[Fluorescent-labeled lipophilic analogues of serotonin, dopamine, and acetylcholine: synthesis, mass spectrometry, and biological activity].
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 (lambda(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 (lambda(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 mass spectrometry mainly proceeds through the elimination of hydrogen fluoride from the fluorescent core of the molecules. Experiments on sea urchin Lytechinus variegatus 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. The English version of the paper: Russian Journal of Bioorganic Chemistry, 2004, vol. 30, no. 5; see also http: // www.maik.ru.
Bezyglov
V V
VV
Gretskaia
N M
NM
Esipov
S E
SE
Poliakov
N B
NB
Nikitina
L A
LA
Buznikov
G A
GA
Lauder
J
J
D000109:Acetylcholine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D016718:Arachidonic Acid / Q000493:pharmacokinetics / Q000494:pharmacology; D001671:Biochemistry / Q000379:methods; D001896:Boron Compounds / Q000737:chemistry; D003593:Cytoplasm / Q000187:drug effects / Q000378:metabolism; D004298:Dopamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D004625:Embryo, Nonmammalian / Q000187:drug effects; D005260:Female; D005456:Fluorescent Dyes / Q000737:chemistry*; D047331:Lytechinus / Q000196:embryology; D013058:Mass Spectrometry; D018377:Neurotransmitter Agents / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology; D012701:Serotonin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D013329:Structure-Activity Relationship
C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D005456:Fluorescent Dyes; D018377:Neurotransmitter Agents; D016718:Arachidonic Acid; D012701:Serotonin; D000109:Acetylcholine; D004298:Dopamine