The Design, Synthesis And Properties Of Novel Polyamine Zinc Phthalocyanine Derivatives With Different Side Chain Structures

Photodynamic therapy(PDT)as a new treatment of cancer is receiving more and more attention.In recent years,phthalocyanines have been known as promising photosensitizers for its superior characteristics and have received more and more attention from researchers.In this paper,to solve the bottleneck of zinc phthalocyanine-polyamine conjugates,a series zinc phthalocyanine derivative were designed and synthsised.On this basis,primary studies about the influences of the number of amine groups and their arrangement manner have been conducted.The main research conclusions are as follows:(1)Six phthalocyanine-polyamine conjugates derivatives have been designed and syntheised.They are quaternized 2(3),9(10),16(17),23(24)-tetra-(4-methoxyphenyl)methanamine)zinc(?)phthalocyanine(ZnPc1)?quaternized 2(3),9(10),16(17),23(24)-tetra-(N,N-bis(2-aminoethyl)-4-methoxybenzamide)zinc(?)phthalocy anine(ZnPc2)?quaternized 2(3),9(10),16(17),23(24)-tetra-(N,-(2-aminoethyl)-N1-(4-methoxybenzyl)ethane-1,2-diamine)zinc(?)phthalocyanine(ZnPc3)?quaternized 2(3),9(10),16(17),23(24)-tetra-(N1-(2-aminoethyl)-N2-(4-methoxybenzyl)ethane-1,2-diamine)zinc(?)phthalocyanine(ZnPc4)?protonated 2(3),9(10),16(17),23(24)-tetra-(N,N-bis(2-aminoethyl)-4-methoxybenzamide)zinc(?)phthalocyanine(ZnPc5)and protonated 2(3),9(10),16(17),23(24)-tetra-(N,N'-(2,2'-(4-methoxybenzylazanediyl)-bis(ethane-2,1-diyl))diacetamide)zinc(?)phthalocyanine(ZnPc6).All phthalocyanine-polyamine conjugates precursors and phthalocyanines were characterized by UV-Vis spectra,IR spectra,NMR and elemental analyses.Characterization results show that the synthesis of precursor and phthalocyanine compounds structure in consistent with expectations.(2)The solubility of ZnPc derivatives was studied and the results showed that these ZnPc derivatives not only have good water solubility but also have oil solubility,show amphipathic property to some degree.(3)The influences about the change of the amino groups on the side chain have been studied.The results showed that the increase of the amino groups can improve the generation ability of the single oxygen and fluorescence intensity.In addition,the increase of amino groups can make the maximum absorption wavelength red-shift.At the same time,we also found that,in water solution,the increase of the load power,don't necessarily lead to the aggregate depolymerization.(4)The influences about the arrangement manner of the amino groups on the side chain have also been studied.The results showed that in water solution,straight chain configuration is more advantageous to depolymerization.Besides,phthalocyanine with straight chain configuration is better than branch chain configuration in the single oxygen generation and fluorescence intensity.(5)The influences about the amido bond on the phthalocyanine-polyamine conjugates hydrochloride derivatives were studied.The results showed that the position of the amido bond can obviously affect the fluorescence intensity of ZnPc derivatives.(6)Comprehensive studies of the properties of the phthalocyanine-polyamine conjugates derivatives indicated that quaternized and hydrochloride derivatives have potential to be used as photosensitizer for PDT.