Synthetic Routes to N-9 Alkylated 8-Oxoguanines; Weak Inhibitors of the Human DNA Glycosylase OGG1
AbstractThe human 8-oxoguanine DNA glycosylase OGG1 is involved in base excision repair (BER), one of several DNA repair mechanisms that may counteract the effects of chemo- and radiation therapy for the treatment of cancer. We envisage that potent inhibitors of OGG1 may be found among the 9-alkyl-8-oxoguanines. Thus we explored synthetic routes to 8-oxoguanines and examined these as OGG1 inhibitors. The best reaction sequence started from 6-chloroguanine and involved N-9 alkylation, C-8 bromination, and finally simultaneous hydrolysis of both halides. Bromination before N-alkylation should only be considered when the N-substituent is not compatible with bromination conditions. The 8-oxoguanines were found to be weak inhibitors of OGG1. 6-Chloro-8-oxopurines, byproducts in the hydrolysis of 2,6-halopurines, turned out to be slightly better inhibitors than the corresponding 8-oxoguanines. View Full-Text
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Mahajan, T.R.; Ytre-Arne, M.E.; Strøm-Andersen, P.; Dalhus, B.; Gundersen, L.-L. Synthetic Routes to N-9 Alkylated 8-Oxoguanines; Weak Inhibitors of the Human DNA Glycosylase OGG1. Molecules 2015, 20, 15944-15965.
Mahajan TR, Ytre-Arne ME, Strøm-Andersen P, Dalhus B, Gundersen L-L. Synthetic Routes to N-9 Alkylated 8-Oxoguanines; Weak Inhibitors of the Human DNA Glycosylase OGG1. Molecules. 2015; 20(9):15944-15965.Chicago/Turabian Style
Mahajan, Tushar R.; Ytre-Arne, Mari E.; Strøm-Andersen, Pernille; Dalhus, Bjørn; Gundersen, Lise-Lotte. 2015. "Synthetic Routes to N-9 Alkylated 8-Oxoguanines; Weak Inhibitors of the Human DNA Glycosylase OGG1." Molecules 20, no. 9: 15944-15965.