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E7131 Sigma-Aldrich

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

≥95% (HPLC)

Synonym: DADLE

  • CAS Number 94825-57-7

  • Empirical Formula (Hill Notation) C29H39N5O7

  • Molecular Weight 569.65

  •  MDL number MFCD00133947

  •  PubChem Substance ID 329799004

  •  NACRES NA.32

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Properties

Related Categories Cell Biology, Cell Signaling and Neuroscience, Enkephalins, Neuropeptides, Opioid Peptides,
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)

Description

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

[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.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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