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DPDPE (trifluoroacetate salt)

(Synonyms: D-Pen2,D-Pen5Enkephalin) Catalog No.: GC43568

DPDPE is a synthetic enkephalin peptide and δ-opioid receptor agonist (Ki = 2.7 nM in rat brain homogenates).

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DPDPE (trifluoroacetate salt) Chemical Structure

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DPDPE is a synthetic enkephalin peptide and δ-opioid receptor agonist (Ki = 2.7 nM in rat brain homogenates). DPDPE has greater than 250-fold selectivity for the δ-opioid receptor over the μ- and κ-opioid receptors in rat brain homogenates (Kis = 713 and >1,500 nM, respectively). It also selectively inhibits electrically-evoked contractions in mouse vas deferens over guinea pig myenteric plexus (IC50s = 4.14 and 3,000 nM, respectively), which does not express the δ-opioid receptor. In vivo, DPDPE (140 nmol, i.v.) completely blocks tonic hindlimb extension induced by maximal electroshock (MES) in 50% of tested rats and increases the flurothyl-induced seizure threshold by 15-20% in rats, effects that can be blocked by the selective δ-opioid receptor antagonist ICI 154129. DPDPE (1-10 μg, i.v) dose-dependently reduces formalin-induced paw licking and lifting, indicating analgesia, in rats. However, DPDPE (15 μg, i.v.) increases the latency to tail withdrawal in the tail-immersion test in both wild-type and δ-opioid receptor knockout mice by 6.74 and 7.6 seconds, respectively, compared to a saline control, but not in μ-opioid receptor knockout mice, and the effect can be blocked by the μ-opioid receptor antagonist CTOP.

Chemical Properties

Cas No. SDF
Synonyms D-Pen2,D-Pen5Enkephalin
Canonical SMILES CC([C@H](C(O)=O)NC1=O)(C)SSC(C)(C)[C@@H](NC([C@@H](N)CC2=CC=C(O)C=C2)=O)C(NCC(N[C@H]1CC3=CC=CC=C3)=O)=O.FC(F)(C(O)=O)F
Formula C30H39N5O7S2•XCF3COOH M.Wt 645.8
Solubility Water: 1 mg/ml Storage Store at -20°C
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
Shipping Condition Evaluation sample solution : ship with blue ice
All other available size: ship with RT , or blue ice upon request

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Research Update

The role of nitric oxide in the local antiallodynic and antihyperalgesic effects and expression of delta-opioid and cannabinoid-2 receptors during neuropathic pain in mice

J Pharmacol Exp Ther 2010 Sep 1;334(3):887-96.PMID:20498253DOI:10.1124/jpet.110.167585

Both delta-opioid receptor (DOPr) and cannabinoid-2 receptor (CB2R) agonists attenuate neuropathic pain, but the precise mechanism implicated in these effects is not completely elucidated. We investigated whether nitric oxide synthesized by neuronal (NOS1) or inducible (NOS2) nitric-oxide synthases could modulate DOPr and/or CB2R antiallodynic and antihyperalgesic effects through the peripheral nitric oxide-cGMP-protein kinase G (PKG) pathway activation and affect their expression during neuropathic pain. In wild-type (WT) mice at 21 days after chronic constriction of sciatic nerve, we evaluated the effects of [d-Pen(2),d-Pen(5)]-enkephalin (DPDPE); (2-methyl-1-propyl-1H-indol-3-yl)-1-naphthalenylmethanone (JWH-015); and a NOS1 [N-[(4S)-4-amino-5-[(2-aminoethyl)amino]pentyl]-N'-nitroguanidine tris(trifluoroacetate) salt; NANT], NOS2 [l-N(6)-(1-iminoethyl)-lysine; l-NIL], l-guanylate cyclase [1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one; ODQ], or PKG [(Rp)-8-(para-chlorophenylthio)guanosine-3',5'-cyclic monophosphorothioate; Rp-8-pCPT-cGMPs] inhibitor administered alone or combined. Expression of DOPr and CB2R mRNA in the spinal cord and dorsal root ganglia of naive and nerve-injured WT, NOS1-knockout (KO), and NOS2-KO mice, also was assessed. The subplantar administration of NANT, l-NIL, ODQ, or Rp-8-pCPT-cGMPs dose-dependently inhibited neuropathic pain and enhanced the local effects of DPDPE or JWH-015. Moreover, although the basal levels of DOPr and CB2R mRNA were similar between WT and NOS-KO animals, nerve injury only decreased (DOPr) or increased (CB2R) their expression in the dorsal root ganglia of WT and NOS2-KO mice, and not in NOS1-KO mice. Results suggest that inactivation of the nitric oxide-cGMP-PKG peripheral pathway triggered by NOS1 and NOS2 enhanced the peripheral actions of DOPr and CB2R agonists and that nitric oxide synthesized by NOS1 is implicated in the peripheral regulation of DOPr and CB2R gene transcription during neuropathic pain.


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Average Rating: 5 ★★★★★ (Based on Reviews and 14 reference(s) in Google Scholar.)

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