Hydroxylation of guanine in nucleosides and DNA at the C-8 position by heated glucose and oxygen radical-forming agents.
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Abstract:
Heated glucose is mutagenic to Salmonella typhimurium TA 100 in the absence of S-9 mix. For identifying unknown mutagens in heated glucose (dry solid, 200 degrees C, 20 min), reaction with isopropylideneguanosine (IPG) was followed by isolation and characterization of the mutagen-IPG adduct. Two adducts, glyoxal-IPG and 8-hydroxy-IPG, were identified in the reaction mixture by this technique. To elucidate the mechanism of this hydroxylation reaction, we investigated the abilities of various agents to hydroxylate deoxyguanosine or guanine base in DNA. Various reducing agents, metals, asbestoses, polyphenols, aminophenols, and X-ray were effective for hydroxylation, and an oxygen radical seems to be the reactive species. For sensitive detection of 8-hydroxyguanine, a monoclonal antibody for it was prepared.Keywords:
Hydroxylation
Deoxyguanosine
Glyoxal
Deoxyguanosine
Deoxyribose
Glycosidic bond
Ribose
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Deoxyguanosine
8-Hydroxy-2'-deoxyguanosine
Electrochemical gas sensor
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Abstract Acylation of the adduct (III) with the acid anhydrides (IV) yields the homogenous tetraacylated derivatives (Va) and (Vb).
Glyoxal
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The C8-2'-deoxyguanosine adduct of the food mutagen 2-amino-3-methylimadazo[4,5-f]-quinoline (IQ) has been synthesized. The key step is a palladium-catalyzed N-arylation of a suitably protected 8-bromo-2'-deoxygunaosine derivative.
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Journal Article A novel photoproduct of 2'-deoxyguanosine induced by acetone photosensitization: 8-(2,3,4-trihydroxybutyl)guanine Get access Narain D. Sharma, Narain D. Sharma Search for other works by this author on: Oxford Academic PubMed Google Scholar R. Jeremy, R. Jeremy Search for other works by this author on: Oxford Academic PubMed Google Scholar H. Davies, H. Davies * *To whom correspondence should be addressed Search for other works by this author on: Oxford Academic PubMed Google Scholar Dennis R. Phillips, Dennis R. Phillips 1Departments of Medicinal Chemistry and Biochemistry, University of UtahSalt Lake City, UT 84112, USA Search for other works by this author on: Oxford Academic PubMed Google Scholar James A. McCloskey James A. McCloskey 1Departments of Medicinal Chemistry and Biochemistry, University of UtahSalt Lake City, UT 84112, USA Search for other works by this author on: Oxford Academic PubMed Google Scholar Nucleic Acids Research, Volume 17, Issue 3, 11 February 1989, Pages 955–967, https://doi.org/10.1093/nar/17.3.955 Published: 11 February 1989 Article history Received: 08 November 1988 Revision received: 03 January 1989 Accepted: 03 January 1989 Published: 11 February 1989
Deoxyguanosine
Cleavage (geology)
Derivative (finance)
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The [math] radical specifically oxidizes 2'-deoxyguanosine at its guanylic moiety. The guanylic radical resulting from this one-electron oxidation is followed by a first-order kinetics process. This is distinctively observed in alkaline solutions (pH ≥ 11) where a new transient could be characterized. This transient exhibits spectra that are similar to those observed with guanine. It is suggested that the oxidized nucleoside radical undergoes a monomolecular process to form an oxidized guanine radical.
Deoxyguanosine
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Radical ion
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A platinum(IV) complex with a high reduction potential, d,l-1,2-diaminocyclohexyltetrachloroplatinum(IV) (PtIV(dach)Cl4), oxidizes guanine in guanosine-5'-monophosphate (GMP), 2'-deoxyguanosine-5'-monophosphate (dGMP), d(GG), and a double-stranded oligonucleotide to 8-oxo-guanine. To the best of our knowledge, this is the first report that provides unambiguous evidence of DNA oxidation by a PtIV complex. This oxidative damage may differentiate the anticancer activity of PtIV complexes from their PtII analogues.
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Guanosine monophosphate
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The reaction of 3-methyl-1,2,3-oxadiazolinium tosylate 10, a close model for a putative reactive intermediate in the carcinogenic activation of ethanol nitrosamines such as (2-hydroxyethyl)methylnitrosamine 1, with various guanine derivatives, including acycloguanosine 12, deoxyguanosine, deoxyguanosine monophosphate, and cyclic guanosine monophosphate, various DNA oligomers, and calf-thymus DNA has been examined to determine whether this compound methylates and hydroxyethylates guanine residues as proposed. In all of the transformations, 7-(2-(methylnitrosamino)ethyl)guanine (14) is the major product, following acidic hydrolysis, and exceeds the formation of 7-methylguanine by ratios ranging from 4:1 to 48:1, depending upon the guanine bearing substrate. O6-(2-(Methylnitrosamino)ethyl)deoxyguanosine (20) was prepared from the Mitsunobu coupling of 1 and a protected deoxyguanosine derivative. 20 is not produced in the reaction of 10 and deoxyguanosine and decomposes to 1 and guanine upon mild acid treatment, suggesting possible neighboring group participation in its facile hydrolytic cleavage. All of the major products from the reaction of 10 and 12 have been characterized, including the direct alkylation product, 7-(2-(methylnitrosamino)ethyl)acycloguanosine (13), and N2-(2-(methylnitrosamino)ethyl)guanine, which was independently synthesized. Elucidation of the reactions of DNA with 10 and other electrophiles was facilitated by the development of both partial and total enzymatic hydrolysis assays utilizing 32P-5'-labeled DNA oligotetramers containing one of each base type and HPLC with radiometric detection. The partial hydrolysis assay gives information as to the type of base being modified, and the total hydrolysis assay permits a determination of the number of adducts produced for a given base. The assays permit a comparison between reactions where the same type of base adduct could be expected. Comparisons of the reactions of ethylene oxide and 10 using this methodology showed that 10 does not hydroxyethylate guanine in DNA.
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After bioactivation, the potent dietary mutagen 2-amino-3-methylimidazo[4,5-f]-quinoline (IQ) reacts with DNA to give two regioisomeric adducts of deoxyguanosine. The synthesis of the minor N2-adduct has been achieved utilizing the Buchwald−Hartwig palladium-catalyzed N-arylation reaction as the key step.
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Quinoline
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A partir de glyoxal et de N 2 -acetyl guanine, synthese d'acetyl-5 dihydroxy-6,7 tetrahydro-5,6,7,9 imidazo [1,2-a] purinone-9 (A) (adduit glyoxal-guanine); acylation par des anhydrides d'acides en derives acyl-3 di-O-acyl-6,7 de A
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