Synthesis and Biological Evaluation of Chlorinated Analogs of Leukotoxin Diol

Christian Nilewski; Camille Le Chapelain; Susanne Wolfrum; Erick M Carreira

doi:10.1021/acs.orglett.5b02814

Synthesis and Biological Evaluation of Chlorinated Analogs of Leukotoxin Diol

Org Lett. 2015 Nov 20;17(22):5602-5. doi: 10.1021/acs.orglett.5b02814. Epub 2015 Oct 30.

Authors

Christian Nilewski¹, Camille Le Chapelain¹, Susanne Wolfrum¹, Erick M Carreira¹

Affiliation

¹ Vladimir Prelog Weg 3, Laboratory of Organic Chemistry, ETH-Zürich , CH-8093 Zurich, Switzerland.

PMID: 26517019
DOI: 10.1021/acs.orglett.5b02814

Abstract

This study documents that chlorinated analogs of leukotoxin diol 1, in which the vic-diol has been replaced with vic-chlorides (2), induce caspase 3 activity and apoptosis on HepG2 cells in a dose-dependent manner in analogy to the parent diol. This suggests that chlorides may substitute for hydroxyls in certain lipids as bioisosteres in defined biological settings.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Apoptosis
Exotoxins / chemical synthesis*
Exotoxins / chemistry
Exotoxins / pharmacology
Halogenation
Humans
Molecular Structure
Stearic Acids / chemical synthesis*
Stearic Acids / chemistry
Stearic Acids / pharmacology
Stearic Acids / toxicity*

Substances

9,10-dihydroxy-12-octadecenoic acid
Exotoxins
Stearic Acids
leukotoxin