1970
DOI: 10.1126/science.167.3925.1622
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Oncogenic Purine Derivatives: Evidence for a Possible Proximate Oncogen

Abstract: Two additional urinary metabolites of the chemical oncogen 3-hydroxyxanthine are now identified as 8-chloroxanthine and 8-methylmercaptoxanthine. Such products are thought to be derived from a reactive intermediate which can be tentatively considered to be a proximate oncogen. Since each of these 8-substituted xanthines has also been obtained in vitro by reactions of 3-acetoxyxanthine with chloride ion or methionine, their production in vivo can be explained as resulting through the metabolic formation of an a… Show more

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Cited by 31 publications
(6 citation statements)
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“…The two isomers can be isolated together in 25% yield. Simultaneously, a portion of T J-he potent oncogen 3-hydroxyxanthine (Brown et al, 1973) is activated in vivo to a sulfate ester (Stohrer et al, 1972) which reacts with methionine to yield 8-methylmercaptoxanthine as a urinary metabolite (Stohrer and Brown, 1970) and 8-methylmercaptoxanthine can be released from tissue proteins (Stohrer et al, 1972). In this communication we describe two of the products of the reaction of L-tryptophan and 3-acetoxyxanthine, a chemically prepared model of the activated oncogen (Wólcke et al, 1969;Birdsall et al, 1971).…”
Section: -Acetoxyxanthinefmentioning
confidence: 99%
“…The two isomers can be isolated together in 25% yield. Simultaneously, a portion of T J-he potent oncogen 3-hydroxyxanthine (Brown et al, 1973) is activated in vivo to a sulfate ester (Stohrer et al, 1972) which reacts with methionine to yield 8-methylmercaptoxanthine as a urinary metabolite (Stohrer and Brown, 1970) and 8-methylmercaptoxanthine can be released from tissue proteins (Stohrer et al, 1972). In this communication we describe two of the products of the reaction of L-tryptophan and 3-acetoxyxanthine, a chemically prepared model of the activated oncogen (Wólcke et al, 1969;Birdsall et al, 1971).…”
Section: -Acetoxyxanthinefmentioning
confidence: 99%
“…Methylsulfonylation, the process leading to the formation of mercapto-(-SH), methylthio-(-SCH3), methylsulfinyl-(-SOCH3) and methylsulfonyl-(SO2CH3) metabolites of xenobiotics, is one of the many novel biological pathways of metabolism discovered during the past several years. The serial methylsulfonyl pathway for xenobiotic metabolism has been studied in numerous laboratories for numerous compounds such as the drugs cafffeine (1), bromazepam (2), bromovalerylurea (3), acetoaminophen (4), alfoqualone (5), and 3-hydroxy- xanthine (6); pesticides and fungicides, including propachlor (7), napthalene (8), AF-2 (9) and PCNB (10); and pollutants such as DDE (11), PCBs (11)(12)(13), HCB (14) and monochlorodibenzo-p-dioxin (15). During the time that xenobiotic thioether derivatives were discovered, precursors including glutathione, cysteinylglycine, cysteine and N-acetylcysteine (mercapturic acid) conjugates (2,4,5,7,14) have been reported.…”
Section: Introductionmentioning
confidence: 99%
“…Reactions in which the nucleophile is a halogen (20,21), oxygen (22), sulfur (23,24), nitrogen (25) reported. Few of these reactions involved cyclic hydroxylamines.…”
Section: H Me Oacmentioning
confidence: 99%