title: Synthesis and in Vitro Studies of a Series of Carborane-Containing Boron Dipyrromethenes (BODIPYs).
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.
authors: Department of Chemistry, Louisiana State University , Baton Rouge, Louisiana 70803, United States.
authors: Sunting
authors: S
authors: Xuan
authors: Department of Chemistry, Louisiana State University , Baton Rouge, Louisiana 70803, United States.
authors: Ning
authors: N
authors: Zhao
authors: Department of Chemistry, Louisiana State University , Baton Rouge, Louisiana 70803, United States.
authors: Zehua
authors: Z
authors: Zhou
authors: Department of Chemistry, Louisiana State University , Baton Rouge, Louisiana 70803, United States.
authors: Frank R
authors: FR
authors: Fronczek
authors: Department of Chemistry, Louisiana State University , Baton Rouge, Louisiana 70803, United States.
authors: M Graça H
authors: MG
authors: Vicente
mesh_terms: D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002463:Cell Membrane Permeability / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D018360:Crystallography, X-Ray; D004305:Dose-Response Relationship, Drug; D005910:Glioma / Q000188:drug therapy* / Q000473:pathology; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D008958:Models, Molecular; D015394:Molecular Structure; D017319:Photosensitizing Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D017319:Photosensitizing Agents