DNA modification promoted by water-soluble nickel(II) salen complexes: a switch to DNA alkylation.
Reaction of a 17-base hairpin-forming oligonucleotide with [N,N'-bis(salicylaldehyde)-meso-1,2-bis(4- trimethylaminophenyl)ethylenediimino]nickel(II) perchlorate, 2, and KHSO5 produced two types of high molecular weight products, an alkaline-labile species and a nonalkaline-labile species, which co-migrated on gel electrophoresis. Upon treatment with piperidine, the base-labile derivative led to strand scission products only at accessible guanine residues that were not part of a Watson-Crick duplex. The formation of higher molecular weight species is proposed to occur via a highly reactive ligand-centered radical acting as a DNA alkylating agent.
Department of Chemistry, State University of New York at Stony Brook 11794-3400.
J G
JG
Muller
S J
SJ
Paikoff
S E
SE
Rokita
C J
CJ
Burrows
D000478:Alkylation; D001483:Base Sequence; D004247:DNA / Q000737:chemistry / Q000187:drug effects / Q000378:metabolism*; D004563:Electrochemistry; D005029:Ethylenediamines / Q000378:metabolism*; D008969:Molecular Sequence Data; D009532:Nickel / Q000378:metabolism* / Q000494:pharmacology; D009690:Nucleic Acid Conformation; D010084:Oxidation-Reduction; D010472:Perchlorates; D012995:Solubility; D013431:Sulfates; D014867:Water
D005029:Ethylenediamines; D010472:Perchlorates; D013431:Sulfates; D014867:Water; C031512:potassium sulfate; D009532:Nickel; D004247:DNA; C011452:disalicylaldehyde ethylenediamine