444898

Mastoparan

A cell-permeable synthetic peptide with sequence identical to Vespula lewisii.

• Synonym(s): Mastoparan, INLKALAALAKKIL
• Empirical Formula (Hill Notation): C₇₀H₁₃₁N₁₉O₁₅
• CAS Number: 72093-21-1
• Molecular Weight: 1478.91
• UNSPSC Code: 51111800
• NACRES: NA.77
• MDL number: MFCD00076865
• Assay: ≥97% (HPLC)
• Form: solid
• Storage condition: OK to freeze

Properties

• Quality Segment: 100
• assay: ≥97% (HPLC)
• form: solid
• potency: 7.5 μM IC₅₀
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: white
• solubility: water: 5 mg/mL
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: N([C@@H](C(CC)C)C(=O)N[C@@H](CC(C)C)C(=O)N)C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](N)[C@H](CC)C)CC(=O)N)CC(C)C)CCCCN)C)CC(C)C)C)C)CC(C)C)C)C
• InChI: 1S/C70H131N19O15/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/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)/t40-,41?,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-,55-,56-/m0/s1
• InChI key: MASXKPLGZRMBJF-HDSAQESISA-N

Description

General description

A cell-permeable synthetic peptide with a sequence identical to Vespula lewisii. Amphiphilic wasp venom tetradecapeptide capable of directly activating pertussis toxin-sensitive G-proteins by a mechanism analogous to that of G-protein-coupled receptors. Acts preferentially on G_i and G_o rather than G_s. Potent factor in mitochondrial permeability transition pore. Inhibits calmodulin and activates phospholipase A₂. Causes a transient Ca²⁺ release from the sarcoplasmic reticulum.

A cell-permeable synthetic peptide with sequence identical to Vespula lewisii. Amphiphilic wasp venom tetradecapeptide capable of directly activating pertussis toxin-sensitive G-proteins by a mechanism analogous to that of G-protein-coupled receptors. Acts preferentially on G_i and G_o rather than G_s. Potent facilitator of the mitochondrial permeability transition pore that is reported to induce apoptosis in cultured cerebellar granule neurons by causing a dramatic increase in intracellular Ca²⁺. Acts as a calmodulin antagonist and activates phospholipase A₂. Causes a transient Ca²⁺ release from the sarcoplasmic reticulum. Also reported to inhibit Na⁺,K⁺-ATPase activity (IC₅₀ = 7.5 µM).

Biochem/physiol Actions

Cell permeable: yes

Primary Target
Na⁺,K⁺-ATPase activity

Product does not compete with ATP.

Reversible: no

Packaging

Yes

Physical form

Supplied as a trifluoroacetate salt.

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

H-Ile-Asn-Leu-Lys-Ala-Leu-Ala-Ala-Leu-Ala-Lys-Lys-Ile-Leu-NH₂

Hirata, Y., et al. 2000. Mol. Pharmacol. 57, 1235.
Liz, S.Z., et al. 1997. Brain Res.771, 184.
Klinker, J.F., et al. 1996. Biochem. Pharmacol. 51, 217.
Langel, U., et al. 1996. Regul. Peptides 62, 47.
Pfeiffer, D.R., et al. 1995. J. Biol. Chem. 270, 4923.
Igarashi, M., et al. 1993. Science259, 77.
Komatsu, M., et al. 1992. Endocrinology130, 221.
Adolfo Garcia-Sainz, J., et al. 1991. Biochem. Biophys. Res. Commun.179, 852.
Gil, J., et al. 1991. J. Cell Biol. 113, 943.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

Safety Information

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