178270

Apamin, Bee Venom

Polypeptide neurotoxin known to pass through the blood-brain barrier.

• Synonym(s): Apamin, Bee Venom, CNCKAPETALCARRCQQH-NH₂
• Empirical Formula (Hill Notation): C₇₉H₁₃₁N₃₁O₂₄S₄
• CAS Number: 24345-16-2
• Molecular Weight: 2027.34
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD00167944

Properties

• Product Name: Apamin, Bee Venom, Polypeptide neurotoxin known to pass through the blood-brain barrier.
• SMILES string: S1SCC(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C3NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C4N(CCC4)C(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(CSSC3)N)CC(=O)N)C1)CCCCN)C)CCC(=O)O)C(O)C)C)CC(C)C)C)CCCN=C(N)N)CCCN=C(N)N)C(=O)NC(CCC(=O)N)C(=O)NC(CCC(=O)N)C(=O)NC(Cc2nc[nH]c2)C(
• 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)
• InChI key: YVIIHEKJCKCXOB-UHFFFAOYSA-N
• description: Merck USA index - 14, 725
• assay: ≥98% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; desiccated (hygroscopic)
• color: white, with dark tan cast
• solubility: 5% acetic acid: 2 mg/mL
• shipped in: ambient
• storage temp.: −20°C
• Quality Level: 100

Description

Biochem/physiol Actions

Cell permeable: no

Primary Target
AHP-type Ca2+-activated K+ channel

Product does not compete with ATP.

Reversible: no

Disclaimer

Toxicity: Harmful (C)

General description

A polypeptide neurotoxin known to pass through the blood-brain barrier. Blocks the AHP-type Ca²⁺-activated K⁺ channel; however, it does not block the TEA and voltage-sensitive Ca²⁺-activated K⁺ channel. Known to induce the secretion of prolactin in a dose-dependent manner.

Polypeptide neurotoxin known to pass through the blood-brain barrier. Blocks the AHP-type Ca²⁺-activated K⁺ channel; does not block the TEA and voltage-sensitive Ca²⁺-activated K⁺ channel. Reported to induce neurodegeneration of Purkinje cells in rat brain. Known to induce the secretion of prolactin in a dose-dependent manner.

Other Notes

H-Cys¹-Asn-Cys³-Lys-Ala-Pro-Glu-Thr-Ala-Leu-Cys¹¹-Ala-Arg-Arg-Cys¹⁵-Gln-Gln-His-NH₂ (disulfide bonds: 1 → 11; 3 → 15)

Mourre, C., et al. 1997. Brain Res. 778, 405.
Silva, E.G., et al. 1994. Br. J. Pharmacol. 113, 1022.
Wang, X., et al. 1994. Brain Res. 662, 83.

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Acetic acid stock solutions are stable for up to 3 days at -20°C.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable