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A1289 Sigma-Aldrich

Apamin

from bee venom, ≥95% (HPLC)

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Properties

Related Categories Bee, Cell Biology, Cell Signaling and Neuroscience, Ion Channel Modulating Peptides, Ion Channels,
Quality Level   200
biological source   bee venom
assay   ≥95% (HPLC)
storage temp.   −20°C
SMILES string   CC(C)C[C@@H]1NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H]2CCC[N@H]2C(=O)[C@H](C)NC(=O)[C@H](CCCCN)NC(=O)[C@@H]3CSSC[C@H](NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CSSC[C@H](N)C(=O)N[C@@H](CC(N)=O)C(=O)N3)NC1=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](Cc4cnc[nH]4)C(N)=O)[C@@H](C)O
InChI   1S/C79H131N31O24S4/c1-35(2)26-49-70(127)107-51-31-136-135-30-41(81)63(120)105-50(28-57(84)114)71(128)108-53(73(130)99-42(12-7-8-22-80)64(121)96-38(5)77(134)110-25-11-15-54(110)75(132)102-47(18-21-58(115)116)69(126)109-59(39(6)111)76(133)95-37(4)62(119)104-49)33-138-137-32-52(106-66(123)44(14-10-24-92-79(88)89)98-65(122)43(13-9-23-91-78(86)87)97-61(118)36(3)94-72(51)129)74(131)101-45(16-19-55(82)112)67(124)100-46(17-20-56(83)113)68(125)103-48(60(85)117)27-40-29-90-34-93-40/h29,34-39,41-54,59,111H,7-28,30-33,80-81H2,1-6H3,(H2,82,112)(H2,83,113)(H2,84,114)(H2,85,117)(H,90,93)(H,94,129)(H,95,133)(H,96,121)(H,97,118)(H,98,122)(H,99,130)(H,100,124)(H,101,131)(H,102,132)(H,103,125)(H,104,119)(H,105,120)(H,106,123)(H,107,127)(H,108,128)(H,109,126)(H,115,116)(H4,86,87,91)(H4,88,89,92)/t36-,37-,38-,39+,41-,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-,54-,59-/m0/s1
InChI key   YVIIHEKJCKCXOB-STYWVVQQSA-N
Gene Information   rat ... Kcnn1(54261)

Description

Amino Acid Sequence

Cys-Asn-Cys-Lys-Ala-Pro-Glu-Thr-Ala-Leu-Cys-Ala-Arg-Arg-Cys-Gln-Gln-His-NH2 [Disulfide Bridges: 1-11, 3-15]

General description

Apamin is a bee venom component and is strongly basic in nature. It has 18 amino acid residues and two disulphide bonds.

Application

Apamin has been used:
• As a selective inhibitor of small conductance (SKCa) channels in HEK cells.
• To inhibit endothelium-derived relaxing factor (EDHF) mediated responses.
• To block small-conductance Ca2-activated K current (ISK) in electrophysiological studies in hyperstriatum ventrale, pars caudalis (HVc) neurons.

Biochem/physiol Actions

Apamin is a neurotoxin and is cytotoxic to erythrocytes. Exposure to apamin leads to hypermotility and convulsions.

The only polypeptide neurotoxin that is known to pass the blood-brain barrier. Blocks ATP-type Ca+2-activated K+ channels.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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92210 Timestrip Plus 0 °C
06693 Timestrip Plus -20 °C

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