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Safety Information

A9459

Sigma-Aldrich

Apamin

synthetic, ≥97% (HPLC)

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Empirical Formula (Hill Notation):
C79H131N31O24S4
CAS Number:
24345-16-2
Molecular Weight:
2027.34
MDL number:
MFCD00167944
UNSPSC Code:
12352200
PubChem Substance ID:
24891455
NACRES:
NA.32

biological source

synthetic

Quality Level

200

Assay

≥97% (HPLC)

form

powder

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

Apamin, a bee venom is a polypeptide, that is made of 18 amino acids with two disulfide bridges.

Application

Apamin has been used in microbiological assays for the determination of antimicrobial activity of synthetic apamin and as a standard for MALDI (matrix-assisted laser desorption/ionization matrix assisted laser desorption ionization-time of flight mass spectrometry (MALDI-TOF MS) and electrospray ionisation mass spectrometry (ESI-MS) analysis.

Biochem/physiol Actions

Apamin is a neurotoxin which can pass the blood-brain barrier. In human, it might cause peripheral nerve dysfunction, mainly seen after bee stings.
The only polypeptide neurotoxin that is known to pass the blood-brain barrier. Blocks ATP-type Ca+2-activated K+ channels.

Other Notes

Lyophilized from 0.1% TFA in H2O

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 as a selective blocker of the calcium-dependent potassium channel in neuroblastoma cells: voltage-clamp and biochemical characterization of the toxin receptor
Hugues M, et al.
Proceedings of the National Academy of Sciences of the USA, 79(4), 1308-1312 (1982)
Claudio A Villalobos et al.
Cell reports, 39(3), 110699-110699 (2022-04-21)
We report that increasing inhibition from the basal ganglia (BG) to the superior colliculus (SC) through the substantia nigra pars reticulata (nigra) using in vivo optogenetic activation of GABAergic terminals in mice produces contralateral orienting movements. These movements are unexpected because
Top-down sequencing of Apis dorsata apamin by MALDI-TOF MS and evidence of its inactivity against microorganisms
Baracchi D, et al.
Toxicon, 105-112 (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
Haeyeong Lee et al.
The Journal of physiology, 591(2), 503-513 (2012-11-14)
We sought to characterize molecular expression and ionic conductances in a novel population of interstitial cells (PDGFRα(+) cells) in murine bladder to determine how these cells might participate in regulation of detrusor excitability. PDGFRα(+) cells and smooth muscle cells (SMCs)
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