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P2928

Sigma-Aldrich

Paxilline

powder, ≥98% (HPLC)

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About This Item

Fórmula empírica (notación de Hill):
C27H33NO4
Número de CAS:
57186-25-1
Peso molecular:
435.56
MDL number:
MFCD00083464
UNSPSC Code:
12352200
PubChem Substance ID:
24898374
NACRES:
NA.77

Quality Level

200

assay

≥98% (HPLC)

form

powder

color

faintly yellow

storage temp.

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

InChI key

ACNHBCIZLNNLRS-UBGQALKQSA-N

General description

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.

Application

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 Actions

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

Features and Benefits

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.

Other Notes

Major toxin in Penicillium paxilli

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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)
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
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)
Paxilline inhibits BK channels by an almost exclusively closed-channel block mechanism
Zhou Y and Lingle CJ
The Journal of General Physiology, 144(5), 415-440 (2014)
A concise approach to paxilline indole diterpenes
George DT, et al.
Journal of the American Chemical Society, 137(49), 15410-15413 (2015)
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