title: Compound instability in dimethyl sulphoxide, case studies with 5-aminopyrimidines and the implications for compound storage and screening.
abstract: The oxidation reactions of 5-aminopyrimidine derivatives in dimethyl sulphoxide (DMSO) were studied. The DMSO solutions of the studied compounds became deeply coloured within a few hours or days. The oxidation products can undergo further condensation reactions with the starting pyrimidines to yield bipyrimidines and/or pyrimidopteridines. The reaction mechanism of the oxidation-condensation reaction was also supported by reactions of the 5-aminopyrimidines with alloxan (2,4,5,6-tetraoxopyrimidine). DMSO is often used as the solvent in in vitro tests of biological activities, but it is also an oxidising agent and may react with solute molecules and significantly affect the quality of the generated biochemical data.
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague, Czech Republic.
authors.forename: Eliška
authors.initials: E
authors.lastname: Procházková
authors.forename: Petr
authors.initials: P
authors.lastname: Jansa
authors.forename: Anna
authors.initials: A
authors.lastname: Březinová
authors.forename: Lucie
authors.initials: L
authors.lastname: Cechová
authors.forename: Helena
authors.initials: H
authors.lastname: Mertlíková-Kaiserová
authors.forename: Antonín
authors.initials: A
authors.lastname: Holý
authors.forename: Martin
authors.initials: M
authors.lastname: Dračínský
mesh_terms: D000631:Aminopyridines / Q000737:chemistry*; D004121:Dimethyl Sulfoxide / Q000737:chemistry*; D016877:Oxidants / Q000737:chemistry*; D010084:Oxidation-Reduction; D012997:Solvents / Q000737:chemistry
chemical_list: D000631:Aminopyridines; D016877:Oxidants; D012997:Solvents; D004121:Dimethyl Sulfoxide