Chiral resolution of a caged xanthone and evaluation across a broad spectrum of breast cancer subtypes

Oraphin Chantarasriwong, Tanis J. Dorwart, Theodore Habarth Morales, Stephanie F. Maggio, Aspen L. Settle, Andrew T. Milcarek, Mary L. Alpaugh, Maria A. Theodoraki, Emmanuel A. Theodorakis

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Racemic resolution of (+/−)-MAD28, a representative caged xanthone, was accomplished using (1S, 4R)-(−)-camphanic chloride as the chiral agent. Selective crystallization of the resulting diastereomers in acetonitrile produced, after hydrolysis, the pure enantiomers. Screening of racemic MAD28 and both enantiomers across a broad spectrum of breast cancer cell lines revealed that they: (a) are equipotent in each of the breast cancer subtypes examined; and (b) exhibit a higher degree of cytotoxicity against breast cancer cell lines of basal-like subtype and triple negative receptor status. The results support the notion that MAD28 and related caged xanthones are promising drug leads against chemoresistant and metastatic cancers.

Original languageEnglish (US)
Article number103303
JournalBioorganic Chemistry
Volume93
DOIs
StatePublished - Dec 2019

All Science Journal Classification (ASJC) codes

  • Drug Discovery
  • Molecular Biology
  • Biochemistry
  • Organic Chemistry

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