Synthesis, Structure and Cytotoxic Activity of New Acetylenic Derivatives of Betulin

被引：75

作者：

Boryczka, Stanislaw ^{[1
]}

Bebenek, Ewa ^{[1
]}

Wietrzyk, Joanna ^{[2
]}

Kempinska, Katarzyna ^{[2
]}

Jastrzebska, Maria ^{[3
]}

Kusz, Joachim ^{[4
]}

Nowak, Maria ^{[3
,4
]}

机构：

[1] Med Univ Silesia, Dept Organ Chem, PL-41200 Sosnowiec, Poland

[2] Polish Acad Sci, Dept Expt Oncol, Ludwik Hirszfeld Inst Immunol & Expt Therapy, PL-53114 Wroclaw, Poland

[3] Univ Silesia, Inst Phys, Dept Solid State Phys, PL-40007 Katowice, Poland

[4] Univ Silesia, Inst Phys, Dept Phys Crystals, PL-40007 Katowice, Poland

来源：

MOLECULES | 2013年 / 18卷 / 04期

关键词：

acetylenic betulins; synthesis; crystal structure; cytotoxic activity; IN-VITRO; CRYSTAL-STRUCTURE; ACID; TRITERPENOIDS; INHIBITOR; AGENTS;

D O I：

10.3390/molecules18044526

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

070307 [化学生物学]; 071010 [生物化学与分子生物学];

摘要：

A new series of betulin derivatives containing one or two pharmacophores bearing an acetylenic and carbonyl function at the C-3 and/or C-28 positions has been synthesized and characterized by H-1- and C-13-NMR, IR, MS and elemental analyses. The crystal structure of 28-O-propynoylbetulin was determined by X-ray structural analysis. All new compounds, as well as betulin, were tested in vitro for their antiproliferative activity against human SW707 colorectal, CCRF/CEM leukemia, T47D breast cancer, and against murine P388 leukemia and Balb3T3 normal fibroblasts cell lines. Most of the compounds showed better cytotoxicity than betulin and cisplatin used as reference agent. 28-O-Propynoylbetulin was the most potent derivative, being over 500 times more potent than betulin and about 100 times more cytotoxic than cisplatin against the human leukemia (CCRF/CEM) cell line, with an ID50 value of 0.02 mu g/mL.

引用

页码：4526 / 4543

页数：18

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