E7131

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

≥95% (HPLC)

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

Properties

• Quality Segment: 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)

Description

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 p70^s6k 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]

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)