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Merck

A1289

Sigma-Aldrich

Apamin

from bee venom, ≥95% (HPLC)

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About This Item

Fórmula empírica (notación de Hill):
C79H131N31O24S4
Número de CAS:
Peso molecular:
2027.34
Número CE:
Número MDL:
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
NACRES:
NA.32

origen biológico

bee venom

Nivel de calidad

Ensayo

≥95% (HPLC)

Formulario

powder

mol peso

2027.34 g/mol

técnicas

inhibition assay: suitable

nota de secuencia

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]

Nº de acceso UniProt

temp. de almacenamiento

−20°C

cadena SMILES

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

Clave InChI

YVIIHEKJCKCXOB-STYWVVQQSA-N

Información sobre el gen

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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]

Descripción general

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.

Aplicación

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).

Acciones bioquímicas o fisiológicas

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.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


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Visite la Librería de documentos

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

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