| Identification | Back Directory | [Name]
APAMIN | [CAS]
24345-16-2 | [Synonyms]
APAMIN
apamine
APAMIN, BEE VENOM
Apamin, ≥97% (HPLC)
APAMIN FROM BEE VENOM
CNCKAPETALCARRCQQH-NH2
APAMIN FROM HONEY BEE VENOM
Apamin (trifluoroacetate salt)
M.W. 2027.34 C79H131N31O24S4
APAMIN (HONEY BEE, APIS MELIFERA)
APAMIN (HONEYBEE, APIS MELLIFERA)
Apamin, Bee Venom - CAS 24345-16-2 - Calbiochem
CNCKAPETALCARRCQQH-NH2 (DISULFIDE BRIDGE: 1-11,3-15)
CYS-ASN-CYS-LYS-ALA-PRO-GLU-THR-ALA-LEU-CYS-ALA-ARG-CYS-GLN-GLN-HIS-NH2
CYS-ASN-CYS-LYS-ALA-PRO-GLU-THR-ALA-LEU-CYS-ALA-ARG-ARG-CYS-GLN-GLN-HIS-NH2
H-CYS-ASN-CYS-LYS-ALA-PRO-GLU-THR-ALA-LEU-CYS-ALA-ARG-ARG-CYS-GLN-GLN-HIS-NH2
H-+CYS-ASN-++CYS-LYS-ALA-PRO-GLU-THR-ALA-LEU-+CYS-ALA-ARG-ARG-++CYS-GLN-GLN- HIS-NH2
[CYS-ASN-(CYS-LYS-ALA-PRO-GLU-THR-ALA-LEU-CYS]CYCL-ALA-ARG-ARG-CYS)CYCL-GLN-GLN-HIS-NH2
H-Cys-Asn-Cys-Lys-Ala-Pro-Glu-Thr-Ala-Leu-Cys-Ala-Arg-Arg-Cys-Gln-Gln-His-NH2 (Cys1-Cys11, Cys3-Cys15)
H-CYS-ASN-CYS-LYS-ALA-PRO-GLU-THR-ALA-LEU-CYS-ALA-ARG-ARG-CYS-GLN-GLN-HIS-NH2 (DISULFIDE BRIDGE: 1-11, 3-15)
L-Cys-L-Asn-L-Cys-L-Lys-L-Ala-L-Pro-L-Glu-L-Thr-L-Ala-L-Leu-L-Cys-L-Ala-L-Arg-L-Arg-L-Cys-L-Gln-L-Gln-L-His-NH2
CYS-ASN-CYS-LYS-ALA-PRO-GLU-THR-ALA-LEU-CYS-ALA-ARG- ARG-CYS-GLN-GLN-HIS-NH2(DISULFIDE BRIDGE:CYS1-CYS11, CYS3-CYS15)
L-Cysteinyl-L-asparaginyl-L-cysteinyl-L-lysyl-L-alanyl-L-prolyl-L-alpha-glutamyl-L-threonyl-L-alanyl-L-leucyl-L-cysteinyl-L-alanyl-L-arginyl-L-arginyl-L-cysteinyl-L-glutaminyl-L-glutaminyl-L-histidinamide cyclic (1-11) (3-15)-bis(disulfide) = Cys-Asn-Cys-Lys-Ala-Pro-Glu-Thr-Ala-leu-Cyc-Ala-Arg-Arg-Cys-Gln-Gln-His-NH2 | [EINECS(EC#)]
246-182-7 | [Molecular Formula]
C79H131N31O24S4 | [MDL Number]
MFCD00167944 | [MOL File]
24345-16-2.mol | [Molecular Weight]
2027.34 |
| Chemical Properties | Back Directory | [Boiling point ]
847.17°C (rough estimate) | [density ]
1.63 | [refractive index ]
1.5530 (estimate) | [storage temp. ]
-20°C | [solubility ]
0.05 M acetic acid: 5 mg/mL, clear, colorless to faintly yellow
| [form ]
White solid with dark tan cast | [Water Solubility ]
Soluble to 1 mg/ml in water | [Merck ]
13,732 |
| Safety Data | Back Directory | [Safety Statements ]
22-24/25 | [RIDADR ]
2811 | [WGK Germany ]
3
| [RTECS ]
CD6899900
| [F ]
3-10 | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [Toxicity]
LD50 i.v. in mice: 4 mg/kg (Habermann, Reiz); LD50 intracerebroventricularly in mice: 12 ng/animal (Labbé-Jullié) |
| Hazard Information | Back Directory | [Chemical Properties]
Small, highly potent, highly basic polypeptide. | [Uses]
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 (ISK) in electrophysiological studies in hyperstriatum ventrale, pars caudalis (HVc) neurons.
| [Definition]
Occurs in the venom of the honey bee, Apis mellifera; molecular weight of 2027.38. | [General Description]
Apamin is a bee venom component and is strongly basic in nature. It has 18 amino acid residues and two disulphide bonds. | [Hazard]
Central nervous system poison able to cross the blood–brain barrier; neurotoxic; poison. | [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. | [Safety Profile]
Poison by intravenous, parenteral,intracerebral, and intraperitoneal routes. When heated todecomposition it emits toxic fumes of SOx and NOx. | [Enzyme inhibitor]
This bee venom octadecapeptide toxin (FW = 2027.34 g/mol; CAS 24345- 16-2; NCBI Reference Sequence: NP_001011612.1) potently blocks the small-conductance Ca 2+ -activated potassium ion (or SK) channels hSK1 as well as rSK2, with IC50 values of 3.3 nM and 83 pM. It shows greater effectiveness at the SK2 channel (IC50 = 0.06-0.4 nM) than SK1 (IC50 = 1- 12 nM). SK3 (IC50 = 1-13 nM), and SK4 (IC50 = 1 μM) channels, and is active against channels within neurons, vascular endothelium, bladder smooth muscle, and certain cancers. Apamin does not inhibit human cardiac Na + current, L-type Ca 2+ current or other major K+ currents. Structurally, apamin forms a stable structure, consisting of a C-terminal a- helix and two reverse turns, that is stabilized by two disulfide bonds connecting Cys-1 to Cys-11 and Cys-3 to Cys-15. A minor constituent of venom of the bee (Apis mellifera), apamin amounts to only 2-3% (w/w) of its dry venom. The smallest known neurotoxic polypeptide, apamin is derived by proteolytic processing of the 48-residue pre-pro-protein. The precursors of the bee venom constituents apamin and MCD peptide are encoded by two genes in tandem which share the same 3'-exon. | [storage]
-20°C (desiccate) |
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