Metenkefalin
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 319923

CAS#: 58569-55-4

Description: Met-enkephalin, also known as metenkefalin, sometimes referred to as opioid growth factor (OGF), is a naturally occurring, endogenous opioid peptide that has opioid effects of a relatively short duration. It is one of the two forms of enkephalin, the other being leu-enkephalin. The enkephalins are considered to be the primary endogenous ligands of the δ-opioid receptor, due to their high potency and selectivity for the site over the other endogenous opioids.

Chemical Structure

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Metenkefalin
CAS# 58569-55-4
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 319923
Name: Metenkefalin
CAS#: 58569-55-4
Chemical Formula: C27H35N5O7S
Exact Mass: 573.23
Molecular Weight: 573.665
Elemental Analysis: C, 56.53; H, 6.15; N, 12.21; O, 19.52; S, 5.59

Price and Availability

Size Price Availability Quantity
25mg USD 305 2 weeks
50mg USD 550 2 weeks
100mg USD 950 2 weeks
Bulk inquiry

Synonym: (Met5)-enkephalin; CCRIS 4225; Enkephalin methionine; Lupex; MET-enkephalin; NSC 374896; Porcine beta-endorphin 1-5; Tyr-Gly-Gly-Phe-Met-OH; Metenkefalin

IUPAC/Chemical Name: D-tyrosylglycylglycyl-L-phenylalanyl-L-methionine

InChi Key: YFGBQHOOROIVKG-FSSWDIPSSA-N

InChi Code: InChI=1S/C27H35N5O7S/c1-40-12-11-21(27(38)39)32-26(37)22(14-17-5-3-2-4-6-17)31-24(35)16-29-23(34)15-30-25(36)20(28)13-18-7-9-19(33)10-8-18/h2-10,20-22,33H,11-16,28H2,1H3,(H,29,34)(H,30,36)(H,31,35)(H,32,37)(H,38,39)/t20-,21+,22+/m1/s1

SMILES Code: CSCC[C@@H](C(O)=O)NC([C@H](CC1=CC=CC=C1)NC(CNC(CNC([C@@H](CC2=CC=C(O)C=C2)N)=O)=O)=O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Certificate of Analysis:
View CoA: current batch, Lot#A7F11L30
Safety Data Sheet (SDS):
View Safety Data Sheet (SDS)
Instruction:
View handling instruction
Biological target: Tyr-Gly-Gly-Phe-Met-OH regulates human immune function and inhibits tumor growth via binding to the opioid receptor.
In vitro activity: In this study, the mechanism that Met-enkephalin (M-ENK) inhibits ROS production through Wnt/β-catenin signaling was investigated in the ZF4 cells of zebrafish. The cell viability was significantly increased by 10, 20, 40, 80, and 160 μM M-ENK. After ZF4 cells were exposed to 0, 20, 40, and 80 μM M-ENK for 24 h, the mRNA expression of Wnt10b, β-catenin, and CCAAT/enhancer binding protein α (C/EBPα) was significantly increased by 40 and 80 μM M-ENK. The results showed that M-ENK could induce Wnt/β-catenin signaling, which further inhibited ROS production through the induction of C/EBPα, MMP, and the activities of antioxidant enzymes. Reference: Fish Shellfish Immunol. 2019 May;88:432-440. https://pubmed.ncbi.nlm.nih.gov/15806307/
In vivo activity: The present study showed that MetEnk (Met-enkephalin) effectively prevented high fat diet (HFD) induced C57BL/6J mice weight gain, clearly enhanced glucose tolerance and insulin sensitivity, and dramatically reduced hepatic steatosis in HFD fed mice. Mechanically, MetEnk restored protein kinase A (PKA) signaling pathway in HFD challenged mice and promoted subcutaneous white adipose tissue (WAT) browning. Reference: Toxicol Appl Pharmacol. 2018 Nov 15;359:12-23. https://pubmed.ncbi.nlm.nih.gov/30222981/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 40.0 69.73
Water 6.7 11.63

Preparing Stock Solutions

The following data is based on the product molecular weight 573.67 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Liu Z, Liu Y, Gu Y, Gao L, Li A, Liu D, Kang C, Pang Q, Wang X, Han Q, Yu H. Met-enkephalin inhibits ROS production through Wnt/β-catenin signaling in the ZF4 cells of zebrafish. Fish Shellfish Immunol. 2019 May;88:432-440. doi: 10.1016/j.fsi.2019.03.016. Epub 2019 Mar 9. PMID: 30862518. 2. Malendowicz LK, Rebuffat P, Tortorella C, Nussdorfer GG, Ziolkowska A, Hochol A. Effects of met-enkephalin on cell proliferation in different models of adrenocortical-cell growth. Int J Mol Med. 2005 May;15(5):841-5. PMID: 15806307. 3. Suo J, Zhao X, Guo X, Zhao X. Met-enkephalin improves metabolic syndrome in high fat diet challenged mice through promotion of adipose tissue browning. Toxicol Appl Pharmacol. 2018 Nov 15;359:12-23. doi: 10.1016/j.taap.2018.09.015. Epub 2018 Sep 14. PMID: 30222981. 4. Martinić R, Sošić H, Turčić P, Konjevoda P, Fučić A, Stojković R, Aralica G, Gabričević M, Weitner T, Stambuk N. Hepatoprotective effects of Met-enkephalin on acetaminophen-induced liver lesions in male CBA mice. Molecules. 2014 Aug 7;19(8):11833-45. doi: 10.3390/molecules190811833. PMID: 25105920; PMCID: PMC6270943.
In vitro protocol: 1. Liu Z, Liu Y, Gu Y, Gao L, Li A, Liu D, Kang C, Pang Q, Wang X, Han Q, Yu H. Met-enkephalin inhibits ROS production through Wnt/β-catenin signaling in the ZF4 cells of zebrafish. Fish Shellfish Immunol. 2019 May;88:432-440. doi: 10.1016/j.fsi.2019.03.016. Epub 2019 Mar 9. PMID: 30862518. 2. Malendowicz LK, Rebuffat P, Tortorella C, Nussdorfer GG, Ziolkowska A, Hochol A. Effects of met-enkephalin on cell proliferation in different models of adrenocortical-cell growth. Int J Mol Med. 2005 May;15(5):841-5. PMID: 15806307.
In vivo protocol: 1. Suo J, Zhao X, Guo X, Zhao X. Met-enkephalin improves metabolic syndrome in high fat diet challenged mice through promotion of adipose tissue browning. Toxicol Appl Pharmacol. 2018 Nov 15;359:12-23. doi: 10.1016/j.taap.2018.09.015. Epub 2018 Sep 14. PMID: 30222981. 2. Martinić R, Sošić H, Turčić P, Konjevoda P, Fučić A, Stojković R, Aralica G, Gabričević M, Weitner T, Stambuk N. Hepatoprotective effects of Met-enkephalin on acetaminophen-induced liver lesions in male CBA mice. Molecules. 2014 Aug 7;19(8):11833-45. doi: 10.3390/molecules190811833. PMID: 25105920; PMCID: PMC6270943.

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