Chem. J. Chinese Universities ›› 2012, Vol. 33 ›› Issue (04): 732.doi: 10.3969/j.issn.0251-0790.2012.04.016

• Organic Chemistry • Previous Articles     Next Articles

Synthesis and Characterization of Curcumin Bridged Porphyrins as Photosensitizers

HUANG Qi-Mao, WANG Si-Wei, LI Qing, PAN Wei, DENG Peng-Xing, ZHOU Hong, PAN Zhi-Quan   

  1. Key Laboratory for Green Chemical Process, Ministry of Education, Wuhan Institute of Technology, Wuhan 430073, China
  • Received:2011-06-01 Online:2012-04-10 Published:2012-04-10
  • Supported by:

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

Abstract: 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.

Key words: Porphyrin, Curcumin, Photosensitivity

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