A mast cell degranulating peptide
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Mastoparan (trifluoroacetate salt)

Item No. 20240

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Molecular Formula
C70H131N19O15 • XCF3COOH
Formula Weight
1478.9
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2) (1:3): 0.25 mg/ml
λmax
203 nm
SMILES
O=C(N[C@@H]([C@@H](C)CC)C(N[C@H](C(N)=O)CC(C)C)=O)[C@H](CCCCN)NC([C@H](CCCCN)NC([C@H](C)NC([C@H](CC(C)C)NC([C@H](C)NC([C@H](C)NC([C@H](CC(C)C)NC([C@H](C)NC([C@H](CCCCN)NC([C@H](CC(C)C)NC([C@H](CC(N)=O)NC([C@@H](N)[C@@H](C)CC)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O.FC(F)(C(O)=O)F
InChi Code
InChI=1S/C70H131N19O15.C2HF3O2/c1-17-40(11)55(75)69(103)88-53(35-54(74)90)68(102)87-52(34-39(9)10)67(101)83-46(25-19-22-28-71)62(96)78-45(16)61(95)86-50(32-37(5)6)65(99)79-42(13)58(92)77-43(14)60(94)85-51(33-38(7)8)66(100)80-44(15)59(93)81-47(26-20-23-29-72)63(97)82-48(27-21-24-30-73)64(98)89-56(41(12)18-2)70(104)84-49(57(76)91)31-36(3)4;3-2(4,5)1(6)7/h36-53,55-56H,17-35,71-73,75H2,1-16H3,(H2,74,90)(H2,76,91)(H,77,92)(H,78,96)(H,79,99)(H,80,100)(H,81,93)(H,82,97)(H,83,101)(H,84,104)(H,85,94)(H,86,95)(H,87,102)(H,88,103)(H,89,98);(H,6,7)/t40-,41-,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-,55-,56-;/m0./s1
InChi Key
WZPKLDWYLMDLDU-UVXXMCETSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Cayman Chemical
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    Product Description

    Mastoparan is a mast cell degranulating peptide originally isolated from Vespid wasp venom.1 It promotes degranulation by increasing GTPase activity for Gi and Go signaling independent of G protein-coupled receptor binding.2,3 Mastoparan also binds calmodulin (Kd = 0.3 nM) and inhibits the calmodulin-induced activation of phosphodiesterase (IC50 = 0.02 µM).4,5 In vitro, mastoparan was effective in killing leukemia, myeloma, and breast cancer cells (IC50s = 8-9.2, 11, and 20-24 µM, respectively).6 It worked synergistically with gemcitabine in a mouse model of mammary carcinoma.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hirai, Y., Yashuhara, T., Yoshida, H., et al. A new mast cell degranulating peptide "mastoparan" in the venom of Vespula lewisii. Chem. Pharm. Bull. (Tokyo) 27(8), 1942-1944 (1979).

    2. Higashijima, T., Uzu, S., Nakajima, T., et al. Mastoparan, a peptide toxin from wasp venom, mimics receptors by activating GTP-binding regulatory proteins (G proteins). The Journal of Biological Chemisty 263(14), 6491-6494 (1988).

    3. Higashijima, T., Burnier, J., and Ross, E.M. Regulation of Gi and Go by mastoparan, related amphiphilic peptides, and hydrophobic amines. Mechanism and structural determinants of activity. The Journal of Biological Chemisty 265(24), 14176-14186 (1990).

    4. Malencik, D.A., and Anderson, S.R. High affinity binding of the mastoparans by calmodulin. Biochem. Biophys. Res. Commun. 114(1), 50-56 (1983).

    5. Barnette, M.S., Daly, R., and Weiss, B. Inhibition of calmodulin activity by insect venom peptides. Biochem. Pharmacol. 32(19), 2929-2933 (1983).

    6. Hilchie, A.L., Sharon, A.J., Haney, E.F., et al. Mastoparan is a membranolytic anti-cancer peptide that works synergistically with gemcitabine in a mouse model of mammary carcinoma. Biochim. Biophys. Acta 1858(12), 3195-3204 (2016).