Synthesis and activity of novel C-1 analogs of pancratistatin and 7-deoxypancratistatin

Synthesis and activity of novel C-1 analogs of pancratistatin and 7-deoxypancratistatin

Project 2011

Principal Investigator/Inventor: Dr. Tomas Hudlicky, Department of Chemistry

Novel C-1 analogs of pancratistatin and 7-deoxypancratistatin, their synthesis, and their use in selective cancer cell death.

Pancratistatin is a naturally occurring compound isolated from the Amaryllidaceae family of plants and is known to be active against cancer cell lines. Its development as a cancer therapeutic has been hampered by the difficulty in isolating and purifying sufficient quantities from natural sources and its poor bioavailability. Hudlicky’s research group has focused on producing a variety of novel fully synthetic analogues of pancratistatin, in promising yields, with more desirable bioavailability and solubility characteristics. Data show that the novel analogues have significant activity against pancreatic, prostate, lung, breast, neuroblastoma and melanoma cell lines in vitro.

Patent Status

Hudlicky et al., “Novel C-1 analogs of pancratistatin and 7-deoxypancratistatin and process for their preparation.” Applications in: Europe, 09832768.7; US, 61/138774, 13/140209; Canada, 2647655, 2747565.

References and Publications

Vshyvenko, S., et al., (2011). Synthesis of C-1 homologues of pancratistatin and their preliminary biological evaluation. Bioorg Med. Chem. Lett. 21: 4750-2

Vshyvenko, S., et al., (2012). Unnatural C-1 homologues of pancratistatin – Synthesis and promising biological activities. Can. J. Chem. In Press.

 

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