姜黄素桥连卟啉光敏剂的合成及表征  

Synthesis and Characterization of Curcumin Bridged Porphyrins as Photosensitizers

作　　者：黄齐茂[1] 王司卫[1] 李清[1] 潘威[1] 邓鹏星[1] 周红[1] 潘志权[1] 

机构地区：[1]武汉工程大学绿色化工过程省部共建教育部重点实验室,武汉430073

出　　处：《高等学校化学学报》2012年第4期732-737,共6页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金(批准号:20471045);湖北省自然科学基金青年杰出人才项目(批准号:2008CDB072)资助

摘　　要：为了开发新的高效光动力治疗光敏剂,以2-(2-羟基萘基)-5,10,15,20-四苯基卟啉及其Cu(Ⅱ),Ni(Ⅱ),Zn(Ⅱ)配合物为原料,利用1,6-二溴己烷桥连具有抗癌活性的小分子姜黄素,设计合成4个新型的天然产物桥连卟啉化合物.通过UV,1H NMR,IR,MS及元素分析等手段对该新型光敏药剂进行了结构表征;在此基础上,采用凝胶电泳法考察了化合物在光照和无光照条件下对pBR322质粒DNA的切割能力.作为潜在光敏剂与DNA相互作用的初步研究表明,其与DNA结合能力较强,具有明显的光敏切割效果.Photodynamic therapy（PDT） is a promising modality with minimally invasive approach to the clinical treatment of oncology generally based on the activation of photosensitizers,as they can utilize the administration and selective accumulation in cancer tissues to form cytotoxic reactive oxygen species such as singlet oxygen when followed by exposure to suitable visible light,causing tissue injury and cell death.To improve this treatment,new efficient photosensitizers were synthesized and tested for their important role in PDT.Porphyrins have considerable attractive properties in biological systems derived from unique characteristic π-system and coordinating metals,which can be used for a broad range of applications,and modification of porphyrins to tune or change the properties has been investigated extensively.To develop new porphyrin photosensitizers of PDT,four novel porphyrin compounds containing structural unit of natural product curcumin were synthesized using 2-（2-hydroxy-naphthyl）-5,10,15,20-tetraphenyl porphyrin and its Cu（Ⅱ）,Ni（Ⅱ）,Zn（Ⅱ） complexes as starting materials.In these compounds,porphyrin and small molecule curcumin with anticancer activity were bridged by 1,6-dibromo-hexane.These compounds were characterized by UV,1H NMR,IR,MS,and elemental analysis.Based on the confirmation,their cleavage abilities to pBR322 plasmid DNA were investigated by gel electrophoresis under photo irradiation and in dark,respectively.The results show that the novel porphyrin compounds as potential photosensitizers have both obvious photosensitive cleavage activity and effective binding interaction with DNA.

关 键 词：卟啉 姜黄素 光敏活性 

分 类 号：O625[理学—有机化学] O614[理学—化学]