Synthesis and characterization of a carboranyl-tetrabenzoporphyrin

• Published in: Bioorganic & medicinal chemistry letters Vol. 15; no. 6; pp. 1665 - 1668
• Main Authors: Ongayi, Owendi, Gottumukkala, Vijay, Fronczek, Frank R., Vicente, M. Graça H.
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 15.03.2005; Elsevier
• Subjects: Animals; Biological and medical sciences; BNCT; Boron Neutron Capture Therapy; Carborane; Cell Line; Cricetinae; Medical sciences; Models, Chemical; Models, Molecular; Molecular Structure; PDT; Photochemotherapy; Photoradiation therapy and photosensitizing agent; Photosensitizing Agents - chemical synthesis; Photosensitizing Agents - pharmacology; Porphyrins - chemical synthesis; Porphyrins - pharmacology; Radiation therapy and radiosensitizing agent; Radiation-Sensitizing Agents - chemical synthesis; Radiation-Sensitizing Agents - pharmacology; Tetrabenzoporphyrin; Treatment with physical agents; Treatment. General aspects; Tumors; PDT; BNCT; Carborane; Tetrabenzoporphyrin; Cage compound; Lung; Cytotoxicity; Fluorescence spectrometry; V79-Cell line; Chemical synthesis; Boron neutron capture therapy; Photodynamic therapy; Rodentia; Radiotherapy; Biological activity; Water soluble compound; Absorption spectrometry; Vertebrata; Mammalia; Porphyrin; Animal; Boron Organic compounds; Fibroblast; Hamster; Crystalline structure
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2005.01.043

The synthesis of a novel water-soluble carboranyl-tetrabenzoporphyrin is reported. This compound shows characteristic absorption and emission spectra and low dark toxicity toward V79 cells. The X-ray structure of a precursor Cu(II)–carboranyl-tetrabenzoporphyrin is presented. An expeditious synthetic route to a carboranyl-substituted tetrabenzoporphyrin is reported. The absorption and emission spectra of water-soluble tetrabenzoporphyrin 4 are distinct from those of a known carboranylporphyrin ( 5). Both tetrabenzoporphyrin 4 and porphyrin 5 were found to be non-toxic toward V79 hamster lung fibroblast cells at 300 μM, using an MTT assay. The X-ray structure of a Cu(II)–carboranyl-tetrabenzoporphyrin is presented and discussed.