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E3888

Sigma-Aldrich

[D-Pen2,5]-Enkephalin hydrate

≥95% (HPLC)

Synonyme(s) :

DPDPE

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About This Item

Formule empirique (notation de Hill):
C30H39N5O7S2 · xH2O
Poids moléculaire :
645.79 (anhydrous basis)
Numéro MDL:
MFCD00076430
Code UNSPSC :
12352209
ID de substance PubChem :
329799055
Nomenclature NACRES :
NA.32

Niveau de qualité

200

Pureté

≥95% (HPLC)

Température de stockage

−20°C

Chaîne SMILES 

CC1(C)SSC(C)(C)[C@@H](NC(=O)[C@@H](N)Cc2ccc(O)cc2)C(=O)NCC(=O)N[C@@H](Cc3ccccc3)C(=O)N[C@H]1C(O)=O

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

Clé InChI

MCMMCRYPQBNCPH-WMIMKTLMSA-N

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Amino Acid Sequence

Tyr-Pen-Gly-Phe-Pen [Disulfide Bridge: 2-5]

Description générale

[D-Pen2,5]-Enkephalin hydrate, also called DPDPE, is a peptide and acts as a δ1-opioid receptor agonist. Opioid receptors are divided into three types called, μ, κ and δ, depending upon their ligands. These ligands are peptides and are classified as enkephalins, endorphins and dynorphins.

Application

[D-Pen2,5]-Enkephalin hydrate (DPDPE) has been used to study the pharmacodynamic and pharmacokinetic capabilities of polyethylene glycol (PEG) conjugate of DPDPE in rodents. It has been used to study the tendency of opiate self-administration in male Long-Evans rats, in ventral tegmental area (VTA).

Actions biochimiques/physiologiques

Antinociceptive activity mediated through the δ1 receptor while the modulatory activity is mediated through the δ2 receptor. Tritiated [D-Pen2,5]-enkephalin is used as a δ1 ligand.

Autres remarques

Lyophilized from 0.1% TFA in H2O

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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S Allouche et al.
Biochemical pharmacology, 59(8), 915-925 (2000-02-29)
The two pharmacological delta-opioid receptor subtypes, delta1 and delta2, have been defined on the basis of pharmacological tools but remain to be characterized at the molecular level, since only a single cDNA has been cloned. The present study aimed to
D C Jewett et al.
Psychopharmacology, 127(3), 225-230 (1996-10-01)
The present study assessed the discriminative stimulus effects of the delta-opioid agonist [D-Pen2-D-Pen5]enkephalin (DPDPE) in pigeons. Food-restricted pigeons were trained to discriminate between i.c.v injections of 100 micrograms [D-Pen2-D-Pen5]enkephalin (DPDPE) and saline in a two-key operant procedure; acquisition of discriminative
B Gao et al.
The Journal of pharmacology and experimental therapeutics, 294(1), 73-79 (2000-06-28)
Organic anion-transporting polypeptides (Oatps) are a rapidly growing gene family of polyspecific membrane transporters. In rat brain, Oatp1 (gene symbol Slc21a1) and Oatp2 (Slc21a5) are localized at the apical and basolateral domains, respectively, of the choroid plexus epithelium. Furthermore, Oatp2
K A Witt et al.
The Journal of pharmacology and experimental therapeutics, 298(2), 848-856 (2001-07-17)
Poly(ethylene glycol), or PEG, conjugation to proteins and peptides is a growing technology used to enhance efficacy of therapeutics. This investigation assesses pharmacodynamic and pharmacokinetic characteristics of PEG-conjugated [D-Pen2,D-Pen5]-enkephalin (DPDPE), a met-enkephalin analog, in rodent (in vivo, in situ) and
D P Devine et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 14(4), 1978-1984 (1994-04-01)
Intracranial self-administration of mu- and delta-opioid agonists was demonstrated in male Long-Evans rats. Independent groups were allowed to lever-press for ventral tegmental area (VTA) microinfusions of morphine, the selective mu agonist [D-Ala2,N-Me-Phe4-Gly5-ol]-enkephalin (DAMGO), the selective delta-agonist [D-Pen2,D-Pen5]-enkephalin (DPDPE), or ineffective
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