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.
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
DPDPE (D-Pen2, D-Pen5-enkephalin) is a synthetic peptide belonging to the class of enkephalin analogs, specifically designed to mimic endogenous opioid peptides. Structurally, it incorporates D-amino acid substitutions that confer enhanced metabolic stability and receptor selectivity, making it a valuable tool in opioid receptor research. The compound exhibits high affinity and selectivity for the delta-opioid receptor (DOR), distinguishing it from other opioid peptides and allowing researchers to dissect the physiological and pharmacological roles of delta-opioid signaling pathways. Due to its unique biochemical properties, DPDPE has become a staple in neuropharmacology and peptide-receptor interaction studies, facilitating the exploration of opioid mechanisms at the molecular and cellular levels.
Receptor Binding Studies: DPDPE is widely employed in binding assays to characterize the selectivity and affinity of ligands for the delta-opioid receptor. Its well-defined interaction profile enables precise mapping of receptor-ligand binding domains, supporting the development of new opioid ligands with improved pharmacological properties. Researchers utilize this peptide to benchmark the efficacy of novel compounds, investigate competitive binding dynamics, and elucidate the structural determinants of receptor specificity, thereby advancing the understanding of opioid receptor pharmacology.
Signal Transduction Analysis: In cellular and biochemical assays, DPDPE serves as a potent agonist for the delta-opioid receptor, making it instrumental in studying receptor-mediated signal transduction pathways. By activating DORs, the peptide allows researchers to monitor downstream effects such as G-protein coupling, second messenger production, and modulation of ion channel activity. These insights are crucial for unraveling the intracellular mechanisms underlying opioid receptor signaling and for identifying potential targets for selective modulation of neural pathways.
Peptide Structure-Activity Relationship (SAR) Investigations: The inclusion of D-amino acids in DPDPE provides a model system for exploring the impact of stereochemical modifications on peptide stability, receptor binding, and functional activity. Researchers leverage this compound to systematically assess how specific structural changes influence peptide-receptor interactions, informing the rational design of next-generation peptide therapeutics and research probes. Such studies contribute to a deeper understanding of the relationship between peptide conformation and biological activity.
Neuropharmacological Research: DPDPE is extensively used in neuropharmacological experiments to probe the physiological roles of delta-opioid receptors in neuronal tissues. Its selectivity enables researchers to isolate DOR-mediated effects from those of other opioid receptor subtypes, facilitating the study of pain modulation, synaptic transmission, and neurochemical signaling. Experimental applications include electrophysiological recordings, neurotransmitter release assays, and behavioral studies in model systems, all aimed at elucidating the functional significance of delta-opioid pathways in the central nervous system.
Peptide Stability and Metabolism Studies: The metabolic stability of DPDPE, owing to its D-amino acid content, makes it a valuable standard for investigating peptide degradation mechanisms and enzymatic processing in biological systems. Researchers use it to analyze the susceptibility of peptides to proteolytic enzymes, compare the stability of different analogs, and develop strategies for enhancing peptide half-life in experimental settings. These studies inform the optimization of peptide-based research tools and contribute to advances in peptide chemistry and pharmacokinetics.
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2. Adipose tissue is a key organ for the beneficial effects of GLP-2 metabolic function
3. High fat diet and GLP-1 drugs induce pancreatic injury in mice
5. TMEM16F and dynamins control expansive plasma membrane reservoirs
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