A1289

Apamin

from bee venom, ≥95% (HPLC)

• Empirical Formula (Hill Notation): C₇₉H₁₃₁N₃₁O₂₄S₄
• CAS Number: 24345-16-2
• Molecular Weight: 2027.34
• NACRES: NA.32
• PubChem Substance ID: 24890526
• UNSPSC Code: 12352200
• EC Number: 246-182-7
• MDL number: MFCD00167944

Properties

• Product Name: Apamin, from bee venom, ≥95% (HPLC)
• InChI key: YVIIHEKJCKCXOB-STYWVVQQSA-N
• 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
• 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
• biological source: bee venom
• assay: ≥95% (HPLC)
• form: powder
• mol wt: 2027.34 g/mol
• technique(s): inhibition assay: suitable
• 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]
• UniProt accession no.: P01500
• storage temp.: −20°C
• Quality Level: 200
• Gene Information: rat ... Kcnn1(54261)

Description

Application

Apamin has been used:

• As a selective inhibitor of small conductance (SKCa) channels in HEK cells.[1]
• To inhibit endothelium-derived relaxing factor (EDHF) mediated responses.[2]
• To block small-conductance Ca²⁺-activated K⁺current (/SK) in electrophysiological studies in hyperstriatum ventrale, pars caudalis (HVc) neurons.[3]
• as a standard for determination of content and compositions of bee venom by high-performance liquid chromatography (HPLC).[4]

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.[5]

Apamin is a neurotoxin[6] and is cytotoxic to erythrocytes. Exposure to apamin leads to hypermotility and convulsions.[7]

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.[7] It has 18 amino acid residues and two disulphide bonds.[6]

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable