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Dynamin inhibitory peptide, myristoylated

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An inhibitor of the GTPase dynamin that competitively blocks binding of dynamin to amphiphysin, preventing endocytosis.

Category

Peptide Inhibitors

Catalog number

BAT-010303

CAS number

251634-22-7

Molecular Formula

C61H107N19O14

Molecular Weight

1330.64

Dynamin inhibitory peptide, myristoylated

Specification
Reference Reading

IUPAC Name

(2S)-N-[(2S)-1-[(2S)-2-[[(2S)-1-[[(2S)-1-[(2S)-2-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-1-oxopropan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-1,4-dioxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-2-(tetradecanoylamino)pentanediamide

Synonyms

AKOS024456771; Dynamin inhibitory peptide,myristoylated; PD079118; S-251634-22-7

Appearance

White Solid

Purity

>99%

Density

1.4±0.1 g/cm3

Sequence

Myr-QVPSRPNRAP-NH2

Storage

Store at -20°C

InChI

InChI=1S/C61H107N19O14/c1-5-6-7-8-9-10-11-12-13-14-15-26-48(84)72-39(27-28-46(62)82)52(87)77-49(36(2)3)59(94)80-33-20-25-45(80)56(91)76-42(35-81)54(89)74-40(22-17-30-70-61(67)68)58(93)79-32-19-24-44(79)55(90)75-41(34-47(63)83)53(88)73-38(21-16-29-69-60(65)66)51(86)71-37(4)57(92)78-31-18-23-43(78)50(64)85/h36-45,49,81H,5-35H2,1-4H3,(H2,62,82)(H2,63,83)(H2,64,85)(H,71,86)(H,72,84)(H,73,88)(H,74,89)(H,75,90)(H,76,91)(H,77,87)(H4,65,66,69)(H4,67,68,70)/t37-,38-,39-,40-,41-,42-,43-,44-,45-,49-/m0/s1

InChI Key

IFTSFTVOMZTNME-ZUSDHBTASA-N

Canonical SMILES

CCCCCCCCCCCCCC(=O)NC(CCC(=O)N)C(=O)NC(C(C)C)C(=O)N1CCCC1C(=O)NC(CO)C(=O)NC(CCCN=C(N)N)C(=O)N2CCCC2C(=O)NC(CC(=O)N)C(=O)NC(CCCN=C(N)N)C(=O)NC(C)C(=O)N3CCCC3C(=O)N

1.Gbetagamma activation of Src induces caveolae-mediated endocytosis in endothelial cells.

Shajahan AN1, Tiruppathi C, Smrcka AV, Malik AB, Minshall RD. J Biol Chem. 2004 Nov 12;279(46):48055-62. Epub 2004 Sep 2.

Caveolae-mediated endocytosis in endothelial cells is stimulated by the binding of albumin to gp60, a specific albumin-binding protein localized in caveolae. The activation of gp60 induces its cell surface clustering and association with caveolin-1, the caveolar-scaffolding protein. This interaction leads to G(i)-induced Src kinase activation, which in turn signals dynamin-2-mediated fission and directed migration of caveolae-derived vesicles from apical to basal membrane. In this study, we investigated the possible role of the Gbetagamma heterodimer in signaling G(i)-induced Src activation and subsequent caveolae-mediated endocytosis. We observed using rat lung microvascular endothelial cells that expression of the C terminus of beta-adrenergic receptor kinase (ct-betaARK), an inhibitor Gbetagamma signaling, prevented gp60-dependent Src activation as well as caveolae-mediated endocytosis and transcellular transport of albumin and uptake of cholera toxin subunit B, a specific marker of caveolae internalization.