Title

Synthesis and cellular studies of porphyrin-cobaltacarborane conjugates

Document Type

Article

Publication Date

11-1-2005

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-C4H8O2-1,2-C 2B9H10)(1′2′-C2B 9H11)]. These unique zwitterionic compounds have one to four cobaltabisdicarbollide anions conjugated to the porphyrin macrocycle via (CH2CH2O)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. © 2005 American Chemical Society.

Publication Source (Journal or Book title)

Bioconjugate Chemistry

First Page

1495

Last Page

1502

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