| Benzene and dopamine catechol quinones could initiate cancer or neurogenic disease. | |
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MedLine Citation:
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PMID: 19909805 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Catechol quinones of estrogens react with DNA by 1,4-Michael addition to form depurinating N3Ade and N7Gua adducts. Loss of these adducts from DNA creates apurinic sites that can generate mutations leading to cancer initiation. We compared the reactions of the catechol quinones of the leukemogenic benzene (CAT-Q) and N-acetyldopamine (NADA-Q) with 2'-deoxyguanosine (dG) or DNA. NADA was used to prevent intramolecular cyclization of dopamine quinone. Reaction of CAT-Q or NADA-Q with dG at pH 4 afforded CAT-4-N7dG or NADA-6-N7dG, which lost deoxyribose with a half-life of 3 h to form CAT-4-N7Gua or 4 h to form NADA-6-N7Gua. When CAT-Q or NADA-Q was reacted with DNA, N3Ade adducts were formed and lost from DNA instantaneously, whereas N7Gua adducts were lost over several hours. The maximum yield of adducts in the reaction of CAT-Q or NADA-Q with DNA at pH 4 to 7 was at pH 4. When tyrosinase-activated CAT or NADA was reacted with DNA at pH 5 to 8, adduct levels were much higher (10- to 15-fold), and the highest yield was at pH 5. Reaction of catechol quinones of natural and synthetic estrogens, benzene, naphthalene, and dopamine with DNA to form depurinating adducts is a common feature that may lead to initiation of cancer or neurodegenerative disease. |
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Authors:
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Muhammad Zahid; Muhammad Saeed; Eleanor G Rogan; Ercole L Cavalieri |
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Publication Detail:
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Type: In Vitro; Journal Article; Research Support, N.I.H., Extramural; Research Support, U.S. Gov't, Non-P.H.S. Date: 2009-11-10 |
Journal Detail:
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Title: Free radical biology & medicine Volume: 48 ISSN: 1873-4596 ISO Abbreviation: Free Radic. Biol. Med. Publication Date: 2010 Jan |
Date Detail:
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Created Date: 2010-02-03 Completed Date: 2010-06-14 Revised Date: 2011-07-20 |
Medline Journal Info:
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Nlm Unique ID: 8709159 Medline TA: Free Radic Biol Med Country: United States |
Other Details:
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Languages: eng Pagination: 318-24 Citation Subset: IM |
Copyright Information:
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Copyright 2009 Elsevier Inc. All rights reserved. |
Affiliation:
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Eppley Institute for Research in Cancer and Allied Diseases, University of Nebraska Medical Center, Omaha, NE 68198-6805, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Aminobutyric Acids
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pharmacology Animals Benzene / chemistry, metabolism* Catechols / chemistry Cattle Cell Transformation, Neoplastic Chromatography, High Pressure Liquid DNA Adducts / adverse effects*, chemistry Dopamine / analogs & derivatives, chemistry, metabolism* Humans Hydrogen-Ion Concentration Mutagenesis / drug effects, genetics Mutagens / adverse effects, chemistry Naphthalenes / chemistry, metabolism Neoplasms / etiology* Neurodegenerative Diseases / etiology* Quinones / chemistry |
| Grant Support | |
ID/Acronym/Agency:
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P01 CA049210-15/CA/NCI NIH HHS; P01 CA49210/CA/NCI NIH HHS; P30 CA36727/CA/NCI NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Aminobutyric Acids; 0/Catechols; 0/DNA Adducts; 0/Mutagens; 0/N(gamma)-acetyl-2,4-diaminobutyric acid; 0/Naphthalenes; 0/Quinones; 120-80-9/catechol; 71-43-2/Benzene; 91-20-3/naphthalene |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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