(2R)-5,6,6aα,7,12,12b,12c,13,14,14aβ-デカヒドロ-4bβ-ヒドロキシ-2-(1-ヒドロキシ-1-メチルエチル)-12bβ,12cα-ジメチル-2H-1-ベンゾピラノ[5',6':6,7]インデノ[1,2-b]インドール-3(4bH)-オン

説明

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.

化学的特性

Powder

使用

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.

生物活性

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).

酵素阻害剤

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.

参考文献

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