Mifamurtide

Mifamurtide is a drug against osteosarcoma, a kind of bone cancer mainly affecting children and young adults, which is lethal in about a third of cases.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: 10-101-165

CAS No:83461-56-7

Synonyms/Alias:83461-56-7;CGP-19835;[(2R)-3-[2-[[(2S)-2-[[(4R)-4-[[(2S)-2-[[(2R)-2-[(3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoyl]amino]propanoyl]amino]ethoxy-hydroxyphosphoryl]oxy-2-hexadecanoyloxypropyl] hexadecanoate;MTP-cephalin;CHEMBL2111100;CHEBI:135906;Mifamurtide; L-Alaninamide, N-(N-acetylmuramoyl)-L-alanyl-D-a-glutaminyl-N-[(7R)-4-hydroxy-4-oxido-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacos-1-yl]-; L-Alaninamide, N-(N-acetylmuramoyl)-L-alanyl-D-a-glutaminyl-N-[4-hydroxy-10-oxo-7-[(1-oxohexadecyl);N-(N-Acetylmuramoyl)-L-alanyl-D-alpha-glutaminyl-N-[(7R)-4-hydroxy-4-oxido-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacos-1-yl]-L-alaninamide;

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M.F/Formula
C59H109N6O19P
M.W/Mr.
1237.5
Labeling Target
Nucleotide-binding oligomerization domain-containing protein 2
Application
Mifamurtide is indicated for the treatment of high-grade, nonmetastasizing, resectable osteosarcoma following complete surgical removal in children, adolescents, and young adults, aged two to 30 years.
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Activity
Agonist
Biological Activity
Mifamurtide is a liposomal formulation containing a muramyl dipeptide (MDP) analogue with potential immunomodulatory and antineoplastic activities.
Areas of Interest
Osteosarcoma

Mifamurtide, also known as muramyl tripeptide phosphatidylethanolamine (MTP-PE), is a synthetic derivative of muramyl dipeptide, which is a naturally occurring component of bacterial cell walls. Engineered to mimic the immunostimulatory properties of its parent compound, Mifamurtide is designed for research and development in the field of immunology and oncology. Its unique structure enables it to interact with immune cells, particularly macrophages and monocytes, triggering a cascade of cellular responses that can be harnessed for various scientific investigations. As a potent activator of the innate immune system, Mifamurtide is valued for its ability to modulate cytokine production and enhance the body's initial defense mechanisms. Researchers utilize this compound to explore cellular signaling pathways, immune modulation, and the interplay between innate immunity and disease progression.

Immunology Research: Mifamurtide is widely employed in immunological studies to elucidate the mechanisms underlying innate immune activation. By binding to pattern recognition receptors such as NOD2 on monocytes and macrophages, it stimulates the production of pro-inflammatory cytokines and chemokines. This property makes it a valuable tool for dissecting the molecular events that govern immune cell activation, differentiation, and communication. Scientists utilize MTP-PE to model the body's response to bacterial infection, investigate the signaling cascades involved in inflammation, and identify potential targets for immunomodulatory therapies. Its ability to trigger a controlled and measurable immune response allows for reproducible experiments in both in vitro and in vivo systems.

Cancer Biology: In the realm of cancer research, Mifamurtide serves as a model compound for studying the role of innate immunity in tumor microenvironments. By activating macrophages, it can induce the release of factors that modulate tumor cell behavior, influence angiogenesis, and affect the recruitment of other immune cells to the tumor site. Researchers employ it to investigate how innate immune activation can alter tumor growth dynamics, promote anti-tumor immunity, and potentially sensitize tumors to other therapeutic interventions. The compound's capacity to simulate aspects of the body's natural defense against malignancies provides valuable insights into the development of novel immunotherapeutic strategies.

Drug Delivery Systems: MTP-PE is frequently incorporated into liposomal formulations and other drug delivery platforms to enhance the immunogenicity of encapsulated agents. Its lipid-soluble properties facilitate integration into phospholipid bilayers, making it an ideal candidate for targeted delivery to immune cells. Scientists exploit this characteristic to design delivery vehicles that can co-activate immune responses alongside the administration of experimental drugs or vaccines. By leveraging its dual role as an immunostimulant and a delivery enhancer, researchers can optimize the efficacy and specificity of their investigational compounds.

Adjuvant Development: The immunostimulatory profile of Mifamurtide has made it a subject of interest in the development of adjuvants for vaccines and immunotherapies. Its ability to potentiate immune responses without introducing pathogenic material enables the creation of safer and more effective adjuvant systems for preclinical studies. Researchers assess its impact on antigen presentation, T-cell priming, and the generation of memory responses. The insights gained from these studies inform the rational design of next-generation adjuvants that can improve the immunogenicity of experimental vaccines or biologics in animal models.

Inflammatory Pathway Analysis: Mifamurtide is also utilized to probe the complex networks of signaling pathways involved in inflammation and immune regulation. By serving as a controlled trigger for innate immune activation, it allows scientists to dissect the downstream effects on gene expression, protein synthesis, and cellular interactions. This approach is instrumental in mapping the intricate balance between pro-inflammatory and anti-inflammatory signals, identifying potential biomarkers, and understanding disease mechanisms at a molecular level.

In summary, Mifamurtide stands out as a versatile research compound with broad applications in immunology, cancer biology, drug delivery, adjuvant development, and inflammatory pathway analysis. Its unique ability to activate innate immune responses positions it as a critical tool for advancing scientific knowledge in these fields. As research continues to uncover the complexities of immune regulation and disease, Mifamurtide remains an indispensable resource for investigators seeking to explore the frontiers of immunomodulation and therapeutic innovation.

Source#
Synthetic
Long-term Storage Conditions
Soluble in DMSO, not in water
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.
Short-term Storage Conditions
Dry, dark and at 0 - 4 °C
Solubility
-20 °C
Organism
Human
InChI
InChI=1S/C59H109N6O19P/c1-7-9-11-13-15-17-19-21-23-25-27-29-31-33-50(69)79-40-46(83-51(70)34-32-30-28-26-24-22-20-18-16-14-12-10-8-2)41-81-85(77,78)80-38-37-61-56(73)42(3)62-49(68)36-35-47(55(60)72)65-57(74)43(4)63-58(75)44(5)82-54-52(64-45(6)67)59(76)84-48(39-66)53(54)71/h42-44,46-48,52-54,59,66,71,76H,7-41H2,1-6H3,(H2,60,72)(H,61,73)(H,62,68)(H,63,75)(H,64,67)(H,65,74)(H,77,78)/t42-,43-,44+,46+,47+,48+,52+,53+,54+,59?/m0/s1
InChI Key
JMUHBNWAORSSBD-WKYWBUFDSA-N
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]1[C@@H]([C@H](OC([C@@H]1NC(=O)C)O)CO)O)OC(=O)CCCCCCCCCCCCCCC
BoilingPoint
N/A
References

Mifamurtide, also known as liposomal muramyl tripeptide phosphatidyl ethanolamine (L-MTP-PE), has been approved for the treatment of osteosarcoma in Europe. Mifamurtide's rational drug design employs MTP-PE for macrophage activation in a multilamellar liposome drug carrier, containing the synthetic phospholipids 1-palmitoyl-2-oleoyl phosphatidyl choline (POPC) and 1,2-dioleoyl phosphatidyl serine (OOPS). Although the drug is not cytotoxic towards normal or tumor cells in vitro, immune activation against osteosarcoma lung metastases in vivo accounts for mifamurtide's antiosteosarcoma effects. Phosphatidyl serine-containing lipids signal macrophage cells that have "flipped phosphatidyl serine" to the outer membrane after apoptosis (e.g., after damage of tumor cells from chemotherapy); thus, both mifamurtide's active and inactive ingredients target immune cells in the lungs.

Mifamurtide in osteosarcoma: a practical review.

Mifamurtide (liposomal muramyl tripeptide phosphatidylethanolamine; L-MTP-PE) is a new agent. L-MTP-PE is a nonspecific immunomodulator, which is a synthetic analog of a component of bacterial cell walls. L-MTP-PE activates macrophages and monocytes as a potent activator of immune response in addition to standard chemotherapy. It also improves the overall survival from 70 to 78% and results in a one-third reduction in the risk of death from osteosarcoma.

Mifamurtide for the treatment of nonmetastatic osteosarcoma

Melting Point
N/A

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