DADLE
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MedKoo CAT#: 574348

CAS#: 63631-40-3

Description: DADLE is a prototypical δ-opioid receptor agonist that displays activity at the μ-opioid receptor and antinociceptive activity in vivo.


Chemical Structure

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DADLE
CAS# 63631-40-3

Theoretical Analysis

MedKoo Cat#: 574348
Name: DADLE
CAS#: 63631-40-3
Chemical Formula: C29H39N5O7
Exact Mass: 569.2849
Molecular Weight: 569.66
Elemental Analysis: C, 61.15; H, 6.90; N, 12.29; O, 19.66

Price and Availability

Size Price Availability Quantity
1.0mg USD 220.0 2 Weeks
5.0mg USD 370.0 2 Weeks
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Synonym: DADLE

IUPAC/Chemical Name: L-tyrosyl-D-alanylglycyl-L-phenylalanyl-D-leucine

InChi Key: ZHUJMSMQIPIPTF-IBURTVSXSA-N

InChi Code: InChI=1S/C29H39N5O7/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/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)/t18-,22+,23+,24-/m1/s1

SMILES Code: [H]N[C@@H](CC1=CC=C(O)C=C1)C(=O)N[C@H](C)C(=O)NCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@H](CC(C)C)C(O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Product Data:

Biological target: DADLE is a peptide agonist of δ-opioid receptors (Ki = 2.06 nM in a radioligand binding assay) that is selective for δ-opioid over κopioid receptors (Ki = 16,000 nM) but also agonizes μ-opioid receptors (Ki = 13.8 nM).
In vitro activity: This study showed that DOR stimulation with DADLE (0.1 μmol/L) for 2 d selectively activates the PI3K/Akt/NF-κB pathway in NaN3-treated neurons; this activation increased Bcl-2 expression, attenuated Cyto c release and promoted neuronal survival. Further investigation revealed that sustained DADLE stimulation increased Bcl-2 expression by enhancing NF-κB binding to the Bcl-2 promoter and upregulating the histone acetylation levels of the Bcl-2 promoter. The results demonstrate that prolonged DADLE exposure epigenetically promotes Bcl-2 expression and elicits neuroprotective effects in the NaN3 model via the PI3K/Akt/NF-κB pathway. Reference: Acta Pharmacol Sin. 2018 Oct; 39(10): 1582–1589. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6289365/
In vivo activity: DADLE postconditioning protection of hippocampal CA1 neurons against transient forebrain ischemia was tested. 6 days after being implanted with cannula at the right lateral ventricle, rats underwent 10 min of forebrain ischemia by four vessel occlusion. The results showed that DADLE at doses of 0.25 and 2.5 nmol, but not 25 nmol, could significantly protect CA1 neurons against ischemia/reperfusion injury. Furthermore, DADLE postconditioning exhibited cognitive benefits in rats with transient forebrain ischemia. The study thus suggested a therapeutic opportunity of postconditioning neuroprotection by DADLE and also provided important information in understanding the mechanism of DADLE action in the ischemic brain. Reference: Eur J Pharmacol. 2011 May 11;658(2-3):140-4. https://pubmed.ncbi.nlm.nih.gov/21349267/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 25.0 43.89
DMF 25.0 43.89

Preparing Stock Solutions

The following data is based on the product molecular weight 569.66 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Wang S, Cao X, Duan Y, Zhang G. Delta Opioid Peptide [d-Ala2, d-Leu5] Enkephalin (DADLE) Exerts a Cytoprotective Effect in Astrocytes Exposed to Oxygen-Glucose Deprivation by Inducing Autophagy. Cell Transplant. 2019 Jun;28(6):775-782. doi: 10.1177/0963689719825619. Epub 2019 Jan 22. PMID: 30666890; PMCID: PMC6686437. 2. Zhu M, Liu M, Guo QL, Zhu CQ, Guo JC. Prolonged DADLE exposure epigenetically promotes Bcl-2 expression and elicits neuroprotection in primary rat cortical neurons via the PI3K/Akt/NF-κB pathway. Acta Pharmacol Sin. 2018 Oct;39(10):1582-1589. doi: 10.1038/aps.2018.7. Epub 2018 May 24. PMID: 29795362; PMCID: PMC6289365. 3. Lai Z, Gu L, Yu L, Chen H, Yu Z, Zhang C, Xu X, Zhang M, Zhang M, Ma M, Zhao Z, Zhang J. Delta opioid peptide [d-Ala2, dLeu5] enkephalin confers neuroprotection by activating delta opioid receptor-AMPK-autophagy axis against global ischemia. Cell Biosci. 2020 Jun 15;10:79. doi: 10.1186/s13578-020-00441-z. PMID: 32549974; PMCID: PMC7294676. 4. Wang S, Duan Y, Su D, Li W, Tan J, Yang D, Wang W, Zhao Z, Wang X. Delta opioid peptide [D-Ala2, D-Leu5] enkephalin (DADLE) triggers postconditioning against transient forebrain ischemia. Eur J Pharmacol. 2011 May 11;658(2-3):140-4. doi: 10.1016/j.ejphar.2011.02.006. Epub 2011 Feb 22. PMID: 21349267.
In vitro protocol: 1. Wang S, Cao X, Duan Y, Zhang G. Delta Opioid Peptide [d-Ala2, d-Leu5] Enkephalin (DADLE) Exerts a Cytoprotective Effect in Astrocytes Exposed to Oxygen-Glucose Deprivation by Inducing Autophagy. Cell Transplant. 2019 Jun;28(6):775-782. doi: 10.1177/0963689719825619. Epub 2019 Jan 22. PMID: 30666890; PMCID: PMC6686437. 2. Zhu M, Liu M, Guo QL, Zhu CQ, Guo JC. Prolonged DADLE exposure epigenetically promotes Bcl-2 expression and elicits neuroprotection in primary rat cortical neurons via the PI3K/Akt/NF-κB pathway. Acta Pharmacol Sin. 2018 Oct;39(10):1582-1589. doi: 10.1038/aps.2018.7. Epub 2018 May 24. PMID: 29795362; PMCID: PMC6289365.
In vivo protocol: 1. Lai Z, Gu L, Yu L, Chen H, Yu Z, Zhang C, Xu X, Zhang M, Zhang M, Ma M, Zhao Z, Zhang J. Delta opioid peptide [d-Ala2, dLeu5] enkephalin confers neuroprotection by activating delta opioid receptor-AMPK-autophagy axis against global ischemia. Cell Biosci. 2020 Jun 15;10:79. doi: 10.1186/s13578-020-00441-z. PMID: 32549974; PMCID: PMC7294676. 2. Wang S, Duan Y, Su D, Li W, Tan J, Yang D, Wang W, Zhao Z, Wang X. Delta opioid peptide [D-Ala2, D-Leu5] enkephalin (DADLE) triggers postconditioning against transient forebrain ischemia. Eur J Pharmacol. 2011 May 11;658(2-3):140-4. doi: 10.1016/j.ejphar.2011.02.006. Epub 2011 Feb 22. PMID: 21349267.

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Mulder et al (1991) Pharmacological profile of various κ-agonists at κ-, μ- and δ-opioid receptors mediating presynaptic inhibition of neurotransmitter release in the rat brain. Br.J.Pharmacol. 102 518 PMID: 1673074

Ke et al (2009) Delta opioid agonist [D-Ala2, D-Leu5] enkephalin (DADLE) reduced oxygen-glucose deprivation caused neuronal injury through the MAPK pathway. Brain Res. 1292 100 PMID: 19619518

Suh and Tseng (1990) Different types of opioid receptors mediating analgesia induced by morphine, DAMGO, DPDPE, DADLE and beta-endorphin in mice. Naunyn-Schmied.Arch.Pharmacol. 342 67

DADLE

1.0mg / USD 220.0