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Design, synthesis, and photophysical characterization of water-soluble chlorins

机译:水溶性二氢卟酚的设计,合成和光物理特性

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The use of chlorins as photosensitizers or fluorophores in a range of biological applications requires facile provisions for imparting high water solubility. Two free base chlorins have been prepared wherein each chlorin bears a geminal dimethyl group in the reduced ring and a water-solubilizing unit at the chlorin 10-position. In one design (FbC1-PO3H2), the water-solubilizing unit is a 1,5-diphosphonopent-3-yl ("swallowtail") unit, which has previously been used to good effect with porphyrins. In the other design (FbC2-PO3H2), the water-solubilizing unit is a 2,6-bis(phosphonomethoxy)phenyl unit. Two complementary routes were developed for preparing FbC2-PO3H2 that entail introduction of the protected phosphonate moieties either in the Eastern-half precursor to the chlorin or by derivatization of an intact chlorin. Water-solubilization is achieved in the last step of each synthesis upon removal of the phosphonate protecting groups. The chlorins FbC1-PO3H2 and FbC(2)-PO3H2 are highly water-soluble (> 10 mM) as shown by H-1 NMR spectroscopy (D2O) and UV-vis absorption spectroscopy. The photophysical properties of the water-soluble chlorins in phosphate-buffered saline solution (pH 7.4) at room temperature were investigated using static and time-resolved absorption and fluorescence spectroscopic techniques. Each chlorin exhibits dominant absorption bands in the blue and the red region (lambda = 398, 626 nm), a modest fluorescence yield (Phi(f) approximate to 0.11), a long singlet excited-state lifetime (tau = 7.5 ns), and a high yield of intersystem crossing to give the triplet state (Phi(isc) = 0.9). The properties of the water-soluble chlorins in aqueous media are comparable to those of hydrophobic chlorins in toluene. The high aqueous solubility combined with the attractive photophysical properties make these compounds suitable for a wide range of biomedical applications.
机译:在许多生物学应用中,使用二氢卟酚作为光敏剂或荧光团需要提供高水溶性的简便设备。已经制备了两种游离碱二氢卟酚,其中每个二氢卟酚在还原环上具有双甲基二甲基基团,并且在二氢卟酚的10位上具有水溶性单元。在一种设计(FbC1-PO3H2)中,水增溶单元是1,5-二膦基叔丁基-3-基(“燕尾”)单元,其先前已被用于与卟啉良好地作用。在另一种设计中(FbC2-PO3H2),水溶性单元是2,6-双(膦酰基甲氧基)苯基单元。已开发出两条互补的路线来制备FbC2-PO3H2,这需要在二氢卟酚的东部东部前体中引入受保护的膦酸酯部分,或通过完整二氢卟酚的衍生化而引入。除去膦酸酯保护基团后,在每个合成的最后一步中都实现了水溶性。二氢卟酚FbC1-PO3H2和FbC(2)-PO3H2具有高度水溶性(> 10 mM),如H-1 NMR光谱(D2O)和UV-vis吸收光谱所示。使用静态和时间分辨吸收和荧光光谱技术研究了室温下磷酸盐缓冲盐溶液(pH 7.4)中水溶性二氢卟酚的光物理性质。每个二氢卟酚在蓝色和红色区域(λ= 398,626 nm)显示出主要的吸收带,适度的荧光产率(Phi(f)约为0.11),单线态激发态寿命长(tau = 7.5 ns),并以较高的系统间交叉产率获得三重态(Phi(isc)= 0.9)。水性介质中的水溶性二氢卟酚的性能与甲苯中的疏水性二氢卟酚相当。高水溶性和吸引人的光物理特性使这些化合物适合广泛的生物医学应用。

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