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Anti-tumor triterpenoids substituted with nitrogen substituents

INTRODUCTION: 
Triterpenoids are natural compounds with a number of biological activities including anticancer. Most of the triterpenoids are not suffi ciently water soluble, which makes the biological tests diffi cult and also is a reason for low bioavailability. Therefore it is important to improve the solubility by modifying the compounds with polar functional groups such as quarternary ammonium salts.

TECHNOLOGY (INVENTION) DESCRIPTION: 
The invention is based on the introduction of quarternaty ammonium salts into the triterpenic structure of active compounds. Those ammonium salts are connected to the 18-carboxylic acid via alkylester linker. Compounds containing both aliphatic and aromatic quarternary ammonium salts were studied and patented and they showed high in vitro cytotoxic activities.

ADVANTAGES OVER EXISTING SOLUTIONS: 
The invention provides a large group of novel compounds active on broad spectrum of cancer cell lines. New anti-cancer pharmaceuticals can be based on the invention as well as abnormal proliferation therapeutics.

DEVELOPMENT STATUS (STAGE): 
Laboratory scale, data on cell lines, primarily human tumors, orientational pharmacology/toxicology on rodents.

PUBLICATIONS: 
Kvasnica, M., Urban, M., Dickinson, N. J., Sarek, J. Pentacyclic triterpenoids with nitrogen- and sulfur-containing heterocycles: synthesis and medicinal signifi cance. Nat Prod Rep. 2015 Jun 1. PubMed PMID: 26030604 Borkova, L., Jasikova, L., Rehulka, J., Frisonsova, K., Urban, M., Frydrych, I., Popa, I., Hajduch, M., Dickinson, N. J., Vlk, M., Dzubak, P., Sarek, J. Synthesis of cytotoxic 2,2-difl uoroderivatives of dihydrobetulinic acid and allobetulin and study of their impact on cancer cells. Eur J Med Chem. 2015 May 26, doi: 10.1016/j.ejmech.2015.03.068. Epub 2015 Apr 1. PubMed PMID: 25942059. Biedermann, D., Eignerova, B., Hajduch, M., Sarek, J. Synthesis and Evaluation of Biological Activity of the Quaternary Ammonium Salts of Lupane-, Oleanane-, and Ursane-Type Acids. Synthesis – Stuttgart 2010, 22, 3839

IP PROTECTION STATUS: 
Patents: CZ 301158

TECHNOLOGY / IP OWNERS : 
Palacky University Olomouc - Institution of Molecular and Translational Medicine (IMTM), Faculty of Medicine and Dentistry Charles University Prague