Synthesis and in vitro photocytotoxicity of coumarin derivatives for one- and two-photon excited photodynamic therapy.

作者: Qianli Zou , Yanyan Fang , Yuxia Zhao , Hongyou Zhao , Ying Wang

DOI: 10.1021/JM400025G

关键词:

摘要: Triethylene glycol functionalized coumarin derivatives 1-5 were synthesized and investigated as photosensitizers for one- two-photon excited photodynamic therapy (PDT). Their absorption, fluorescence, triplet-state quantum yields, singlet oxygen yields found to be significantly related the substituent at 7-position of ring. In vitro photocytotoxicity these toward HepG2 cells was examined compared with a clinical drug. generation reactive species (ROS), cellular uptake, intracellular distribution also characterized fully reveal their structure-property relationships. The results showed that derivative 5, absorption cross section value 1556 GM, could powerful PDT agent both superficial diseases solid tumors.

参考文章(32)
D. H. Oh, B. A. King, S. G. Boxer, P. C. Hanawalt, Spatially localized generation of nucleotide sequence-specific DNA damage. Proceedings of the National Academy of Sciences of the United States of America. ,vol. 98, pp. 11271- 11276 ,(2001) , 10.1073/PNAS.201409698
Mamta Khurana, Hazel A Collins, Aliaksandr Karotki, Harry L Anderson, David T Cramb, Brian C Wilson, None, Quantitative in vitro demonstration of two-photon photodynamic therapy using photofrin and visudyne. Photochemistry and Photobiology. ,vol. 83, pp. 1441- 1448 ,(2007) , 10.1111/J.1751-1097.2007.00185.X
Madhukar A. Pathak, Thomas B. Fitzpatrick, The evolution of photochemotherapy with psoralens and UVA (PUVA): 2000 BC to 1992 AD Journal of Photochemistry and Photobiology B: Biology. ,vol. 14, pp. 3- 22 ,(1992) , 10.1016/1011-1344(92)85080-E
Ajesh P. Thomas, P. S. Saneesh Babu, S. Asha Nair, S. Ramakrishnan, Danaboyina Ramaiah, Tavarekere K. Chandrashekar, A. Srinivasan, M. Radhakrishna Pillai, Meso-tetrakis(p-sulfonatophenyl)N-confused porphyrin tetrasodium salt: a potential sensitizer for photodynamic therapy. Journal of Medicinal Chemistry. ,vol. 55, pp. 5110- 5120 ,(2012) , 10.1021/JM300009Q
Robert S. Stern, Khanh T. Nichols, Liisa H. Väkevä, Malignant Melanoma in Patients Treated for Psoriasis with Methoxsalen (Psoralen) and Ultraviolet A Radiation (PUVA) New England Journal of Medicine. ,vol. 336, pp. 1041- 1045 ,(1997) , 10.1056/NEJM199704103361501
Dennis E.J.G.J. Dolmans, Dai Fukumura, Rakesh K. Jain, Photodynamic therapy for cancer Nature Reviews Cancer. ,vol. 3, pp. 380- 387 ,(2003) , 10.1038/NRC1071
Yuxia Zhao, Weijia Wang, Feipeng Wu, Yang Zhou, Naiyan Huang, Ying Gu, Qianli Zou, Wei Yang, Polyethylene glycol-functionalized benzylidene cyclopentanone dyes for two-photon excited photodynamic therapy Organic and Biomolecular Chemistry. ,vol. 9, pp. 4168- 4175 ,(2011) , 10.1039/C0OB01278E
Xue Li, Yuxia Zhao, Jie Wu, Mengquan Shi, Feipeng Wu, Two-photon photopolymerization using novel asymmetric ketocoumarin derivatives Journal of Photochemistry and Photobiology A: Chemistry. ,vol. 190, pp. 22- 28 ,(2007) , 10.1016/J.JPHOTOCHEM.2007.03.007
W. G. Fisher, W. P. Partridge, C. Dees, E. A. Wachter, Simultaneous Two-Photon Activation of Type-I Photodynamic Therapy Agents Photochemistry and Photobiology. ,vol. 66, pp. 141- 155 ,(1997) , 10.1111/J.1751-1097.1997.TB08636.X
Adam Wright, Clare L Hawkins, Michael J Davies, None, Photo-oxidation of cells generates long-lived intracellular protein peroxides Free Radical Biology and Medicine. ,vol. 34, pp. 637- 647 ,(2003) , 10.1016/S0891-5849(02)01361-8