{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,19]],"date-time":"2026-05-19T04:27:05Z","timestamp":1779164825280,"version":"3.51.4"},"reference-count":39,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2006,1,12]],"date-time":"2006-01-12T00:00:00Z","timestamp":1137024000000},"content-version":"vor","delay-in-days":407,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Annals of the New York Academy of Sciences"],"published-print":{"date-parts":[[2004,12]]},"abstract":"<jats:p><jats:bold>A<jats:sc>bstract<\/jats:sc>: <\/jats:bold> The first step in cancer initiation is the reaction of chemical carcinogens with DNA to form stable adducts, which remain in DNA unless removed by repair, and depurinating adducts, which detach from DNA following destabilization of the glycosyl bond. Depurinating DNA adducts of polycyclic aromatic hydrocarbons play a major role in the initiation of cancer, as shown by the correlation between depurinating adducts and oncogenic mutations of the H\u2010ras oncogene in mouse skin. Following these results, experiments on the metabolism of estrogens, formation of depurinating DNA adducts, carcinogenicity, mutagenicity, and cellular transformation have led us to the hypothesis that certain metabolites of endogenous estrogens\u2014in particular, estradiol(estrone)\u20103,4\u2010quinones\u2014can react with DNA to form depurinating adducts at the N\u20103 of Ade and the N\u20107 of Gua. Depurination of these adducts can generate critical mutations by error\u2010prone repair to initiate breast, prostate, and other cancers. The oxidation mechanism of catechols to quinone compounds includes not only natural estrogens, but also synthetic estrogens, such as hexestrol and the human carcinogen diethylstilbestrol, which react with DNA to form N3Ade and N7Gua adducts, presumably to initiate cancer. Furthermore, the initiating mechanism of the leukemogen benzene involves oxidation of catechol to catechol quinone, which reacts with DNA to form N3Ade and N7Gua adducts. The quinone of the neurotransmitter dopamine can also react with DNA to form N3Ade and N7Gua adducts. The subsequent mutations could be at the origin of Parkinson's and other neurodegenerative diseases. In summary, the apurinic sites produced in DNA from the loss of these depurinating adducts can be converted into mutations by error\u2010prone repair, which may initiate cancer and other diseases.<\/jats:p>","DOI":"10.1196\/annals.1322.029","type":"journal-article","created":{"date-parts":[[2005,1,13]],"date-time":"2005-01-13T20:08:46Z","timestamp":1105646926000},"page":"247-257","source":"Crossref","is-referenced-by-count":81,"title":["A Unifying Mechanism in the Initiation of Cancer and Other Diseases by Catechol Quinones"],"prefix":"10.1111","volume":"1028","author":[{"given":"ERCOLE L.","family":"CAVALIERI","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"ELEANOR G.","family":"ROGAN","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2006,1,12]]},"reference":[{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/0163-7258(93)90057-K"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1093\/carcin\/19.1.1"},{"key":"e_1_2_8_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/tx010042g"},{"key":"e_1_2_8_5_2","doi-asserted-by":"publisher","DOI":"10.1093\/carcin\/22.9.1573"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1093\/carcin\/23.2.329"},{"key":"e_1_2_8_7_2","doi-asserted-by":"publisher","DOI":"10.1093\/carcin\/bgg004"},{"key":"e_1_2_8_8_2","doi-asserted-by":"publisher","DOI":"10.1210\/er.21.1.40"},{"key":"e_1_2_8_9_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.94.20.10937"},{"key":"e_1_2_8_10_2","doi-asserted-by":"publisher","DOI":"10.1093\/carcin\/bgg191"},{"key":"e_1_2_8_11_2","doi-asserted-by":"crossref","unstructured":"Cavalieri E. K. Frenkel J. G. Liehr et al.2000. Estrogens as endogenous genotoxic agents: DNA adducts and mutations.InJNCI Monograph: Estrogens as Endogenous Carcinogens in the Breast and Prostate. E. Cavalieri & E. Rogan Eds.: 75\u201093. Oxford University Press. New York.","DOI":"10.1093\/oxfordjournals.jncimonographs.a024247"},{"key":"e_1_2_8_12_2","doi-asserted-by":"publisher","DOI":"10.1093\/carcin\/22.6.905"},{"key":"e_1_2_8_13_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00018-002-8456-0"},{"key":"e_1_2_8_14_2","doi-asserted-by":"crossref","unstructured":"Cavalieri E. E. Rogan & D. Chakravarti. 2004. The role of endogenous catechol quinones in the initiation of cancer and neurodegenerative diseases.InMethods in Enzymology Vol. 382: Quinones and Quinone Enzymes Part B. H. Sies & L. Packer Eds.: 293\u2010319. Elsevier. 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