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P2928

Sigma-Aldrich

Paxilline

powder, ≥98% (HPLC)

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About This Item

Empirische Formel (Hill-System):
C27H33NO4
CAS-Nummer:
57186-25-1
Molekulargewicht:
435.56
MDL-Nummer:
MFCD00083464
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24898374
NACRES:
NA.77

Qualitätsniveau

200

Assay

≥98% (HPLC)

Form

powder

Farbe

faintly yellow

Lagertemp.

2-8°C

SMILES String

CC(C)(O)C1OC2CCC3(C)C(O)(CCC4Cc5c([nH]c6ccccc56)C34C)C2=CC1=O

InChI

1S/C27H33NO4/c1-24(2,30)23-20(29)14-18-21(32-23)10-11-25(3)26(4)15(9-12-27(18,25)31)13-17-16-7-5-6-8-19(16)28-22(17)26/h5-8,14-15,21,23,28,30-31H,9-13H2,1-4H3/t15-,21-,23-,25+,26+,27+/m0/s1

InChIKey

ACNHBCIZLNNLRS-UBGQALKQSA-N

Allgemeine Beschreibung

Paxilline is an indole diterpene metabolite produced by fungi. It has a functionalized pentacyclic core and is a template for the synthesis of a wide variety of derivatives.

Anwendung

Paxilline has been used to block large conductance calcium activated potassium channels (BKCa) in murine smooth muscle cells and in myometrial cells of uterine samples. Paxilline acts as an agonist and activates liver X receptor in atlantic salmon.

Biochem./physiol. Wirkung

Paxilline is a selective blocker of high-conductance Ca2+-activated (Maxi-K) potassium channels. It also blocks big potassium (BK) channels.

Leistungsmerkmale und Vorteile

This compound is featured on the Potassium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Sonstige Hinweise

Major toxin in Penicillium paxilli

Piktogramme

Skull and crossbonesCorrosion
GHS06,GHS05

Signalwort

Danger

Gefahreneinstufungen

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Die Dokumentenbibliothek aufrufen

Membrane-delimited inhibition of maxi-K channel activity by the intermediate conductance Ca2+-activated K channel
Thompson J and Begenisich T
The Journal of General Physiology, 127(2), 159-169 (2006)
Sonal Shruti et al.
Neurobiology of disease, 30(3), 323-330 (2008-04-05)
A heritable gain-of-function in BK channel activity has been associated with spontaneous seizures in both rodents and humans. We find that chemoconvulsant-induced seizures induce a gain-of-function in BK channel current that is associated with abnormal, elevated network excitability. Action potential
Electrophysiological and functional effects of the KCNQ channel blocker XE991 on murine portal vein smooth muscle cells
Yeung SYM and Greenwood IA
British Journal of Pharmacology, 146(4), 585-595 (2005)
A concise approach to paxilline indole diterpenes
George DT, et al.
Journal of the American Chemical Society, 137(49), 15410-15413 (2015)
Contribution of the functional coupling between the human myometrial beta2-adrenoreceptor and the BKCa channel to uterine quiescence
Chanrachakul B, et al.
American Journal of Physiology. Cell Physiology, 287(C1747?C1752), 585-595 (2004)
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