Paxilline
Product Code: AG-CN2-0167
Product Group: Natural Products and Extracts
Supplier: AdipoGen Life Sciences
| Code | Size | Price |
|---|
| AG-CN2-0167-M001 | 1 mg | £50.00 |
Quantity:
| AG-CN2-0167-M005 | 5 mg | £130.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
+4°C
Documents
Further Information
Alternate Names/Synonyms:
BRN 5317894; NSC 658707
Appearance:
Off-white solid.
CAS:
57186-25-1
Class:
6.1
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS05,GHS06
Handling Advice:
Keep cool and dry.Protect from light and moisture.
Hazards:
H301, H311, H315, H318, H331, H335
InChi:
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
InChiKey:
ACNHBCIZLNNLRS-UBGQALKQSA-N
Long Description:
Chemical. CAS: 57186-25-1. Formula: C27H33NO4. MW: 435.6. Isolated from Penicillium sp. Tremorgenic. Potent, selective and reversible inhibitor of high-conductance calcium-activated potassium (BKCa) channels. Reversible inhibitor of inositol 1,4,5-trisphosphate receptor (InsP(3)). Sarco/endoplasmic reticulum Ca2+ ATPase (SERCA) inhibitor. Liver X receptor (LXRalpha and LXRbeta; NR1H3 and NR1H2) agonist in biochemical and in vitro cell-based assays. Anticonvulsant. Apoptosis enhancer. Can sensitize various glioma cells to TRAIL-mediated apoptosis. Shown to protect neuronal cells against glutamate-induced cell death.
MDL:
MFCD00083464
Molecular Formula:
C27H33NO4
Molecular Weight:
435.6
Package Type:
Vial
PG:
III
Precautions:
P261, P280, P301, P310, P305, P351, P338, P405
Product Description:
Tremorgenic [1]. Potent, selective and reversible inhibitor of high-conductance calcium-activated potassium (BKCa) channels [2]. Reversible inhibitor of inositol 1,4,5-trisphosphate receptor (InsP(3)) [3]. Sarco/endoplasmic reticulum Ca2+ ATPase (SERCA) inhibitor [4]. Liver X receptor (LXRalpha and LXRbeta; NR1H3 and NR1H2) agonist in biochemical and in vitro cell-based assays [5]. Anticonvulsant [6]. Apoptosis enhancer. Can sensitize various glioma cells to TRAIL-mediated apoptosis [7]. Shown to protect neuronal cells against glutamate-induced cell death [8].
Purity:
>95% (HPLC)
Signal word:
Danger
SMILES:
[H][C@]12CC3=C(NC4=C3C=CC=C4)[C@]1(C)[C@@]1(C)CC[C@]3([H])O[C@@H](C(=O)C=C3[C@]1(O)CC2)C(C)(C)O
Solubility Chemicals:
Soluble in DMSO, methanol or ethanol (all at least 1mg/ml).
Source / Host:
Isolated from Penicillium sp.
Transportation:
Excepted Quantity
UN Nummer:
UN 2811
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C. Working aliquots are stable for up to 3 months when stored at -20°C.
References
A new tremorgenic metabolite from Penicillium paxilli: R.J. Cole, et al.; Can. J. Microbiol. 20, 1159 (1974) | Tremorgenic indole alkaloids potently inhibit smooth muscle high-conductance calcium-activated potassium channels: H.G. Knaus, et al.; Biochemistry 33, 5819 (1994) | The mycotoxin paxilline inhibits the cerebellar inositol 1,4, 5-trisphosphate receptor: C.L. Longland, et al.; Eur. J. Pharmacol. 408, 219 (2000) | The mechanism of inhibition of the sarco/endoplasmic reticulum Ca2+ ATPase by paxilline: J.G. Bilmen, et al.; Arch. Biochem. Biophys. 406, 55 (2002) | A natural product ligand of the oxysterol receptor, liver X receptor: K.S. Bramlett, et al.; J. Pharmacol. Exp. Ther. 307, 291 (2003) | Anticonvulsant effects of the BK-channel antagonist paxilline: J.J. Sheehan, et al.; Epilepsia 50, 711 (2009) | Paxilline enhances TRAIL-mediated apoptosis of glioma cells via modulation of c-FLIP, survivin and DR5: Y.J. Kang, et al.; Exp. Mol. Med. 43, 24 (2011) | Glutamate-induced cell death in HT22 mouse hippocampal cells is attenuated by paxilline, a BK channel inhibitor: B. Kulawiak & A. Szewczyk; Mitochondrion 12, 169 (2012)