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Key Documents

P2928

Sigma-Aldrich

Paxilline

powder, ≥98% (HPLC)

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About This Item

Formula empirica (notazione di Hill):
C27H33NO4
Numero CAS:
Peso molecolare:
435.56
Numero MDL:
Codice UNSPSC:
12352200
ID PubChem:
NACRES:
NA.77

Livello qualitativo

Saggio

≥98% (HPLC)

Forma fisica

powder

Colore

faintly yellow

Temperatura di conservazione

2-8°C

Stringa SMILE

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
ACNHBCIZLNNLRS-UBGQALKQSA-N

Descrizione generale

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.

Applicazioni

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.

Azioni biochim/fisiol

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

Caratteristiche e vantaggi

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.

Altre note

Major toxin in Penicillium paxilli

Pittogrammi

CorrosionSkull and crossbones

Avvertenze

Danger

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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


Certificati d'analisi (COA)

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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
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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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