title: Bio-orthogonal phosphatidylserine conjugates for delivery and imaging applications.
abstract: The syntheses of phosphatidylserine (PS) conjugates are described, including fluorescent derivatives for potential cellular delivery and bioimaging applications. Installation of terminal functional groups (amine, thiol, or alkyne) onto the sn-2 chain provides reactive sites for bio-orthogonal conjugation of cargo with suitably protected PS derivatives. An amine-containing PS forms amide bonds with peptidic cargo, a thiol derivative is designed for conjugation to cargo that contain alpha-halo carbonyls or Michael acceptors, and the terminal alkyne PS analogue permits "click" conjugation with any azide-tagged molecule. This latter conjugation method is quite versatile as it can be performed without PS headgroup protection, in aqueous media, and with acid-labile cargo.
authors.affiliation: Department of Chemistry and Biochemistry and Walther Cancer Research Center, 251 Nieuwland Science Hall, University of Notre Dame, Notre Dame, Indiana 46556, USA.
authors.forename: Andrew J
authors.initials: AJ
authors.lastname: Lampkins
authors.forename: Edward J
authors.initials: EJ
authors.lastname: O'Neil
authors.forename: Bradley D
authors.initials: BD
authors.lastname: Smith
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry; D001386:Azides / Q000138:chemical synthesis / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry; D010713:Phosphatidylcholines / Q000737:chemistry; D010718:Phosphatidylserines / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000480:Alkynes; D000588:Amines; D001386:Azides; D005456:Fluorescent Dyes; D010713:Phosphatidylcholines; D010718:Phosphatidylserines; D013438:Sulfhydryl Compounds