Anti-tumor triterpenoids substituted with nitrogen substituents
Triterpenoids are natural compounds with a number of biological activities including anticancer. Most of the triterpenoids are not sufficiently water soluble, which makes the biological tests difficult 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.
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.
Laboratory scale, data on cell lines, primarily human tumors, orientational pharmacology/toxicology on rodents.
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.
Exclusive/non-exclusive licence to the patent, related know-how and data
Kvasnica, M., Urban, M., Dickinson, N. J., Sarek, J. Pentacyclic triterpenoids with nitrogen- and sulfur-containing heterocycles: synthesis and medicinal significance. 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-difluoroderivatives 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
Institute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry, Palacky University, Olomouc
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