The principal cytotoxic component of bee venom
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Melittin (trifluoroacetate salt)

Item No. 17494

Technical Information
Molecular Formula
C131H229N39O31 • XCF3COOH
Formula Weight
Purity
≥95%
A crystalline solid
DMF: 25 mg/mlDMSO: 25 mg/mlPBS (pH 7.2): 3 mg/ml
SMILES
NC([C@H](CCC(N)=O)NC([C@H](CCC(N)=O)NC([C@H](CCCNC(N)=N)NC([C@H](CCCCN)NC([C@H](CCCNC(N)=N)NC([C@H](CCCCN)NC([C@@]([C@H](CC)C)([H])NC([C@@H](NC([C@H](CO)NC([C@@]([C@H](CC)C)([H])NC([C@H](CC(C)C)NC([C@@H](NC([C@@H]1CCCN1C([C@H](CC(C)C)NC(CNC([C@@]([C@@H](C)O)([H])NC([C@@]([C@@H](C)O)([H])NC([C@H](CC(C)C)NC([C@H](C(C)C)NC([C@H](CCCCN)NC([C@H](CC(C)C)NC([C@H](C(C)C)NC([C@@H](NC(CNC([C@@]([C@H](CC)C)([H])NC(CN[H])=O)=O)=O)C)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)C)=O)=O)=O)=O)CC2=CNC3=C2C=CC=C3)=O)=O)=O)=O)=O)=O)=O)=O.OC(C(F)(F)F)=O
InChi Code
InChI=1S/C131H229N39O31.C2HF3O2/c1-23-71(16)102(163-97(176)60-135)122(194)146-62-98(177)148-74(19)109(181)164-100(69(12)13)124(196)160-88(55-65(4)5)116(188)155-84(41-30-33-51-134)115(187)165-101(70(14)15)125(197)161-90(57-67(8)9)118(190)168-106(77(22)173)128(200)169-105(76(21)172)123(195)147-63-99(178)150-92(58-68(10)11)129(201)170-54-36-44-94(170)121(193)149-75(20)108(180)158-89(56-66(6)7)117(189)166-104(73(18)25-3)127(199)162-93(64-171)120(192)159-91(59-78-61-145-80-38-27-26-37-79(78)80)119(191)167-103(72(17)24-2)126(198)157-83(40-29-32-50-133)111(183)154-85(42-34-52-143-130(139)140)112(184)152-82(39-28-31-49-132)110(182)153-86(43-35-53-144-131(141)142)113(185)156-87(46-48-96(137)175)114(186)151-81(107(138)179)45-47-95(136)174;3-2(4,5)1(6)7/h26-27,37-38,61,65-77,81-94,100-106,145,171-173H,23-25,28-36,39-60,62-64,132-135H2,1-22H3,(H2,136,174)(H2,137,175)(H2,138,179)(H,146,194)(H,147,195)(H,148,177)(H,149,193)(H,150,178)(H,151,186)(H,152,184)(H,153,182)(H,154,183)(H,155,188)(H,156,185)(H,157,198)(H,158,180)(H,159,192)(H,160,196)(H,161,197)(H,162,199)(H,163,176)(H,164,181)(H,165,187)(H,166,189)(H,167,191)(H,168,190)(H,169,200)(H4,139,140,143)(H4,141,142,144);(H,6,7)/t71-,72-,73-,74-,75-,76+,77+,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,100-,101-,102-,103-,104-,105-,106-;/m0./s1
InChi Key
ABMAJLCYJGUBMU-CTOWXMLOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Melittin is a small protein that is the principal cytotoxic component of venom of the honey bee, A. mellifera.1 Structurally, melittin consists of two α-helical segments forming a bent rod, with hydrophilic residues on the convex side and hydrophobic sites on the concave side.1,2 This allows melittin molecules to assemble as tetramers on membrane surfaces and form pores, resulting in cell death. Bee venom is also known to stimulate phospholipase A2 (PLA2) activity, and this may be linked to melittin-mediated pore production as well as the presence of low molecular weight PLA2 enzymes in the venom.2,3 Melittin also has antimicrobial properties, which, combined with its cytolytic properties, extends its potential for therapeutic applications.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Terwilliger, T.C., and Eisenberg, D. The structure of melittin. II. Interpretation of the structure. The Journal of Biological Chemisty 257(11), 6016-6022 (1982).

    2. Kourie, J.I., and Shorthouse, A.A. Properties of cytotoxic peptide-formed ion channels. Am. J. Physiol. Cell Physiol. 278, C1063-C1087 (2000).

    3. Moreno, M., and Giralt, E. Three valuable peptides from bee and wasp venoms for therapeutic and biotechnological use: Melittin, apamin and mastoparan. Toxins 7, 1126-1150 (2015).