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ProductsBack/Paxilline [57186-25-1]
Chemical Structure
Chemical Structure
Chemical Structure

Paxilline [57186-25-1]

Research Use Only
AG-CN2-0167
AdipoGen Life Sciences
CAS Number57186-25-1
DownloadMSDS
Product group Chemicals
Estimated Purity>95%
Molecular Weight435.6
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Paxilline [57186-25-1]
  • Delivery Days Customer
    10
  • ADR Class
    6.1
  • CAS Number
    57186-25-1
  • Certification
    Research Use Only
  • Estimated Purity
    >95%
  • Hazard Information
    Danger,Excepted quantity
  • Molecular Formula
    C27H33NO4
  • Molecular Weight
    435.6
  • Scientific 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. - 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].
  • 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
  • Storage Instruction
    2°C to 8°C,-20°C
  • UN Number
    UN 2811
  • UNSPSC
    12352200

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)