Conjugates of the fungal cytotoxin illudin M with improved tumour specificity

Bioorganic & Medicinal Chemistry
Rainer SchobertMatthias Ocker

Abstract

A simplified procedure for the isolation of gram quantities of illudin M from culture broths of basidiomycete Omphalotus olearius is described. Esters of illudin M with docosahexaenoic acid, chlorambucil, demethylcantharidinic acid (endothall) and 2,2'-bipyridyl-5,5'-dicarboxylic acid were synthesised and tested for cytotoxicity and induction of apoptosis in two clinically relevant tumour cell lines (Panc-1 pancreas carcinoma and HT-29 colon carcinoma) and in non-malignant human foreskin fibroblasts. The demethylcantharidin and the bipyridine conjugates retained the cytotoxicity of the parent illudin M while displaying an improved specificity for the tumour cells over the fibroblasts.

References

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Mar 9, 2002·Breast Cancer Research and Treatment·Maryanne C S HerzigJan M Woynarowski
May 4, 2004·Prostaglandins, Leukotrienes, and Essential Fatty Acids·Undurti N Das

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Citations

Apr 10, 2012·Chemical Reviews·Marina Tanasova, Shana J Sturla
Aug 19, 2011·Journal of Medicinal Chemistry·Rainer SchobertThomas Mueller
Jul 17, 2009·Anti-cancer Drugs·Sebastian KnauerRainer Schobert
Mar 7, 2014·PloS One·Malgorzata Sztiller-SikorskaMalgorzata Czyz
Aug 21, 2009·Natural Product Reports·Braulio M Fraga
Jul 17, 2019·Chemistry : a European Journal·Philipp LeStephan A Sieber
Jul 30, 2020·Journal of Controlled Release : Official Journal of the Controlled Release Society·Nadia FattahiHélder A Santos

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