Mifamurtide sodium - ≥98% , CAS No.90825-43-7

CAS: 90825-43-7 Cat. No.: M650522 Molecular Weight: 1259.48 PubChem CID: 76972714

GRADE & PURITY ≥98%

Synonyms

MURAMYL TRIPEPTIDE PHOSPHATIDYLETHANOLAMINE S | sodium;2-[[(2S)-2-[[(4R)-4-[[(2S)-2-[[(2R)-2-[(2R,3R,4R,5R)-2-acetamido-4,5,6-trihydroxy-1-oxohexan-3-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoyl]amino]propanoyl]amino]ethyl [(2R)-2,3-di(he

Storage

Store at 2-8°C,Desiccated

Shipped In

Wet ice

Overview

Mifamurtide sodium (MTP-PE sodium), an analog of the muramyl dipeptide (MDP), is a nonspecific immunomodulator by stimulating the immune response activating macrophages and monocytes. Mifamurtide sodium, an orphan agent, is a specific ligand of NOD2 used as an insulin sensitizer. Mifamurtide sodium has the potential for osteosarcoma research

In Vitro

Mifamurtide sodium (MTP-PE sodium; 100 µM) induces a reduction of MG63 cells number when co-cultured with macrophages. Mifamurtide sodium (100 µM) increases both the M1 polarization marker iNOS and the M2 polarization marker CD206 mRNAs; both pro-inflammatory (IL-1β, IL-6) and anti-inflammatory (IL-4, IL-10) cytokines. Mifamurtide sodium increases the iron transporter DMT1 protein. L-mifamurtide sodium (5, 5000 nM; for 48 hours) alone has no direct effect on the proliferation rate of the two osteosarcoma cell lines MOS-J and KHOS in vitro or in vivo. Mifamurtide sodium acts as a nonspecific immunomodulator by activating macrophages and monocytes related to the upregulation of tumoricidal activity and secretion of pro-inflammatory cytokines including tumor necrosis factor (TNF)-a, interleukin (IL)-1, IL-6, IL-8, IL-12, nitric oxide (NO), prostaglandin E2 (PGE2) and PGD2. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Mifamurtide sodium (MTP-PE sodium; 1 mg/kg; i.v.; twice per week for 4 weeks) causes a trend of diminished spontaneous lung metastasis dissemination . Mifamurtide sodium (50 μg/mouse) improves glucose tolerance during endotoxemia in mice. Mifamurtide sodium (equivalent to 20 μg MDP; 4 times per week for 5 weeks) improves glucose tolerance in HFD-fed mice without altering body mass. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: C57BL/6, BALB/c mice with KHOS osteosarcoma cells Dosage: 1 mg/kg Administration: IV; twice per week for 4 weeks Result: Caused a trend of diminished spontaneous lung metastasis dissemination in xenogeneic (KHOS) and syngeneic (MOS-J) models.

Form:Solid

IC50& Target:NOD2

Specifications

Synonyms

MURAMYL TRIPEPTIDE PHOSPHATIDYLETHANOLAMINE S | sodium;2-[[(2S)-2-[[(4R)-4-[[(2S)-2-[[(2R)-2-[(2R, 3R, 4R, 5R)-2-acetamido-4, 5, 6-trihydroxy-1-oxohexan-3-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoyl]amino]propanoyl]amino]ethyl [(2R)-2, 3-di(he

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Mifamurtide sodium (MTP-PE sodium), an analog of the muramyl dipeptide (MDP), is a nonspecific immunomodulator by stimulating the immune response activating macrophages and monocytes. Mifamurtide sodium, an orphan agent, is a specific ligand of NOD2 used

Storage

Store at 2-8°C, Desiccated

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CCCCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCCNC(=O)C(C)NC(=O)CCC(C(=O)N)NC(=O)C(C)NC(=O)C(C)OC(C(C=O)NC(=O)C)C(C(CO)O)O)OC(=O)CCCCCCCCCCCCCCC.[Na+]
• IUPAC Name: sodium;2-[[(2S)-2-[[(4R)-4-[[(2S)-2-[[(2R)-2-[(2R,3R,4R,5R)-2-acetamido-4,5,6-trihydroxy-1-oxohexan-3-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoyl]amino]propanoyl]amino]ethyl [(2R)-2,3-di(hexadecanoyloxy)propyl] phosphate
• InChIKey: LRSAONQAUPMYDK-XNLRRNFISA-M
• INCHI: 1S/C59H109N6O19P.Na/c1-7-9-11-13-15-17-19-21-23-25-27-29-31-33-52(71)80-41-47(84-53(72)34-32-30-28-26-24-22-20-18-16-14-12-10-8-2)42-82-85(78,79)81-38-37-61-57(75)43(3)62-51(70)36-35-48(56(60)74)65-58(76)44(4)63-59(77)45(5)83-55(54(73)50(69)40-67)49(39-66)64-46(6)68;/h39,43-45,47-50,54-55,67,69,73H,7-38,40-42H2,1-6H3,(H2,60,74)(H,61,75)(H,62,70)(H,63,77)(H,64,68)(H,65,76)(H,78,79);/q;+1/p-1/t43-,44-,45+,47+,48+,49-,50+,54+,55+;/m0./s1
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCCNC(=O)[C@H](C)NC(=O)CC[C@H](C(=O)N)NC(=O)[C@H](C)NC(=O)[C@@H](C)O[C@H]([C@H](C=O)NC(=O)C)[C@@H]([C@@H](CO)O)O)OC(=O)CCCCCCCCCCCCCCC.[Na+]
• Alternate CAS: 90825-43-7
• PubChem CID: 76972714
• MeSH Entry Terms: CGP 19835 A;CGP-19835A;Mepact;mifamurtide;mifamurtide acid;mifamurtide anhydrous;mifamurtide free acid anhydrous;mifamurtide sodium;mifamurtide sodium salt;MLV 19835;muramyl tripeptide phosphatidylethanolamine;muramyl tripeptide phosphatidylethanolamine,
• Molecular Weight: 1259.48

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Peptides
          • Level6 Dipeptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Peptides
• Direct Parent: Dipeptides
• Alternative Parents: N-acyl-phosphatidylethanolamines Glutamine and derivatives N-acyl-alpha amino acids and derivatives Alpha amino acid amides Hexoses Alanine and derivatives Monosaccharide phosphates Phosphoethanolamines Aminosaccharides Dialkyl phosphates Fatty acid esters Dicarboxylic acids and derivatives N-acyl amines Acetamides Secondary carboxylic acid amides Carboxylic acid esters Primary carboxylic acid amides Secondary alcohols Polyols Dialkyl ethers Organic zwitterions Hydrocarbon derivatives Organonitrogen compounds Organopnictogen compounds Primary alcohols Aldehydes Organic sodium salts Organic oxides
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Alpha-dipeptide - N-acyl-phosphatidylethanolamine - Glycero-3-phospho-n-acyl-ethanolamine - Glutamine or derivatives - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - Hexose monosaccharide - Alanine or derivatives - Monosaccharide phosphate - N-substituted-alpha-amino acid - Alpha-amino acid or derivatives - Glycerophospholipid - Phosphoethanolamine - Fatty acid ester - Amino saccharide - Dialkyl phosphate - Monosaccharide - Alkyl phosphate - Organic phosphoric acid derivative - Fatty amide - Fatty acyl - N-acyl-amine - Phosphoric acid ester - Dicarboxylic acid or derivatives - Acetamide - Primary carboxylic acid amide - Secondary alcohol - Secondary carboxylic acid amide - Carboxylic acid ester - Carboxamide group - Dialkyl ether - Organic alkali metal salt - Ether - Polyol - Organic zwitterion - Organic salt - Organic sodium salt - Aldehyde - Alcohol - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organopnictogen compound - Organic oxygen compound - Primary alcohol - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: DMSO : 50 mg/mL (39.70 mM; Need ultrasonic)