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| 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 Chemical Properties |
Fp | 2℃ | storage temp. | 2-8°C | solubility | Soluble in DMSO, acetone or chloroform. | form | powder | color | faint yellow |
| PAXILLINE Usage And Synthesis |
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. | Uses | Potent blocker of high-conductance calcium-activated potassium (BKCa) channels | 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 |
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