DPDPE

DPDPE is a selective δ-opioid receptor agonist peptide that inhibits electrically stimulated contraction of mouse vas deferens in vitro and is antinociceptive in vivo. DPDPE is a heterodetic cyclic peptide that is a cyclic enkephalin analogue, having D-penicillaminyl residues located at positions 2 and 5, which form the heterocycle via a disulfide bond. It has a role as a delta-opioid receptor agonist.

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CAT#	R1918
Chemical Structure
CAS	88373-73-3
Synonyms/Alias	DPDPE; [D-Pen2,5]Enkephalin; [D-Pen2,D-Pen5]Enkephalin
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
M.F/Formula	C30H39N5O7S2
M.W/Mr.	645.79
Sequence	One Letter Code: YXGFX Three Letter Code: H-Tyr-D-Pen(1)-Gly-Phe-D-Pen(1)-OH
Application	Opioid Research
Appearance	Solid powder
Activity	Agonist
Biological Activity	Prototypical selective δ-opioid receptor agonist peptide. Inhibits electrically stimulated contraction of mouse vas deferens in vitro (EC50 = 5.2 nM), and is antinociceptive in vivo.

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Storage	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
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.
InChI	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
InChI Key	MCMMCRYPQBNCPH-WMIMKTLMSA-N
Canonical SMILES	CC1(C(C(=O)NCC(=O)NC(C(=O)NC(C(SS1)(C)C)C(=O)O)CC2=CC=CC=C2)NC(=O)C(CC3=CC=C(C=C3)O)N)C
Isomeric 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
References	1. Chandrakumar et al (1992) Analogs of the δ opioid receptor selective cyclic peptide [2-D-penicillamine,5-D-penicillamine]-enkephalin: 2',6'-dimethyltyrosine and Gly3-Phe4 amide bond isostere substitutions. J.Med.Chem. 35 2928 PMID: 1323677 2. Clark et al (1986) [D-Pen2,D-Pen5]enkephalin (DPDPE): a δ-selective enkephalin with low affinity for μ1 opiate binding sites. Eur.J.Pharmacol. 128 303 PMID: 3025000 3. Fraser et al (2000) Supraspinal antinociceptive response to [D-Pen2,5]-enkephalin (DPDPE) is pharmacologically distince from that to other δ-agonists in the rat. J.Pharmacol.Exp.Ther. 295 1135 PMID: 11082450