期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 9, 期 20, 页码 7028-7032出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1ob05955f
关键词
-
资金
- Chinese University of Hong Kong [2009/10]
Treatment of 4,5-bis[4-(methoxycarbonyl) phenoxy] phthalonitrile and 4,5-bis[3,5-bis(methoxycarbonyl)phenoxy]phthalonitrile with an excess of 1,3-diiminoisoindoline in the presence of Zn(OAc)(2)center dot 2H(2)O and 1,8-diazabicyclo[5.4.0]undec-7-ene in triethylene glycol monomethyl ether or polyethylene glycol monomethyl ether (with an average molecular weight of 550) led to 3 + 1 mixed cyclisation and transesterification in one pot, affording the corresponding di-beta-substituted zinc(II) phthalocyanines in 7-23% yield. As shown by absorption spectroscopy, these compounds were essentially non-aggregated in N,N-dimethylformamide and could generate singlet oxygen effectively. The singlet oxygen quantum yields (Phi(Delta) = 0.53-0.57) were comparable with that of the unsubstituted zinc(II) phthalocyanine (Phi(Delta) = 0.56). These compounds in Cremophor EL emulsions also exhibited photocytotoxicity against HT29 human colorectal adenocarcinoma and HepG2 human hepatocarcinoma cells with IC(50) values in the range of 0.25-3.72 mu M. The analogue with four triethylene glycol chains was the most potent photosensitiser and localised preferentially in the mitochondria of HT29 cells. The bis(polyethylene glycol)-counterpart could form surfactant-free nanoparticles both in water and in the culture medium. The hydrodynamic radii, as determined by dynamic laser light scattering, ranged from 6.3 to 79.8 nm depending on the preparation methods and conditions. The photocytotoxicity of these nanoparticles (IC(50) = 0.43-0.56 mu M) was comparable with that of the Cremophor EL-formulated system (IC(50) = 0.34 mu M).
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据