Document Detail


Antinociceptive activities of alpha-truxillic acid and beta-truxinic acid derivatives.
MedLine Citation:
PMID:  16508173     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Our recent study demonstrated that the dimeric structure of alpha-truxillic acid derivatives played an important role in the expression of their anti-inflammatory activities. In the present report, to investigate the correlation between the structure and anti-inflammatory activity, alpha-truxillic acid (1) and its derivatives (2-6), beta-truxinic acid (7) and its derivatives (8-10) were prepared, and their activities were evaluated in the formalin test. All compounds showed only weak or no activities against the neurogenic pain response, but demonstrated significant activities against the inflammatory pain response induced by formalin. The highest anti-inflammatory activities were observed for alpha-truxillic acid (1) and its derivative 4,4'-dihydroxy-alpha-truxillic acid (2). In addition, alpha-truxillic acid (1) and its derivative, alpha-truxillic acid bis(p-nitrophenyl)ester (5), showed higher anti-inflammatory activities than beta-truxinic acid (7) and the corresponding derivative (10). Furthermore, free carboxylic acids (1, 2) showed higher activities than their dimethyl esters (3, 4) and bis(p-nitrophenyl)ester (5). These results confirmed that the alpha-formation of dimeric structure and the free carboxylic acid were also important for the expression of anti-inflammatory activities. Otherwise, 4,4'-dichloro-beta-truxinic acid (8) had higher activity than its parent compound 7; furthermore, 1,3-dibenzoyl-2,4-di(4-chlorophenyl)cyclobutane (6) also showed strong anti-inflammatory activity. These results suggested that substituents in the phenyl groups were also important for the expression of anti-inflammatory activity. In order to gain information about their activity intensity, the anti-inflammatory activities of 2 and 4,4'-dichlorolated derivatives (6, 8) were compared with that of indomethacin (a nonsteroidal anti-inflammatory drug) in the formalin test. As a result, compounds 2, 6 and 8 showed stronger anti-inflammatory activities than indomethacin. These results suggested that alpha-truxillic acid and beta-truxinic acid derivatives might be developed into a new type of anti-inflammatory drug.
Authors:
Yu-Ming Chi; Motoyuki Nakamura; Xi-Ying Zhao; Toyokichi Yoshizawa; Wen-Mei Yan; Fumio Hashimoto; Junei Kinjo; Toshihiro Nohara; Shinobu Sakurada
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Biological & pharmaceutical bulletin     Volume:  29     ISSN:  0918-6158     ISO Abbreviation:  Biol. Pharm. Bull.     Publication Date:  2006 Mar 
Date Detail:
Created Date:  2006-03-01     Completed Date:  2006-05-17     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9311984     Medline TA:  Biol Pharm Bull     Country:  Japan    
Other Details:
Languages:  eng     Pagination:  580-4     Citation Subset:  IM    
Affiliation:
Seiwa Pharmaceutical Ltd., Kitaibaraki, Ibaraki, Japan. chi-59@unimatec.co.jp
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MeSH Terms
Descriptor/Qualifier:
Analgesics*
Animals
Anti-Inflammatory Agents, Non-Steroidal / pharmacology
Cyclobutanes / chemical synthesis,  pharmacology*
Formaldehyde / diagnostic use
Indicators and Reagents
Indomethacin / pharmacology
Male
Mice
Pain Measurement / drug effects
Chemical
Reg. No./Substance:
0/Analgesics; 0/Anti-Inflammatory Agents, Non-Steroidal; 0/Cyclobutanes; 0/Indicators and Reagents; 4462-95-7/truxillic acid; 50-00-0/Formaldehyde; 53-86-1/Indomethacin

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