title: Oxidative DNA cleavage by Cu(II) complexes: Effect of periphery substituent groups.
abstract: A series of structurally-related [Cu(R-benzyl-dipicolylamine)(NO3)2] complexes, where R=methoxy- (1), methyl- (2), H- (3), fluoro- (4), and nitro-group (5), were synthesized, and their activity on DNA cleavage was investigated by linear dichroism (LD) and electrophoresis. The addition of a benzyl group to the dipicolylamine ligand of the [Cu(dipicolylamine)(NO3)2] complex (A), i.e., the [Cu(benzyl-dipicolylamine)(NO3)2] complex (3), caused significant enhancement in the efficiency of oxidative cleavage of both super-coiled (sc) and double stranded (ds) DNA, as evidenced by the electrophoresis pattern and faster decrease in the LD intensity at 260nm. The efficiency in DNA cleavage was also altered with further modifications of the benzyl group by the introduction of various substituents at the para-position. The cleavage efficiency appeared to be the largest when the methyl group was attached. The order of efficiency in DNA cleavage was methyl>methoxy≈H>fluoro≈nitro group. When an electron-withdrawing group was introduced, the cleavage efficiency decreased remarkably. The reactive oxygen species involved in the cleavage process were the superoxide radical and singlet oxygen. A possible mechanism for this variation in the DNA cleavage efficiency was proposed.
authors.affiliation: Department of Chemistry, Yeungnam University, Gyeongsan City, Gyeong-buk 712-749, Republic of Korea.
authors.forename: Wei
authors.initials: W
authors.lastname: Wang
authors.affiliation: Department of Chemistry, Yeungnam University, Gyeongsan City, Gyeong-buk 712-749, Republic of Korea.
authors.forename: Young Ae
authors.initials: YA
authors.lastname: Lee
authors.affiliation: Department of Chemistry, Yeungnam University, Gyeongsan City, Gyeong-buk 712-749, Republic of Korea.
authors.forename: Gyeongwon
authors.initials: G
authors.lastname: Kim
authors.affiliation: Department of Chemistry, Yeungnam University, Gyeongsan City, Gyeong-buk 712-749, Republic of Korea. Electronic address: seogkim@yu.ac.kr.
authors.forename: Seog K
authors.initials: SK
authors.lastname: Kim
authors.affiliation: Department of Chemistry and Nano Science, Ewha Womans University, Seoul 120-750, Republic of Korea.
authors.forename: Ga Ye
authors.initials: GY
authors.lastname: Lee
authors.affiliation: Department of Chemistry and Nano Science, Ewha Womans University, Seoul 120-750, Republic of Korea.
authors.forename: Jinheung
authors.initials: J
authors.lastname: Kim
authors.affiliation: Department of Chemistry and Nano Science, Ewha Womans University, Seoul 120-750, Republic of Korea.
authors.forename: Youngmee
authors.initials: Y
authors.lastname: Kim
authors.affiliation: Department of Fine Chemistry, Seoul National University of Science and Technology, Seoul 139-743, Republic of Korea; Department of Interdisciplinary Bio IT Materials, Seoul National University of Science and Technology, Seoul 139-743, Republic of Korea.
authors.forename: Gyeong Jin
authors.initials: GJ
authors.lastname: Park
authors.affiliation: Department of Fine Chemistry, Seoul National University of Science and Technology, Seoul 139-743, Republic of Korea; Department of Interdisciplinary Bio IT Materials, Seoul National University of Science and Technology, Seoul 139-743, Republic of Korea. Electronic address: chealkim@seoultech.ac.kr.
authors.forename: Cheal
authors.initials: C
authors.lastname: Kim
mesh_terms: D014013:1,2-Dihydroxybenzene-3,5-Disulfonic Acid Disodium Salt / Q000737:chemistry; D002374:Catalase / Q000737:chemistry; D056831:Coordination Complexes / Q000138:chemical synthesis / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D053837:DNA Cleavage; D004278:DNA, Superhelical / Q000737:chemistry*; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D016166:Free Radical Scavengers / Q000737:chemistry; D010084:Oxidation-Reduction; D010957:Plasmids; D019810:Sodium Azide / Q000737:chemistry
chemical_list: D056831:Coordination Complexes; D004278:DNA, Superhelical; D016166:Free Radical Scavengers; D014013:1,2-Dihydroxybenzene-3,5-Disulfonic Acid Disodium Salt; D003300:Copper; D019810:Sodium Azide; D002374:Catalase; D004121:Dimethyl Sulfoxide
keywords: Cu complexes; DNA cleavage; Dipicolylamine; Linear dichroism