Abstract
N-oleoyl-dopamine (OLDA) is a novel lipid derivative of dopamine. Its biological action includes the interaction with dopamine and the transient receptor potential vanilloid (TRPV1) receptors. It seems to be synthesized in a dopamine-like manner, but there has been no information on its degradation. The aim of the study was, therefore, to determine whether OLDA metabolism proceeds the way dopamine proper does. We addressed the issue by examining the occurrence of O-methylation of exogenously supplemented OLDA via catechol-O-methyltransferase (COMT) under in vitro, ex vivo, and in vivo conditions using rat brain tissue. The results show that OLDA was methylated by COMT in all conditions studied, yielding the O-methylated derivative. The methylation was reversed by tolcapone, a potent COMT inhibitor, in a dose-dependent manner. We conclude that OLDA enters the metabolic pathway of dopamine. Methylation of OLDA may enhance its bioactive properties, such as the ability to interact with TRPV1 receptors.
Highlights
The subject of the present study was N-oleoyl-dopamine (OLDA), N-[2-(3,4-dihydroxyphenyl) ethyl]-9Z-octadecenamide, a novel lipid derivative of dopamine [1,2,3]
The study gave a positive answer to the question posed, which gives supportive evidence for a dopaminelike metabolic pathway of OLDA and raises the possibility that pre-methylation of OLDA facilitates its affinity to transient receptor potential vanilloid V1 (TRPV1) receptors
Localization of the minimum changed from 262 nm in the control mixture to 260 nm in the reaction mixture. The minimum of the latter matched neither that of OLDA nor O-Me-OLDA (Fig. 1A), but was identical with the minimum of an artificially produced 1:1 mixture of OLDA and O-Me-OLDA (Fig. 1B), which points to the occurrence of a reaction of O-methylation of OLDA via COMT, yielding both OLDA and O-Me-OLDA in the assay
Summary
The subject of the present study was N-oleoyl-dopamine (OLDA), N-[2-(3,4-dihydroxyphenyl) ethyl]-9Z-octadecenamide, a novel lipid derivative of dopamine [1,2,3]. OLDA is a ligand for the transient receptor potential vanilloid V1 (TRPV1) receptors [4,10,11] These receptors seem to favor the compounds that have the 3-methoxy-4-hydroxybenzyl (homovanillyl) and the 3,4dihydroxybenzyl (catechol) groups [12,13], which they are affiliated with. The latter group is present in OLDA and in its methylated metabolite – 3-methoxy-N-oleoyl-dopamine (O-MeOLDA). The question arises of whether O-methylation of OLDA could occur in the biological setting and whether it is catechol-O-methyltransferase (COMT)-dependent. The study gave a positive answer to the question posed, which gives supportive evidence for a dopaminelike metabolic pathway of OLDA and raises the possibility that pre-methylation of OLDA facilitates its affinity to TRPV1 receptors
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