M5280

Mastoparan, Vespula lewisii

Name: Mastoparan, <I>Vespula lewisii</I>
Brand: SIGMA
Price: 665 PLN

≥97% (HPLC), powder

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Informacje o tej pozycji

Wzór empiryczny (zapis Hilla):

C₇₀H₁₃₁N₁₉O₁₅

Numer CAS:

72093-21-1

Masa cząsteczkowa:

1478.91

UNSPSC Code:

41106300

NACRES:

NA.32

PubChem Substance ID:

329818006

MDL number:

MFCD00076865

Beilstein/REAXYS Number:

5491949

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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

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 key

MASXKPLGZRMBJF-MVSGICTGSA-N

biological source

synthetic

assay

≥97% (HPLC)

form

powder

color

white

storage temp.

−20°C

Quality Level

200

Gene Information

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

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Ta pozycja	M4171	M212	A9459
Sigma-Aldrich M5280 Mastoparan, Vespula lewisii	Sigma-Aldrich M4171 Melittin	Sigma-Aldrich M212 Mastoparan-7	Sigma-Aldrich A9459 Apamin
assay ≥97% (HPLC)	assay ≥97% (HPLC)	assay ≥97% (HPLC)	assay ≥97% (HPLC)
biological source synthetic	biological source -	biological source -	biological source synthetic
Quality Level 200	Quality Level 200	Quality Level 200	Quality Level 200
form powder	form -	form lyophilized powder	form powder
storage temp. −20°C	storage temp. −20°C	storage temp. −20°C	storage temp. −20°C
Gene Information human ... CALM1(801), PLA2R1(22925) mouse ... CALM1(12313), PLA2R1(18779) rat ... CALM1(24242), PLA2R1(295631)	Gene Information human ... ATP1A1(476), CALM1(801) mouse ... ATP1A1(11928), CALM1(12313) rat ... ATP1A1(24211), CALM1(24242)	Gene Information -	Gene Information rat ... Kcnn1(54261)

General description

Mastoparan is a cationic, amphiphilic, tetradecapeptide amide. It is composed of the restricted amino acid and the repeated sequence.[1] This protein is a nonspecific secretagogue isolated from venom of wasp.[2]

Application

Mastoparan has been used as a calmodulin antagonist.[3]

Biochem/physiol Actions

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

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.[2] 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.[4][5][6] Mastoparan helps in mitochondrial permeability transition by enhancing an apparent bimodal mechanism of action.[7]

Other Notes

Lyophilized from 0.1% TFA in H2O

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Klasa składowania

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Dokumenty związane z niedawno zakupionymi produktami zostały zamieszczone w Bibliotece dokumentów.

Odwiedź Bibliotekę dokumentów

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)

Enantiomer-specific bioactivities of peptidomimetic analogues of mastoparan and mitoparan: characterization of inverso mastoparan as a highly efficient cell penetrating peptide.

Sarah Jones et al.

Bioconjugate chemistry, 23(1), 47-56 (2011-12-14)

Retro-inverso transformation has commonly been employed as a strategy both for the synthesis of proteolytically stable peptide analogues and for the detailed investigation of structure activity relationships. Herein, we adopted a similar strategy to probe the structure activity relationships of

Activation of Phospholipase A2 by Auxin and Mastoparan in Hypocotyl Segments from Zucchini and Sunflower

Scherer GFE

Journal of Plant Physiology, 145, 483-490 (1995)

Single-transmembrane domain IGF-II/M6P receptor: potential interaction with G protein and its association with cholesterol-rich membrane domains.

Asha Amritraj et al.

Endocrinology, 153(10), 4784-4798 (2012-08-21)

The IGF-II/mannose 6-phosphate (M6P) receptor is a single-transmembrane domain glycoprotein that plays an important role in the intracellular trafficking of lysosomal enzymes and endocytosis-mediated degradation of IGF-II. The receptor may also mediate certain biological effects in response to IGF-II binding

Influence of the bilayer composition on the binding and membrane disrupting effect of Polybia-MP1, an antimicrobial mastoparan peptide with leukemic T-lymphocyte cell selectivity.

Marcia Perez dos Santos Cabrera et al.

Biochemistry, 51(24), 4898-4908 (2012-05-29)

This study shows that MP-1, a peptide from the venom of the Polybia paulista wasp, is more toxic to human leukemic T-lymphocytes than to human primary lymphocytes. By using model membranes and electrophysiology measurements to investigate the molecular mechanisms underlying

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Mastoparan, Vespula lewisii