三甲基氨基苯氧基取代的锌（II）酞菁的合成与性质
Syntheses and properties of trimethylaminophenoxy-substituted Zn((II))-phthalocyanines.
作者信息
Ongarora Benson G, Hu Xiaoke, Li Hairong, Fronczek Frank R, Vicente M Graça H
机构信息
Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.
出版信息
Medchemcomm. 2012;3(2):179-194. doi: 10.1039/C1MD00232E.
Abstract
The syntheses, photophysical properties and in vitro biological behavior of a series of nine Zn((II))-phthalocyanines (ZnPcs) bearing one to eight positively-charged trimethylaminophenoxy groups are reported. All ZnPcs are highly soluble in polar organic solvents, and show fluorescence and singlet oxygen quantum yields in the ranges 0.11-0.21 and 0.16-0.47, respectively. The cytotoxicity of the ZnPcs depends on both the number of charges and their site of substitution (α vs. β) on the Pc isoindole units; the most promising for PDT application are the α-substituted di-cationic ZnPcs 6a and 17a.
摘要
报道了一系列九个带有一至八个带正电荷的三甲基氨基苯氧基的锌（II）酞菁（ZnPc）的合成、光物理性质及体外生物学行为。所有的ZnPc在极性有机溶剂中都具有高溶解性，并且分别显示出荧光量子产率在0.11 - 0.21范围内以及单线态氧量子产率在0.16 - 0.47范围内。ZnPc的细胞毒性取决于电荷数量及其在酞菁异吲哚单元上的取代位置（α位与β位）；对于光动力疗法（PDT）应用最有前景的是α位取代的二价阳离子ZnPc 6a和17a。
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2
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Bioorg Med Chem. 2010 Apr 1;18(7):2672-7. doi: 10.1016/j.bmc.2010.02.020. Epub 2010 Feb 18.
3
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Met Based Drugs. 2008;2008:276109. doi: 10.1155/2008/276109.
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Chemistry. 2008;14(30):9431-41. doi: 10.1002/chem.200800835.
5
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Bioconjug Chem. 2008 Mar;19(3):705-13. doi: 10.1021/bc700393u. Epub 2008 Feb 13.
6
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Bioorg Med Chem. 2008 Mar 15;16(6):3191-208. doi: 10.1016/j.bmc.2007.12.020. Epub 2008 Feb 21.
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Interaction of cationic meso-porphyrins with liposomes, mitochondria and erythrocytes.
J Bioenerg Biomembr. 2007 Apr;39(2):175-85. doi: 10.1007/s10863-007-9075-0. Epub 2007 Apr 14.
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Bioconjug Chem. 2007 Mar-Apr;18(2):410-20. doi: 10.1021/bc060297b. Epub 2007 Feb 6.
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