Oxidation of 7,8-dihydroneopterin by hypochlorous acid yields neopterin.
In vitro, interferon-gamma stimulates primate monocytes/macrophages to produce the pteridines neopterin and 7,8-dihydroneopterin. These pteridines are capable of modulating the oxidative potential of reactive species. Neopterin is pro-oxidative whereas 7, 8-dihydroneopterin is an effective antioxidant. In the presence of oxygen, 7,8-dihydroneopterin is rapidly oxidized and after loosing the side chain 7,8-dihydroxanthopterin is formed. It is considered that under physiological conditions, 7,8-dihydroneopterin cannot be a source for neopterin production. In this study it is demonstrated that hypochlorous acid is capable to oxidize 7,8-dihydroneopterin yielding neopterin. Neopterin is less affected by hypochlorous acid, and in a mixture of both pteridines similar to the in vivo situation, only 7,8-dihydroneopterin is oxidized, thereby increasing the ratio towards neopterin. The findings may beat relevance for the in vivo situation since hypochlorous acid shifts the neopterin/7, 8-dihydroneopterin ratio towards the side of neopterin, hence probably increasing the oxidative potential in a micro-environment.
Widner
B
B
Institute of Medical Chemistry and Biochemistry, University of Innsbruck, Fritz Pregl Strasse 3, Innsbruck, A-6020, Austria.
Mayr
C
C
Wirleitner
B
B
Fuchs
D
D
D002851:Chromatography, High Pressure Liquid; D006997:Hypochlorous Acid / Q000737:chemistry*; D019798:Neopterin / Q000138:chemical synthesis* / Q000031:analogs & derivatives; D010084:Oxidation-Reduction; D011621:Pteridines / Q000737:chemistry*; D011863:Radioimmunoassay
D011621:Pteridines; C000976:7,8-dihydroneopterin; D019798:Neopterin; D006997:Hypochlorous Acid