Bicuculline
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| Surname | Bicuculline | |||||||||||||||||||||
| other names |
(6 R ) - 6- [(5 S ) - 6-methyl-5, 6, 7, 8-tetrahydro [1,3] dioxolo [4.5- g ] isoquinolin-5-yl] furo [3.4 - e ] [1,3] benzodioxol- 8 (6 H ) - one ( IUPAC ) |
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| Molecular formula | C 20 H 17 NO 6 | |||||||||||||||||||||
| Brief description |
white to yellowish powder |
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| properties | ||||||||||||||||||||||
| Molar mass | 367.35 g mol −1 | |||||||||||||||||||||
| Physical state |
firmly |
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| solubility |
Soluble in ethanol to 5 mM and in DMSO to 100 mM, also in benzene, chloroform and ethyl acetate |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||||||||||||||
Bicuculline is an alkaloid and a potent, selective and competitive GABA A receptor - antagonist .
Occurrence
The pale yellowish, light-sensitive substance was first found in 1932 in an extract from the hooded heart flower ( Dicentra cucullaria ) that gave it its name. Besides there it occurs in other types of heart flowers as well as in the lark spurs , which also belong to the earth smoke family .
effect
Bicuculline blocks GABA A receptors. These receptors are ion channels that allow ions, in this case negatively charged chloride , to pass into the cell interior. The transport of negative charge into the cell interior hyperpolarizes nerve cells and makes them less excitable. Blockage of the channels blocks the inhibition and thus has an exciting and convulsive effect on the nervous system. The symptoms of bicuculline poisoning are similar to those of epilepsy .
As a GABA antagonist, bicuculline is similar to the plant poison picrotoxin from the myrtle and the synthetic agent gabazine . Important GABA agonists are muscimol , one of the toxins of the fly agaric , and the active ingredient baclofen .
Applications
Bicuculline is used in basic research, for example in laboratory tests to study epilepsy in vivo and to block GABA A receptors in vitro .
In addition to its selective effect on GABA A receptor channels, it also blocks Ca 2+ -activated potassium channels and suppresses the growth of fungal spores.
Pharmacologically effective concentrations of bicuculline on the GABA A receptor are a few μM. Since bicuculline is extremely poorly soluble in water, it is often applied in DMSO .
GABA A receptors are the primary target of benzodiazepines and related anxiolytic pharmaceuticals. Bicuculline, in its role as a GABA A receptor antagonist, can neutralize the effects of these substances.
See also
Individual evidence
- ↑ a b Datasheet (+) - Bicuculline at Enzo Life Sciences, accessed December 3, 2014.
- ↑ a b c data sheet (+) - Bicuculline from Sigma-Aldrich , accessed on October 22, 2016 ( PDF ).
- ↑ Abcam: Bicuculline , accessed October 4, 2014.
- ↑ Tocris: bicuculline , accessed on October 4, 2014.
- ↑ K. Starke: Fundamentals of the pharmacology of the nervous system. In: K. Aktories, U. Förstermann, F. Hofmann and K. Starke (eds.): General and special pharmacology and toxicology. 11th edition, Munich, Elsevier GmbH 2013, pp. 95–125, here pp. 115–116. ISBN 978-3-437-42523-3 .
- ^ Manske, RHF: The Alkaloids of Fumaraceous Plants. II. Dicentra cucullaria (L.) Bernh. . In: Canadian Journal of Research . 7, 1932, pp. 265-269. doi : 10.1139 / cjr32-078 .
- ↑ Israilov, IA, Melikov FM, Murav'eva DA: Alkaloids of Dicentra . In: Chemistry of Natural Compounds . 20, 1984, pp. 74-76. doi : 10.1007 / BF00574796 .
- ↑ a b Basha SA, Mishra RK, Jha RN, Pandey VB, Singh UP: Effect of berberine and (±) -bicuculline isolated from Corydalis chaerophylla on spore germination of some fungi . In: Folia Microbiologica . 47, 2002, pp. 161-165. doi : 10.1007 / BF02817675 .
- ^ W. Bautista, J. Aguilar, JE Loeza-Alcocer, R. Delgado-Lezama: Pre- and postsynaptic modulation of monosynaptic reflex by GABAA receptors on turtle spinal cord. In: The Journal of Physiology. Volume 588, Pt 14 July 2010, pp. 2621-2631, doi: 10.1113 / jphysiol.2010.188979 , PMID 20519320 , PMC 2916992 (free full text).
- ^ Makoto Taketani: Advances in Network Electrophysiology. Springer Science & Business Media, 2006, ISBN 978-0-387-25858-4 , pp. 305f ( limited preview in Google book search).
- ^ BH Liu, GK Wu, R. Arbuckle, HW Tao, LI Zhang: Defining cortical frequency tuning with recurrent excitatory circuitry. In: Nature Neuroscience . Volume 10, number 12, December 2007, pp. 1594–1600, doi: 10.1038 / nn2012 , PMID 17994013 , PMC 2447868 (free full text).
- ↑ Söder Feldt example, Kalimo H., Olsson Y., Siesjö BK: bicuculline-induced epileptic brain injury . In: Acta Neuropathologica . 62, 1983, pp. 87-95. doi : 10.1007 / BF00684924 .
- ↑ R. Khawaled, A. Bruening-Wright, JP Adelman, J. Maylie: Bicuculline block of small-conductance calcium-activated potassium channels. In: Pflügers Archive - European Journal of Physiology . Volume 438, Number 3, August 1999, pp. 314-321, PMID 10398861 .
- ^ H. Dickinson-Anson, MH Mesches, K. Coleman, JL McGaugh: Bicuculline administered into the amygdala blocks benzodiazepine-induced amnesia. In: Behavioral and neural biology. Volume 60, Number 1, July 1993, pp. 1-4, PMID 8216155 .
