title: Tumor promoting effect of N-nitroso-N-(2-hexanonyl)-3'-nitrotyramine (a nitrosated Maillard reaction product) in benzo(a)pyrene-initiated mouse skin carcinogenesis.
abstract: N-nitroso-N-(2-hexanonyl)-3'-nitrotyramine (NO-HNTA) is a product generated in a model browning system in the presence of sodium nitrite. The chemical structure of this compound has been confirmed by UV, mass, nuclear magnetic resonance and infrared spectroscopy in our study. Twenty weeks, twice weekly, topical application of NO-HNTA at the concentration of 10, 50 and 250 mumol to mice previously initiated with benzo(a)pyrene (B[a]P) increased their tumor formation by 3.2-, 4.6- and 5.8-fold respectively. Application of the same amount of NO-HNTA not only caused significant induction of hyperplasia but also the activity of epidermal ornithine decarboxylase (ODC). Treatment of mouse skin with various amounts of NO-HNTA (10, 50 and 250 mumol) caused production of hydrogen peroxide by 1.38-, 1.95- and 3.26-fold respectively, and induction myeloperoxidase (MPO) by 24-, 63- and 102-fold. These results indicate that the formation of NO-HNTA or its derivatives derived from the reaction of tyrosine and glucose in the presence of sodium nitrite has the potential as a tumor promoter.
authors.affiliation: Institute of Biochemistry, Chung Shan Medical and Dental College, Taichung, Taiwan, ROC.
authors.forename: T H
authors.initials: TH
authors.lastname: Tseng
authors.forename: M C
authors.initials: MC
authors.lastname: Chang
authors.forename: J D
authors.initials: JD
authors.lastname: Hsu
authors.forename: M J
authors.initials: MJ
authors.lastname: Lee
authors.forename: C L
authors.initials: CL
authors.lastname: Hsu
authors.forename: K P
authors.initials: KP
authors.lastname: Lan
authors.forename: C J
authors.initials: CJ
authors.lastname: Wang
mesh_terms: D000818:Animals; D001564:Benzo(a)pyrene / Q000633:toxicity*; D002273:Carcinogens / Q000737:chemistry / Q000633:toxicity*; D003043:Cocarcinogenesis; D004305:Dose-Response Relationship, Drug; D004423:Ear; D004487:Edema / Q000139:chemically induced; D004817:Epidermis / Q000187:drug effects / Q000201:enzymology; D005260:Female; D006861:Hydrogen Peroxide / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015416:Maillard Reaction; D013058:Mass Spectrometry; D051379:Mice; D009955:Ornithine Decarboxylase / Q000096:biosynthesis; D012878:Skin Neoplasms / Q000139:chemically induced*; D012977:Sodium Nitrite / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D014439:Tyramine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity
chemical_list: D002273:Carcinogens; C115660:N-nitroso-N-(2-hexanonyl)-3'-nitrotyramine; D001564:Benzo(a)pyrene; D006861:Hydrogen Peroxide; D009955:Ornithine Decarboxylase; D012977:Sodium Nitrite; D014439:Tyramine