Synthesis and cellular studies of porphyrin-cobaltacarborane conjugates.
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.
Hao
Erhong
E
Department of Chemistry, Louisiana State University, Baton Rouge 70803, USA.
Jensen
Timothy J
TJ
Courtney
Brandy H
BH
Vicente
M Graça H
MG
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
D001880:Boranes; D009942:Organometallic Compounds; D011166:Porphyrins