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E7131

Sigma-Aldrich

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

≥95% (HPLC)

Synonym(s):

DADLE

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About This Item

Empirical Formula (Hill Notation):
C29H39N5O7
CAS Number:
94825-57-7
Molecular Weight:
569.65
MDL number:
MFCD00133947
UNSPSC Code:
12352209
PubChem Substance ID:
329799004
NACRES:
NA.32

Quality Level

200

Assay

≥95% (HPLC)

storage temp.

−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

InChI key

YRZBXSPTRALQEX-IIKZURRYSA-N

Gene Information

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

Amino Acid Sequence

Tyr-Ala-Gly-Phe-Leu

General description

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

Application

[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 Actions

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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
L Vinod Kumar Reddy et al.
Life sciences, 191, 195-204 (2017-10-22)
Nutritional deprivation and inflammation-rich zones are the major causative reasons for poor survivability of transplanted mesenchymal stem cells (MSCs). Therefore in the present study, we demonstrated the cytoprotective and anti-inflammatory effects of activated delta (δ)-opioid receptor (DOR) with synthetic peptide
N A Shahabi et al.
Journal of neuroimmunology, 94(1-2), 48-57 (1999-06-22)
Delta opioid receptors (DOR) are G-protein coupled 7-transmembrane receptors (GPCR), expressed by thymic and splenic T cells, that modulate interleukin (IL)-2 production and proliferation in response to concanavalin A or crosslinking the TCR. Mitogen-activated protein kinases (MAPKs) are involved in
Mei-Rong Lv et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 93, 230-237 (2017-06-24)
The central objective was to identify the role of the PI3K-Akt activation pathway on the neuroprotection of δ-opioid receptor agonist (DADLE) against cerebral ischemia-reperfusion (I/R) injury in a rat model. Fifty-five male Sprague-Dawley (SD) rats were included to establish a
Zelin Lai et al.
Cell & bioscience, 10, 79-79 (2020-06-19)
Ischemic stroke poses a severe risk to human health worldwide, and currently, clinical therapies for the disease are limited. Delta opioid receptor (DOR)-mediated neuroprotective effects against ischemia have attracted increasing attention in recent years. Our previous studies revealed that DOR
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