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PAXILLINE

CAS No.
57186-25-1
Chemical Name:
PAXILLINE
Synonyms
PAXILINE;mycillin;PAXILLINE;Paxicillin;Paxilline solution;Paxilline in Methanol;PAXILLINE, PENICILLIUM PAXILLI;paxilline from penicillium paxilli;4b-beta,6a-alpha,12b-beta,12c-alpha,14a-beta)-2-alph;14,14a-decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-(
CBNumber:
CB2402640
Molecular Formula:
C27H33NO4
Molecular Weight:
435.56
MDL Number:
MFCD00083464
MOL File:
57186-25-1.mol
MSDS File:
SDS
Last updated:2024-10-23 13:36:13

PAXILLINE Properties

Flash point 2℃
storage temp. 2-8°C
solubility Soluble in DMSO, acetone or chloroform.
form powder
color faint yellow
FDA UNII 3T9U9Z96L7

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS05,GHS06
Signal word  Danger
Hazard statements  H301+H311+H331-H315-H318-H335
Precautionary statements  P261-P280-P301+P310-P302+P352+P312-P304+P340+P311-P305+P351+P338
Hazard Codes  T,Xn,F
Risk Statements  23/24/25-36/37/38-41-36-20/21/22-11
Safety Statements  26-36/37/39-45-36/37-16
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
RTECS  DJ2830000
HazardClass  6.1(b)
PackingGroup  III
HS Code  29419090
NFPA 704
0
4 0

PAXILLINE price More Price(19)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich P2928 Paxilline powder, ≥98% (HPLC) 57186-25-1 5mg $414 2024-03-01 Buy
Alfa Aesar J61341 Paxilline, 97+% 57186-25-1 5mg $216.65 2024-03-01 Buy
Alfa Aesar J61341 Paxilline, 97+% 57186-25-1 25mg $639 2021-12-16 Buy
Cayman Chemical 11345 Paxilline ≥98% 57186-25-1 1mg $45 2024-03-01 Buy
Cayman Chemical 11345 Paxilline ≥98% 57186-25-1 5mg $121 2024-03-01 Buy
Product number Packaging Price Buy
P2928 5mg $414 Buy
J61341 5mg $216.65 Buy
J61341 25mg $639 Buy
11345 1mg $45 Buy
11345 5mg $121 Buy

PAXILLINE Chemical Properties,Uses,Production

Description

A complex alkaloid, paxilline occurs in the mycelium of the mold Penicillium paxilli. The structure has been confirmed by X-ray crystallography. The crystals are orthorhombic with space group P2 12 121 and a = 31.009, b = 11.522 and c = 7.70 A.

Description

Paxilline is an indole diterpene from fungi which potently and reversibly inhibits large conductance Ca2+-activated K+ (BKCa) channels, as shown in patch clamp (Ki = 1.9 nM) and whole smooth muscle cell studies (Ki = 35.7 nM). It also enhances the binding of charybdotoxin , a peptidyl neurotoxin, to BKCa channels. Paxilline is currently used to evaluate the role of BKCa channels in various cell processes and responses.

Chemical Properties

Powder

Uses

Potent blocker of high-conductance calcium-activated potassium (BKCa) channels

Uses

Paxilline is a tremorgenic mycotoxin isolated from species of Penicillium, Acremonium and Emericella. Paxilline selectively blocks high-conductance Ca2+-activated potassium channels and inhibits binding to the cerebellar inositol 1,4,5-triphosphate (InsP(3)) receptor.

Definition

ChEBI: Paxilline is an indole diterpene alkaloid with formula C27H33NO4 isolated from Penicillium paxilli. It is a potent inhibitor of large conductance Ca2(+)- and voltage-activated K(+) (BK)-type channels. It has a role as a mycotoxin, a Penicillium metabolite, an anticonvulsant, an Aspergillus metabolite, a potassium channel blocker, a genotoxin, a geroprotector and an EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor. It is an organic heterohexacyclic compound, a tertiary alcohol, a terpenoid indole alkaloid, an enone and a diterpene alkaloid.

Biological Activity

Potent blocker of high-conductance Ca 2+ -activated K + (BK Ca ) channels. Binds to the α -subunit of BK Ca (K i = 1.9 nM for block of currents in α -subunit-expressing oocytes) and enhances binding of charybdotoxin to BK Ca channels in vascular smooth muscle. Also inhibits sarco/endoplasmic reticulum Ca 2+ -ATPase (IC 50 = 5-50 μ M).

Enzyme inhibitor

This BKCa/KCa1.1) channel blocker (FW = 435.56 g/mol; CAS 57186-25-1; Solubility: 100 mM in DMSO), also named (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, binds to the α-subunit of BKCa, exhibiting a Ki value of 1.9 nM in blocking currents in α-subunit-expressing oocytes and enhancing binding of to BKCa channels in vascular smooth muscle. (See Charybdotoxin) Paxilline also inhibits sarco/endoplasmic reticulum Ca2+-ATPase, IC50 = 5 - 50 μM.

storage

-20°C (desiccate)

References

Springer et ai., Tetrahedron Lett., 2531 (1975)

PAXILLINE Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 116)Suppliers
Supplier Tel Email Country ProdList Advantage
TargetMol Chemicals Inc.
+1-781-999-5354 +1-00000000000 marketing@targetmol.com United States 32161 58
BOC Sciences
16314854226; +16314854226 inquiry@bocsci.com United States 19741 58
TargetMol Chemicals Inc.
support@targetmol.com United States 38631 58
Shaanxi Cuikang Pharmaceutical Technology Co., Ltd
+86-18791163155 +86-13119157289 13119157289@163.com China 2973 58
Aladdin Scientific
+1-+1(833)-552-7181 sales@aladdinsci.com United States 52924 58
J & K SCIENTIFIC LTD. 010-82848833 400-666-7788 jkinfo@jkchemical.com China 96815 76
3B Pharmachem (Wuhan) International Co.,Ltd. 821-50328103-801 18930552037 3bsc@sina.com China 15839 69
Dalian Meilun Biotech Co., Ltd. 0411-62910999 13889544652 meilunui@163.com China 4727 58
Sigma-Aldrich 021-61415566 800-8193336 orderCN@merckgroup.com China 51456 80
EMMX Biotechnology LLC 888-539-0666 info@emmx.com United States 8447 60

View Lastest Price from PAXILLINE manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Paxilline pictures 2024-10-24 Paxilline
57186-25-1
US $399.00 / mg 10g TargetMol Chemicals Inc.
  • Paxilline pictures
  • Paxilline
    57186-25-1
  • US $399.00 / mg
  • TargetMol Chemicals Inc.
(2R)-5,6,6aα,7,12,12b,12c,13,14,14aβ-Decahydro-4bβ-hydroxy-2-(1-hydroxy-1-methylethyl)-12bβ,12cα-dimethyl-2H-1-benzopyrano[5',6':6,7]indeno[1,2-b]indol-3(4bH)-one 2h-1-benzopyrano(5’,6’:6,7)indeno(1,2-b)indol-3(4bh)-one,5,6,6a,7,12,12b,12c,1 4b-beta,6a-alpha,12b-beta,12c-alpha,14a-beta)-2-alph paxilline from penicillium paxilli PAXILINE Paxicillin (2R,4bS,6aS,12bS,12cR,14aS)-4b-Hydroxy-2-(1-hydroxy-1-methylethyl)-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 solution Paxilline solution PAXILLINE PAXILLINE, PENICILLIUM PAXILLI (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 14,14a-decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-( 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,(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 4b-Hydroxy-2-(1-hydroxy-1-methylethyl)-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 mycillin Paxilline in Methanol 57186-25-1 C27H33NO4 BioChemical Cell Biology Cell Signaling and Neuroscience Monovalent Ion Channels Potassium Channel Modulators Ion Channels Voltage-gated Ion Channels MoldVoltage-gated Ion Channels Cell Signaling and Neuroscience Monovalent Ion Channels Potassium Channel Modulators Toxins and Venoms Potassium channel antibiotic