| Identification | Back Directory | [Name]
PAXILLINE | [CAS]
57186-25-1 | [Synonyms]
PAXILINE
PAXILLINE
Paxicillin
Paxilline solution
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-(
2h-1-benzopyrano(5’,6’:6,7)indeno(1,2-b)indol-3(4bh)-one,5,6,6a,7,12,12b,12c,1
(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
(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
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)-
(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
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 | [EINECS(EC#)]
637-206-0 | [Molecular Formula]
C27H33NO4 | [MDL Number]
MFCD00083464 | [MOL File]
57186-25-1.mol | [Molecular Weight]
435.56 |
| Chemical Properties | Back Directory | [Fp ]
2℃ | [storage temp. ]
2-8°C
| [solubility ]
Soluble in DMSO, acetone or chloroform. | [form ]
powder
| [color ]
faint yellow
| [InChIKey]
ACNHBCIZLNNLRS-UBGQALKQSA-N | [SMILES]
N1C2=C(C=CC=C2)C2C[C@@]3([H])[C@](C)(C1=2)[C@@]1(C)CC[C@]2([H])O[C@H](C(O)(C)C)C(=O)C=C2[C@]1(O)CC3 |
| Hazard Information | Back Directory | [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]
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]
Desiccate at -20°C | [References]
Springer et ai., Tetrahedron Lett., 2531 (1975) |
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