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 No: R1918

CAS No: 88373-73-3

Synonyms/Alias: DPDPE;88373-73-3;(D-Pen2,D-Pen5)-Enkephalin;2,5-Pen-enkephalin;DPLPE;Bis-penicillamine-enkephalin;Enkephalin, D-penicillamine (2,5)-;D-penicillamine-(2,5)-enkephalin;c[D-Pen(2,5)]-enkephalin;(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;(4s,7s,13s)-7-benzyl-3,3,14,14-tetramethyl-6,9,12-trioxo-13-(l-tyrosylamino)-1,2-dithia-5,8,11-triazacyclotetradecane-4-carboxylic acid;CHEBI:73356;cyclo-[D-Pen(2,5)]-enkephalin;[D-Pen(2)-D-Pen(5)]-enkephaline;H-Tyr-c(D-Pen-Gly-Phe-D-Pen)-OH;Pen(2),pen(5)-enkephalin;CHEMBL31421;H-Tyr-cyclo-(D-Pen-Gly-Phe-D-Pen)-OH;cyclo-[D-Pen2,5]-enkephalin;[D-Pen2-D-Pen5]-enkephaline;Enkephalin, penicillamine(2,5)-;DTXSID201008102;(D-Pen(2),D-pen(5))enkephalin;LY 198572;[3H]DPDPE;D-Valine, L-tyrosyl-3-mercapto-D-valylglycyl-L-phenylalanyl-3-mercapto-, cyclic (2-5)-disulfide;L-tyrosyl-3-mercapto-D-valylglycyl-L-phenylalanyl-3-mercapto-D-valine, cyclic (2-5)-disulfide;(D-Pen2,Pen5)-Enkephalin;c(D-Pen(2,5))-enkephalin;cyclo-(D-Pen2,5)-enkephalin;(D-Pen2-D-Pen5)-enkephaline;cyclo-(D-Pen(2,5))-enkephalin;(D-Pen(2)-D-Pen(5))-enkephaline;Bis-pen-enkephalin;Bis Pen Enkephalin;(4S,7S,13S)-13-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-3,3,14,14-tetramethyl-6,9,12-trioxo-7-(phenylmethyl)-1,2-dithia-5,8,11-triazacyclotetradecane-4-carboxylic acid;Dpdpe(SH)2;D-Pen5-Enkephalin D-Pen2;D Pen2, D Pen5 Enkephalin;D-Pen2, D-Pen5-Enkephalin;D-Pen2, L-Pen5-Enkephalin;D-Penicillamine (2,5)-Enkephalin;(4S,7S,13S)-13-(((2S)-2-amino-3-(4-hydroxyphenyl)propanoyl)amino)-3,3,14,14-tetramethyl-6,9,12-trioxo-7-(phenylmethyl)-1,2-dithia-5,8,11-triazacyclotetradecane-4-carboxylic acid;Enkephalin, Penicillamine (2,5)-;DPDPE-Cl;DPDPE-OH;[D-Pen2,5]Enkephalin;D-Pen2,D-Pen5]enkephalin;[D-Pen2,D-Pen5]enkephalin;SCHEMBL727022;[D-Pen2, D-Pen5]enkephalin;GTPL1608;BDBM21008;DTXCID501434946;Cyclic [D-Pen2, D-Pen5]enkephalin;Cyclic(D-penicillamine2,5)enkephalin;DB08861;BP108798;DA-63010;H-Tyr-D-Pen(1)-Gly-Phe-D-Pen(1)-OH;NS00071889;C20164;G12225;[2-D-Penicillamine, 5-D-penicillamine]enkephalin;[D-Pen2,5]-Enkephalin hydrate, >=95% (HPLC);Tyr-D-Pen-Gly-Phe-D-Pen [Disulfide Bridge: 2-5];Q27077106;1,2-Dithia-5,8,11-triazacyclotetradecane, cyclic peptide deriv.;Enkephalin, [Tyrosyl-2,6-3H(N)]- (2-D-Penicillamine, 5-D-Penicillamine);L-Tyrosyl-D-penicillamyl-glycyl-L-phenylalanyl-D-penicillamine (2->5)-disulfide;(4S,7S,13S)-13-((S)-2-amino-3-(4-hydroxyphenyl)propanamido)-7-benzyl-3,3,14,14-tetramethyl-6,9,12-trioxo-1,2-dithia-5,8,11-triazacyclotetradecane-4-carboxylic acid;(4S,7S,13S)-13-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-7-benzyl-3,3,14,14-tetramethyl-6,9,12-trioxo-1,2-dithia-5,8,11-triazacyclotetradecane-4-carboxylic acid;1,2-dithia-5,8,11-triazacyclotetradecane-4-carboxylic acid, 13-[[(2S)-2-amino-3-(4-hydroxyphenyl)-1-oxopropyl]amino]-3,3,14,14-tetramethyl-6,9,12-trioxo-7-(phenylmethyl)-, (4S,7S,13S)-;D-Valine, L-tyrosyl-3-mercapto-D-valylglycyl-L-phenylalanyl-3- mercapto-, cyclic (2-5)-disulfide;D-Valine, L-tyrosyl-3-mercapto-D-valylglycyl-L-phenylalanyl-3-mercapto-, cyclic (2>5)-disulfide (9CI);D-Valine, L-tyrosyl-3-mercapto-D-valylglycyl-L-phenylalanyl-3-mercapto-, cyclic (2?5)-disulfide;

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

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Specification Technical Data Publications Customer reviews and Q&A
M.F/FormulaC30H39N5O7S2
M.W/Mr.645.8
SequenceOne Letter Code:YXGFX
Three Letter Code:H-Tyr-D-Pen(1)-Gly-Phe-D-Pen(1)-OH
ApplicationOpioid Research
AppearanceSolid powder
ActivityAgonist
Biological ActivityPrototypical 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.
Long-term Storage ConditionsSoluble in DMSO
Shipping ConditionShipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
InChIInChI=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 KeyMCMMCRYPQBNCPH-WMIMKTLMSA-N
Canonical SMILESCC1(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 SMILESCC1([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
References1. 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

1. C-Peptide replacement therapy and sensory nerve function in type 1 diabetic neuropathy

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3. Myotropic activity and immunolocalization of selected neuropeptides of the burying beetle Nicrophorus vespilloides (Coleoptera: Silphidae)

4. Store-operated Ca2+ entry sustains the fertilization Ca2+ signal in pig eggs

5. An Open-label, Single-center, Safety and Efficacy Study of Eyelash Polygrowth Factor Serum

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