Ac-RYYRWK-NH2 - 200959-47-3

Ac-RYYRWK-NH2

Catalog Number: EVT-242109
CAS Number: 200959-47-3
Molecular Formula: C49H69N15O9
Molecular Weight: 1012.2 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.

Product Introduction

Description

The hexapeptide Ac-RYYRWK-NH2 has garnered significant attention in the field of neuropharmacology due to its interaction with the nociceptin/orphanin FQ (N/OFQ) receptor, also known as the ORL1 receptor. This receptor is a G protein-coupled receptor (GPCR) that plays a crucial role in various physiological processes, including pain modulation, cardiovascular function, and stress response. Understanding the mechanism of action and potential applications of Ac-RYYRWK-NH2 can provide insights into the development of new therapeutic agents for treating a range of conditions.

Applications in Various Fields

Analgesia and Neuropathic Pain

Ac-RYYRWK-NH2 and its analogs have been explored as potential analgesic and antineuropathic drugs. The peptide library-based antagonist Ac-RYYRIK-NH2, which shares a similar sequence with Ac-RYYRWK-NH2, inhibits nociceptin activity mediated through ORL1 receptors, indicating its potential for pain management5. Modifications to the peptide structure have led to analogs with enhanced receptor-binding affinity and strong antagonist activity, which could be more potent in clinical applications5.

Cardiovascular Research

The ability of Ac-RYYRWK-NH2 to fully inhibit the chronotropic effect of nociceptin on cardiomyocytes points to its potential application in cardiovascular research. By antagonizing nociceptin's action, it may be possible to modulate heart rate and other cardiac functions, which could be beneficial in the treatment of certain cardiovascular diseases1.

Neuropharmacology

In neuropharmacological studies, Ac-RYYRWK-NH2 has been used to investigate the role of the nociceptin receptor in various central nervous system (CNS) functions. For instance, the ligand has been shown to affect spontaneous locomotor activity in mice, suggesting its influence on motor control and behavior4. Additionally, the regional distribution of [3H]ac-RYYRWK-NH2 binding in rat brain sections correlates with that of nociceptin, indicating its relevance in studying brain function and disorders2.

Drug Development

The structural requirements for receptor binding of Ac-RYYRWK-NH2 have been extensively studied, providing valuable information for the design of new therapeutic agents targeting the ORL1 receptor. The importance of the N-terminal acetyl group and the C-terminal amide group has been highlighted, as well as the significance of the N-terminal Arg residue8. These insights can guide the development of more selective and potent drugs with fewer side effects.

Properties

CAS Number

200959-47-3

Product Name

Ac-RYYRWK-NH2

IUPAC 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

Molecular Formula

C49H69N15O9

Molecular Weight

1012.2 g/mol

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

InChI Key

YROQVQIJRORFAZ-SKGSPYGFSA-N

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

Synonyms

Ac-Arg-Tyr-Tyr-Arg-Trp-Lys-NH2
Ac-RYYRWK-NH2
acetyl-arginyl-tyrosyl-tyrosyl--arginyl-tryptophyl-lysinamide
CAM 6369
CAM-6369
CAM6369

Canonical 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

Isomeric SMILES

CC(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)N[C@@H](CC2=CC=C(C=C2)O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)N[C@@H](CCCCN)C(=O)N
Mechanism of Action

Ac-RYYRWK-NH2 has been characterized as a potent partial agonist at the nociceptin receptor, with high specificity and no affinity for other opioid receptors such as µ-, κ-, or δ-opioid receptors2. It has been shown to competitively antagonize the effects of nociceptin, a neuropeptide that acts as a hyperalgesic agent, by inhibiting G protein activation in rat brain preparations1. Furthermore, Ac-RYYRWK-NH2 has been radiolabelled to create [3H]ac-RYYRWK-NH2, which has been used in receptor-binding experiments to reveal a single high-affinity site for the ligand in rat cortical membranes2. This ligand has also been shown to inhibit the chronotropic effect of nociceptin on neonatal rat cardiomyocytes, suggesting its potential as a starting point for the development of specific antagonists1.

Method of Synthesis or Extraction
Ac-RYYRWK-NH2 can be synthesized using various methods, including solid-phase peptide synthesis (SPPS), liquid-phase peptide synthesis (LPPS), and recombinant DNA technology. SPPS is the most commonly used method, which involves the stepwise addition of amino acids to a solid support. LPPS, on the other hand, involves the synthesis of peptides in solution phase. Recombinant DNA technology involves the use of genetically modified organisms to produce peptides. The efficiency and yield of each method vary, with SPPS being the most efficient and yielding the highest amount of peptide. However, all methods have environmental and safety considerations, such as the use of hazardous chemicals and waste disposal.
Chemical Structure and Biological Activity
Ac-RYYRWK-NH2 is a hexapeptide with the chemical formula C33H49N11O8. It has a molecular weight of 747.86 g/mol and a net charge of +2. Ac-RYYRWK-NH2 has been shown to have various biological activities, including antimicrobial, antiviral, and anticancer properties. Its mechanism of action involves binding to specific receptors on the cell surface and activating intracellular signaling pathways. Ac-RYYRWK-NH2 has been found to target various biological molecules, including enzymes, receptors, and transcription factors.
Biological Effects
Ac-RYYRWK-NH2 has been shown to have significant effects on cell function and signal transduction. It has been found to regulate cell proliferation, differentiation, and apoptosis. Ac-RYYRWK-NH2 has also been shown to modulate immune responses and inflammation. However, its potential therapeutic and toxic effects depend on the dose and duration of exposure. Ac-RYYRWK-NH2 has been found to have potential therapeutic effects in various diseases, including cancer, infectious diseases, and autoimmune disorders. However, it also has potential toxic effects, such as cytotoxicity and immunotoxicity.
Future Perspectives and Challenges
Despite the promising applications of Ac-RYYRWK-NH2, there are still limitations in its use and study. One of the main challenges is the potential toxicity and side effects, which need to be further investigated. Another challenge is the cost and scalability of the synthesis or extraction methods. However, possible solutions and improvements include the development of more efficient and cost-effective methods of synthesis or extraction. Future trends and prospects in the application of Ac-RYYRWK-NH2 in scientific research include the development of novel therapeutic agents and the exploration of its potential in various fields, such as agriculture and food science.
Conclusion
Ac-RYYRWK-NH2 is a promising peptide with various potential applications in medical, environmental, and industrial research. Its method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, future perspectives, and challenges have been discussed in this paper. Further research is needed to fully understand the potential of Ac-RYYRWK-NH2 and its limitations.

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