PL 017Selective μ agonist CAS# 83397-56-2 |
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Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 83397-56-2 | SDF | Download SDF |
PubChem ID | 115335 | Appearance | Powder |
Formula | C29H37N5O5 | M.Wt | 535.64 |
Type of Compound | N/A | Storage | Desiccate at -20°C |
Solubility | Soluble to 1 mg/ml in water | ||
Sequence | YPFP (Modifications:Phe-3 = N-methyl-Phe, Pro-4 = C-terminal amide) | ||
Chemical Name | (2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]-N-[(2S)-1-[(2R)-2-carbamoylpyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]-N-methylpyrrolidine-2-carboxamide | ||
SMILES | CN(C(CC1=CC=CC=C1)C(=O)N2CCCC2C(=O)N)C(=O)C3CCCN3C(=O)C(CC4=CC=C(C=C4)O)N | ||
Standard InChIKey | JAKBYSTWCHUQOK-NDBXHCKUSA-N | ||
Standard InChI | InChI=1S/C29H37N5O5/c1-32(25(18-19-7-3-2-4-8-19)29(39)33-15-5-9-23(33)26(31)36)28(38)24-10-6-16-34(24)27(37)22(30)17-20-11-13-21(35)14-12-20/h2-4,7-8,11-14,22-25,35H,5-6,9-10,15-18,30H2,1H3,(H2,31,36)/t22-,23+,24-,25-/m0/s1 | ||
General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. |
Description | Selective μ opioid receptor agonist (IC50 values are 5.5 and > 10000 nM for inhibition of 125I-FK 33,824 and 125I-DADLE binding to μ and δ sites respectively). Produces naloxone-reversible analgesia, catalepsy and hyperthermia following central administration in rats in vivo. |
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Immunohistochemical evidence of down-regulation of mu-opioid receptor after chronic PL-017 in rats.[Pubmed:9600647]
Eur J Pharmacol. 1998 Mar 5;344(2-3):137-42.
In a previous study, mu-opioid receptor binding was decreased by chronic treatment of rats with a mu-opioid receptor-selective agonist [CH3Phe3, D-Pro4]morphiceptin (PL-017) [Tao, P.L., Lee, H.Y., Chang, L.R., Loh, H.H., 1990. Decrease in mu-opioid receptor binding capacity in rat brain after chronic PL-017 treatment. Brain Res. 526, 270-275]. However, there was a lack of correlation between the time course of receptor down-regulation and the loss of pharmacological effects of the drug. In the current study, we used immunohistochemistry to reinvestigate this issue. Male Sprague-Dawley rats were chronically treated with PL-017 i.c.v. for 1, 3 or 5 days, using an escalating dosage paradigm (0.75-6.0 microg), which resulted in a 1.4 to 32-fold increase in the AD50. Rat brains were removed, frozen, coronally sectioned (14 microm) and processed for mu-, delta- or kappa-opioid receptor immunohistochemistry by the avidin-biotin complex (ABC) method. Significant decreases in OP3 immunodensity were found in many brain regions which are enriched with OP3 after chronic treatment of PL-017. Time-dependent decreases in OP3 were detected and reached a plateau around 3 days of PL-017 treatment. No significant change in OP1 or OP2 immunodensity after chronic treatment with PL-017 was found. Our conclusion is that chronic treatment with PL-017 of rats selectively down-regulates mu-opioid receptors in the brain. This may be an important mechanism for PL-017 tolerance.
Body temperature and analgesic effects of selective mu and kappa opioid receptor agonists microdialyzed into rat brain.[Pubmed:9103537]
J Pharmacol Exp Ther. 1997 Apr;281(1):499-507.
Opioids administered by i.c.v. injection produce body temperature (Tb) changes and analgesic responses in rats. The present study was undertaken to investigate the effects on Tb and analgesia of highly selective mu and kappa opioid receptor agonists and antagonists delivered directly into the preoptic anterior hypothalamus (POAH) and periaqueductal gray (PAG) by the intracerebral microdialysis method. Microdialyzed into the POAH, the mu receptor agonist Tyr-Pro-N-MePhe-D-Pro-NH2 induced dose-related hyperthermia that could be prevented or antagonized by the mu receptor antagonist cyclic D-Phe-Cys-Tyr-D-Trp-Arg-Thr-Pen-Thr-NH2 or by naloxone, but not by the kappa receptor antagonist nor-binaltorphimine. The kappa receptor agonist dynorphin A(1-17), microdialyzed into the POAH, induced dose-related hypothermia that was prevented or antagonized by nor-binaltorphimine but not cyclic D-Phe-Cys-Tyr-D-Trp-Arg-Thr-Pen-Thr-NH2. Neither Tyr-Pro-N-MePhe-D-Pro-NH2 nor dynorphin A(1-17) microdialyzed into the PAG produced significant changes in Tb. However, these agonists microdialyzed into the PAG produced analgesic responses that did not occur after administration into the POAH. These results support the hypothesis that the hyperthermic response to opioids is mediated by the mu receptor and the hypothermic response is mediated by the kappa receptor in rats. The POAH is a primary functional area in Tb, but not in analgesic, responses to opioids, whereas the PAG is a sensitive area for analgesic, but not for Tb, responses to opioids.
Behavioral effects of the mu-opioid peptide agonists DAMGO, DALDA, and PL017 on locomotor activities.[Pubmed:8265694]
Pharmacol Biochem Behav. 1993 Oct;46(2):391-5.
The relative role of central mu-opioid receptor agonists Tyr-D-Ala-Gly-N-Methyl-Phe-Gly-ol (DAMGO), Tyr-D-Arg-Phe-Lys (DALDA), and Tyr-Pro-MePhe-D-Pro (PL017) (0.00, 0.01, 01, or 1.0 micrograms, ICV) on behavior was investigated in rats for 60 min in activity monitors. DAMGO (0.1 and 1.0 micrograms) and PL017 (1.0 micrograms) resulted in biphasic effects, inhibition followed by hyperactivity for linear locomotor, whereas the 0.01-micrograms dosage was associated with hyperactivity. On the other hand, DALDA (0.1 and 1.0 micrograms) suppressed locomotor activity over the 60-min session.
Potent morphiceptin analogs: structure activity relationships and morphine-like activities.[Pubmed:6313901]
J Pharmacol Exp Ther. 1983 Nov;227(2):403-8.
Morphiceptin (Tyr-Pro-Phe-Pro-NH2), a nonenkephalin peptide, is an opioid agonist highly selective for mu opiate receptors. Chemical modification of Tyr-Pro-Phe-Pro-NH2 was carried out by substituting structurally related amino acids at residues 2, 3 and 4. The morphiceptin analogs synthesized were then examined for receptor binding activities using 125I-labeled FK 33,824 (Tyr-D-Ala-Gly-NMePhe-Met(O)-ol) as the mu-ligand and 125I-labeled D-Ala2,D-Leu5-enkephalin as the delta-ligand, and for inhibitory activities on electrically evoked smooth muscle contraction of mouse vas deferens and isolated myenteric plexus-longitudinal muscle strips of guinea-pig ileum. All of these analogs showed virtually no activity at delta opiate receptor binding sites. Methylation of the nitrogen atom of phenylalanine and the substitution at the C-terminal of L-proline by D-proline produced potent mu-agonists, the prototype analog being Tyr-Pro-NMePhe-D-Pro-NH2 (PL017). The IC50 values of morphiceptin and its analogs for mu receptor binding were correlated to the ED50 values in the guinea-pig ileum assay, suggesting that the ileum effects were mediated by mu receptor interactions. A similar correlation between mu receptor binding activity and the ED50 values in the mouse vas deferens assay suggested that morphiceptin and its analogs also acted on mu receptors in this tissue. This idea is supported by the observation that naloxone has a high pA2 value of 8.71 against PL017 in mouse vas deferens. In in vivo studies, PL017 administered centrally into the rostral portion of the 4th ventricle produced long-lasting, naloxone-reversible analgesia in rats.(ABSTRACT TRUNCATED AT 250 WORDS)