Synthesis And Evaluation Of Sugar And Amino Acid-modified Poly BODIPY Compounds

BODIPY with characteristics of high molar extinction coefficient, high fluorescence quantum yield, wide range of wavelengths, not easily affected by the polarity of the environment and the PH, good stability to light, oxygen and heat etc., in which halogenated BODIPY compounds are suitable for being photosensitizer, while nonhalogenated BODIPY compounds are appropriate for being fluorescence labeling molecules. However the lower water solubility limits the application of this kind of compounds.In this thesis, two ways are reported to improve the water solubility and biocompatibility of BODIPY compounds. One way is modification of BODIPY with sugar moieties,12BODIPY conjugated with glucose, xylose, galactose, lactose respevtively were reported. The other way is BODIPYconjugated with poly amino acid, either single replaced or double replaced, totally12target compounds were synthesized. Their structure were all characterized by HNMR、HRMS、IR、UV, and the photophysical proerties like fluorescence quantum yield、photobleaching rate、singlet oxygen quantum yield, were measured. Their photodynamic therapeutic effect in vitro and in vivo were performed. The results show that either glucose, xylose, galactose, lactose modified BODIPY or poly amino acids substances (EDTAa/DTPAa/TTHAa) can effectively improve their water solubility; experiments in cell and animal show that iodine and bromine BODIPY have significant phototoxcity as photo sens it izer, indicates that they have potential applications in the field of photodyanmic therapy. Nonhalogenated BODIPY compounds have good optical imaging capability. Living optical imaging experiments on mice bearing H22tumor show that different sugar modified BODIPY compounds have certain target effect at tumor tissue in vivo, while tissue imaging in dissection organs further confirmed these results. Sumary above showed that poly amino acids or sugar modification could effectively improve the water solubility of BODIPY compounds, this will make it possible for BODIPY as photosensiter in PDT or as imging probe in optical imaging.