P2928

Sigma-Aldrich

Paxilline

powder, ≥98% (HPLC)

Empirical Formula (Hill Notation):
C27H33NO4
CAS Number:
Molecular Weight:
435.56
MDL number:
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

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

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.

Packaging

5, 10 mg in glass bottle

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

Signal Word

Danger

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

T

Risk Statement

23/24/25-36/37/38-41

Safety Statement

26-36/37/39-45

RIDADR

UN 2811 6.1 / PGII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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)
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)
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)
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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