Synthesis and cellular studies of an octa-anionic 5,10,15,20-tetra[3,5- (nido-carboranylmethyl)phenyl]porphyrin (H2OCP) for application in BNCT
The total synthesis of 5,10,15,20-tetra[3,5-(carboranylmethyl)phenyl] porphyrins 2-5 containing 36-43% boron by weight are reported. All compounds were characterized by spectroscopic methods and, in the case of 2, by X-ray crystallography. The water-soluble nido-carboranylporphyrin 5 (H2OCP) was found to have low dark toxicity toward V79 lung fibroblasts (CS 50 ≥ 250 μM), to be readily taken up by human glioblastoma T98G cells in culture and to localize subcellularly preferentially in the cell lysosomes. In comparison with a known tetra(nido-carboranyl)porphyrin (6), H2OCP (5) is taken up slower and to a lower extent by T98G cells, possibly as a result of its higher hydrophilic character. The metal-free H 2OCP (5) was also found to accumulate to a higher extent in T98G cells compared with its zinc(II) complex analog 4. Our studies show that carboranylporphyrins bearing eight nido-carborane cages can still accumulate intracellularly and have low dark toxicity toward cells in culture, and therefore might have promise for application in BNCT. © 2004 Elsevier Ltd. All rights reserved.
Publication Source (Journal or Book title)
Bioorganic and Medicinal Chemistry
Gottumukkala, V., Luguya, R., Fronczek, F., & Vicente, M. (2005). Synthesis and cellular studies of an octa-anionic 5,10,15,20-tetra[3,5- (nido-carboranylmethyl)phenyl]porphyrin (H2OCP) for application in BNCT. Bioorganic and Medicinal Chemistry, 13 (5), 1633-1640. https://doi.org/10.1016/j.bmc.2004.12.016