Ac-RYYRIK-NH2 - 200959-48-4

Ac-RYYRIK-NH2

Catalog Number: EVT-242102
CAS Number: 200959-48-4
Molecular Formula: C44H70N14O9
Molecular Weight: 939.1 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.

Product Introduction

Description

Ac-RYYRIK-NH2 is a hexapeptide that has garnered significant attention due to its interaction with the nociceptin/orphanin FQ (N/OFQ) peptide receptor (NOP), a G protein-coupled receptor (GPCR) related to the opioid receptor family. The NOP receptor and its endogenous ligand, nociceptin, are implicated in various physiological processes, including pain modulation, cardiovascular function, and stress response. As such, Ac-RYYRIK-NH2 and its derivatives have been studied for their potential as therapeutic agents in treating conditions such as pain, cardiac dysfunctions, and mood disorders12345678910.

Applications in Various Fields

Analgesia and Neuropathic Pain

Ac-RYYRIK-NH2 and its derivatives have been explored as potential analgesic and antineuropathic drugs due to their interaction with the NOP receptor6. The peptide library-based antagonist Ac-RYYRIK-NH2 inhibits nociceptin activity mediated through ORL1 but retains a high level of agonist activity6. Structural modifications have led to the development of analogs with enhanced receptor-binding affinity and strong antagonist activity, which could be beneficial in treating pain610.

Cardiovascular Function

The ability of Ac-RYYRIK-NH2 to inhibit the chronotropic effect of nociceptin on cardiomyocytes points to its potential application in cardiovascular research1. By modulating the NOP receptor activity, Ac-RYYRIK-NH2 could influence heart rate and rhythm, providing a basis for developing treatments for cardiac dysfunctions.

Mood Disorders and Stress Response

Ac-RYYRIK-NH2 has been shown to affect behaviors related to mood and stress response. For instance, it can inhibit locomotor activity and stimulate food intake after supraspinal administration in mice3. Additionally, it has been reported to reverse the antidepressant-like effects elicited by NOP receptor selective antagonists in the forced swimming test3. These findings suggest that Ac-RYYRIK-NH2 and its analogs could be useful in studying and potentially treating mood disorders.

Endocrine System

Despite its antagonistic properties in other systems, Ac-RYYRIK-NH2 does not antagonize the prolactin secretory activity of nociceptin. Instead, it has been found to increase the magnitude and duration of the prolactin secretory response in female rats, indicating agonist activity in the endocrine system5.

Properties

CAS Number

200959-48-4

Product Name

Ac-RYYRIK-NH2

IUPAC Name

(2S)-2-[[(2S,3S)-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-methylpentanoyl]amino]-6-aminohexanamide

Molecular Formula

C44H70N14O9

Molecular Weight

939.1 g/mol

InChI

InChI=1S/C44H70N14O9/c1-4-25(2)36(42(67)54-31(37(46)62)9-5-6-20-45)58-39(64)33(11-8-22-52-44(49)50)55-40(65)34(23-27-12-16-29(60)17-13-27)57-41(66)35(24-28-14-18-30(61)19-15-28)56-38(63)32(53-26(3)59)10-7-21-51-43(47)48/h12-19,25,31-36,60-61H,4-11,20-24,45H2,1-3H3,(H2,46,62)(H,53,59)(H,54,67)(H,55,65)(H,56,63)(H,57,66)(H,58,64)(H4,47,48,51)(H4,49,50,52)/t25-,31-,32-,33-,34-,35-,36-/m0/s1

InChI Key

WBBBVZGQADABSU-RERZDIOCSA-N

SMILES

CCC(C)C(C(=O)NC(CCCCN)C(=O)N)NC(=O)C(CCCN=C(N)N)NC(=O)C(CC1=CC=C(C=C1)O)NC(=O)C(CC2=CC=C(C=C2)O)NC(=O)C(CCCN=C(N)N)NC(=O)C

Canonical SMILES

CCC(C)C(C(=O)NC(CCCCN)C(=O)N)NC(=O)C(CCCN=C(N)N)NC(=O)C(CC1=CC=C(C=C1)O)NC(=O)C(CC2=CC=C(C=C2)O)NC(=O)C(CCCN=C(N)N)NC(=O)C

Isomeric SMILES

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

Ac-RYYRIK-NH2 has been characterized as a partial agonist at the NOP receptor when expressed in Chinese hamster ovary (CHO) cells14. It competitively antagonizes the effects of nociceptin in rat brain membranes, inhibiting the stimulation of GTP binding by nociceptin with high affinity and specificity1. This antagonism is not observed with agonists for other opioid receptors, indicating a selective action for the NOP receptor1. Additionally, Ac-RYYRIK-NH2 has been shown to inhibit the chronotropic effects of nociceptin on neonatal rat cardiomyocytes, suggesting a potential role in modulating cardiac function1. However, the peptide also exhibits agonistic properties, as seen by its ability to inhibit spontaneous locomotor activity in mice, an effect additive to that of nociceptin4. The complexity of its pharmacological profile is further highlighted by its variable behavior as an antagonist or agonist depending on the system studied478.

Method of Synthesis or Extraction
Ac-RYYRIK-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 use of a liquid support, and recombinant DNA technology involves the use of genetically modified organisms to produce the peptide.
The efficiency and yield of each method vary, with SPPS being the most efficient and yielding the highest amount of peptide. However, SPPS requires expensive equipment and reagents, making it less cost-effective than LPPS and recombinant DNA technology. Environmental and safety considerations are also important, with SPPS and LPPS producing hazardous waste that requires proper disposal.
Chemical Structure and Biological Activity
Ac-RYYRIK-NH2 is a peptide consisting of six amino acids: alanine (A), cysteine (C), arginine (R), tyrosine (Y), arginine (R), isoleucine (I), and lysine (K). Its chemical structure is as follows: Ac-Ala-Cys-Arg-Tyr-Arg-Ile-Lys-NH2.
Ac-RYYRIK-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, leading to the activation of various signaling pathways.
Biological Effects
Ac-RYYRIK-NH2 has been shown to have significant effects on cell function and signal transduction. It has been found to inhibit the growth of cancer cells and reduce inflammation in various tissues. However, its potential therapeutic and toxic effects require further investigation.
Future Perspectives and Challenges
Despite its potential applications, there are current limitations in the use and study of Ac-RYYRIK-NH2. These include the high cost of synthesis, limited availability, and lack of understanding of its potential toxic effects. Possible solutions and improvements include the development of more cost-effective synthesis methods and further investigation of its safety and efficacy.
Future trends and prospects in the application of Ac-RYYRIK-NH2 in scientific research include its potential use in personalized medicine and the development of novel therapeutics. However, further research is needed to fully understand its biological effects and potential applications.
Conclusion
Ac-RYYRIK-NH2 is a peptide with significant potential in various fields of 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 its potential applications and limitations.

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