Ac-muramyl-Ala-D-Glu-NH2

Names

[ Name ]:
Ac-muramyl-Ala-D-Glu-NH2

[Synonym ]:
2-Acetamido-2-deoxy-3-O-(D-2-propionyl-L-alanyl-D-isoglutamine)-D-glucopyranose
AC-MURAMYL-ALA-D-GLN
Adjuvant Peptide,Muramyl dipeptide
N-AC-MURAMYL-ALA-D-GLU-NH2
L-18-MDP
MFCD00077638
AC-MURAMYL-ALA-D-GLU-NH2
ADJUVANT PEPTIDE
MDP
AC-MURAMYL-ALA-D-ISOGLN-OH
N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE
Nod2 ligand muramyl dipeptide
N2-[N-(N-Acetylmuramoyl)-L-alanyl]-D-a-glutamine
EINECS 258-696-9
(4R)-4-{[(2S)-2-{[(2R)-2-{[(3R,4R,5S,6R)-3-Acetamido-2,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl]oxy}propanoyl]amino}propanoyl]amino}-5-amino-5-oxopentanoic acid

Biological Activity

[Description]:

Muramyl dipeptide (MDP) is a synthetic immunoreactive peptide, consisting of N-acetyl muramic acid attached to a short amino acid chain of L-Ala-D-isoGln. Muramyl dipeptide is an inducer of bone formation through induction of Runx2. Muramyl dipeptide directly enhances osteoblast differentiation by up-regulating Runx2 gene expression through MAPK pathways. Muramyl dipeptide indirectly attenuates osteoclast differentiation through a decreased RANKL/OPG ratio[1].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> MAPK/ERK Pathway >> p38 MAPK

Signaling Pathways >> MAPK/ERK Pathway >> ERK

Signaling Pathways >> MAPK/ERK Pathway >> JNK

Signaling Pathways >> Stem Cell/Wnt >> ERK

[In Vitro]

Muramyl dipeptide (0.1-10 µg/mL; 24 hours) increases protein expression of Runx2 in a dose-dependent manner[1]. Muramyl dipeptide (0.1-10 µg/mL; 6 hours) increases mRNA levels of Runx2 in a dose-dependent manner[1]. Western Blot Analysis[1] Cell Line: MC3T3-E1 cells Concentration: 0.1, 1, 10 µg/mL Incubation Time: 24 hours Result: Increased protein expression of Runx2 in a dose-dependent manner. RT-PCR[1] Cell Line: MC3T3-E1 cells Concentration: 0.1, 1, 10 µg/mL Incubation Time: 6 hours Result: Increases mRNA levels of Runx2 in a dose-dependent manner.

[In Vivo]

Muramyl dipeptide (1.25 mg/kg; i.p.; twice) alleviates bone loss induced by osteoporosis[1]. Animal Model: RANKL-induced osteoporosis model (Five-week-old C57BL/6 mice)[1] Dosage: 1.25 mg/kg Administration: i.p.; twice (RANKL-induced osteoporosis for 3 weeks and euthanized at 4 weeks) Result: Significantly enhanced the trabecular bone volume (BV/TV) and trabecular number (Tb.N).

[References]

[1]. Park OJ, et al. 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.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
1023.8±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₉H₃₂N₄O₁₁

[ Molecular Weight ]:
492.478

[ Flash Point ]:
572.9±34.3 °C

[ Exact Mass ]:
492.206757

[ PSA ]:
246.84000

[ LogP ]:
-2.97

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.578

[ Storage condition ]:
−20°C

[ Water Solubility ]:
H2O: 10 mg/mL, clear, colorless

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MA2275260

CHEMICAL NAME :: D-alpha-Glutamine, N(sup 2)-(N-(N-acetylmuramoyl)-L-alanyl)-

CAS REGISTRY NUMBER :: 53678-77-6

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C19-H32-N4-O11

MOLECULAR WEIGHT :: 492.55

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intratesticular

DOSE :: 800 ug/kg

SEX/DURATION :: male 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)

REFERENCE :: IJMRAQ Indian Journal of Medical Research. (Indian Council of Medical Research, Ansari Nagar, New Delhi 110 029, India) V.1- 1913- Volume(issue)/page/year: 74,251,1981

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
MA2275260

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