Ac-RYYRWK-NH2Potent, selective NOP partial agonist peptide CAS# 200959-47-3 |
2D Structure
- Amyloid β-Protein (1-15)
Catalog No.:BCC1003
CAS No.:183745-81-5
- Beta-Amyloid (1-11)
Catalog No.:BCC1002
CAS No.:190436-05-6
Quality Control & MSDS
3D structure
Package In Stock
Number of papers citing our products
Cas No. | 200959-47-3 | SDF | Download SDF |
PubChem ID | 9811889 | Appearance | Powder |
Formula | C49H69N15O9 | M.Wt | 1012.17 |
Type of Compound | N/A | Storage | Desiccate at -20°C |
Solubility | Soluble to 1 mg/ml in water | ||
Sequence | RYYRWK (Modifications: Arg-1 = C-terminal Ac, Lys-6 = C-terminal amide) | ||
Chemical Name | (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-6-aminohexanamide | ||
SMILES | CC(=O)NC(CCCN=C(N)N)C(=O)NC(CC1=CC=C(C=C1)O)C(=O)NC(CC2=CC=C(C=C2)O)C(=O)NC(CCCN=C(N)N)C(=O)NC(CC3=CNC4=CC=CC=C43)C(=O)NC(CCCCN)C(=O)N | ||
Standard InChIKey | YROQVQIJRORFAZ-SKGSPYGFSA-N | ||
Standard InChI | InChI=1S/C49H69N15O9/c1-28(65)59-37(11-6-22-56-48(52)53)43(69)62-40(25-30-15-19-33(67)20-16-30)46(72)63-39(24-29-13-17-32(66)18-14-29)45(71)61-38(12-7-23-57-49(54)55)44(70)64-41(26-31-27-58-35-9-3-2-8-34(31)35)47(73)60-36(42(51)68)10-4-5-21-50/h2-3,8-9,13-20,27,36-41,58,66-67H,4-7,10-12,21-26,50H2,1H3,(H2,51,68)(H,59,65)(H,60,73)(H,61,71)(H,62,69)(H,63,72)(H,64,70)(H4,52,53,56)(H4,54,55,57)/t36-,37-,38-,39-,40-,41-/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. |
||
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. |
||
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 | Potent, selective partial agonist peptide for the NOP receptor (Ki = 0.71 nM). Selective over μ, δ and κ opioid receptors (IC50 > 4000 nM). Increases food intake in vivo. |
Ac-RYYRWK-NH2 Dilution Calculator
Ac-RYYRWK-NH2 Molarity Calculator
Calcutta University
University of Minnesota
University of Maryland School of Medicine
University of Illinois at Chicago
The Ohio State University
University of Zurich
Harvard University
Colorado State University
Auburn University
Yale University
Worcester Polytechnic Institute
Washington State University
Stanford University
University of Leipzig
Universidade da Beira Interior
The Institute of Cancer Research
Heidelberg University
University of Amsterdam
University of Auckland
TsingHua University
The University of Michigan
Miami University
DRURY University
Jilin University
Fudan University
Wuhan University
Sun Yat-sen University
Universite de Paris
Deemed University
Auckland University
The University of Tokyo
Korea University
- SB 243213 dihydrochloride
Catalog No.:BCC6035
CAS No.:200940-23-4
- m-3M3FBS
Catalog No.:BCC7209
CAS No.:200933-14-8
- (D)-(+)-Neopterin
Catalog No.:BCC7960
CAS No.:2009-64-5
- Xanthotoxol
Catalog No.:BCN4881
CAS No.:2009-24-7
- Epinodosin
Catalog No.:BCN3282
CAS No.:20086-60-6
- Diosbulbin C
Catalog No.:BCN4880
CAS No.:20086-07-1
- Diosbulbin B
Catalog No.:BCN4879
CAS No.:20086-06-0
- Epicurzerenone
Catalog No.:BCN3521
CAS No.:20085-85-2
- Pseudoneolinderane
Catalog No.:BCN8034
CAS No.:20082-45-5
- 16-Nor-15-oxodehydroabietic acid
Catalog No.:BCN3943
CAS No.:200813-31-6
- 7-Hydroxy-PIPAT maleate
Catalog No.:BCC6760
CAS No.:200722-46-9
- (-)-Phyllocladene
Catalog No.:BCN7661
CAS No.:20070-61-5
- Ac-RYYRIK-NH2
Catalog No.:BCC5736
CAS No.:200959-48-4
- Fmoc-Lys(Me)3-OH Chloride
Catalog No.:BCC3267
CAS No.:201004-29-7
- SB-269970
Catalog No.:BCC1927
CAS No.:201038-74-6
- Ravenine
Catalog No.:BCN6666
CAS No.:20105-22-0
- cis-Methylkhellactone
Catalog No.:BCN7690
CAS No.:20107-13-5
- 2-Amino-2'-chloro-5-nitro benzophenone
Catalog No.:BCC8521
CAS No.:2011-66-7
- 4-PPBP maleate
Catalog No.:BCC6723
CAS No.:201216-39-9
- 3-AQC
Catalog No.:BCC6743
CAS No.:201216-42-4
- Diosmetin-7-O-beta-D-glucopyranoside
Catalog No.:BCN5328
CAS No.:20126-59-4
- H-Thr-OBzl.oxalate
Catalog No.:BCC3103
CAS No.:201274-07-9
- 1-(3,4-Dimethoxyphenyl)propane-1,2-diol
Catalog No.:BCN1507
CAS No.:20133-19-1
- Fmoc-D-Tyr(Me)-OH
Catalog No.:BCC3269
CAS No.:201335-88-8
Tryptophan replacement in the nociceptin/orphanin FQ receptor ligand Ac-RYYRWK-NH2.[Pubmed:15946194]
J Pept Res. 2005 Jul;66(1):39-47.
In the present study we describe the in vitro pharmacological characterization of the nociceptin/orphanin FQ (N/OFQ) receptor (NOP) ligand Ac-RYYRWK-NH2 and the synthesis and biological evaluation of 13 Trp5 substituted Ac-RYYRWK-NH2 analogs. Results indicate that Ac-RYYRWK-NH2 behaves as a highly potent and selective partial agonist at the NOP receptors and that the whole indole moiety of the Trp5 side chain is not required, being a phenyl-ethyl side chain already sufficient for maintaining high potency.
[3H]ac-RYYRWK-NH2, a novel specific radioligand for the nociceptin/orphanin FQ receptor.[Pubmed:11138846]
Naunyn Schmiedebergs Arch Pharmacol. 2000 Dec;362(6):538-45.
The hexapeptide Ac-RYYRWK-NH2 has been described as a potent partial agonist at the nociceptin (NC)/orphanin FQ receptor which has no affinity for mu-, kappa- or delta-opioid receptors. However, it is not clear whether Ac-RYYRWK-NH2 is truly selective for the NC receptor, and Ac-RYYRWK-NH2 has therefore been radiolabelled and characterised in receptor-binding experiments. Saturation experiments with [3H]Ac-RYYRWK-NH2 binding to rat cortical membranes revealed a single high affinity site for [3H]Ac-RYYRWK-NH2 (Kd=0.071 +/- 0.018 nM; Bmax=22+/-2 fmol/mg protein). Uncoupling of the G-proteins resulted in a significant 45% increase in Kd and no change in Bmax. [3H]Ac-RYYRWK-NH2 binding to rat cortical membranes or to membranes from baby hamster kidney cells expressing human orphan opioid receptor-like (ORL1) was displaced by NC and Ac-RYYRWK-NH2 to the same extent. The following rank order of potency was observed: Ac-RYYRWK-NH2 > [Tyr14]NC-OH = NC-OH = NC-NH2 > NC, H-(1-13)-NH2 > NC(1-12)-NH2 >> NC(1-11)-NH2 and, thus, displayed a typical NC receptor pharmacology. Novel cyclic analogues of Ac-RYYRWK-NH2 were prepared but these structures were much less active when compared to Ac-RYYRWK-NH2. In vitro receptor autoradiography with [3H]Ac-RYYRWK-NH2 to rat brain sections revealed high levels of binding in the cerebral cortex, amygdala, hypothalamus and superior colliculus, but low levels in the cerebellum and striatum. Overall, the regional distribution was very similar to that of [3H]NC. Ac-RYYRWK-NH2 seems indeed to be selective for the NC receptor and [3H]Ac-RYYRWK-NH2 is a novel radioligand which may be useful for further exploring the pharmacology and receptor-ligand interaction of the NC receptor.
Characterization of the ORL(1) receptor on adrenergic nerves in the rat anococcygeus muscle.[Pubmed:10991930]
Br J Pharmacol. 2000 Sep;131(2):349-55.
1. Nociceptin, the endogenous ORL(1) receptor agonist inhibited the motor response to electrical-field stimulation in the rat anococcygeus muscle. This effect was characterized using the peptide ligands acetyl-Arg-Tyr-Tyr-Arg-Trp-Lys-NH(2) (Ac-RYYRWK-NH(2)), acetyl-Arg-Tyr-Tyr-Arg-Ile-Lys-NH(2) (Ac-RYYRIK-NH(2)) and [Phe(1)psi(CH(2)-NH)Gly(2)]nociceptin(1-13)NH(2) ([F/G]NC(1-13)NH(2)), and the non-selective opioid antagonist naloxone benzoylhydrazone (NalBzOH). 2. Nociceptin produced a concentration-dependent inhibition of the adrenergic motor response to electrical-field stimulation (EC(50) 19 nM, pEC(50) 7.7+/-0.1, n=8), but the response to exogenous noradrenaline (0.2 - 1 microM) was unaffected. The inhibitory nerve response was not affected by up to 1 microM nociceptin. 3. After inhibition of nitric oxide synthase (N(omega)-nitro-L-arginine 100 microM), and in the presence of peptidase inhibitors, nociceptin produced full inhibition of the pure adrenergic motor response (EC(50) 4 nM; pEC(50) 8.4+/-0.1, E(max) 98.3+/-1.2%, n=12). Ac-RYYRWK-NH(2) was a potent partial-agonist (pEC(50) 9.0+/-0.1, E(max) 66.4+/-5.2; n=11) but the efficacy of Ac-RYYRIK-NH(2) (pEC(50) 8.0+/-0.2, E(max) 36.7+/-3.5; n=12) was lower and the peptide could be tested as an antagonist (pA(2) 9.01). 4. [F/G]NC(1-13)NH(2) and NalBzOH had little or no efficacy and were competitive antagonists with pK(B) values of 7.4 (95% c.l. 7.1, 7.7) and 6.9 (95% c.l. 6.7, 7.1) respectively. Both increased the response to field stimulation at high concentrations, suggesting the release of an endogenous agonist for the ORL(1) receptor during stimulation. 5. Rat nocistatin did not affect the response to electrical-field stimulation, nor did it modify the inhibitory action of nociceptin. 6. Our findings suggest there is a significant endowment of ORL(1) receptors on sympathetic terminals of the rat anococcygeus, where nociceptin mediates a powerful inhibitory effect on adrenergic neuromuscular transmission.
Binding and in vitro activities of peptides with high affinity for the nociceptin/orphanin FQ receptor, ORL1.[Pubmed:9353393]
J Pharmacol Exp Ther. 1997 Nov;283(2):735-41.
Fifteen hexapeptides having high affinity for the opioid-like receptor ORL1 were identified from a combinatorial library containing more than 52 million different hexapeptides. The five compounds with the highest affinity were characterized further by use of a variety of in vitro models. Binding studies indicated that these five peptides have affinity for ORL1 in the nanomolar range, similar to the recently discovered endogenous ligand called nociceptin and orphanin FQ (N/OFQ). The activity of these compounds was investigated in three different assays: stimulation of [35S]GTPgammaS binding and inhibition of forskolin-stimulated cAMP accumulation in Chinese hamster ovary cells transfected with ORL1, and inhibition of electrically induced contractions in the mouse vas deferens. In each assay, the five hexapeptides acted as partial agonists. The EC50 values for stimulation of [35S]GTPgammaS binding and inhibition of cAMP accumulation were in the range of that for N/OFQ, but maximal effects ranged from 70 to 90% of N/OFQ in the cAMP assay, and 30 to 60% of N/OFQ in the GTPgammaS assay. The positive hexapeptides identified were found to have minimal structural similarity to N/OFQ. The peptides are positively charged, which could enable them to bind to the negatively charged second extracellular loop thought to be a likely binding site for N/OFQ.