Synthesis of novel carboranylchlorins with dual application in boron neutron capture therapy (BNCT) and photodynamic therapy (PDT).
Total synthesis of carboranylchlorins 3 and 4, from readily available starting materials, are described and the molecular structures of two key intermediates are presented. Chlorins 3 and 4 show similar spectroscopic behavior but differ considerably in their solubility properties; whereas closo-carboranylchlorin 3 is completely insoluble in water, its nido derivative 4 has good water-solubility. Carboranylchlorin 3 absorbs in the red region of the optical spectrum (at lambda(max)=642 nm) six times more strongly than porphyrin 1, and displays a fluorescence emission band at lambda(max)=651 nm, upon excitation at 642 nm. The water-soluble carboranylchlorin 4 also displays intense absorption and emission bands at lambda(max)=642 and 651 nm, respectively, in ethanol solution. It is concluded that carboranylchlorins 3 and 4 have higher promise for the dual application in PDT and BNCT than do comparable porphyrins.
Department of Chemistry, Louisiana State University, 433 Choppin Hall, Baton Rouge, LA 70803, USA.
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Luguya
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Fronczek
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Smith
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MG
Vicente
D016754:Boron Neutron Capture Therapy; D018360:Crystallography, X-Ray; D006801:Humans; D008958:Models, Molecular; D015394:Molecular Structure; D010778:Photochemotherapy; D017319:Photosensitizing Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D011838:Radiation-Sensitizing Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D013050:Spectrometry, Fluorescence; D013053:Spectrophotometry
D017319:Photosensitizing Agents; D011166:Porphyrins; D011838:Radiation-Sensitizing Agents