Fluorescent-Labeled Lipophilic Analogues of Serotonin,Dopamine, and Acetylcholine: Synthesis,Mass Spectrometry,and Biological Activity |
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Authors: | Bezuglov V. V. Gretskaya N. M. Esipov S. E. Polyakov N. B. Nikitina L. A. Buznikov G. A. Lauder J. |
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Affiliation: | (1) Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul. Miklukho-Maklaya 16/10, Moscow, 117997, Russia;(2) School of Medicine, University of North Carolina, Chapel Hill, NC, USA;(3) Kol'tsov Institute of Developmental Biology, Russian Academy of Sciences, ul. Vavilova 26, Moscow, 117808, Russia |
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Abstract: | 4,4-Difluoro-5,7-dimethyl-4-bora-3a,4a-diaza-s-indacene-3-dodecanoyl derivatives of serotonin, dopamine, choline, and N,N-dimethylaminoethanol, with the fluorescence maximum at 512 nm (exc 470 nm), and 4,4-difluoro-5,7-diphenyl-4-bora-3a,4a-diaza-s-indacene-3-dodecanoyl derivatives of choline and N,N-dimethylaminoethanol, with the fluorescence maximum at 554 nm (exc 470 nm), were synthesized. These compounds yield protonated molecular ions of 100% intensity upon mass spectrometry with electrospray ionization at atmospheric pressure. The fragmentation of molecular ions under the conditions of secondary ion mass spectrometry mainly proceeds through the elimination of hydrogen fluoride from the fluorescent core of the molecules. Experiments on sea urchin Lytechinusvariegatus embryos and larvae showed that these compounds easily penetrate into the cells and are accumulated in the cytoplasm. They do not differ in their biological activity from similar derivatives of arachidonic acid described previously and are agonists of serotonin or acetylcholine or antagonists of nicotinic acetylcholine receptors. |
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Keywords: | acylated neurotransmitters BODIPY choline esters dopamine nicotine sea urchin serotonin |
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