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Usage

Uses

Used in Pharmaceutical Industry:
(DES-TYR1)-MET-ENKEPHALIN is used as an analgesic agent for its ability to bind and activate opioid receptors, which helps in regulating pain perception. This makes it a potential candidate for the development of pain management therapies.
Used in Research Applications:
(DES-TYR1)-MET-ENKEPHALIN is used as a research tool for studying the mechanisms of opioid receptor binding and activation, as well as the role of these receptors in pain regulation and other physiological processes. This can aid in the development of new therapeutic strategies for pain management and other conditions related to the opioid system.
Used in Drug Development:
(DES-TYR1)-MET-ENKEPHALIN is used as a lead compound in the development of new drugs targeting the opioid receptors. Its metabolic stability and duration of biological activity make it a valuable starting point for designing more effective and longer-lasting pain management medications.

InChI:InChI=1/C18H26N4O5S/c1-28-8-7-13(18(26)27)22-17(25)14(9-12-5-3-2-4-6-12)21-16(24)11-20-15(23)10-19/h2-6,13-14H,7-11,19H2,1H3,(H,20,23)(H,21,24)(H,22,25)(H,26,27)/t13-,14-/m0/s1

Upstream product

• 22248-60-8 L-phenylalanyl-L-methionine methyl ester 
• 70035-45-9 N-tert-Butyloxycarbonyl-glycyl-glycyl-L-phenylalanyl-L-methionin-methylester 
• 82362-17-2 (S)-2-[(S)-2-(2-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methylsulfanyl-butyric acid; compound with acetic acid 
• 68800-26-0 N-tert-butoxycarbonylglycylglycylphenylalanylmethionine 

Downstream Products

• 906794-23-8 [(trifluoroacetate-κO)(dipyrido[3,2-a:2',3'-c]phenazine)(pentamethylcyclopentadienyl)iridium(III)] trifluoromethanate 

Relevant academic research and scientific papers

Phosphorylation of enkephalins enhances their proteolytic stability

Pharmacological action of enkephalins as opioid peptides is limited because of their rapid degradation by endoproteases. A novel approach is used in this study to prolong the life of those peptides. Phosphorylation of N-terminal tyrosine residue is found to have a profound influence in improving the stability of [Met]enkephalin and [Leu]enkephalin against the action of aminopeptidase M. Whereas, breakdown of [Met]enkephalin and [Leu]enkephalin is essentially complete in less than one min when incubated at 37°C with purified aminopeptidase M (EC 3.4.11.2; substrate:enzyme = 1:0.1) in Tris buffer (pH 7.02), the corresponding phospho analogs are still detected 60 min after start of incubation. The rate of disappearance of phospho-[Met]enkephalin and phospho-[Leu]enkephalin follows first-order kinetics with half-lives of 7.3 and 8.8 min, respectively.

Transmucosal delivery of methionine enkephalin. I: Solution stability and kinetics of degradation in various rabbit mucosa extracts

To evaluate the feasibility of transmucosal delivery of methionine enkephalin (Tyr-Gly-Gly-Phe-Met; Met-Enk), it is important to first investigate its physicochemical and enzymatic stability. The kinetics of degradation of Met-Enk in aqueous solution was determined at pH 2.01-9.84 and 37-45 °C by high-performance liquid chromatography. The first-order rate constant (k) was calculated, and the log k-pH profile showed that Met-Enk is most stable at pH ~5.0. Various mucosae excised from rabbit were mounted on Valia-Chien permeation cells and exposed to isotonic phosphate buffer at physiologic pHs. Mucosal and serosal extracts were collected from the donor and receptor solutions, respectively. The degradation of Met-Enk in the extracts followed first-order kinetics, but no significant difference in the degradation rates was observed between mucosal and serosal extracts, regardless of the type of mucosa used. Degradation was most rapid in the extracts of rectal mucosa, followed by vaginal and nasal mucosae. The major metabolites were Des-Tyr-Met-Enk and Tyrosine (Tyr), indicating the enzymatic hydrolysis by aminopeptidases. However, the data also suggested that dipeptidyl peptidase and dipeptidyl carboxypeptidase could play some roles in the degradation of Met-Enk. The degradation pathways of Met-Enk were further explored by concomitantly determining the formation of smaller metabolites of primary hydrolytic fragments of Met-Enk in the mucosal extracts.