Reaction kinetics of alkyl epoxides with DNA and other nucleophiles

1,2-Epoxy alkanes from C3 to C8 were reacted with DNA, deoxyguanosine and 4-( p-nitrobenzyl) pyridine (NBP). DNA was hydrolyzed at neutral pH to release 7-alkylguanines. The products were analyzed by HPLC. The epoxides reacted largely according to the chain length, shorter epoxides being more reacti...

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Veröffentlicht in:	Chemico-biological interactions 1994-10, Vol.93 (1), p.51-58
Hauptverfasser:	Hemminki, Akseli, Väyrynen, Taneli, Hemminki, Kari
Format:	Artikel
Sprache:	eng
Schlagworte:	4-( p-Nitrobenzyl)pyridine 7-Alkylguanine Alkanes - chemistry Alkyl epoxide Biological and medical sciences Carcinogenesis, carcinogens and anticarcinogens Chemical agents Chromogenic Compounds Deoxyguanosine - chemistry DNA - chemistry DNA adduct Epoxide Epoxy Compounds - chemistry Kinetics Medical sciences Pyridines - chemistry Structure-Activity Relationship Tumors
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Beschreibung
Zusammenfassung:	1,2-Epoxy alkanes from C3 to C8 were reacted with DNA, deoxyguanosine and 4-( p-nitrobenzyl) pyridine (NBP). DNA was hydrolyzed at neutral pH to release 7-alkylguanines. The products were analyzed by HPLC. The epoxides reacted largely according to the chain length, shorter epoxides being more reactive. Substitutions through carbon 1 predominated. Reactivity with NBP was almost equal between the epoxides.
ISSN:	0009-2797 1872-7786
DOI:	10.1016/0009-2797(94)90085-X