Toward "best-in-class" Hsp90 inhibitors: Design, biosynthesis and preclinical profiles

MEDI 351

Christine J Martin, christine.martin@biotica.com1, Sabine Gaisser1, William A Vousden1, Lesley S Sheehan1, Teresa Foster1, Rose M Sheridan1, Mohammad Nur-E-Alam1, Nigel Coates1, Steven J Moss, steven.moss@biotica.com1, Christoph Beckmann1, Barrie Wilkinson1, Matthew A Gregory1, Chris Prodromou2, Laurence Pearl2, Thomas Greiner3, Niko Bausch3, and Ming Q Zhang1. (1) Biotica Technology Ltd, Chesterford Research Park, Little Chesterford, CB10 1XL, United Kingdom, (2) Institute of Cancer Research, London, United Kingdom, (3) Oncotest GmbH, Freiburg, Germany
Hsp90 inhibitors in advanced development for cancer can broadly be classified into two groups: semi-synthetic derivatives of naturally occurring ansamycins and small molecules, such as mimetics of adenosine and non-purine based resorcinol compounds. Semi-synthetic ansamycins such as 17-DMAG and 17-AAG, contain a common quinone ‘toxicophore'. Through genetic engineering of the macbecin biosynthetic pathway we have now prepared a series of derivatives that lack the undesired quinone moiety. The most potent compound of this series has a binding affinity (Kd) of 3 nM to Hsp90, and is much better tolerated in vivo than 17-AAG (MTTD ≥ 250 mg/kg vs ~50 mg/kg i.p. in mice). It showed equivalent in vivo tumor growth inhibition in xenograft models at ≤ 1/3 MTTD to that of 17-AAG at MTTD. The improved therapeutic index coupled with its potent inhibition of Hsp90 makes the compound potentially the ‘best-in-class' Hsp90 inhibitor described to-date.
 

Poster Session
7:00 PM-9:00 PM, Wednesday, August 22, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Medicinal Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007