title: Bioconjugates of enantiomerically pure organopalladium compounds by metal-assisted positional selective transesterifications at palladium enolates.
abstract: The synthesis of enantiomerically pure palladatricyclo[4.1.0.0(2,4)]heptanes and their modification by an unprecedented and very efficient positional selective transesterification is described. The mild reaction conditions are most probably based on an acceleration of the transesterification due to assistance by the metal. This novel approach allows straightforward access to a large number of structurally diverse organometallic complexes. The functional groups on the newly installed ester moieties were modified by using standard peptide synthesis protocols, Sonogashira reactions, and nucleophilic substitution reactions. The cellular uptake of these organometallic species was traced by confocal microscopy and their biological activity was evaluated by using different cell lines. Inhibition of cell growth and induction of apoptotic cell death by these novel palladium heterocycles are equivalent to Cisplatin.
authors.affiliation: Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany. hashmi@hashmi.de
authors.forename: A Stephen K
authors.initials: AS
authors.lastname: Hashmi
authors.forename: Dominic
authors.initials: D
authors.lastname: Riedel
authors.forename: Marc A
authors.initials: MA
authors.lastname: Grundl
authors.forename: Bärbel C
authors.initials: BC
authors.lastname: Wittel
authors.forename: Andreas
authors.initials: A
authors.lastname: Föll
authors.forename: Jana
authors.initials: J
authors.lastname: Lubkoll
authors.forename: Telisha
authors.initials: T
authors.lastname: Traut
authors.forename: Raymond
authors.initials: R
authors.lastname: Hewer
authors.forename: Frank
authors.initials: F
authors.lastname: Rominger
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Frey
authors.forename: Jan W
authors.initials: JW
authors.lastname: Bats
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D017209:Apoptosis / Q000187:drug effects*; D002384:Catalysis; D045744:Cell Line, Tumor / Q000187:drug effects*; D003508:Cycloheptanes / Q000737:chemistry*; D004951:Esterification; D006801:Humans; D008670:Metals / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D003508:Cycloheptanes; D008670:Metals; D009942:Organometallic Compounds; D010165:Palladium