Back to Search
Start Over
Synthesis and in Vitro Studies of a Series of Carborane-Containing Boron Dipyrromethenes (BODIPYs).
- Source :
-
Journal of Medicinal Chemistry . Mar2016, Vol. 59 Issue 5, p2109-2117. 9p. - Publication Year :
- 2016
-
Abstract
- A series of seven BODIPYs functionalized with ortho-carborane groups at the 8(meso) or 3/5(α) position were synthesized and characterized by NMR, HRMS, HPLC, and in the cases of 2b and 5b, by X-ray analysis. The BODIPYs exhibited low dark toxicity and phototoxicity toward human glioma T98G cells, and their cellular uptake varied significantly, with 5b accumulating the most and 7 the least. All BODIPYs localized mainly within the cell ER. The BODIPYs showed higher permeabilities than lucifer yellow across human hCMEC/D3 brain endothelial cell monolayers as the BBB model. Among this series, 1b showed the highest BBB permeability (Pe = 16.4 × 10-5 cm/s), probably as a result of its lower MW (366 Da) and favorable hydrophobicity (log P = 1.5). The combination of low cytotoxicity, amphiphilicity, high boron content, high cellular uptake, and moderate BBB permeability renders these compounds promising boron delivery agents for the BNCT of brain tumors. [ABSTRACT FROM AUTHOR]
- Subjects :
- *CARBORANES
*BORON
*DIPYRRINS
*ENDOTHELIAL cells
*BRAIN tumors
Subjects
Details
- Language :
- English
- ISSN :
- 00222623
- Volume :
- 59
- Issue :
- 5
- Database :
- Academic Search Index
- Journal :
- Journal of Medicinal Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 114321983
- Full Text :
- https://doi.org/10.1021/acs.jmedchem.5b01783