DADLE | CAS# 63631-40-3 | Antinociceptive

MedKoo Cat#: 574348 | Name: DADLE

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Chemical Structure

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
10mg	USD 450.00	2 Weeks

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Synonym

DADLE; [D-Ala2, D-Leu5]-Enkephalin; H-TYR-D-ALA-GLY-PHE-D-LEU-OH

IUPAC/Chemical Name

(2R)-2-[[(2S)-2-[[2-[[(2R)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoic acid

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

More Info

Product Data

Product Data

Instruction

View handling instruction

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/

	Solvent	mg/mL	mM
Solubility
	DMSO	25.0	43.89
	DMF	25.0	43.89

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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:

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.

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