Synthesis of psymberin analogues

Probing a functional correlation with the pederin/mycalamide family of natural products

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64 Citations (Scopus)

Abstract

(Chemical Equation Presented) In this letter we describe an efficient synthesis of "psympederin", a hybrid between the novel antitumor natural product psymberin and the blister beetle toxin pederin. Evaluation of antiproliferative activity reveals that the dihydroisocoumarin fragment is important for psymberin toxicity and the cyclic pederate fragment is important for pederin/mycalamide toxicity. On the basis of preliminary results described herein, we speculate that, despite their structural resemblance, psymberin and pederin/mycalamide induce toxicity through different mechanisms.

Original languageEnglish (US)
Pages (from-to)227-230
Number of pages4
JournalOrganic Letters
Volume9
Issue number2
DOIs
StatePublished - Jan 18 2007

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Biological Products
toxicity
Toxicity
analogs
synthesis
products
fragments
beetles
blisters
Beetles
Blister
evaluation
psymberin
pederin

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

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AU - Jiang, Xin

AU - Williams, Noelle

AU - De Brabander, Jef K.

PY - 2007/1/18

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AB - (Chemical Equation Presented) In this letter we describe an efficient synthesis of "psympederin", a hybrid between the novel antitumor natural product psymberin and the blister beetle toxin pederin. Evaluation of antiproliferative activity reveals that the dihydroisocoumarin fragment is important for psymberin toxicity and the cyclic pederate fragment is important for pederin/mycalamide toxicity. On the basis of preliminary results described herein, we speculate that, despite their structural resemblance, psymberin and pederin/mycalamide induce toxicity through different mechanisms.

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