An inhibitor of KCa2.2/SK2 channels
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Apamin (trifluoroacetate salt)

Item No. 17082

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
L-cysteinyl-L-asparaginyl-L-cysteinyl-L-lysyl-L-alanyl-L-prolyl-L-α-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), trifluoroacetate salt
CAS Number
24345-16-2
Synonyms
  • Ro 23-6721
Molecular Formula
C79H131N31O24S4 • XCF3COOH
Formula Weight
2027.3
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Water: 1 mg/ml
SMILES
O=C([C@]1(N(CCC1)C([C@H](C)NC([C@H](CCCCN)NC([C@@]([H])(NC([C@@H](CC(N)=O)NC([C@@](N)([H])CSSC2)=O)=O)CSSC[C@@H](C(N[C@H](C(N[C@H](C(N[C@@H](CC3=CNC=N3)C(N)=O)=O)CCC(N)=O)=O)CCC(N)=O)=O)NC([C@H](CCCNC(N)=N)NC4=O)=O)=O)=O)=O)[H])N[C@@H](CCC(O)=O)C(N[C@@H]([C@@H](C)O)C(N[C@@H](C)C(N[C@@H](CC(C)C)C(N[C@]2(C(N[C@@H](C)C(N[C@]4(CCCNC(N)=N)[H])=O)=O)[H])=O)=O)=O)=O.FC(F)(C(O)=O)F
InChi Code
InChI=1S/C79H131N31O24S4.C2HF3O2/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;3-2(4,5)1(6)7/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);(H,6,7)/t36-,37-,38-,39+,41+,42-,43-,44-,45-,46-,47-,48-,49-,50+,51+,52-,53-,54-,59-;/m0./s1
InChi Key
GUBJIBRYPCCYMV-ZKPRYNSTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $176

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    Product Description

    Apamin is an 18-amino acid peptide toxin that has been found in honey bee (A. mellifera) venom.1,2 It is an inhibitor of small conductance calcium-activated potassium (KCa2.2/SK2) channels (IC50s = 0.06-0.4 nM).1 It is selective for KCa2.2/SK2 channels over KCa2.1/SK1 and KCa2.3/SK3 channels (IC50s = 1-12 and 1-13 nM, respectively), as well as the intermediate-conductance calcium-activated potassium channel KCa3.1/SK4 at 1 µM but does inhibit voltage-gated potassium channel 1.3 (Kv1.3; IC50 = 13 nM).3,1,4 Apamin (50 µg/kg) reduces CD8+ cell infiltration into the CNS and the severity of experimental autoimmune encephalomyelitis (EAE), as well as increased peripheral blood levels of CD62L-, CD44L-, and CD44+ memory T cells in mice.5 It has commonly been used to determine the role of KCa/SK channels in the brain, vascular endothelium, and bladder.6,7,8,2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wulff, H., and Köhler, R. Endothelial small-conductance and intermediate-conductance KCa channels: An update on their pharmacology and usefulness as cardiovascular targets. J. Biomed. Sci. 61(2), 102-112 (2013).

    2. Gu, H., Han, S.M., and Park, K.-K. Therapeutic effects of apamin as a bee venom component for non-neoplastic disease. Toxins (Basel) 12(3), 195 (2020).

    3. Maylie, J., Bond, C.T., Herson, P.S., et al. Small conductance Ca2+-activated K+ channels and calmodulin. J. Physiol. 554(Pt 2), 255-261 (2004).

    4. Voos, P., Yazar, M., Lautenschläger, R., et al. The small neurotoxin apamin blocks not only small conductance Ca2+ activated K+ channels (SK type) but also the voltage dependent Kv1.3 channel. Eur. Biophys. J. 46(6), 517-523 (2017).

    5. Fattahi, H., Esmaeil, N., and Aliomrani, M. Apamin as a BBB shuttle and its effects on T cell population during the experimental autoimmune encephalomyelitis-induced model of multiple sclerosis. Neurotox. Res. 39(6), 1881-1891 (2021).

    6. Triggle, C.R., Hollenberg, M., Anderson, T.J., et al. The endothelium in health and disease - a target for therapeutic intervention. J. Smooth Muscle Res. 39(6), 249-267 (2003).

    7. Pedarzani, P., and Stocker, M. Molecular and cellular basis of small- and intermediate-conductance, calcium-activated potassium channel function in the brain. Cell. Mol. Life Sci. 65(20), 3196-3217 (2008).

    8. Thorneloe, K.S., Knorn, A.M., Doetsch, P.E., et al. Small-conductance, Ca2+-activated K+ channel 2 is the key functional component of SK channels in mouse urinary bladder. Am. J. Physiol. Regul. Integr. Comp. Physiol. 294(5), R1737-R1743 (2008).