Title:

Cytotoxicity of semisynthetic betulin derivatives

Author:

Achrem-Achremowicz, Jacek

Subject:

betulin ; triterpenes ; cytotoxicity

Abstract:

Betulin is a pentacyclic triterpene of the lupane type present as the main ingredient of the outer bark of birch trees (Betula sp.). In recent years there have been published several articles about pharmacological activity of the lupane type triterpenes concerning mainly cytotoxicity against cancer cells, antimalarial and antiinflammatory activities, etc. From the purified betulin isolated from the bark of Betula verrucosa Erh. 18 derivatives were synthesized. Identity of the compounds was confirmed on the basis of chromatographic (TLC) and spectroscopic (NMR, MS i IR) data, and theoretical values of log P were calculated, whereas for some of the compounds the values of molar lipophilicity (RM0) were determined with the use of reversed thin layer chromatography. Cytotoxicity was measured with MTT and LDH tests on NCI-H292 and ARPE-19 human cell lines. TB test was performed on murine cells B16, XC and 3T3. Most of the derivatives showed strong and often selective cytotoxic activity that was comparable to doxorubicine and colchicine. In the series of derivatives several correlations structure-activity (SAR) were found; additionally cytotoxicity of betulin derivatives measured in TB test was found to be dependant on the lipophilicity. Two models describing cytotoxicity as a function of lipophilicity were presented.

Place of publishing:

Kraków

Level of degree:

2 - studia doktoranckie

Degree discipline:

farmakologia

Degree grantor:

Wydział Farmaceutyczny

Promoter:

Janeczko, Zbigniew

Date:

2008

Date issued:

2007

Type:

Praca doktorska

Call number:

ZB-107454

Language:

pol

Access rights:

nieograniczony