Novel 6-formylpterin derivatives: chemical synthesis and O2 to ROS conversion activities

Organic & Biomolecular Chemistry
Mitsuru NonogawaKeisuke Makino

Abstract

6-Formylpterin (6FP) has been demonstrated to have strong neuroprotective effects against transient ischemia-reperfusion injury in gerbils. Also it has been shown that in rats, 6FP protected retinal neurons even when it was administered after the ischemic insult. Since there is a significant need for such a compound that effectively suppresses the events caused by the lack of oxygen supply, 6FP has attracted further investigation. Unfortunately, however, 6FP is hardly soluble in water at neutral pH and in organic solvents because of its self-assembling ability. Although a several mM solution of 6FP is available in alkaline water, it is unstable. In the present study, a novel chemical derivatization of 6FP has been developed which maintains the formyl group on the 6-position of 6FP, which is essential for the physiological activities of 6FP, and increases solubility in water and organic solvents. In the method, the 2- and 3-positions of 6FP were modified by a three component coupling reaction: 6FP was subjected to the reaction with acid chloride and N,N-dimethylformamide. The derivatives synthesized here, 2-(N,N-dimethylaminomethyleneamino)-6-formyl-3-pivaloylpteridine-4-one 1, 2-(N,N-dimethylaminomethyleneamino)-6-formyl-3-isob...Continue Reading

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Citations

Sep 12, 2007·The Journal of Physical Chemistry. a·Frederick A VillamenaJay L Zweier
Jan 9, 2007·Biochemical and Biophysical Research Communications·Mitsuru NonogawaKeisuke Makino
Jun 12, 2008·Journal of Pharmacological Sciences·Takashi MiyoshiMasataka Sasada
May 10, 2021·Free Radical Biology & Medicine·Jean-François GoossensChristian Bailly

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