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Merck

A1289

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
NACRES:
NA.32
PubChem Substance ID:
24890526
UNSPSC Code:
12352200
EC Number:
246-182-7
MDL number:
MFCD00167944

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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)

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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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

A1289-.5MG-PW: + A1289-5MG: + A1289-VAR: + A1289-.5MG: + A1289-5MG-PW: + A1289-BULK: + A1289-1MG: + A1289-1MG-PW:

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Certificates of Analysis (COA)

Lot/Batch Number
0000339712
0000339713
0000339714
0000339712
0000339714

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Electrophysiological characterization and computational models of HVC neurons in the zebra finch
Daou A, et al.
Journal of Neurophysiology, 110(5), 1227-1245 (2013)
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)
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)
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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