Antioxidative effects of purine bases on hydrogen peroxide oxidation of pyrimidine bases

Melzer, Marvin S.; Tomlinson, Raymond V.

doi:10.1016/s0003-9861(66)81061-5

Cited by 9 publications

(6 citation statements)

References 6 publications

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“…The remaining s2T content was calculated from the peak areas of s2T, by comparing them with those of guanosine, which was added to the sample solution beforehand as a standard for quantitative analysis. Guanosine was stable against H202 with the buffer used (Melzer & Tomlinson, 1966) and did not influence the rate constant of s2T. The results are summarized in the insert in Figure 1, showing a good correlation between the magnitude of the CD band at 319 nm and the s2T content analyzed by LC. If we assume that the H202-altered nucleoside is the only one which appeared in the elution profiles in Figure 2, the sum of s2T and the nucleoside must be constant throughout the reaction.…”

Section: Resultsmentioning

confidence: 76%

“…At the same time, an aliquot of the reaction mixture was taken up at appropriate intervals and loaded onto the chromatograph to check the decrease of s2T and the increase of its H202-altered nucleoside quantitatively (Figure 2). EDTA was added to the reaction buffer to minimize the reactivity of H202 with the usual nucleosides (Melzer & Tomlinson, 1966) except thiopyrimidines.…”

Section: Resultsmentioning

confidence: 99%

“…In order to suppress these side reactions, EDTA was added to prevent any activity of contaminating metal ions (Melzer & Tomlinson, 1966). The H202 concentration was lowered to 0.1 M, and the reaction was carried out at 20 °C.…”

Section: Discussionmentioning

confidence: 99%

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Reactions of 2-thioribothymidine and 4-thiouridine with hydrogen peroxide in transfer ribonucleic acids from Thermus thermophilus and Escherichia coli as studied by circular dichroism

Watanabe¹

1980

Biochemistry

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Section: Resultsmentioning

confidence: 76%

Section: Resultsmentioning

confidence: 99%

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Reactions of 2-thioribothymidine and 4-thiouridine with hydrogen peroxide in transfer ribonucleic acids from Thermus thermophilus and Escherichia coli as studied by circular dichroism

Watanabe¹

1980

Biochemistry

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“…Marked damage of DNA has been induced with H202 or the organic peroxide, ascaridole (10); H202 destroys the pyrimidine moieties of nucleotides, and has other effects on the DNA molecule (11)(12)(13). The chemical linkage of the polycyclic hydrocarbons, benzo(a)pyrene, 3-methylcholanthrene, and dimethylbenzanthracene, to calf-thymus DNA has been induced by incubation with dilute solutions of H202 (14).…”

mentioning

confidence: 99%

Carcinogen-Induced Chromosomal Breakage Decreased by Antioxidants

Shamberger

Baughman

Kalchert

et al. 1973

Proc. Natl. Acad. Sci. U.S.A.

117

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Blood leukocyte cultures were incubated with antioxidants and the carcinogens sodium cyclamate and 7,12-dimethylbenz(a) The antioxidants, selenium (1-3), dl-a-tocopherol (1, 2), and ascorbic acid (4), applied to mouse skin, significantly reduced tumor formation induced by 7,12-dimethylbenz(a)anthracene and croton oil. Dietary selenium has decreased the number of mouse-skin tumors induced by dimethylbenzanthracene-croton oil (1), rat-liver tumors induced by N-2-fluorenylacetamide (5), and liver tumors induced by diethylaminoazobenzene (6). Rats fed tocopherol-rich wheat-germ oil had fewer mixed tumors (7) after intraperitoneal injection of 3-methylcholanthrene than rats fed a control diet. Haber and Wissler (8) have reported that a tocopherol-supplemented diet had an inhibitory effect on subcutaneous sarcoma from injection of methylcholanthrene in mice. The incidence of gastric cancer in mice decreased after the mice were given the potent food antioxidants, butylated hydroxyanisole and butylated hydroxytoluene (9). After application of dimethylbenzanthracene to mouse skin on day 1, an increase of peroxidation (4) was observed until day 20. When antioxidants were applied to mice treated with dimethylbenzanthracene on days 2-21, the number of tumors developed with croton oil in the mice treated with antioxidant was considerably decreased (2).The current belief about the mechanism of carcinogenesis is that a carcinogen, virus, or other factors alter a macromolecule such as DNA, and change the inherent information that can be transmitted to daughter cells or change the encoded information needed for metabolic function and control during the life of the cell. Marked damage of DNA has been induced with H202 or the organic peroxide, ascaridole (10); H202 destroys the pyrimidine moieties of nucleotides, and has other effects 1461 on the DNA molecule (11-13). The chemical linkage of the polycyclic hydrocarbons, benzo(a)pyrene, 3-methylcholanthrene, and dimethylbenzanthracene, to calf-thymus DNA has been induced by incubation with dilute solutions of H202 (14). Because antioxidants prevent carcinogenesis in animals (1-9) and possibly prevent certain types of human cancer (15-17) Procedure. Several tubes containing about 4.5 ml of heparinized blood were drawn from a 38-year-old male volunteer each morning before breakfast throughout the experiment. A modified macrotechnique of chromosome production was then used (18). Phytohemagglutinin M, 0.2 ml, was injected through the stopper. The tubes were inverted several times, and then placed into an ice-water bath for 1 hr. The blood samples, with the rubber stoppers intact to minimize bacterial contamination, were centrifuged in a Phillips Drucker model L-708 table centrifuge at 400 rpm for 5 min. The stoppers were removed, and 2.0 ml of plasma was transferred aseptically to a tube of chromosomal medium 1A.The tubes containing the chromosomal medium were incubated at 37 for 3 days. About 15 hr before harvest, the antioxidants and carcinogens were added separately in 0.2 ...

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“…However, it is important to note that at 365 nm other photoproducts are quite important in these systems (see review by Webb, reference 18), and it is likely that these photoproducts are not without effect after 325-nm irradiation. Treatment of DNA with Hydrogen Peroxide Hydrogen peroxide breaks down to produce oxygen radicals which in turn have been shown to cause DNA damage by way of altered bases (17), particularly pyrimidines (19). A preliminary study has indicated that hydrogen peroxide produces thymidine glycol from thymidine (20).…”

Section: Irradiation Of Dna With Near Uv Lightmentioning

confidence: 99%

5,6-Saturated thymine lesions in DNA: production by ultraviolet light or hydrogen peroxide

1982

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Thymine analogs with saturated 5-6 bonds are important types of DNA damage that are recognized by the DNA N-glycosylase activity of E. coli endonuclease III. Seeking agents which could preferentially form 5,6-hydrated thymine residues in duplex DNA both in vivo and in vitro, we exposed purified duplex DNA to 325- or 313-nm light; however, after such exposure pyrimidine dimers greatly predominated over 5,6-hydrated thymine. Hydrogen peroxide, on the other hand, formed significant numbers of endonuclease III-sensitive sites in vitro which were not apurinic/apyrimidinic lesions and thus were likely to be 5,6-hydrated thymines.

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Antioxidative effects of purine bases on hydrogen peroxide oxidation of pyrimidine bases

Cited by 9 publications

References 6 publications

Reactions of 2-thioribothymidine and 4-thiouridine with hydrogen peroxide in transfer ribonucleic acids from Thermus thermophilus and Escherichia coli as studied by circular dichroism

Reactions of 2-thioribothymidine and 4-thiouridine with hydrogen peroxide in transfer ribonucleic acids from Thermus thermophilus and Escherichia coli as studied by circular dichroism

Carcinogen-Induced Chromosomal Breakage Decreased by Antioxidants

5,6-Saturated thymine lesions in DNA: production by ultraviolet light or hydrogen peroxide

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