Peroxide induced binding of hydrocarbons to DNA

Morreal, Charles E.; Dao, Thomas L.; Eskins, Kenneth; King, Charles L.; Dienstag, Jules L.

doi:10.1016/0005-2787(68)90024-5

Cited by 25 publications

(3 citation statements)

References 8 publications

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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). Because antioxidants prevent carcinogenesis in animals (1-9) and possibly prevent certain types of human cancer (15)(16)(17) Procedure.…”

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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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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“…During the completion of this manuscript, Morreal et al (1968) have reported the induction of a chemical linkage of the polycyclic hydrocarbons 3,4-benzpyrene, 3-methylcholanthrene, and 9,10-dimethyl-l ,2-benzanthracene to calf thymus DNA with dilute solutions of H202.…”

Section: Discussionmentioning

confidence: 99%

Interaction of nucleic acids. V. Chemical linkage of 3,4-benzopyrene to deoxyribonucleic acid in aqueous solution

Lesko¹,

Ts’o²,

Umans³

1969

Biochemistry

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“…The hydrocarbons have relatively low ionization potentials, and it has been suggested that radical cations ( Fig. 3) arising from reactions with oxidants in the cells might playa primary role in hydrocarbon carcinogenesis (Fried and Schumm, 1967;Morreal et al, 1969;Wilk and Girke, 1969;Wilk and Hoppe, 1969). On the other hand, Boyland and Sims (1962 have presented evidence that a number of epoxides are formed in the metabolism of phenanthrene, benz(a)anthracene, and dibenz(a,h) anthracene and, by analogy, epoxides are probably formed in the metabolism of many carcinogenic hydrocarbons.…”

Section: F Polycyclic Aromatic Hydrocarbonsmentioning

confidence: 99%

Chemical Mutagens

1971

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Peroxide induced binding of hydrocarbons to DNA

Cited by 25 publications

References 8 publications

Carcinogen-Induced Chromosomal Breakage Decreased by Antioxidants

Carcinogen-Induced Chromosomal Breakage Decreased by Antioxidants

Interaction of nucleic acids. V. Chemical linkage of 3,4-benzopyrene to deoxyribonucleic acid in aqueous solution

Chemical Mutagens

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