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P2928

Sigma-Aldrich

Paxilline

powder, ≥98% (HPLC)

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Empirical Formula (Hill Notation):
C27H33NO4
CAS Number:
Molecular Weight:
435.56
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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This Item
C7861A0263PZ0312
Paxilline powder, ≥98% (HPLC)

P2928

Paxilline

Citalopram hydrobromide ≥98% (HPLC)

C7861

Citalopram hydrobromide

Aflatoxin G2

A0263

Aflatoxin G2

(S)-PFI-2

PZ0312

(S)-PFI-2

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

-

assay

≥98% (HPLC)

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

color

faintly yellow

color

-

color

-

color

white to beige

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

CorrosionSkull and crossbones

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


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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)
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)
A concise approach to paxilline indole diterpenes
George DT, et al.
Journal of the American Chemical Society, 137(49), 15410-15413 (2015)
Conservation of lipid metabolic gene transcriptional regulatory networks in fish and mammals
Carmona-Antonanzas, Greta and Tocher, Douglas R and Martinez-Rubio, Laura and Leaver, Michael J
Gene, 534(1), 1-9 (2014)
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)

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