Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

E7131

Sigma-Aldrich

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

≥95% (HPLC)

Synonym(s):

DADLE

Sign Into View Organizational & Contract Pricing
All Photos(1)

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
Pricing and availability is not currently available.

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.[1]

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[2] and to assess the analgesic effect of WIN55,212-2 in mice.[3]

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.[1] 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.[4]

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SLBZ8480
SLBR0070V
SLBK8814V
SLBF0742V
091M5066V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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 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
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
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
View All Related Papers

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service