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E3888

Sigma-Aldrich

[D-Pen2,5]-Enkephalin hydrate

≥95% (HPLC)

Synonym(s):

DPDPE

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About This Item

Empirical Formula (Hill Notation):
C30H39N5O7S2 · xH2O
Molecular Weight:
645.79 (anhydrous basis)
MDL number:
MFCD00076430
UNSPSC Code:
12352209
PubChem Substance ID:
329799055
NACRES:
NA.32

Quality Level

200

Assay

≥95% (HPLC)

storage temp.

−20°C

SMILES string

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

InChI key

MCMMCRYPQBNCPH-WMIMKTLMSA-N

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Amino Acid Sequence

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

General description

[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).

Biochem/physiol Actions

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.

Other Notes

Lyophilized from 0.1% TFA in H2O

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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