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Muramyl Dipeptide (MDP) is a novel and potent NOD2 agonist. It is a synthetic peptidoglycan immunoadjuvant that also causes arthritis and stimulates cellular and humorally bioavailable immunity. It has been demonstrated that NOD2 can recognize MDP, but not TLR2, TLR2/1, or TLR2/6 associations [1, 2]. There is no reaction to the D-D or L-L analogs in this recognition, which is highly stereospecific for the L-D isomer.
| Targets |
p38 MAPK; NLRP1
|
|---|---|
| ln Vitro |
MDP directly augments osteoblast differentiation and bone-forming gene expression by Runx2 activation. MDP has no direct effect, but it indirectly inhibits osteoclast differentiation by lowering the RANKL/OPG ratio. The MDP receptor, Nod2, is expressed more frequently when MDP is present, and Nod2-deficient individuals do not experience MDP-induced bone formation or osteoblast activation. [1]
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| ln Vivo |
Muramyl dipeptide (MDP)-treated mice show increased bone and mineral density due to enhanced bone formation. Surprisingly, pre- or post-treatment with MDP reduces bone loss in mouse models of RANKL-induced osteoporosis.[1]
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| Enzyme Assay |
Enzyme-linked immunosorbent assay[1]
The levels of OPG and RANKL in culture supernatant and bone marrow extracellular fluid were measured using Quantikine enzyme-linked immunosorbent assay (ELISA) kits according to the manufacturer's instructions. Real-time reverse transcriptase–polymerase chain reaction[1] The mRNA expression of ALP, BSP, Runx2, Nod2, and GAPDH in osteoblasts was determined by using real-time reverse transcriptase–polymerase chain reaction (real-time RT-PCR) as described.28 The sequences of each primer are as follows: ALP: forward 5′-CCAACTCTTTTGTGCCAGAGA-3′ and reverse 5′-GGCTACATTGGTGTTGAGCTTTT-3′; BSP, forward 5′-GAATGCTGTGTCCTCTGAAG-3′ and reverse 5′-AATCCTCGCTCTCTGCATGG-3′; Runx2: forward 5′-AACGATCTGAGATTTGTGGGC-3′ and reverse 5′-CCTGCGTGGGATTTCTTGGTT-3′; Nod2: forward 5′-CCTGGTACGTGCCCAAAGTAG-3′ and reverse 5′-GCCAAGTAGAAAGCGGCAAA-3′; and GAPDH: forward 5′-AGGTCGGTGTGAACCGGATTTG-3′ and reverse 5′-TGTAGACCATGTAGTTGAGGTCA-3′. |
| Cell Assay |
In 48-well plates with 2×104 cells/400 l per well, MC3T3-E1 cells, BMSCs, or primary osteoblast precursors from mouse calvaria are plated before being incubated with osteoblast induction medium in the absence or presence of MDP. Every two days, half of the medium is replaced with brand-new osteoblast induction medium. At days 6 and 12, the cells are stained with alizarin red S to detect bone mineralization and with ALP to detect osteoblast differentiation.
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| Animal Protocol |
Five-week-old C57BL/6 mice, one-day-old neonatal mice, B6.129S1-Nod2tm1Flv/J mice
1.25 mg/kg IP |
| References |
| Molecular Formula |
C19H34N4O10
|
|---|---|
| Molecular Weight |
492.47800
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| Exact Mass |
478.23
|
| Elemental Analysis |
C, 47.69; H, 7.16; N, 11.71; O, 33.44
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| CAS # |
53678-77-6
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| Related CAS # |
53678-77-6
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| Appearance |
White to off-white solid powder
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| LogP |
-2.97
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| tPSA |
246.840
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| SMILES |
C[C@@H](C(=O)N[C@H](CCC(=O)O)C(=O)N)NC(=O)[C@@H](C)O[C@H]1[C@@H]([C@H](OC([C@@H]1NC(=O)C)O)CO)O
|
| InChi Key |
BSOQXXWZTUDTEL-QAQREVAFSA-N
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| 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
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| Chemical Name |
(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-oxopentanoic acid
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| Synonyms |
Adjuvant Peptide; Muramyl Dipeptide; N-Acetylmuramyl-L-alanyl-D-isoglutamine; Ac-muramyl-Ala-D-Glu-NH2
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: 98~260 mg/mL (199~527.9 mM)
Ethanol: ~98 mg/mL (~199 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 6.5 mg/mL (13.20 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 65.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 6.5 mg/mL (13.20 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 65.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 6.5 mg/mL (13.20 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0305 mL | 10.1527 mL | 20.3054 mL | |
| 5 mM | 0.4061 mL | 2.0305 mL | 4.0611 mL | |
| 10 mM | 0.2031 mL | 1.0153 mL | 2.0305 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT04924686 | Unknown | Other: Observational studies, no intervention |
Colorectal Cancer Type2 Diabetes Mellitus |
Zhujiang Hospital | May 10, 2020 |
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