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E7131

Sigma-Aldrich

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

≥95% (HPLC)

Sinonimo/i:

DADLE

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About This Item

Formula empirica (notazione di Hill):
C29H39N5O7
Numero CAS:
94825-57-7
Peso molecolare:
569.65
Numero MDL:
MFCD00133947
Codice UNSPSC:
12352209
ID PubChem:
329799004
NACRES:
NA.32

Livello qualitativo

200

Saggio

≥95% (HPLC)

Temperatura di conservazione

−20°C

Stringa SMILE

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
YRZBXSPTRALQEX-IIKZURRYSA-N

Informazioni sul gene

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

Amino Acid Sequence

Tyr-Ala-Gly-Phe-Leu

Descrizione generale

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

Applicazioni

[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.

Azioni biochim/fisiol

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
SLBZ8480
SLBR0070V
SLBK8814V
SLBF0742V
091M5066V

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Naltrexone solution 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material, Cerilliant®

Supelco

N-007

Naltrexone solution

β-Endorphin rat ≥97% (HPLC)

Sigma-Aldrich

E1142

β-Endorphin rat

Ser-Phe-Leu-Leu-Arg-Asn-Pro-Asn-Asp-Lys-Tyr-Glu-Pro-Phe ≥97% (HPLC)

Sigma-Aldrich

S7152

Ser-Phe-Leu-Leu-Arg-Asn-Pro-Asn-Asp-Lys-Tyr-Glu-Pro-Phe

HPLC peptide standard mixture analytical standard

Supelco

H2016

HPLC peptide standard mixture

Sieroalbumina heat shock fraction, protease free, fatty acid free, essentially globulin free, pH 7, ≥98%

Sigma-Aldrich

A7030

Sieroalbumina

Perossido di idrogeno 30 % (w/w) in H2O, contains stabilizer

Sigma-Aldrich

H1009

Perossido di idrogeno

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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