新型碳硼烷二氢卟吩的合成及其在硼中子俘获疗法（BNCT）和光动力疗法（PDT）中的双重应用

Synthesis of novel carboranylchlorins with dual application in boron neutron capture therapy (BNCT) and photodynamic therapy (PDT).

作者信息

Luguya R, Fronczek F R, Smith K M, Vicente M G H

机构信息

Department of Chemistry, Louisiana State University, 433 Choppin Hall, Baton Rouge, LA 70803, USA.

出版信息

Appl Radiat Isot. 2004 Nov;61(5):1117-23. doi: 10.1016/j.apradiso.2004.05.068.

DOI:10.1016/j.apradiso.2004.05.068

PMID:15308202

Abstract

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.

摘要

本文描述了从易得的起始原料全合成碳硼烷二氢卟吩3和4，并给出了两种关键中间体的分子结构。二氢卟吩3和4表现出相似的光谱行为，但它们的溶解性有很大差异；巢式碳硼烷二氢卟吩3完全不溶于水，而其棱式衍生物4具有良好的水溶性。碳硼烷二氢卟吩3在光谱的红色区域（λ(max)=642 nm）的吸收强度比卟啉1强六倍，并且在642 nm激发时，在λ(max)=651 nm处显示出荧光发射带。水溶性碳硼烷二氢卟吩4在乙醇溶液中也分别在λ(max)=642和651 nm处显示出强烈的吸收和发射带。得出的结论是，与类似的卟啉相比，碳硼烷二氢卟吩3和4在光动力疗法（PDT）和硼中子俘获疗法（BNCT）中的双重应用具有更高的前景。