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A1289

Sigma-Aldrich

Apamin

from bee venom, ≥95% (HPLC)

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About This Item

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

biological source

bee venom

Quality Level

200

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

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)

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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

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.

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.
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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

高风险级别生物产品--毒素类产品

Certificates of Analysis (COA)

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Apamin from bee venom. Effects of the neurotoxin on subcellular particles of neural cultures
Spoerri E, et al.
Febs Letters, 53(2), 143-147 (1975)
Chemical composition and antibacterial activity of bee venom against multi-drug resistant pathogens
Gokmen TG, et al.
The Onderstepoort Journal of Veterinary Research, 90(1), e1-e5 (2023)
Chemical composition and antibacterial activity of bee venom against multi-drug resistant pathogens
Gokmen TG, et al.
The Onderstepoort Journal of Veterinary Research, 90(1), e1-e5 (2023)
Ramesh C Mishra et al.
Cardiovascular research, 97(2), 339-348 (2012-11-03)
Endothelial SK(Ca) and IK(Ca) channels play an important role in the regulation of vascular function and systemic blood pressure. Based on our previous findings that small molecule activators of SK(Ca) and IK(Ca) channels (i.e. NS309 and SKA-31) can inhibit myogenic
Jung-Yeon Kim et al.
Molecules (Basel, Switzerland), 25(23) (2020-12-09)
Sepsis is the major cause of acute kidney injury (AKI) in severely ill patients, but only limited therapeutic options are available. During sepsis, lipopolysaccharide (LPS), an endotoxin derived from bacteria, activates signaling cascades involved in inflammatory responses and tissue injury.
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