Crosslinking of DNA by busulfan. Formation of diguanyl derivatives.
High-pressure liquid chromatography has been used to separate the derivatives of guanosine which are formed when this nucleoside is reacted with busulfan. Derivatives which have been identified by a combination of ultraviolet and mass spectrometry include: 7-(delta-hydroxybutyl)guanosine, 1,4-di(7-guanosyl)butane, and 1-(7-guanyl)-4-(7-guanosinyl)butane. The latter two derivatives can be converted to 1,4-di(7-guanyl)butane by mild acid hydrolysis. Using 1,4-di(7-guanyl)butane as a marker for high-pressure liquid chromatography, we have identified this compound as a product of the reaction between DNA and busulfan. These findings verify the previously unconfirmed report that busulfan is a crosslinking agent for DNA and strengthen the hypothesis that differences in the biological properties of alkylating agents result from differences in their reactions with DNA.
D000818:Animals; D002066:Busulfan; D002417:Cattle; D002851:Chromatography, High Pressure Liquid; D004247:DNA; D006151:Guanosine / Q000031:analogs & derivatives / Q000032:analysis*; D013058:Mass Spectrometry; D013056:Spectrophotometry, Ultraviolet; D013950:Thymus Gland
D006151:Guanosine; C026027:7-(delta-hydroxybutyl)guanosine; C026026:1,4-di(7-guanosyl)butane; C026028:1-(7-guanyl)-4-(7-guanosinyl)butane; D004247:DNA; D002066:Busulfan