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E7131

Sigma-Aldrich

[D-Ala2, D-Leu5]-Enkephalin acetate salt

≥95% (HPLC)

Synonym(e):

DADLE

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About This Item

Empirische Formel (Hill-System):
C29H39N5O7
CAS-Nummer:
94825-57-7
Molekulargewicht:
569.65
MDL-Nummer:
MFCD00133947
UNSPSC-Code:
12352209
PubChem Substanz-ID:
329799004
NACRES:
NA.32

Qualitätsniveau

200

Assay

≥95% (HPLC)

Lagertemp.

−20°C

SMILES String

CC(O)=O.CC(C)C[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@@H](C)NC(=O)[C@@H](N)Cc2ccc(O)cc2)C(O)=O

InChI

1S/C29H39N5O7.C2H4O2/c1-17(2)13-24(29(40)41)34-28(39)23(15-19-7-5-4-6-8-19)33-25(36)16-31-26(37)18(3)32-27(38)22(30)14-20-9-11-21(35)12-10-20;1-2(3)4/h4-12,17-18,22-24,35H,13-16,30H2,1-3H3,(H,31,37)(H,32,38)(H,33,36)(H,34,39)(H,40,41);1H3,(H,3,4)/t18-,22+,23+,24-;/m1./s1

InChIKey

YRZBXSPTRALQEX-IIKZURRYSA-N

Angaben zum Gen

human ... OPRD1(4985)
mouse ... OPRD1(18386)
rat ... OPRD1(24613)

Amino Acid Sequence

Tyr-Ala-Gly-Phe-Leu

Allgemeine Beschreibung

[D-Ala2, D-Leu5]-Enkephalin acetate salt, also called DADLE, is an analog of endogenous δ-opioid peptide encephalin, and is metabolically stable.

Anwendung

[D-Ala2, D-Leu5]-Enkephalin or DADLE has been used for use in immunocomplex kinetic assay, to determine the activation of p70s6k by DADLE in the cell clones D2 and DOE and in non-transfected parental Rat-1 fibroblasts and to assess the analgesic effect of WIN55,212-2 in mice.

Biochem./physiol. Wirkung

Prototypical δ-agonist; more potent and selective than Leu-enkephalin and Met-enkephalin.
[D-Ala2, D-Leu5]-Enkephalin can induce hibernation in ground squirrels, during summers, when they do not normally hibernate. In multiorgan block preparation, it can prolong the survival time of organs such as, heart, lung, liver, spleen and kidney, up to 46hrs. It aids in tolerance development of myocardium to ischemia. It might have tissue protective role in central nervous system. It prevents and reverses methamphetamine (METH)-induced damage of dopaminergic terminals of brain. It prevents naltrexone-sensitive PC12 cell apoptosis in serum deprivation conditions. Thus, it might play an essential role in the survival of neurons and organs.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

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M A Wilson et al.
The Biochemical journal, 325 ( Pt 1), 217-222 (1997-07-01)
The regulation of mitogenic signalling pathways by G-protein-coupled receptors has been studied in Rat-1 fibroblasts stably transfected with the murine delta opioid receptor. We showed recently that stimulation of this receptor led to the activation of the p42 and p44
L I Tsao et al.
The Journal of pharmacology and experimental therapeutics, 287(1), 322-331 (1998-10-09)
Delta opioid peptide [D-Ala2,D-leu5]enkephalin (DADLE) can prolong organ preservation and increases myocardial tolerance to ischemia. Our study examined the protective property of DADLE against methamphetamine- (METH) induced dopaminergic terminal damage in the central nervous system. Because the neurotoxicity of METH
Yi Zhou et al.
Molecular medicine reports, 16(5), 6214-6221 (2017-09-14)
Hepatic ischemia/reperfusion (I/R) injury is a common pathophysiological process that occurs following liver surgery, which is associated with oxidative stress, and can cause acute liver injury and lead to liver failure. Recently, the development of drugs for the prevention of
Erfath Thanjeem Begum Moghal et al.
Cell biology international, 42(5), 543-569 (2017-12-23)
Parkinson's disease (PD) is the second most progressive neurodegenerative disease characterized by the loss of dopaminergic neurons and accumulation of misfolded proteins in endoplasmic reticulum (ER) leading to activation of the unfolded protein response (UPR). In the present study, we
T P Su
Journal of biomedical science, 7(3), 195-199 (2000-05-16)
By studying the hibernation in ground squirrels, a protein factor termed hibernation induction trigger (HIT) was found to induce hibernation in summer-active ground squirrels. Further purification of HIT yielded an 88-kD peptide that is enriched in winter hibernator. Partial sequence
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