Peptide derivatives of dopamine (DA) and serotonin (5-hydroxytryptamine, 5-HT) acylated with lauric acid (LA) and oleic acid (OA), including LA-Gly-Pro-DA, LA-Gly-Pro-5-HT, OA-Gly-Pro-DA, and OA-Gly-Pro-5-HT, were synthesized. A mass spectrometric method for assessing the content of the DA and 5-HT derivatives in phosphate buffered saline (PBS Am-E404 – 100, pH 7.4) was developed. It was shown that these compounds could penetrate through artificial membranes. A special mixture of these compounds was used for modeling a situation where the molecules of DAand 5-HT derivatives diffused through the membrane as a result of their competitive interaction, which allowed a reliable determination of which compounds in the mixture penetrated more easily through artificial membranes. The comparative permeability of the blood–brain barrier (BBB) was evaluated by the method of parallel artificial membrane permeability assay (PAMPA). It was established that derivatives LA-Gly-Pro-5-HT and LA-Gly-Pro-DA, which were acylated by LA, were most promising for overcoming the BBB.
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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 56, No. 5, pp. 29 – 33, May, 2022.
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Shevchenko, V.P., Andreeva, L.A., Shevchenko, K.V. et al. Investigation of the Membranotropic Properties of Acylated Peptide Derivatives of Dopamine and Serotonin Using the Pampa Method. Pharm Chem J 56, 602–606 (2022). https://doi.org/10.1007/s11094-022-02683-2
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DOI: https://doi.org/10.1007/s11094-022-02683-2