Synthesis And Characterization Of Axial Substituted Metal Phthalocyanine

Phthalocyanine (Pc) and their substituted derivatives had aroused extensive interest in the lastdecade, as they were widely used as photosensitizers in photodynamic therapy (PDT) of canceror macular degeneration. Our research group is aim to. developing a series of newphotosensitizers for therapy choroidal neovascularization. It has been shown that, for betterperformance in tissue selectivity, the presence of both hydrophobic and hydrophilic group wouldbe of benefit. According to that concept, an axial group seems to be interesting for itshydrophobic characteristic, or for the possibility of high interaction with proteins or covalentbonding with monoclonal antibodies. Therefore, two types of axial substitution metalphthalocyanines were synthesized and characterized. One is hydrophobic principle substitutedcomplex axial dioxypridiyl-tetra-(α-pentyloxy) tin phthalocyanine, the other is hydrophilicprinciple substituted compounds: axial hematoxylin-tetrasulfonic titanium phthalocyanine andaxial dioxypridiyl tetrasulfonic titanium phthalocyanine. Their structure were characterized byIR,UV-VIS,TG, HPLC and MS. The axial substitution Pcs has the advantegous ofstability, disaggregation and red shifted maximal absorption wavelength. It was found that theaxial electron-withdrawing groups caused the maximal absorption wavelength red shift, whileaxial electron-donor groups caused the maximal absorption wavelength blue shift.The interactionof tetrasulfonated metal phathalocyanine (TiOPcS4)and TiOPcS4-hematoxylin with bovineserum albumin(BSA) was studied .The association constants of two metal phthalocyanines weredetermined by both UV/Vis and fluorescence spectrascopic methods, the similar results wereobtained. The binding site of tetrasulfonated metal phathalocyanine on the BSA were determinedby using Hemin chloride(HE), Ibuprofen(IB)and L-tryptophan(TRP) as ligands and competitivebinding method.