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A1289

Apamin

Name: Apamin
Brand: SIGMA

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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Properties

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)

Description

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 is a neurotoxin and is cytotoxic to erythrocytes. Exposure to apamin leads to hypermotility and convulsions.

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.

The only polypeptide neurotoxin that is known to pass the blood-brain barrier. Blocks ATP-type Ca⁺²-activated K⁺ channels.

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Storage Class

11 - Combustible Solids

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

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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)

A Comparison of the Ability of Leu8-and Pro8-Oxytocin to Regulate Intracellular Ca2+ and Ca2+-Activated K+ Channels at Human and Marmoset Oxytocin Receptors

Pierce ML, et al.

Molecular Pharmacology, 95(4), 376-385 (2019)

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)

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Global Trade Item Number

SKU	GTIN
A1289-.5MG	04061833342053
A1289-1MG	04061833342060
A1289-5MG	04061833342077