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Mastoparan-7

Name: Mastoparan-7
Brand: SIGMA

≥97% (HPLC), lyophilized powder

Synonym(s):

Mas 7

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About This Item

Empirical Formula (Hill Notation):

C₆₇H₁₂₄N₁₈O₁₅

CAS Number:

145854-59-7

Molecular Weight:

1421.81

MDL number:

MFCD00144726

UNSPSC Code:

41106300

PubChem Substance ID:

329817929

NACRES:

NA.77

Quality Level

200

Assay

≥97% (HPLC)

form

lyophilized powder

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

InChI

1S/C67H124N18O15/c1-18-38(12)53(71)67(100)85-51(32-52(70)86)66(99)84-50(31-37(10)11)64(97)79-45(24-20-22-26-69)61(94)75-42(16)58(91)82-47(28-34(4)5)62(95)76-39(13)55(88)73-40(14)57(90)81-48(29-35(6)7)63(96)77-41(15)56(89)78-44(23-19-21-25-68)60(93)74-43(17)59(92)83-49(30-36(8)9)65(98)80-46(54(72)87)27-33(2)3/h33-51,53H,18-32,68-69,71H2,1-17H3,(H2,70,86)(H2,72,87)(H,73,88)(H,74,93)(H,75,94)(H,76,95)(H,77,96)(H,78,89)(H,79,97)(H,80,98)(H,81,90)(H,82,91)(H,83,92)(H,84,99)(H,85,100)/t38-,39-,40-,41-,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,53-/m0/s1

InChI key

HOLQXBRPSSZJMZ-FGRXCANLSA-N

Amino Acid Sequence

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

General description

Mastoparan-7 is an analog of the mastoparan peptide. It is present in the venom of Vespula lewisii. It was originally isolated from wasp venom.

Application

Mastoparan-7 has been used to study mastoparan-stimulated nucleotide binding to G proteins.

Biochem/physiol Actions

Mastoparan-7 (Mas-7) stimulates the G protein subunit Gα_o/i by its mode of action (to bind to the plasma membrane). It possesses antiviral activity and is associated with histamine release from mast cells. It is also involved in the induction of potent mitochondrial permeability and tumor cell cytotoxicity.

Analysis Note

More potent analog of mastoparan.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Activation of GTP formation and high-affinity GTP hydrolysis by mastoparan in various cell membranes. G-protein activation via nucleoside diphosphate kinase, a possible general mechanism of mastoparan action.

J F Klinker et al.

Biochemical pharmacology, 51(3), 217-223 (1996-02-09)

The wasp venom, mastoparan (MP), is a direct activator of reconstituted pertussis toxin-sensitive G-proteins and of purified nucleoside diphosphate kinase (NDPK) [E.C. 2.6.4.6.]. In HL-60 membranes, MP activates high-affinity GTPase [E.C. 3.6.1.-] and NDPK-catalyzed GTP formation, but not photolabeling of

The heterotrimeric G-protein Gi is localized to the insulin secretory granules of beta-cells and is involved in insulin exocytosis.

R J Konrad et al.

The Journal of biological chemistry, 270(21), 12869-12876 (1995-05-26)

Mastoparan, a tetradecapeptide found in wasp venom that stimulates G-proteins, increases insulin secretion from beta-cells. In this study, we have examined the role of heterotrimeric G-proteins in mastoparan-induced insulin secretion from the insulin-secreting beta-cell line beta-TC3. Mastoparan stimulated insulin secretion

Drosophila GoLoco-protein Pins is a target of Galpha(o)-mediated G protein-coupled receptor signaling.

Damir Kopein et al.

Molecular biology of the cell, 20(17), 3865-3877 (2009-07-03)

G protein-coupled receptors (GPCRs) transduce their signals through trimeric G proteins, inducing guanine nucleotide exchange on their Galpha-subunits; the resulting Galpha-GTP transmits the signal further inside the cell. GoLoco domains present in many proteins play important roles in multiple trimeric

Mastoparan may activate GTP hydrolysis by Gi-proteins in HL-60 membranes indirectly through interaction with nucleoside diphosphate kinase.

J F Klinker et al.

The Biochemical journal, 304 ( Pt 2), 377-383 (1994-12-01)

The wasp venom, mastoparan (MP), activates reconstituted pertussis toxin (PTX)-sensitive G-proteins in a receptor-independent manner. We studied the effects of MP and its analogue, mastoparan 7 (MP 7), on G-protein activation in HL-60 cells and a reconstituted system and on

Fluorescent BODIPY-GTP analogs: real-time measurement of nucleotide binding to G proteins.

D P McEwen et al.

Analytical biochemistry, 291(1), 109-117 (2001-03-23)

Three BODIPY GTPgammaS analogs (FL, 515, and TR), BODIPY FL GppNHp and BODIPY FL GTP molecules were synthesized as possible fluorescent probes to study guanine nucleotide binding spectroscopically. Binding to G(alphao) increases baseline analog fluorescence by 6-, 8.5-, 2.8-, 3.5-

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