Abstract: The present invention relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, intermediates thereto, and uses thereof. QS-7 is a potent immuno-adjuvant that is significantly less toxic than QS-21, a related saponin that is currently the favored adjuvant in anticancer and antiviral vaccines. Tedious isolation and purification protocols have hindered the clinical development of QS-7. A novel semi-synthetic method is provided wherein a hydrolyzed prosapogenin mixture is used to synthesize QS-7, QS-21, and related analogs, greatly facilitating access to QS-7 and QS-21 analogs for preclinical and clinical evaluation.
Type:
Grant
Filed:
September 24, 2014
Date of Patent:
August 1, 2017
Assignee:
MEMORIAL SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH
Inventors:
David Gin, Michelle Adams, Kai Deng, Philip Livingston, Govindaswami Ragupathi, Eric Chea, Alberto Fernandez-Tejada, Lars Ulrik Nordstroem, William Walkowicz, Jeffrey Gardner, Derek Tan
Abstract: The present invention provides a method of synthesizing an allyl pentasaccharide having the structure:
as well as related oligosaccharide ceramides and other glycoconjugates useful as vaccines for inducing antibodies to epithelial cancer cells in an adjuvant therapy therefor, and in a method for preventing recurrence of epithelial cancer.
Type:
Grant
Filed:
July 24, 1995
Date of Patent:
October 16, 2001
Assignee:
Memorial Sloan-Kettering Institute for Cancer Research
Inventors:
Samuel J. Danishefsky, Victor Behar, Kenneth O. Lloyd