N-Caffeoyl serotonin as selective COX-2 inhibitor.

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Takahashi T, Miyazawa M

N-Caffeoyl serotonin as selective COX-2 inhibitor.

Bioorg Med Chem Lett. 2012 Apr 1;22(7):2494-6. doi: 10.1016/j.bmcl.2012.02.002. Epub 2012 Feb 9.

PubMed ID
22386242 [ View in PubMed
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Abstract

The inhibitory effects of the synthetic serotonin analogues (1-8) on COX (1 and 2) were evaluated. Two serotonin derivatives (4 and 8) showed inhibitory effect of COX (1 and 2). Especially, 4 exhibited excellent inhibitions on COX-2 with extremely high potency (IC(50)=42.5 muM). The inhibitory activities of cinnamic acid derivatives and serotonin were evaluated to clarify whether inhibitory activities of compound 4 and 8 are due to cinnamic acid moiety or serotonin moiety. Caffeic acid and N-caffeoyl serotonin (4) exhibited selective inhibition of COX-2 compared to aspirin. Comparison caffeic acid with 4 suggested that the linkage of caffeic acid and serotonin enhance COX-2 inhibition. Comparison of structures of caffeic acid and sinapic acid implied that catechol moiety of cinnamic acid derivatives is a major contributing factor for selective inhibition of COX-2. The selective COX-2 inhibitory activity of compound 4 is significant and could be employed as drugs against inflammatory and allergy.

DrugBank Data that Cites this Article

Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
Acetylsalicylic acidProstaglandin G/H synthase 1IC 50 (nM)560100N/AN/ADetails
Acetylsalicylic acidProstaglandin G/H synthase 2IC 50 (nM)1413300N/AN/ADetails