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Sugar-modified phthalocyanine synthesis, spectroscopic properties and biological activity of

Author: LiYanZhou
Tutor: LiuTianJun
School: Beijing Union Medical College
Course: Medicinal Chemistry
Keywords: Sugar phthalocyanine Optical Properties Photodynamic therapy Near -infrared fluorescence imaging
CLC: R318.51
Type: Master's thesis
Year: 2011
Downloads: 52
Quote: 0
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Abstract


Optical imaging and photodynamic therapy with its non-ionic low-energy radiation, high sensitivity, non-invasive or minimally invasive, side effects and other advantages in cancer diagnosis and treatment plays an increasingly important role. Optical imaging and photodynamic therapy photosensitizers are the key factors, so synthesis of novel photosensitizer, photosensitizer structure-activity relationship studies can push optical imaging and photodynamic therapy development. Commenting on this optical imaging and photodynamic therapy research status, based on the combined experience of many years of research by our group designed and synthesized a series of certain bioactive galactose substituted phthalocyanine compounds. And around the synthesis of such compounds, photophysical properties and photodynamic inactivation of chemical tumor cells with the ability to expand the near-infrared imaging in vivo studies, the main tasks include the following aspects: 1, with 4 - nitro phthalonitrile and 1,2:3,4-O-double-isopropylidene-α-D-galactose was synthesized through nucleophilic substitution reaction synthesis of 4 - substituted phthalonitrile sugar with 4 - Sugar Substitute phthaloyl nitrile and anhydrous zinc chloride as raw materials by condensation probability phthalocyanine synthesized four kinds of sugar, and each compound was characterized. Since the introduction of galactose, to greatly increase the solubility of the phthalocyanine, and galactose as the increase in number of the substituent, gradually increased its water solubility, four galactose substituted phthalocyanines can be dissolved in water, the better. 2, the determination of the four sugar phthalocyanine UV absorption and fluorescence spectra, the results showed the phthalocyanine of Sugar ultraviolet absorption maximum wavelength of about 680nm, the fluorescence emission wavelength of about 690nm, which qualify as UV absorption and fluorescence spectra of the photosensitizer in the near infrared region (600 ~ 900nm) requirements; determination of Sugar phthalocyanine fluorescence quantum yield, and its value is greater than 0.2; phthalocyanine of Sugar photobleaching experiments shown, they both have a light stability sex, for photodynamic therapy and near-infrared fluorescence imaging, will not cause too much damage to normal tissue. 3, using the MTT assay method of Sugar phthalocyanine conducted in vitro photodynamic tumor evaluation showed that the compound T3, T4 of gastric HGC-27 no dark toxicity, and after the light show significant inhibition of the cytotoxic rate 2.5μmol / L concentrations inhibition rate reached 90% or more. Compound T1 has a dark toxicity and phototoxicity is also very strong, T2 at a concentration of 1.25-5μmol / L when the light is displayed after a significant cytotoxicity inhibition rate reached 80% or more. In addition, four kinds of sugar phthalocyanine on melanoma A375, A549 lung and liver HepG-2 were also different degrees of inhibition; hepatocellular tumors in nude mice as experimental animal models in vivo imaging system through animal (Kodak invivo FX) for the compound T4 carried out in vivo fluorescence imaging results showed that one hour tumor, liver, kidney and other tissues have certain fluorescence, three hours later, with the metabolism of tumor fluorescence probe reaches the strongest, 12 hours a fluorescent tumor site collection waning.

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