Document Detail

Quantum chemical studies of methylbenz[a]anthracenes: metabolism and correlations with carcinogenicity.
MedLine Citation:
PMID:  7408039     Owner:  NLM     Status:  MEDLINE    
In the context of the bay region, K-region and radical cation hypotheses for polycyclic aromatic carcinogens, molecular properties were calculated for fourteen methyl derivatives of benz[a]anthracene (BA) related to (1) intrinsic substrate reactivities towards activating and detoxifying metabolism and (2) the stabilities of the putative carbocation ultimate carcinogens. All-valence electron methods were used, avoiding the inherent difficulties found in the pi-electron methods. The calculated substrate reactivities were found to predict major metabolites successfully, supporting the validity of their use in attempted correlations with observed carcinogenic potencies. Positive correlations were found between observed carcinogenic potencies smf (1) the reactivities of the parent polycyclic aromatic hydrocarbons (PAH) towards the initial distal bay region epoxidation and (2) the stabilities of the diol epoxide carbocations. This latter correlation holds when both the methyl derivatives of BA and previously studied unsubstituted PAH are considered together, indicating its potential usefulness as a screening parameter for carcinogenic activity.
G Loew; M Poulsen; J Ferrell; D Chaet
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Chemico-biological interactions     Volume:  31     ISSN:  0009-2797     ISO Abbreviation:  Chem. Biol. Interact.     Publication Date:  1980 Sep 
Date Detail:
Created Date:  1980-11-25     Completed Date:  1980-11-25     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  0227276     Medline TA:  Chem Biol Interact     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  319-40     Citation Subset:  IM    
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MeSH Terms
Benz(a)Anthracenes / metabolism*,  toxicity
Chemistry, Physical
Physicochemical Phenomena
Quantum Theory
Structure-Activity Relationship
Grant Support
Reg. No./Substance:
0/Benz(a)Anthracenes; 0/Carcinogens

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