Antinociceptive properties of caffeic acid derivatives in mice

被引：52
作者：
Buzzi, Fatima de Campos [1 ]
Franzoi, Caroline Liandra [1 ]
Antonini, Graziele [1 ]
Fracasso, Mauricio [1 ]
Cechinel Filho, Valdir [1 ]
Yunes, Rosendo Augusto [2 ]
Niero, Rivaldo [1 ]
机构：
[1] Univ Vale Itajai, Programa Mestrado Ciencias Farmaceut & Nucl Inves, CCS, BR-88302202 Itajai, SC, Brazil
[2] Univ Fed Santa Catarina, Curso Posgrad Quim, BR-88040900 Florianopolis, SC, Brazil
来源：
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2009年 / 44卷 / 11期
关键词：
Antinociceptive action; Caffeic acid derivatives; Structure-activity relationship; FORMALIN TEST; IN-VITRO; CAPSAICIN; EXTRACT; PAIN; PREDICTION; MECHANISM; ANALOGS; ESTERS; AMIDE;
D O I：
10.1016/j.ejmech.2009.06.029
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Ten ester derivatives from caffeic acid were synthesized, and their antinociceptive properties are evaluated in mice. The most active compound, dodecyl ester derivative, exhibited potent and dose-related activity against the writhing test, with a calculated ID50 value of 15.1 (11.9-19.1) mu mol/kg and MI of 78.8% being several times more active than reference drugs. It was also effective in other experimental models, such as formalin, capsaicin and glutamate-induced pain tests, but was inactive in the hot-plate test. Although the mechanism of action has still not been elucidated, these results appear to support its therapeutic potential against painful diseases. (C) 2009 Elsevier Masson SAS. All rights reserved.
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收藏
页码：4596 / 4602
页数：7
相关论文
共 33 条
[1]   Spinal and supraspinal antinociceptive action of dipyrone in formalin, capsaicin and glutamate tests. Study of the mechanism of action [J].
Beirith, A ;
Santos, ARS ;
Rodrigues, ALS ;
Creczynski-Pasa, TB ;
Calixto, JB .
EUROPEAN JOURNAL OF PHARMACOLOGY, 1998, 345 (03) :233-245
[2]   The capsaicin receptor: a heat-activated ion channel in the pain pathway [J].
Caterina, MJ ;
Schumacher, MA ;
Tominaga, M ;
Rosen, TA ;
Levine, JD ;
Julius, D .
NATURE, 1997, 389 (6653) :816-824
[3]   ABDOMINAL CONSTRICTION RESPONSE AND ITS SUPPRESSION BY ANALGESIC DRUGS IN MOUSE [J].
COLLIER, HOJ ;
DINNEEN, LC ;
JOHNSON, CA ;
SCHNEIDER, C .
BRITISH JOURNAL OF PHARMACOLOGY, 1968, 32 (02) :295-+
[4]   Caffeic acid derivatives:: In vitro and in vivo anti-inflammatory properties [J].
Da Cunha, FM ;
Duma, D ;
Assreuy, J ;
Buzzi, FC ;
Niero, R ;
Campos, MM ;
Calixto, JB .
FREE RADICAL RESEARCH, 2004, 38 (11) :1241-1253
[5]  
de Souza MT, 2007, Z NATURFORSCH C, V62, P550
[6]   Synthesis of new 1-phenyl-3-{4-[(2E)-3-phenylprop-2-enoyl] phenyl}-thiourea and urea derivatives with anti-nociceptive activity [J].
dos Santos, Lorena ;
Lima, Luise Azevedo ;
Cechinel-Filho, Valdir ;
Correa, Rogerio ;
Buzzi, Fatima de Campos ;
Nunes, Ricardo Jose .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (18) :8526-8534
[7]  
EDDY NB, 1953, J PHARMACOL EXP THER, V107, P385
[8]   Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties [J].
Ertl, P ;
Rohde, B ;
Selzer, P .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (20) :3714-3717
[9]   Mechanism of toxicity of esters of caffeic and dihydrocaffeic acids [J].
Etzenhouser, B ;
Hansch, C ;
Kapur, S ;
Selassie, CD .
BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (01) :199-209
[10]   Evaluation of caffeic acid amide analogues as anti-platelet aggregation and anti-oxidative agents [J].
Hung, CC ;
Tsai, WJ ;
Kuo, LMY ;
Kuo, YH .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (05) :1791-1797
1234