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Quantitative structure‐activity relationships for skin sensitization potential of urushiol analogues

 

作者: David W. Roberts,   Claude Benezra,  

 

期刊: Contact Dermatitis  (WILEY Available online 1993)
卷期: Volume 29, issue 2  

页码: 78-83

 

ISSN:0105-1873

 

年代: 1993

 

DOI:10.1111/j.1600-0536.1993.tb03487.x

 

出版商: Blackwell Publishing Ltd

 

关键词: quantitative structure‐activity relationships;relative alleviation index;guinea pig sensitization;urushiols;orthoquinones;overload effect

 

数据来源: WILEY

 

摘要:

The relative alkylation index (RAI), a theoretically derived parameter intended to quantify the relative extent of carrier haptenation resulting from a given dose of a given sensitizer, has previously been successfully applied to the analysis of relative sensitization potential and dose‐response data for a variety of contact allergens which are directly electrophilic. Here the RAI concept is applied to analysis of data on compounds related to urushiol (i.e., 3‐substituted catechols), the naturally occurring mixture of allergens responsible for contact allergy to poison ivy and poison oak. These allergens are believed to act as pro‐electrophiles, being oxidized to electrophilic orthoquinones in vivo. It is found that the various types of urushiol derivatives fit the same sort of RAI‐sensitization relationships as expected theoretically and as found previously with direct acting electrophiles. There is evidence that in many cases, the test conditions were such that overload effects, whereby the degree of sensitization induced decreases with increasing carrier haptenation, applied. It is also concluded that the question as to the relative sensitization potencies of the naturally occurring urushiols remains open. The commonly held view that with these materials, sensitization potential increases with increasing unsaturation in the 3‐hydrocarbyl chain of the 3‐hydrocarbyl catechols, is based on evidence that is capable of alternative int

 

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