PAXILLINE

PAXILLINE Basic information
Product Name:PAXILLINE
Synonyms:(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
CAS:57186-25-1
MF:C27H33NO4
MW:435.56
EINECS:637-206-0
Product Categories:MoldVoltage-gated Ion Channels;Cell Signaling and Neuroscience;Monovalent Ion Channels;Potassium Channel Modulators;Toxins and Venoms;Potassium channel;antibiotic
Mol File:57186-25-1.mol
PAXILLINE Structure
PAXILLINE Chemical Properties
Fp 2℃
storage temp. 2-8°C
solubility Soluble in DMSO, acetone or chloroform.
form powder
color faint yellow
Safety Information
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
MSDS Information
ProviderLanguage
SigmaAldrich English
PAXILLINE Usage And Synthesis
DescriptionA 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.
DescriptionPaxilline 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 PropertiesPowder
UsesPaxilline 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.
UsesPotent blocker of high-conductance calcium-activated potassium (BKCa) channels
DefinitionChEBI: 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 ActivityPotent 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 inhibitorThis 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)
ReferencesSpringer et ai., Tetrahedron Lett., 2531 (1975)
PAXILLINE Preparation Products And Raw materials
Ampicillin 4-tert-Butylcyclohexanol 2-TERT-BUTYL-1H-INDOLE 4-Methyl-3-decen-5-ol PAXILLINE 3-N-OCTYLPYRROLE 3,3-DIMETHYLCYCLOHEXYLIDENEACETALDEHYDE 4-TERT-AMYLCYCLOHEXANOL 1-VINYLCYCLOHEXANOL 97 5,6-dihydro-2H-pyran-3-methanol TRANS-4-TERT-BUTYLCYCLOHEXANOL 1 2 3 4-TETRAHYDROCYCLOPENT(B) INDOLE 2,7-dimethyloct-5-en-4-one 4-METHYL-4-HEPTEN-3-OL 3-HEPTYLPYRROLE TRANS-4-TERT-PENTYLCYCLOHEXANOL 2-CYCLOHEXYL-1H-INDOLE Diacetone Alcohol

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