Synthesis And Photosensitivity Of Phthalocyanine Zinc Substituted With Quinoxaline

Photodynamic therapy?PDT?is a new type of therapy for clinical treatment of tumors.Phthalocyanine compounds are one of the important photosensitizers.Indoline-2,3-dione is an important skeleton of active compounds with many organisms,of which bioisosteres quinoxaline have been developed some targeted anticancer drugs,which have been showed to be better resistant to range of endometrial cancer,solid tumors and breast cancer in clinical studies.In this study,two different anti-cancer drug molecules,quinoxaline and phthalo-cyanine were conjugated to build a new chemical entity to obtain a multi-target anti-tumor drugs by using multi-target drug molecular design and combination principles.The main contents are as follows:?1?2-Hydroxyquinoxaline and 4-nitrophthal-onitrile were used as raw materials to synthesize the corresponding precursors with connection by ethoxy unit or butoxy.The title zinc phthalocyanines were synthesized and characterized by MS and 1H-NMR.?2?The synthesis of intermediates and target compounds was optimized.The intermediates were prepared by traditional refluxing methods and microwave method,which the latter significantly improved the yield and reaction rate of products.?3?Photosensitive properties of the target products were determinated.Compared with ZnPc,maximum absorption wavelength??max?of quinoxalin-2-yloxy substituted phthalocyanine and it derivatives showed bathochromic shift effect,fluorescence quantum yield??F?of the title complexes was similar and ¹O₂ quantum yield????was smaller.?4?The inhibition rate of HepG2 cells was no obvious difference among the title compounds in the concentration of0.2¹6uM with or without light.