{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T13:07:16Z","timestamp":1791292036455,"version":"4.1.0"},"reference-count":26,"publisher":"Wiley","issue":"12","license":[{"start":{"date-parts":[[2011,11,2]],"date-time":"2011-11-02T00:00:00Z","timestamp":1320192000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IUBMB Life"],"published-print":{"date-parts":[[2011,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The neurotransmitter dopamine is oxidized to its quinone (DA\u2010Q), which at neutral pH undergoes intramolecular cyclization by 1,4\u2010Michael addition, followed by oxidation to form leukochrome, then aminochrome, and finally neuromelanin. At lower pH, the amino group of DA is partially protonated, allowing the competitive intermolecular 1,4\u2010Michael addition with nucleophiles in DNA to form the depurinating adducts, DA\u20106\u2010N3Ade and DA\u20106\u2010N7Gua. Catechol estrogen\u20103,4\u2010quinones react by 1,4\u2010Michael addition to form the depurinating 4\u2010hydroxyestrone(estradiol)\u20101\u2010N3Ade [4\u2010OHE<jats:sub>1<\/jats:sub>(E<jats:sub>2<\/jats:sub>)\u20101\u2010N3Ade] and 4\u2010OHE<jats:sub>1<\/jats:sub>(E<jats:sub>2<\/jats:sub>)\u20101\u2010N7Gua adducts, which are implicated in the initiation of breast and other human cancers. The effect of pH was studied by reacting tyrosinase\u2010activated DA with DNA and measuring the formation of depurinating adducts. The most adducts were formed at pH 4, 5, and 6, and their level was nominal at pH 7 and 8. The N3Ade adduct depurinated instantaneously, but N7Gua had a half\u2010life of 3 H. The slow loss of the N7Gua adduct is analogous to that observed in previous studies of natural and synthetic estrogens. The antioxidants <jats:italic>N<\/jats:italic>\u2010acetylcysteine and resveratrol efficiently blocked formation of the DA\u2010DNA adducts. Thus, slightly acidic conditions render competitive the reaction of DA\u2010Q with DNA to form depurinating adducts. We hypothesize that formation of these adducts could lead to mutations that initiate Parkinson's disease. If so, use of <jats:italic>N<\/jats:italic>\u2010acetylcysteine and resveratrol as dietary supplements may prevent initiation of this disease. \u00a9 2011 IUBMB IUBMB Life, 63(12): 1087\u20131093, 2011<\/jats:p>","DOI":"10.1002\/iub.538","type":"journal-article","created":{"date-parts":[[2011,11,2]],"date-time":"2011-11-02T06:21:42Z","timestamp":1320214902000},"page":"1087-1093","source":"Crossref","is-referenced-by-count":40,"title":["Formation of dopamine quinone\u2010DNA adducts and their potential role in the etiology of Parkinson's disease"],"prefix":"10.1002","volume":"63","author":[{"given":"Muhammad","family":"Zahid","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Muhammad","family":"Saeed","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Li","family":"Yang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cheryl","family":"Beseler","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Eleanor","family":"Rogan","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ercole L.","family":"Cavalieri","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2011,11,2]]},"reference":[{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.1093\/carcin\/23.6.1071"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.freeradbiomed.2009.11.002"},{"key":"e_1_2_8_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.neuron.2010.02.012"},{"key":"e_1_2_8_5_2","doi-asserted-by":"publisher","DOI":"10.2217\/fon.09.137"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1038\/sj.onc.1204969"},{"key":"e_1_2_8_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jsbmb.2006.06.019"},{"key":"e_1_2_8_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.steroids.2004.09.011"},{"key":"e_1_2_8_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/tx050229y"},{"key":"e_1_2_8_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/ijc.24113"},{"key":"e_1_2_8_11_2","first-page":"117","article-title":"Melatonin involvement in oxidative processes","volume":"29","author":"Ianas O.","year":"1991","journal-title":"Rom. 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