Paxilline

Modify Date: 2024-01-02 19:51:46

Paxilline Structure
Paxilline structure
Common Name Paxilline
CAS Number 57186-25-1 Molecular Weight 435.555
Density 1.3±0.1 g/cm3 Boiling Point 648.8±55.0 °C at 760 mmHg
Molecular Formula C27H33NO4 Melting Point 252ºC
MSDS Chinese USA Flash Point 346.2±31.5 °C
Symbol GHS05 GHS06
GHS05, GHS06
Signal Word Danger

 Use of Paxilline


Paxilline is an indole alkaloid mycotoxin from Penicillium paxilli, acts as a potent BK channels inhibitor by an almost exclusively closed-channel block mechanism. Paxilline also inhibits the sarco/endoplasmic reticulum Ca2+ ATPase (SERCA) with IC50s between 5μM and 50μM for differing isoforms. Paxilline possesses significant anticonvulsant activity[1][2][3].

 Names

Name Paxilline,(2R,4bS,6aS,12bS,12cR,14aS)-5,6,6a,7,12,12b,12c,13,14,14a-Decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-2H-pyrano[2'',3'':5',6']benz[1',2':6,7]indeno[1,2-b]indol-3(4bH)-one
Synonym More Synonyms

 Paxilline Biological Activity

Description Paxilline is an indole alkaloid mycotoxin from Penicillium paxilli, acts as a potent BK channels inhibitor by an almost exclusively closed-channel block mechanism. Paxilline also inhibits the sarco/endoplasmic reticulum Ca2+ ATPase (SERCA) with IC50s between 5μM and 50μM for differing isoforms. Paxilline possesses significant anticonvulsant activity[1][2][3].
Related Catalog
Target

IC50: 5-50 μM (SERCA)[2], BK channel[1]

References

[1]. Zhou Y, et al. Paxilline inhibits BK channels by an almost exclusively closed-channel block mechanism. J Gen Physiol. 2014 Nov;144(5):415-40.

[2]. Bilmen JG, et al. The mechanism of inhibition of the sarco/endoplasmic reticulum Ca2+ ATPase by paxilline. Arch Biochem Biophys. 2002 Oct 1;406(1):55-64.

[3]. Sheehan JJ, et al. Anticonvulsant effects of the BK-channel antagonist paxilline. Epilepsia. 2009 Apr;50(4):711-20.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 648.8±55.0 °C at 760 mmHg
Melting Point 252ºC
Molecular Formula C27H33NO4
Molecular Weight 435.555
Flash Point 346.2±31.5 °C
Exact Mass 435.240967
PSA 82.55000
LogP 3.77
Vapour Pressure 0.0±2.0 mmHg at 25°C
Index of Refraction 1.661
Storage condition 2-8°C
Water Solubility Soluble in DMSO, acetone or chloroform.

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DJ2830000
CAS REGISTRY NUMBER :
57186-25-1
LAST UPDATED :
199612
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C27-H33-N-O4
MOLECULAR WEIGHT :
435.61

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>227 mg/kg
TOXIC EFFECTS :
Behavioral - tremor
REFERENCE :
JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 41,1868,1988
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
150 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
41KEAL "Toxicology, Biochemistry and Pathology of Mycotoxins," Uraguchi, K. and M. Yamazaki, eds., New York, John Wiley & Sons, Inc., 1978 Volume(issue)/page/year: -,108,1978
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Bird - chicken
DOSE/DURATION :
>100 mg/kg
TOXIC EFFECTS :
Behavioral - tremor
REFERENCE :
JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 41,1868,1988

 Safety Information

Symbol GHS05 GHS06
GHS05, GHS06
Signal Word Danger
Hazard Statements H301-H311-H315-H318-H331-H335
Precautionary Statements P261-P280-P301 + P310-P305 + P351 + P338-P311
Personal Protective Equipment Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes T: Toxic;
Risk Phrases R23/24/25
Safety Phrases 26-36/37/39-45
RIDADR UN 2811 6
WGK Germany 3
RTECS DJ2830000
Packaging Group III
Hazard Class 6.1(b)
HS Code 29419090

 Precursor & DownStream

Precursor  0

DownStream  2

 Articles33

More Articles
Large-conductance calcium-activated potassium current modulates excitability in isolated canine intracardiac neurons.

Am. J. Physiol. Cell Physiol. 304(3) , C280-6, (2013)

We studied principal neurons from canine intracardiac (IC) ganglia to determine whether large-conductance calcium-activated potassium (BK) channels play a role in their excitability. We performed whol...

Mitochondrial K+ channels are involved in ischemic postconditioning in rat hearts.

J. Physiol. Sci. 62(4) , 325-32, (2012)

The mitochondrial calcium-activated potassium channel (mitoK(Ca)) and the mitochondrial ATP-sensitive potassium channel (mitoK(ATP)) are both involved in cardiac preconditioning. Here, we examined whe...

Methamphetamine inhibits voltage-gated potassium currents in NG108-15 cells: possible contribution of large-conductance calcium-activated potassium channels.

Toxicol. Lett. 223(2) , 139-45, (2013)

Methamphetamine (MA), a highly abused amphetamine-like psychostimulant, has surged in popularity worldwide in the last decade. Repeated MA exposure has been shown to affect the alternative splice vari...

 Synonyms

2H-Pyrano(2'',3'':5',6')benz(1',2':6,7)indeno(1,2-b)indol-3(4bH)-one, 5,6,6a,7,12,12b,12c,13,14,14a-decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-, (2R,4bS,6aS,12bS,12cR,14aS)-
PAXILINE
2H-1-Benzopyrano[5',6':6,7]indeno[1,2-b]indol-3(4bH)-one, 5,6,6a,7,12,12b,12c,13,14,14a-decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-, (2R,4bS,6aS,12bS,12cR,14aS)-
PAXILLINE,PENICILLIUM PAXILLI
DPNI-caged-GABA
(2R,4bS,6aS,12bS,12cR,14aS)-4b-Hydroxy-2-(2-hydroxy-2-propanyl)-12b,12c-dimethyl-5,6,6a,7,12,12b,12c,13,14,14a-decahydro-2H-chromeno[5',6':6,7]indeno[1,2-b]indol-3(4bH)-one
MFCD00083464
(2R,4bS,6aS,12bS,12cR,14aS)-4b-Hydroxy-2-(2-hydroxypropan-2-yl)-12b,12c-dimethyl-5,6,6a,7,12,12b,12c,13,14,14a-decahydro-2H-chromeno[5',6':6,7]indeno[1,2-b]indol-3(4bH)-one
paxilline from penicillium paxilli
Paxilline 1
Paxilline
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