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Salinomycin Hydroxamic Acids: Synthesis, Structure, and Biological Activity of Polyether Ionophore Hybrids

Author:
  • Björn Borgström
  • Xiaoli Huang
  • Eduard Chygorin
  • Stina Oredsson
  • Daniel Strand
Publishing year: 2016-04-25
Language: English
Pages: 635-640
Publication/Series: ACS Medicinal Chemistry Letters
Volume: 7
Issue: 6
Document type: Journal article
Publisher: The American Chemical Society (ACS)

Abstract english

The polyether ionophore salinomycin has recently gained attention due to its exceptional ability to selectively reduce the proportion of cancer stem cells within a number of cancer cell lines. Efficient single step strategies for the preparation of hydroxamic acid hybrids of this compound varying in N- and O-alkylation are presented. The parent hydroxamic acid, salinomycin-NHOH, forms both inclusion complexes and well-defined electroneutral complexes with potassium and sodium cations via 1,3-coordination by the hydroxamic acid moiety to the metal ion. A crystal structure of an cationic sodium complex with a noncoordinating anion corroborates this finding and, moreover, reveals a novel type of hydrogen bond network that stabilizes the head-to-tail conformation that encapsulates the cation analogously to the native structure. The hydroxamic acid derivatives display down to single digit micromolar activity against cancer cells but unlike salinomycin selective reduction of ALDH+ cells, a phenotype associated

Keywords

  • Biochemistry and Molecular Biology
  • Medical Biotechnology
  • Salinomycin
  • ALDH+
  • head-to-tail conformation
  • hydroxamic acid derivate

Other

Published
  • ISSN: 1948-5875
Stina Oredsson
E-mail: stina [dot] oredsson [at] biol [dot] lu [dot] se

Professor

Functional zoology

+46 46 222 94 97

B-C208

4

Principal investigator

LUCC - Lund University Cancer Centre

Research group

Animal Physiology

Projects

Cell proliferation

Doctoral students and postdocs

PhD Students, main supervisor

Wendy Soria Sotillo

PhD Students, assistant supervisor

Atena Malakpour Permlid