Bioactive Oleic Derivatives of Dopamine: A Review of the Therapeutic Potential
Lipid derivatives of dopamine are a novel class of compounds raising a research interest due to the potential of their being a vehicle for dopamine delivery to the brain. The aim of the present paper is to review the main features of the two most prominent bioactive members of this family, namely, N-oleoyl-dopamine (OLDA) and 3′-O-methyl-N-oleoyl-dopamine (OMe-OLDA), with emphasis on the possible therapeutic properties.
KeywordsBrain Dopamine receptor Lipid derivatives of dopamine Therapeutic potential TRPV1 receptors
The dopamides reviewed in this article were synthetized in the Laboratory of Natural Products Chemistry, The Faculty of Chemistry, University of Warsaw. We remain appreciative of Dr. Zbigniew Czarnocki and Piotr Roszkowski’s dexterity in the elaboration of de novo synthesis of the dopamides, and we are thankful for the provision of the compounds for our biological studies. We also thank Dr. Agnieszka Stasińska for giving a hand in some of the experiments described herein.
Conflicts of Interest
The authors of this article are the inventors of the European (EP 2324824) and the US patents (US 8697898) covering the potential medical applications of OLDA and OMe-OLDA. The patent procedures were in part financed by the EU Innovative Economy grant POIG 1.3.2.-14–047/11.
- Bisogno T, Melck D, Bobrov M, Gretskaya N, Bezuglov V, De Petrocellis L, Di Marzo L (2000) N-acyl-dopamines: novel synthetic CB1 cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivo. Biochem J 351(Pt 3):817–824CrossRefPubMedPubMedCentralGoogle Scholar
- Bolcskei K, Tékus V, Dézsi L, Szolcsanyi J, Petho G (2010) Antinociceptive desensitizing actions of TRPV1 receptor agonists capsaicin, resiniferatoxin and N-oleoyldopamine as measured by determination of the noxious heat and cold thresholds in the rat. Eur J Pain 14:480–486CrossRefPubMedGoogle Scholar
- Hauer D, Schelling G, Gola H, Campolongo P, Morath J, Roozendaal B, Hamuni G, Karabatsiakis A, Atsak P, Vogeser M, Kolassa IT (2013) Plasma concentrations of endocannabinoids and related primary fatty acid amides in patients with post-traumatic stress disorder. PLoS One 8(5):e62741CrossRefPubMedPubMedCentralGoogle Scholar
- Hu SS, Bradshaw HB, Benton VM, Chen JS, Huang SM, Minassi A, Bisogno T, Masuda K, Tan B, Roskoski R Jr, Cravatt BF, Di Marzo V, Walker JM (2009) The biosynthesis of N-arachidonyl dopamine (NADA), a putative endocannabinoid and endovanilloid, via conjugation of arachidonic acid with dopamine. Prostaglandins Leukot Essent Fatty Acids 81:291–301CrossRefPubMedPubMedCentralGoogle Scholar
- Huang S, Bisogno T, Trevisani M, Al-Hayani A, De Petrocellis L, Fezza F, Tognetto M, Petros T, Krey J, Chu C, Miller J, Davies S, Geppetti P, Walker J, Di Marzo V (2002) An endogenous capsaicin-like substance with high potency at recombinant and native vanilloid VR1 receptors. PNAS 99:8400–8404CrossRefPubMedGoogle Scholar
- Ji D, Jang CG, Lee S (2014) A sensitive and accurate quantitative method to determine N-arachidonoyldopamine and N-oleoyldopamine in the mouse striatum using column-switching LC–MS–MS: use of a surrogate matrix to quantify endogenous compounds. Anal Bioanal Chem 406:4491–4499CrossRefPubMedGoogle Scholar
- Rekawek A, Pokorski M (2011) Influence of 3′-O-methyl-N-oleoyl-dopamine on the hypoxic ventilatory response in the rat. Conference on Advances in Pneumology, Bonn, Germany. http://www.pneumology.pl/bonn/media/doc/a089.pdf. Accessed on 13 Mar 2018 (Conference abstract)
- Szolcsanyi J, Sandora Z, Petho G, Varga A, Bolcskei K, Almasi R, Riedl Z, Hajos G, Czeh G (2004) Direct evidence for activation and desensitization of the capsaicin receptor by N-oleoyldopamine on TRPV1-transfected cell, line in gene deleted mice and in the rat. Neurosci Lett 361:155–158CrossRefPubMedGoogle Scholar
- Visnyei K, Onodera H, Damoiseaux R, Saigusa K, Petrosyan S, De Vries D, Ferrari D, Saxe J, Panosyan EH, Masterman-Smith M, Mottahedeh J, Bradley KA, Huang J, Sabatti C, Nakano I, Kornblum HI (2011) A molecular screening approach to identify and characterize inhibitors of glioblastoma stem cells. Mol Cancer Ther 10(10):1818–1828CrossRefPubMedPubMedCentralGoogle Scholar
- Zajac D (2009) Bioproperties of N-oleoyl-dopamine, a new lipid derivative of dopamine, with special attention to its influence on respiration in rats. PhD thesis, Mossakowski Medical Research Centre, Warsaw, Poland (in Polish)Google Scholar
- Zajac D, Roszkowski P, Czarnocki Z, Pokorski M (2010) Influence of TRPV1 (vanilloid) blockade on the respiratory response to hypoxia after N-oleoyl-dopamine in anesthetized rats. Conference on Advances in Pneumology, Warsaw, Poland. http://www.pneumology.pl/warsaw2010/media/doc/a059.pdf. Accessed on 13 Mar 2018 (Conference abstract)