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M5280

Mastoparan, Vespula lewisii

Name: Mastoparan, <I>Vespula lewisii</I>
Brand: SIGMA

≥97% (HPLC), powder

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About This Item

Empirical Formula (Hill Notation):

C₇₀H₁₃₁N₁₉O₁₅

CAS Number:

72093-21-1

Molecular Weight:

1478.91

UNSPSC Code:

41106300

NACRES:

NA.32

PubChem Substance ID:

329818006

MDL number:

MFCD00076865

Beilstein/REAXYS Number:

5491949

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biological source

synthetic

Quality Level

200

assay

≥97% (HPLC)

form

powder

color

white

storage temp.

−20°C

SMILES string

CC[C@H](C)[C@H](N)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)NC([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(N)=O

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-MVSGICTGSA-N

Gene Information

human ... CALM1(801), PLA2R1(22925)
mouse ... CALM1(12313), PLA2R1(18779)
rat ... CALM1(24242), PLA2R1(295631)

General description

Mastoparan is a cationic, amphiphilic, tetradecapeptide amide. It is composed of the restricted amino acid and the repeated sequence. This protein is a nonspecific secretagogue isolated from venom of wasp.

Application

Mastoparan has been used as a calmodulin antagonist.

Biochem/physiol Actions

Mastoparan effectively stimulates exocytosis from diverse mammalian cells. The encoded protein facilitates the secretion of histamine from mast cells, serotonin from platelets, catecholamines from chromaffin cells and prolactin from the anterior pituitary. In addition, it is also involved in activation of Phospholipase A2 and phosphoinositides (Pl) break down. Mastoparan functions as an inhibitor for calmodulin-stimulated phosphodiesterase. Mastoparan helps in mitochondrial permeability transition by enhancing an apparent bimodal mechanism of action.

Mast cell degranulating peptide. Activates phospholipase A₂; inhibits calmodulin. Cell permeable; stimulates exocytosis and phosphoinositide breakdown.

Other Notes

Lyophilized from 0.1% TFA in H2O

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Inhibition of calmodulin activity by insect venom peptides

Barnette MS

Biochemical Pharmacology, 32, 2929-2933 (1983)

Characterization of heterotrimeric nucleotide-depleted Gα(i)-proteins by Bodipy-FL-GTPγS fluorescence anisotropy.

Lauri Tõntson et al.

Archives of biochemistry and biophysics, 524(2), 93-98 (2012-06-05)

Recombinant heterotrimeric G-protein α(i1), α(i2) and α(i3) subunits were purified in GDP-depleting conditions by affinity chromatography using StrepII-tagged β₁γ₂ subunits. Real-time monitoring of fluorescence anisotropy of Bodipy-FL-GTPγS was used for characterization of nucleotide binding properties and inactivation of the purified

Inhibition of olfactory cyclic nucleotide-activated current by calmodulin antagonists

Kleene SJ

British Journal of Pharmacology, 111, 469-472 (1994)

Simvastatin and GGTI-2133, a geranylgeranyl transferase inhibitor, increase erythrocyte deformability but reduce low O(2) tension-induced ATP release.

K M Clapp et al.

American journal of physiology. Heart and circulatory physiology, 304(5), H660-H666 (2013-01-22)

Statin drugs inhibit 3-hydroxy-3-methylglutaryl CoA reductase, which reduces the synthesis of both cholesterol and isoprenoids (geranylgeranyl pyrophosphate and farnesyl pyrophosphate), with the latter being lipid molecules responsible for the posttranslational modification of small GTP-binding proteins such as Rho. Effects of

A new mast cell degranulating peptide "mastoparan" in the venom of Vespula lewisii.

Y Hirai et al.

Chemical & pharmaceutical bulletin, 27(8), 1942-1944 (1979-08-01)

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Global Trade Item Number

SKU	GTIN
M5280-5MG	04061833421239
M5280-1MG	04061826739013

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