title: Identification of chiral alkenyl- and alkynylcarbinols as pharmacophores for potent cytotoxicity.
abstract: Illumination by acetylene: Systematic structural variations in a series of archetypal acetylenic lipids derived from the naturally occurring (S,E)-icos-4-en-1-yn-3-ol allowed the discovery of a series of 3R-like 1,4-di-unsaturated carbinol units with a significant and systematic enantiomeric effect on cytotoxicity.
authors.affiliation: SPCMIB, UMR-CNRS 5068, Université Paul Sabatier-Toulouse III, 118 route de Narbonne, 31062 Toulouse Cedex 9 (France); LCOA, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fès (Marocco).
authors.forename: Dounia
authors.initials: D
authors.lastname: El Arfaoui
authors.forename: Dymytrii
authors.initials: D
authors.lastname: Listunov
authors.forename: Isabelle
authors.initials: I
authors.lastname: Fabing
authors.forename: Mohamed
authors.initials: M
authors.lastname: Oukessou
authors.forename: Céline
authors.initials: C
authors.lastname: Frongia
authors.forename: Valérie
authors.initials: V
authors.lastname: Lobjois
authors.forename: Arnaud
authors.initials: A
authors.lastname: Samson
authors.forename: Frédéric
authors.initials: F
authors.lastname: Ausseil
authors.forename: Abdeslem
authors.initials: A
authors.lastname: Ben-Tama
authors.forename: El Mestafa
authors.initials: el M
authors.lastname: El Hadrami
authors.forename: Remi
authors.initials: R
authors.lastname: Chauvin
authors.forename: Yves
authors.initials: Y
authors.lastname: Génisson
mesh_terms: D000473:Alkanes / Q000737:chemistry / Q000494:pharmacology; D000475:Alkenes / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D055808:Drug Discovery; D020128:Inhibitory Concentration 50; D000432:Methanol / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D047130:Petrosia / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000473:Alkanes; D000475:Alkenes; D000970:Antineoplastic Agents; D000432:Methanol
keywords: asymmetric synthesis; carbinols; cytotoxicity; lipids; polyacetylene