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-carb...

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Bibliographic Details
Published in:Applied radiation and isotopes 2004-11, Vol.61 (5), p.1117-1123
Main Authors: Luguya, R, Fronczek, F.R, Smith, K.M, Vicente, M.G.H
Format: Article
Language:English
Subjects:
Absorption
BNCT
Boron Neutron Capture Therapy
Carboranylchlorins
Crystallography, X-Ray
Emission
Humans
Models, Molecular
Molecular Structure
PDT
Photochemotherapy
Photosensitizing Agents - chemical synthesis
Photosensitizing Agents - chemistry
Photosensitizing Agents - therapeutic use
Porphyrins - chemical synthesis
Porphyrins - chemistry
Porphyrins - therapeutic use
Radiation-Sensitizing Agents - chemical synthesis
Radiation-Sensitizing Agents - chemistry
Radiation-Sensitizing Agents - therapeutic use
Spectrometry, Fluorescence
Spectrophotometry
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Summary: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 λ max=642 nm) six times more strongly than porphyrin 1, and displays a fluorescence emission band at λ max=651 nm, upon excitation at 642 nm. The water-soluble carboranylchlorin 4 also displays intense absorption and emission bands at λ 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.
ISSN:0969-8043
1872-9800
DOI:10.1016/j.apradiso.2004.05.068