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Apamin

SIGMA/A1289 - from bee venom, ≥95% (HPLC)

CAS Number: 24345-16-2
Empirical Formula (Hill Notation): C79H131N31O24S4
Molecular Weight: 2027.34
EC Number: 246-182-7
MDL Number: MFCD00167944
Linear Formula: C79H131N31O24S4
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-A1289-.5MG 0.5 mg
 $298.00
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45-A1289-1MG 1 mg
 $508.00
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45-A1289-5MG 5 mg
 $2010.00
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assay ≥95% (HPLC)
biological source bee venom
form powder
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
mol wt 2027.34 g/mol
Quality Level 200 
sequence note 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]
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
storage temp. −20°C
technique(s) inhibition assay: suitable
UniProt accession no. P01500 
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]
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 (/SK) in electrophysiological studies in hyperstriatum ventrale, pars caudalis (HVc) neurons.
• as a standard for determination of content and compositions of bee venom by high-performance liquid chromatography (HPLC).
Biochem/physiol Actions: Apamin exhibits anti-inflammatory, anti-apoptotic and antifibrotic properties. These properties aid in various biological processes such as vascular smooth muscle cell migration, biliary fibrosis and activation of hepatic stellate cells, TNFα/interferon (IFN)γ-induced keratinocytes, and macrophage activation. It also inhibits lipopolysaccharide (LPS)-induced neuroinflammatory responses by modulating multiple molecular targets involved in the inflammatory response, including calcium/calmodulin-dependent protein kinase II (CaMKII), toll-like receptor 4 (TLR4), nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB)/signal transducer and activator of transcription 3 (STAT3), and mitogen-activated protein kinases (MAPKs)/ extracellular signal-regulated kinase (ERK)pathways.
Biochem/physiol Actions: Apamin is a neurotoxin and is cytotoxic to erythrocytes. Exposure to apamin leads to hypermotility and convulsions.
Biochem/physiol Actions: The only polypeptide neurotoxin that is known to pass the blood-brain barrier. Blocks ATP-type Ca+2-activated K+ channels.
General description: Research area: neuroscience
Apamin is a bee venom component and is strongly basic in nature. It has 18 amino acid residues and two disulphide bonds.
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity ≥95% (HPLC)
Storage Temp. −20°C
UNSPSC 12352200

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