| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
|
||
| 5mg |
|
||
| Other Sizes |
| Targets |
δ Opioid Receptor/DOR
delta-opioid receptor (DOR). DPDPE is a selective delta-opioid receptor agonist. The D-penicillamine residues at positions 2 and 5 form a disulfide bridge, which stabilizes the cyclic conformation necessary for high delta-receptor selectivity and potency. |
|---|---|
| ln Vitro |
DPDPE inhibits electrically stimulated contraction of the mouse vas deferens in vitro with an EC50 of 5.2 nM. It shows very weak activity at micro- and kappa-opioid receptors, confirming high selectivity for the delta subtype. DPDPE also exhibits anticonvulsant effects in seizure models, which are mediated via delta receptor activation.
|
| ln Vivo |
DPDPE has anticonvulsant effects in rats at doses of 70 or 140 nM (icv; once)[1]. Bicuculline-induced convulsions in mice are enhanced by DPDPE (0.78–25 μg/mouse; icv; once)[2].
DPDPE is antinociceptive in vivo. It produces centrally mediated analgesia in animal models of pain, including the tail-flick and hot-plate tests in mice and rats following intracerebroventricular (i.c.v.) or intrathecal administration. The antinociceptive effects are reversed by the delta-selective antagonist naltrindole, confirming delta receptor involvement. It is not analgesic when administered systemically due to poor CNS penetration. |
| Enzyme Assay |
Cell-free delta-opioid receptor binding assays are performed using membranes from CHO-K1 cells stably expressing the human delta-opioid receptor or from mouse brain (minus cerebellum). Membranes are incubated with 0.5-2 nM [3H]-naltrindole (or [3H]-DPDPE) and increasing concentrations of unlabeled DPDPE (0.01-10,000 nM) in 50 mM Tris-HCl (pH 7.4) containing 1 mM EDTA, 1 mM MgCl2, and 0.1% BSA for 60-90 min at 25degC. Bound radioactivity is separated by GF/B filtration. Ki values are calculated by nonlinear regression using the Cheng-Prusoff equation. DPDPE is highly selective for delta over micro and kappa receptors.
|
| Cell Assay |
Mouse vas deferens functional assay: Male mouse vas deferens is dissected, cleaned, and suspended in organ baths containing oxygenated Krebs solution at 37degC. Tissues are stimulated electrically (0.1 Hz, 1 ms, suprathreshold voltage) through platinum electrodes. After stable twitch responses are achieved, DPDPE (0.1-1000 nM) is added cumulatively to the bath, and inhibition of contraction amplitude is recorded. The EC50 (5.2 nM) is calculated from the concentration-response curve. For cell-based assays, CHO cells expressing delta receptors are loaded with Fluo-4 AM; DPDPE-induced calcium changes or cAMP inhibition (HTRF) can be measured as functional readouts.
|
| Animal Protocol |
Animal/Disease Models: Male Sprague- Dawley rats (225-275 g)[1]
Doses: 70 or 140 nM followed by a 2 μl saline flush Route of Administration: Intracerebroventricular injection Experimental Results: Resulted in a significant, dose-dependent increase in the convulsive threshold to flurothyl. Animal/Disease Models: Male ddY mice weighing 20–30 g, pretreated with 1.5 mg/kg bicuculline (subcutaneous (sc) injection)[2]. Doses: 0.78–25 μg/mouse, once Route of Administration: Intracerebroventricular injection Experimental Results: Caused a dose-dependent increase in the proportion of mice exhibiting convulsions. For antinociception studies, DPDPE is dissolved in sterile saline or artificial CSF. It is administered centrally via i.c.v. (1-20 ug/mouse) or intrathecal (i.t.) injection (0.5-10 ug/mouse). Analgesia is assessed by the tail-flick test (radiant heat) or hot-plate test (55degC) at 5, 10, 15, and 30 min post-injection. Antinociceptive responses are expressed as percentage of maximal possible effect (%MPE). Reversal studies use naltrindole (delta antagonist) administered 10 min prior to DPDPE to confirm delta receptor involvement. For anticonvulsant studies, DPDPE is administered i.c.v. to mice 10 min before seizure induction by pentylenetetrazole (PTZ). Seizure latency and severity are scored. |
| ADME/Pharmacokinetics |
DPDPE is a cyclic peptide and is not orally bioavailable. Following i.c.v. or i.t. administration, DPDPE distributes within the CNS and has an elimination half-life of approximately 20-40 min due to rapid enzymatic degradation by peptidases in brain tissue. It has minimal systemic absorption after central administration. The molecular weight is 645.79 (C30H39N5O7S2). Solubility: H2O 1 mg/mL (sonication recommended). Sequence: Tyr-D-Pen-Gly-Phe-D-Pen (disulfide bridge: Pen2-Pen5). Storage: -20degC, dry, away from moisture.
|
| Toxicity/Toxicokinetics |
No specific toxicity data are reported for DPDPE. In published studies at the doses used for analgesia (1-20 ug/mouse i.c.v.), no overt signs of toxicity (seizures, respiratory depression, or mortality) have been reported. However, standard toxicological assessments (hERG, Ames, repeat-dose toxicity) have not been performed. The compound has not advanced to clinical development. Seizure risk has not been systematically evaluated beyond anticonvulsant studies.
|
| References | |
| Additional Infomation |
DPDPE is a heterocyclic peptide, belonging to the cyclic enkephalin analogues, with D-penicillamine residues linked at positions 2 and 5, forming a heterocyclic ring via disulfide bonds. It is a delta-opioid receptor agonist.
A heterocyclic peptide, belonging to the cyclic enkephalin analogues, with D-penicillamine residues linked at positions 2 and 5, forming a heterocyclic ring via disulfide bonds. A disulfide-bonded opioid pentapeptide that selectively binds to delta-opioid receptors and possesses analgesic activity. Other information: DPDPE (CAS# 88373-73-3) is a research-grade peptide, not FDA-approved. Purity ≥95% (commonly ≥98%). Synonyms: (D-Pen2,D-Pen5)-Enkephalin. DPDPE is a prototypical delta-opioid receptor agonist and a standard reference tool in opioid pharmacology. It is widely used to characterize delta receptor-mediated effects in vitro and in vivo, including analgesia, anticonvulsant activity, and receptor signaling studies. For research use only. |
| Molecular Formula |
C30H39N5O7S2
|
|---|---|
| Molecular Weight |
645.79
|
| Exact Mass |
645.229
|
| CAS # |
88373-73-3
|
| Related CAS # |
DPDPE TFA;172888-59-4
|
| PubChem CID |
104787
|
| Appearance |
White to off-white solid powder
|
| Density |
1.4±0.1 g/cm3
|
| Boiling Point |
1038.6±65.0 °C at 760 mmHg
|
| Flash Point |
581.9±34.3 °C
|
| Vapour Pressure |
0.0±0.3 mmHg at 25°C
|
| Index of Refraction |
1.653
|
| LogP |
2.24
|
| Hydrogen Bond Donor Count |
7
|
| Hydrogen Bond Acceptor Count |
10
|
| Rotatable Bond Count |
7
|
| Heavy Atom Count |
44
|
| Complexity |
1040
|
| Defined Atom Stereocenter Count |
4
|
| SMILES |
CC1([C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(SS1)(C)C)C(=O)O)CC2=CC=CC=C2)NC(=O)[C@H](CC3=CC=C(C=C3)O)N)C
|
| InChi Key |
MCMMCRYPQBNCPH-WMIMKTLMSA-N
|
| InChi Code |
InChI=1S/C30H39N5O7S2/c1-29(2)23(34-25(38)20(31)14-18-10-12-19(36)13-11-18)27(40)32-16-22(37)33-21(15-17-8-6-5-7-9-17)26(39)35-24(28(41)42)30(3,4)44-43-29/h5-13,20-21,23-24,36H,14-16,31H2,1-4H3,(H,32,40)(H,33,37)(H,34,38)(H,35,39)(H,41,42)/t20-,21-,23-,24-/m0/s1
|
| Chemical Name |
(4S,7S,13S)-13-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-7-benzyl-3,3,14,14-tetramethyl-6,9,12-trioxo-1,2-dithia-5,8,11-triazacyclotetradecane-4-carboxylic acid
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
H2O: 10 mg/mL (15.48 mM)
|
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.5485 mL | 7.7425 mL | 15.4849 mL | |
| 5 mM | 0.3097 mL | 1.5485 mL | 3.0970 mL | |
| 10 mM | 0.1548 mL | 0.7742 mL | 1.5485 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
