic derivatives exhibit a cytotoxic activity toward various cancer cell lines. These compounds are a promising and potential anticancer candidates. A series of betulin derivatives was prepared and tested for the antiproliferative activity in vitro against T47D breast cancer, CCRF/CEM leukemia, HL-60 promyelocytic leukemia, SW707 colorectal, murine P388 leukemia, as well as BALB3T3 normal fibroblasts cell lines. Cisplatin and betulin 1 were used as a reference compounds. Some derivatives of betulin showed a higher cytotoxic activity than the parent compound 1. Two derivatives (5 and 17) were 24-fold potent than betulin 1 against the human promyelocytic leukemia cell line (HL-60), with an IC₅₀ value of 0.3 µg/mL.

Keywords: Betulin; Betulone; Cytotoxic activity; Lipophilicity; Synthesis.

Publication types

Review