Photo-induced DNA cleavage by (heterocyclo)carbonyl oxime esters of anthraquinone

作者: Jih Ru Hwu , Jhih-Ren Yang , Shwu-Chen Tsay , Ming-Hua Hsu , Yi-Chieh Chen

DOI: 10.1016/J.TETLET.2008.03.056

关键词:

摘要: Abstract Various (heterocyclo)carbonyl mono-oxime esters of anthraquinone were synthesized, which exhibited an ability for DNA cleavage upon UV irradiation. Their structure–activity relationship was established, in the most potent compound O -9-(1,3-benzothiazole-2-carbonyl)oxime ( 4j ). It can produce radical species and nick at concentration as low 1.0 μM.

参考文章(26)
Lei Wang, Carolina Carrasco, Arvind Kumar, Chad E. Stephens, Christian Bailly, David W. Boykin, W. David Wilson, Evaluation of the influence of compound structure on stacked-dimer formation in the DNA minor groove. Biochemistry. ,vol. 40, pp. 2511- 2521 ,(2001) , 10.1021/BI002301R
Giulio Jori, Clara Fabris, Marina Soncin, Stefania Ferro, Olimpia Coppellotti, Donata Dei, Lia Fantetti, Giacomo Chiti, Gabrio Roncucci, Photodynamic therapy in the treatment of microbial infections: Basic principles and perspective applications Lasers in Surgery and Medicine. ,vol. 38, pp. 468- 481 ,(2006) , 10.1002/LSM.20361
Emmanuel A. Theodorakis, Xin Xiang, Petra Blom, Photochemical cleavage of duplex DNA by N-benzoyloxy-2-thiopyridone linked to 9-aminoacridine Chemical Communications. pp. 1463- 1464 ,(1997) , 10.1039/A702913F
Xuhong Qian, Wei Yao, Gang Chen, Xiayu Huang, Ping Mao, N-Aroyloxynaphthalimides as novel highly efficient DNA photocleavers: substituent effects Tetrahedron Letters. ,vol. 42, pp. 6175- 6178 ,(2001) , 10.1016/S0040-4039(01)01214-X
Peter Meisel, Thomas Kocher, Photodynamic therapy for periodontal diseases: state of the art. Journal of Photochemistry and Photobiology B-biology. ,vol. 79, pp. 159- 170 ,(2005) , 10.1016/J.JPHOTOBIOL.2004.11.023
Yuko Iwamoto, Yoko Yamakoshi, A highly water-soluble C60–NVP copolymer: a potential material for photodynamic therapy Chemical Communications. pp. 4805- 4807 ,(2006) , 10.1039/B614305A
Shinsuke Oba, Mamoru Hatakeyama, Hiroshi Handa, Haruma Kawaguchi, Development of polymer latex particles for selective cleavage of mismatched DNA and their application for DNA diagnosis. Bioconjugate Chemistry. ,vol. 16, pp. 551- 558 ,(2005) , 10.1021/BC049728L
Tom C. Karagiannis, Pavel N. Lobachevsky, Roger F. Martin, DNA targeted UVA photosensitization: characterization of an extremely photopotent iodinated minor groove binding DNA ligand. Journal of Photochemistry and Photobiology B-biology. ,vol. 83, pp. 195- 204 ,(2006) , 10.1016/J.JPHOTOBIOL.2005.12.013
Wendy Knapp Pogozelski, Thomas D. Tullius, Oxidative Strand Scission of Nucleic Acids: Routes Initiated by Hydrogen Abstraction from the Sugar Moiety. Chemical Reviews. ,vol. 98, pp. 1089- 1107 ,(1998) , 10.1021/CR960437I
Giulio Jori, Tumour photosensitizers: approaches to enhance the selectivity and efficiency of photodynamic therapy Journal of Photochemistry and Photobiology B-biology. ,vol. 36, pp. 87- 93 ,(1996) , 10.1016/S1011-1344(96)07352-6