title: Synthesis and cellular studies of porphyrin-cobaltacarborane conjugates.
abstract: The total syntheses of five new porphyrin-cobaltacarborane conjugates (1-5) have been achieved in 88-98% yields in a single-step reaction between a nucleophilic meso-pyridyl-containing porphyrin and zwitterionic cobaltacarborane [3,3'-Co(8-C(4)H(8)O(2)-1,2-C(2)B(9)H(10))(1',2'-C(2)B(9)H(11))]. These unique zwitterionic compounds have one to four cobaltabisdicarbollide anions conjugated to the porphyrin macrocycle via (CH(2)CH(2)O)(2) chains. The X-ray structure of one of these conjugates (1) is presented and discussed. The cellular uptake, cytotoxicity, and subcellular localization of cobaltacarboraneporphyrins 1-5 were investigated in human HEp2 cells. The number and distribution of cobaltacarborane residues linked to the porphyrin macrocycle has a significant effect on the cellular uptake of the conjugates.
authors.affiliation: Department of Chemistry, Louisiana State University, Baton Rouge 70803, USA.
authors.forename: Erhong
authors.initials: E
authors.lastname: Hao
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Jensen
authors.forename: Brandy H
authors.initials: BH
authors.lastname: Courtney
authors.forename: M Graça H
authors.initials: MG
authors.lastname: Vicente
mesh_terms: D001880:Boranes / Q000138:chemical synthesis* / Q000493:pharmacokinetics / Q000633:toxicity; D016754:Boron Neutron Capture Therapy; D002460:Cell Line; D018360:Crystallography, X-Ray; D006801:Humans; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000493:pharmacokinetics / Q000633:toxicity; D011166:Porphyrins / Q000138:chemical synthesis* / Q000493:pharmacokinetics / Q000633:toxicity; D013329:Structure-Activity Relationship
chemical_list: D001880:Boranes; D009942:Organometallic Compounds; D011166:Porphyrins