Document Detail


Identification of the persistently bound form of the carcinogen N-acetyl-2-aminofluorene to rat liver DNA in vivo.
MedLine Citation:
PMID:  975399     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
In this article the structural analysis of the persistently bound form of the carcinogen N-acetyl-2-aminofluorene (AAF) to rat liver DNA in vivo is described. This compound appears to result from the formation of a covalent bond between carbon-3 of the aromatic ring and the amino group of guanine. Experimental evidence from three different approaches had led to the identification of the structure of the persistently DNA-bound AAF moiety. First, [3-3H, 9-14C]N-acetoxy-AAF was reacted with DNA in vitro. As reported previously, a minor product was isolated from enzymatic digests of the reacted DNA, which had chemical and chromatographic properties identical to those of the persistent--AAF moiety in DNA in vivo. The ratio 3H/14C of this product had diminished to the same extent as 3-CH3S-AAF resulting from the reaction of methionine with [o-3H, 9-14C]N-acetoxy-AAF. Secondly, reaction of [9-14C]N-acetoxy-AAF with DNA, which was tritiated in the C-8 positions of the purines, did not result in removal of tritium in the persistent fraction obtained after acid hydrolysis, thus excluding substitution at C-8 and N-7 of guanine. Finally , by reacting N-OSO3-K-AAF with deoxyguanosine in dimethylsulfoxide-triethylamine, a compound could be isolated, which was identified as 3-(deoxyguanosin-N2-yl)-AAF based on its NMR spectrum and on the mass spectrum of the corresponding guanine derivative obtained after removing deoxyribose by acid hydrolysis. This compound appeared to be identical with the persistently bound form present in DNA hydrolysates from rat liver after injection of [2'-3H]N-hydroxy-AAF.
Authors:
J G Westra; E Kriek; H Hittenhausen
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Chemico-biological interactions     Volume:  15     ISSN:  0009-2797     ISO Abbreviation:  Chem. Biol. Interact.     Publication Date:  1976 Oct 
Date Detail:
Created Date:  1977-01-03     Completed Date:  1977-01-03     Revised Date:  2009-10-27    
Medline Journal Info:
Nlm Unique ID:  0227276     Medline TA:  Chem Biol Interact     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  149-64     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
2-Acetylaminofluorene / metabolism*
Animals
Binding Sites
Cattle
DNA / metabolism*
Fluorenes / metabolism*
Fourier Analysis
Liver / metabolism*
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Conformation
Nucleic Acid Conformation
Rats
Thymus Gland
Chemical
Reg. No./Substance:
0/Fluorenes; 53-96-3/2-Acetylaminofluorene; 9007-49-2/DNA

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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