title: Synthesis and Biological Evaluation of Chlorinated Analogs of Leukotoxin Diol.
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.
authors.affiliation: Vladimir Prelog Weg 3, Laboratory of Organic Chemistry, ETH-Zürich , CH-8093 Zurich, Switzerland.
authors.forename: Christian
authors.initials: C
authors.lastname: Nilewski
authors.affiliation: Vladimir Prelog Weg 3, Laboratory of Organic Chemistry, ETH-Zürich , CH-8093 Zurich, Switzerland.
authors.forename: Camille
authors.initials: C
authors.lastname: Le Chapelain
authors.affiliation: Vladimir Prelog Weg 3, Laboratory of Organic Chemistry, ETH-Zürich , CH-8093 Zurich, Switzerland.
authors.forename: Susanne
authors.initials: S
authors.lastname: Wolfrum
authors.affiliation: Vladimir Prelog Weg 3, Laboratory of Organic Chemistry, ETH-Zürich , CH-8093 Zurich, Switzerland.
authors.forename: Erick M
authors.initials: EM
authors.lastname: Carreira
mesh_terms: D017209:Apoptosis; D005098:Exotoxins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D054879:Halogenation; D006801:Humans; D015394:Molecular Structure; D013229:Stearic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology / Q000633:toxicity*
chemical_list: C120038:9,10-dihydroxy-12-octadecenoic acid; D005098:Exotoxins; D013229:Stearic Acids; C018579:leukotoxin