title: Biological Investigations of (+)-Danicalipin A Enabled Through Synthesis.
abstract: A total synthesis of the chlorosulfolipid (+)-danicalipin A has been accomplished in 12 steps and 4.4% overall yield. The efficient and scalable synthesis enabled in-depth investigations of the lipid's biological properties, in particular cytotoxicity towards various mammalian cell lines. Furthermore, the ability of (+)-danicalipin A to increase the uptake of fluorophores into bacteria and mammalian cells was demonstrated, indicating it may enhance membrane permeability. By comparing (+)-danicalipin A with racemic 1,14-docosane disulfate, and the diol precursor of (+)-danicalipin A, we have shown that both chlorine and sulfate functionalities are necessary for biological activity.
authors.affiliation: Laboratorium für Organische Chemie, Eidgenössische Technische Hochschule Zürich, HCI H335, Vladimir-Prelog-Weg 3, 8093 Zürich (Switzerland).
authors.forename: Adrian M
authors.initials: AM
authors.lastname: Bailey
authors.affiliation: Laboratorium für Organische Chemie, Eidgenössische Technische Hochschule Zürich, HCI H335, Vladimir-Prelog-Weg 3, 8093 Zürich (Switzerland).
authors.forename: Susanne
authors.initials: S
authors.lastname: Wolfrum
authors.affiliation: Laboratorium für Organische Chemie, Eidgenössische Technische Hochschule Zürich, HCI H335, Vladimir-Prelog-Weg 3, 8093 Zürich (Switzerland). carreira@org.chem.ethz.ch.
authors.forename: Erick M
authors.initials: EM
authors.lastname: Carreira
mesh_terms: D000818:Animals; D002460:Cell Line; D005456:Fluorescent Dyes / Q000737:chemistry; D019073:HT29 Cells; D006801:Humans; D008055:Lipids / Q000138:chemical synthesis / Q000494:pharmacology*; D051379:Mice
chemical_list: D005456:Fluorescent Dyes; D008055:Lipids; C557671:danicalipin A
keywords: biological function; cell membranes; chlorosulfolipids; natural products; total synthesis