title: The possible role of enantiodiscrimination in bilirubin toxicity.
abstract: The possibility that enantiodiscrimination of bilirubin might be involved in neuronal membrane destabilization, and therefore in bilirubin toxicity, was investigated, by circular dichroism, on model membranes composed of phospholipids. The equilibrium between bilirubin enantiomers is displaced at some extent by the interaction with certain phospholipids. The extent of equilibrium displacement depends on the molecular structure of phospholipids and on the state of charge of bilirubin. The results obtained validate the hypothesis of a possible involvement of chirality in bilirubin toxicity and support a previously suggested model for the molecular mechanism of the interaction of bilirubin with the synaptic membrane.
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Roma La Sapienza, Roma, Italy.
authors.forename: Carlotta
authors.initials: C
authors.lastname: Bernardini
authors.forename: Paola
authors.initials: P
authors.lastname: D'Arrigo
authors.forename: Gioia
authors.initials: G
authors.lastname: Elemento
authors.forename: Giovanna
authors.initials: G
authors.lastname: Mancini
authors.forename: Stefano
authors.initials: S
authors.lastname: Servi
authors.forename: Alessandro
authors.initials: A
authors.lastname: Sorrenti
mesh_terms: D000818:Animals; D001663:Bilirubin / Q000737:chemistry* / Q000633:toxicity*; D002417:Cattle; D002462:Cell Membrane / Q000737:chemistry / Q000187:drug effects; D002942:Circular Dichroism; D006863:Hydrogen-Ion Concentration; D008081:Liposomes / Q000737:chemistry; D010767:Phosphorylcholine / Q000737:chemistry; D013109:Sphingomyelins / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D014867:Water / Q000737:chemistry
chemical_list: D008081:Liposomes; D013109:Sphingomyelins; D014867:Water; D010767:Phosphorylcholine; D001663:Bilirubin