Formation of directly mutagenic α-hydroxy-N-nitrosopiperidine phosphate ester by near-ultraviolet irradiation of N-nitrosopiperidine in phosphate buffer

• Published in: Biochemical and biophysical research communications Vol. 162; no. 3; pp. 1140 - 1146
• Main Authors: Arimoto, Sakae, Shimada, Hiromi, Ukawa, Satoko, Mochizuki, Masataka, Hayatsu, Hikoya
• Format: Journal Article
• Language: English
• Published: San Diego, CA Elsevier Inc 15.08.1989; Elsevier
• Subjects: 560120 - Radiation Effects on Biochemicals, Cells, & Tissue Culture; Biological and medical sciences; BUFFERS; CHEMICAL RADIATION EFFECTS; CHEMISTRY; Chromatography, High Pressure Liquid; ELECTROMAGNETIC RADIATION; ESTERS; Fundamental and applied biological sciences. Psychology; IN VITRO; In Vitro Techniques; Magnetic Resonance Spectroscopy; Miscellaneous; Molecular and cellular biology; Molecular genetics; MUTAGENS; NEAR ULTRAVIOLET RADIATION; Nitrosamines - radiation effects; NITROSO COMPOUNDS; ORGANIC COMPOUNDS; ORGANIC NITROGEN COMPOUNDS; ORGANIC PHOSPHORUS COMPOUNDS; Organophosphates; Organophosphorus Compounds; OXYGEN COMPOUNDS; PHOSPHATES; PHOSPHORIC ACID ESTERS; PHOSPHORUS COMPOUNDS; PHOTOCHEMISTRY; RADIATION CHEMISTRY; RADIATION EFFECTS; RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT; RADIATIONS; Spectrophotometry, Ultraviolet; ULTRAVIOLET RADIATION; Ultraviolet Rays; Phosphates; Ultraviolet irradiation; Molecular structure; Reaction product; HPLC chromatography; Isolation; NMR spectrometry; Mutation; Photochemical reaction; Mutagen; Ultraviolet spectrometry; Structural analysis
• ISSN: 0006-291X; 1090-2104
• DOI: 10.1016/0006-291X(89)90792-4

Previously we found that direct-acting mutagens can be formed from N-nitrosodialkylamines on exposure to near-ultraviolet light in the presence of phosphates. We have now isolated the mutagenic photoproduct formed from N-nitrosopiperidine and inorganic phosphate and identified its structure as the phosphate ester of α-hydroxy-N-nitrosopiperidine. This reaction represents a new, non-enzymatic activation of promutagenic N-nitrosodialkylamines.