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P2928

Sigma-Aldrich

Paxilline

powder, ≥98% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C27H33NO4
CAS Number:
57186-25-1
Molecular Weight:
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

Signal Word

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 Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
C Young et al.
Current genetics, 33(5), 368-377 (1998-06-10)
Using a monoclonal antibody based ELISA, 600 pAN7-1 plasmid-tagged mutants of Penicillium paxilli were screened for paxilline accumulation and one paxilline-negative mutant, YI-20, was identified. A molecular analysis of this mutant showed that pAN7-1 was inserted at a single site
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