Oncogenic Purine Derivatives: Evidence for a Possible Proximate Oncogen

Stöhrer, Gerhard; Brown, George Bosworth

doi:10.1126/science.167.3925.1622

Cited by 31 publications

(6 citation statements)

References 12 publications

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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%

Purine N-oxides. 54. Chemical adduct of tryptophan and the oncogen 3-acetoxyxanthine

Stöhrer¹,

Salemnick²,

Gb³

1973

Biochemistry

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Section: -Acetoxyxanthinefmentioning

confidence: 99%

Purine N-oxides. 54. Chemical adduct of tryptophan and the oncogen 3-acetoxyxanthine

Stöhrer¹,

Salemnick²,

Gb³

1973

Biochemistry

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“…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%

Mechanism of biosynthesis of methylsulfones from PCBs and related compounds.

Mio¹,

Sumino²

1985

Environ Health Perspect

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Mercapto-, methylthio-, methylsulfinyl- and methysulfonyl metabolites of PCBs 2,5,2',5'-tetrachlorobiphenyl, 1,3,5-trichlorobenzene and some other chlorobenzenes were identified in adipose tissues of mice, rats and guinea pigs by using GC/MS/COM systems. By means of administration of CD3-methionine, it was confirmed that the methyl group in methylthio metabolites was derived from the methionine. Moreover, after pretreatment with either esterification of urinary metabolites in guinea pigs with 1,3,5-trichlorobenzene and 1,3-dichlorobenzene or N-acetylation after esterification, it was confirmed that cysteinylglycine, cysteine, N-acetylcysteine, cysteamine, mercaptopyruvate, mercaptolactate, mercaptacetate, thiol and disulfide conjugates were detected as a serial modified derivatives of glutathione moiety. These results are summarized as a metabolic proposed pathway of halogenated aromatic compounds. Three routes in pathway correspond to oxygenation (initial route), glutathione thioether disposition (intermediate route) and sulfoxydation (final route) in connection with both reactive intermediates of epoxide and thiol. Methylation of the thiol by S-adenosylmethionine may be important in inhibiting covalent binding of reactive intermediates with biocomponents, similar to the glutathione conjugation for the detoxification of epoxide.

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“…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%

Derivatives of 2-Pyrazolin-5-one. III. The Preparation and Properties of Some 1′-Phenylspiro[indoline-2,4′-[2]pyrazoline]-5′-ones

Coutts¹,

El-Hawari²,

Biggs³

1975

Can. J. Chem.

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The choice of solvent has a great influence on the nature of the products obtained when suitably substituted aromatic nitro-compounds are reduced by means of sodium borohydride in the presence of palladium–charcoal. When derivatives of 4-(2-nitrobenzylidene)-1-phenyl-2-pyrazolin-5-one are reduced by this reagent in dioxane, three products are obtained. They are identified as derivatives of 1′-phenylspiro[indoline-2,4′-[2]pyrazoline]-5′-one, of 1-hydroxy-1′-phenylspiro[indoline-2,4′-[2]pyrazoline]-5′-one, and of 4-(2-aminobenzyl)-1-phenyl-2-pyrazolin-5-one. The 1-hydroxyspiro[indolinepyrazolones] are very reactive compounds. The products of their oxidation, reductions with various reagents, and reactions with chemical nucleophiles have been isolated and identified. Some preliminary pharmacological properties of four of the synthesized compounds are reported.

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Oncogenic Purine Derivatives: Evidence for a Possible Proximate Oncogen

Cited by 31 publications

References 12 publications

Purine N-oxides. 54. Chemical adduct of tryptophan and the oncogen 3-acetoxyxanthine

Purine N-oxides. 54. Chemical adduct of tryptophan and the oncogen 3-acetoxyxanthine

Mechanism of biosynthesis of methylsulfones from PCBs and related compounds.

Derivatives of 2-Pyrazolin-5-one. III. The Preparation and Properties of Some 1′-Phenylspiro[indoline-2,4′-[2]pyrazoline]-5′-ones

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