MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 561820 | Name: Muramyl Dipeptide
Featured

Description:

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

Muramyl Dipeptide is a peptidoglycan immunoadjuvant. It also acts as pyrogen, causes arthritis, and stimulates both humoral and cellular immunity.

Chemical Structure

Muramyl Dipeptide
Muramyl Dipeptide
CAS#53678-77-6

Theoretical Analysis

MedKoo Cat#: 561820

Name: Muramyl Dipeptide

CAS#: 53678-77-6

Chemical Formula: C19H34N4O10

Exact Mass: 478.2275

Molecular Weight: 478.50

Elemental Analysis: C, 47.69; H, 7.16; N, 11.71; O, 33.44

Price and Availability

Size Price Availability Quantity
1mg USD 450.00 2 Weeks
5mg USD 750.00 2 Weeks
10mg USD 1,250.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Muramyl Dipeptide; Adjuvant Peptide; Ac-muramyl-Ala-D-Glu-NH2; N-Acetylmuramyl-L-alanyl-D-isoglutamine;
IUPAC/Chemical Name
(4R)-4-((2S)-2-(2-(((2S,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)propanamido)propanamido)-5-amino-5-oxopentanoic acid
InChi Key
BSOQXXWZTUDTEL-LLAKEARDSA-N
InChi Code
InChI=1S/C19H32N4O11/c1-7(17(30)23-10(16(20)29)4-5-12(26)27)21-18(31)8(2)33-15-13(22-9(3)25)19(32)34-11(6-24)14(15)28/h7-8,10-11,13-15,19,24,28,32H,4-6H2,1-3H3,(H2,20,29)(H,21,31)(H,22,25)(H,23,30)(H,26,27)/t7-,8?,10+,11+,13+,14+,15+,19-/m0/s1
SMILES Code
CC(N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1O)CO)O)OC(C)C(N[C@@H](C)C(N[C@@H](C(N)=O)CCC(O)=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
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
Instruction
View handling instruction
Biological target:
Muramyl Dipeptide is a peptidoglycan immunoadjuvant.
In vitro activity:
SIM-A9 microglia and SH-SY5Y neuroblastoma cells were cholesterol-enriched using a water-soluble cholesterol complex. After exposure to lipopolysaccharide (LPS) plus muramyl dipeptide or Aβ, activation of the inflammasome pathway was analyzed by immunofluorescence, ELISA and immunoblotting analysis. Fluorescently-labeled Aβ was employed to monitor changes in microglia phagocytosis. Conditioned medium was used to study how microglia-neuron interrelationship modulates the inflammasome-mediated response. Reference: Transl Neurodegener. 2023 Mar 9;12(1):10. https://pubmed.ncbi.nlm.nih.gov/36895045/
In vivo activity:
This study investigated the regulation of bone metabolism by muramyl dipeptide (MDP), which is a shared structural unit of peptidoglycans. Increased bone and mineral density by enhanced bone formation were observed in mice administered with MDP. Remarkably, pretreatment or posttreatment with MDP alleviated bone loss in RANKL-induced osteoporosis mouse models. MDP directly augmented osteoblast differentiation and bone-forming gene expression by Runx2 activation. Reference: J Bone Miner Res. 2017 Jul;32(7):1455-1468. https://pubmed.ncbi.nlm.nih.gov/28337794/
Solvent mg/mL mM
Solubility
DMSO 179.0 374.09
Water 62.7 130.97
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 478.50 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. de Dios C, Abadin X, Roca-Agujetas V, Jimenez-Martinez M, Morales A, Trullas R, Mari M, Colell A. Inflammasome activation under high cholesterol load triggers a protective microglial phenotype while promoting neuronal pyroptosis. Transl Neurodegener. 2023 Mar 9;12(1):10. doi: 10.1186/s40035-023-00343-3. PMID: 36895045; PMCID: PMC9996936. 2. Chedid L, Parant M, Parant F, Lefrancher P, Choay J, Lederer E. Enhancement of nonspecific immunity to Klebsiella pneumoniae infection by a synthetic immunoadjuvant (N-acetylmuramyl-L-alanyl-D-isoglutamine) and several analogs. Proc Natl Acad Sci U S A. 1977 May;74(5):2089-93. doi: 10.1073/pnas.74.5.2089. PMID: 325566; PMCID: PMC431080. 3. Lessard AJ, LeBel M, Egarnes B, Préfontaine P, Thériault P, Droit A, Brunet A, Rivest S, Gosselin J. Triggering of NOD2 Receptor Converts Inflammatory Ly6Chigh into Ly6Clow Monocytes with Patrolling Properties. Cell Rep. 2017 Aug 22;20(8):1830-1843. doi: 10.1016/j.celrep.2017.08.009. PMID: 28834747. 4. Park OJ, Kim J, Yang J, Yun CH, Han SH. Muramyl Dipeptide, a Shared Structural Motif of Peptidoglycans, Is a Novel Inducer of Bone Formation through Induction of Runx2. J Bone Miner Res. 2017 Jul;32(7):1455-1468. doi: 10.1002/jbmr.3137. Epub 2017 Apr 27. Erratum in: J Bone Miner Res. 2019 May;34(5):975. PMID: 28337794.
In vitro protocol:
1. de Dios C, Abadin X, Roca-Agujetas V, Jimenez-Martinez M, Morales A, Trullas R, Mari M, Colell A. Inflammasome activation under high cholesterol load triggers a protective microglial phenotype while promoting neuronal pyroptosis. Transl Neurodegener. 2023 Mar 9;12(1):10. doi: 10.1186/s40035-023-00343-3. PMID: 36895045; PMCID: PMC9996936. 2. Chedid L, Parant M, Parant F, Lefrancher P, Choay J, Lederer E. Enhancement of nonspecific immunity to Klebsiella pneumoniae infection by a synthetic immunoadjuvant (N-acetylmuramyl-L-alanyl-D-isoglutamine) and several analogs. Proc Natl Acad Sci U S A. 1977 May;74(5):2089-93. doi: 10.1073/pnas.74.5.2089. PMID: 325566; PMCID: PMC431080.
In vivo protocol:
1. Lessard AJ, LeBel M, Egarnes B, Préfontaine P, Thériault P, Droit A, Brunet A, Rivest S, Gosselin J. Triggering of NOD2 Receptor Converts Inflammatory Ly6Chigh into Ly6Clow Monocytes with Patrolling Properties. Cell Rep. 2017 Aug 22;20(8):1830-1843. doi: 10.1016/j.celrep.2017.08.009. PMID: 28834747. 2. Park OJ, Kim J, Yang J, Yun CH, Han SH. Muramyl Dipeptide, a Shared Structural Motif of Peptidoglycans, Is a Novel Inducer of Bone Formation through Induction of Runx2. J Bone Miner Res. 2017 Jul;32(7):1455-1468. doi: 10.1002/jbmr.3137. Epub 2017 Apr 27. Erratum in: J Bone Miner Res. 2019 May;34(5):975. PMID: 28337794.
1: Nielsen AE, Hantho JD, Mancini RJ. Synthetic agonists of NOD-like, RIG-I-like, and C-type lectin receptors for probing the inflammatory immune response. Future Med Chem. 2017 Aug;9(12):1345-1360. doi: 10.4155/fmc-2017-0101. Epub 2017 Aug 4. Review. PubMed PMID: 28776416. 2: Al Nabhani Z, Dietrich G, Hugot JP, Barreau F. Nod2: The intestinal gate keeper. PLoS Pathog. 2017 Mar 2;13(3):e1006177. doi: 10.1371/journal.ppat.1006177. eCollection 2017 Mar. Review. PubMed PMID: 28253332; PubMed Central PMCID: PMC5333895. 3: Salem M, Ammitzboell M, Nys K, Seidelin JB, Nielsen OH. ATG16L1: A multifunctional susceptibility factor in Crohn disease. Autophagy. 2015 Apr 3;11(4):585-94. doi: 10.1080/15548627.2015.1017187. Review. PubMed PMID: 25906181; PubMed Central PMCID: PMC4502774. 4: Chavarría-Smith J, Vance RE. The NLRP1 inflammasomes. Immunol Rev. 2015 May;265(1):22-34. doi: 10.1111/imr.12283. Review. PubMed PMID: 25879281. 5: Hrnčířová L, Krejsek J, Šplíchal I, Hrnčíř T. Crohn's disease: a role of gut microbiota and Nod2 gene polymorphisms in disease pathogenesis. Acta Medica (Hradec Kralove). 2014;57(3):89-96. doi: 10.14712/18059694.2014.46. Review. PubMed PMID: 25649363. 6: Cui J, Chen Y, Wang HY, Wang RF. Mechanisms and pathways of innate immune activation and regulation in health and cancer. Hum Vaccin Immunother. 2014;10(11):3270-85. doi: 10.4161/21645515.2014.979640. Review. PubMed PMID: 25625930; PubMed Central PMCID: PMC4514086. 7: Boyle JP, Parkhouse R, Monie TP. Insights into the molecular basis of the NOD2 signalling pathway. Open Biol. 2014 Dec;4(12). pii: 140178. doi: 10.1098/rsob.140178. Review. PubMed PMID: 25520185; PubMed Central PMCID: PMC4281710. 8: Leblanc P, Moise L, Luza C, Chantaralawan K, Lezeau L, Yuan J, Field M, Richer D, Boyle C, Martin WD, Fishman JB, Berg EA, Baker D, Zeigler B, Mais DE, Taylor W, Coleman R, Warren HS, Gelfand JA, De Groot AS, Brauns T, Poznansky MC. VaxCelerate II: rapid development of a self-assembling vaccine for Lassa fever. Hum Vaccin Immunother. 2014;10(10):3022-38. doi: 10.4161/hv.34413. Review. PubMed PMID: 25483693; PubMed Central PMCID: PMC5443105. 9: Behr MA, Divangahi M. Freund's adjuvant, NOD2 and mycobacteria. Curr Opin Microbiol. 2015 Feb;23:126-32. doi: 10.1016/j.mib.2014.11.015. Epub 2014 Dec 5. Review. PubMed PMID: 25483349. 10: Schwendener RA. Liposomes as vaccine delivery systems: a review of the recent advances. Ther Adv Vaccines. 2014 Nov;2(6):159-82. doi: 10.1177/2051013614541440. Review. PubMed PMID: 25364509; PubMed Central PMCID: PMC4212474. 11: Meyers PA, Chou AJ. Muramyl tripeptide-phosphatidyl ethanolamine encapsulated in liposomes (L-MTP-PE) in the treatment of osteosarcoma. Adv Exp Med Biol. 2014;804:307-21. doi: 10.1007/978-3-319-04843-7_17. Review. PubMed PMID: 24924182. 12: Karaulov AV, Kaliuzhin OV. [Immunotherapy for infectious diseases: challenges and prospects]. Ter Arkh. 2013;85(11):100-8. Review. Russian. PubMed PMID: 24432609. 13: Wiest R, Lawson M, Geuking M. Pathological bacterial translocation in liver cirrhosis. J Hepatol. 2014 Jan;60(1):197-209. doi: 10.1016/j.jhep.2013.07.044. Epub 2013 Aug 28. Review. PubMed PMID: 23993913. 14: Bawa M, Saraswat VA. Gut-liver axis: role of inflammasomes. J Clin Exp Hepatol. 2013 Jun;3(2):141-9. doi: 10.1016/j.jceh.2013.03.225. Epub 2013 Apr 15. Review. PubMed PMID: 25755488; PubMed Central PMCID: PMC4216435. 15: Nakano M, Kambe N. [The present and the prospect of study on Blau syndrome/early-onset sarcoidosis]. Nihon Rinsho. 2013 Apr;71(4):737-41. Review. Japanese. PubMed PMID: 23678609. 16: Jakopin Ž. Murabutide revisited: a review of its pleiotropic biological effects. Curr Med Chem. 2013;20(16):2068-79. Review. PubMed PMID: 23531213. 17: Yao Q. Nucleotide-binding oligomerization domain containing 2: structure, function, and diseases. Semin Arthritis Rheum. 2013 Aug;43(1):125-30. doi: 10.1016/j.semarthrit.2012.12.005. Epub 2013 Jan 24. Review. PubMed PMID: 23352252. 18: Salem M, Seidelin JB, Rogler G, Nielsen OH. Muramyl dipeptide responsive pathways in Crohn's disease: from NOD2 and beyond. Cell Mol Life Sci. 2013 Sep;70(18):3391-404. doi: 10.1007/s00018-012-1246-4. Epub 2012 Dec 29. Review. PubMed PMID: 23275943. 19: Contassot E, Beer HD, French LE. Interleukin-1, inflammasomes, autoinflammation and the skin. Swiss Med Wkly. 2012 May 31;142:w13590. doi: 10.4414/smw.2012.13590. Review. PubMed PMID: 22653747. 20: Dzierzbicka K, Wardowska A, Trzonkowski P. Recent developments in the synthesis and biological activity of muramylpeptides. Curr Med Chem. 2011;18(16):2438-51. Review. PubMed PMID: 21568914.