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 quaternary ammonium salts.
The invention is based on the introduction of quaternary ammonium salts into the triterpenic structure of active compounds. Those ammonium salts are connected to the 18-carboxylic acid via alkyl-ester linker. Compounds containing both aliphatic and aromatic quaternary 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 pharmaceu¬ticals 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., M. Urban, N. J. Dickinson, J. Sarek. Pentacyclic triterpenoids with nitrogen- and sulfur-containing heterocycles: synthesis and medicinal significance. Natural Product Reports. 2015, 32(9), 1303-30. ISSN: 1460-4752. IF: 10.986. PMID: 26030604 Borkova, L., L. Jasikova, J. Rehulka, K. Frisonsova, M. Urban, I. Frydrych, I. Popa, M. Hajduch, N. J. Dickinson, M. Vlk, P. Dzubak, J. Sarek. Synthesis of cytotoxic 2,2-difluoroderivatives of dihydrobetulinic acid and allobetulin and study of their impact on cancer cells. European Journal of Medicinal Chemistry. 2015, 96, 482-90. ISSN: 0223-5234. IF: 3.902. PMID: 25942059. Biedermann, D., B. Eignerova, M. Hajduch, J. Sarek. Synthesis and Evaluation of Biological Activity of the Quaternary Ammonium Salts of Lupane-, Oleanane-, and Ursane-Type Acids. Synthesis-Stuttgart. 2010, (22): 3839-3848. ISSN: 0039-7881. IF: 2.260
Institute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry, Palacky University, Olomouc
More information is available upon signing a CDA/NDA. Please contact IMTM´s director (firstname.lastname@example.org) or the technology transfer office (email@example.com)