Adenosine 5'-monophosphate monohydrate

Names

[ Name ]:
Adenosine 5'-monophosphate monohydrate

[Synonym ]:
5'-AMP MONOHYDRATE
5'-AMPH2
5'-AMP
5'-Adenylic acid hydrate (1:1)
MFCD00149360
5'-AMP H2O
AMP.H2O
EINECS 200-500-0
5'-AMP=Adenylicacid
5'-adenylic acid, hydrate (1:1)
Adenosine 5′-monophosphate monohydrate
AMP monohydrate
A-5'-P
ADENYLIC ACID MONOHYDRATE
9H-Purin-6-amine, 9-(5-O-phosphono-β-D-ribofuranosyl)-, monohydrate

Biological Activity

[Description]:

Adenosine 5'-monophosphate monohydrate is an adenosine A1 receptor agonist.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Adenosine Receptor

Research Areas >> Neurological Disease

[Target]

Adenosine A1 receptor[1]

[In Vitro]

Adenosine 5'-monophosphate monohydrate is an adenosine A1 receptor agonist[1]. Adenosine 5'-monophosphate monohydrate (5′-AMP)-induced cell toxicity is negligible at concentrations of 25 to 400 μM in RAW264.7 cells. Adenosine 5'-monophosphate monohydrate significantly attenuates the mRNA expression of tumor necrosis factor-α (TNF-α) and interleukin (IL)-6 in RAW264.7 cells. The dose-dependence of TNF-α and IL-6 mRNA show that at concentration of 400 μM, Adenosine 5'-monophosphate monohydrate exhibits the maximum inhibition. Exposure of cells to Adenosine 5'-monophosphate monohydrate significantly reduces recruitment of NF-κB p65 to TNF-α, IL-6, and IL-1β gene promoters[2].

[In Vivo]

C57BL/6J mice treated with Adenosine 5'-monophosphate monohydrate (5′-AMP) markedly increases hepatic adenosine level. Survival rate in PBS-treated mice (n=15) is 60% (8 h) and 33.3% (24 h), whereas survival rate in Adenosine 5'-monophosphate monohydrate-treated mice (n=15) is 100% (8 h) and 93.3% (24 h). Serum aspartate transaminase (AST) and alanine transaminase (ALT) levels are significantly lowered in the Adenosine 5'-monophosphate monohydrate group than in the vehicle group. The area and extent of necrosis is attenuated and the infiltration of inflammatory cells is reduced in the Adenosine 5'-monophosphate monohydrate group[2].

[Kinase Assay]

RAW264.7 cells are plated in 100-mm dishes and stimulated with lipopolysaccharide (LPS) for 1 h. Cross-linked chromatin are sonicated into DNA fragment of 0.5 to 1.0 kb. For in vitro biochemical experiments, the sonicated cell lysates are incubated with Adenosine 5'-monophosphate monohydrate (5′-AMP) (400 μM) at 37°C for 30 min. Then chromatin is precleared with 50% salmon sperm DNA-saturated protein A agarose beads and immunoprecipitated with 5 μg of antibody[2].

[Cell Assay]

The RAW264.7 cells (a murine macrophage cell line) are maintained in supplemented RPMI 1640 in an atmosphere at 90% humidity containing 5% CO2 at 37°C. At the end of the pre-incubated period, cells are rinsed with PBS and the medium is supplemented with RPMI 1640 without fetal bovine serum. The cells are pretreated with Adenosine 5'-monophosphate monohydrate (5′-AMP) (400 μM) for 30 min[2].

[Animal admin]

Male WT C57BL/6J mice are used at 8 to 10 weeks of age with a body weight of 20 to 25 g in this work. For Adenosine 5'-monophosphate monohydrate (5′-AMP)-pretreated survival experiment, WT mice are randomly divided into two groups (n=15 in each group). Adenosine 5'-monophosphate monohydrate (5 mg/20 g body weight i.p.) or PBS is administered to mice. For general experiment, WT mice are randomly divided into different groups (n=5 in each group): (1) vehicle/vehicle group; (2) Adenosine 5'-monophosphate monohydrate/vehicle group. Mice are killed and the blood is collected from the carotid artery. The liver of each mouse is removed immediately and then is kept at -80°C until analyzed[2].

[References]

[1]. Rittiner JE, et al. AMP is an adenosine A1 receptor agonist. J Biol Chem. 2012 Feb 17;287(8):5301-9.

[2]. Zhan Y, et al. Adenosine 5'-monophosphate ameliorates D-galactosamine/lipopolysaccharide-induced liver injury through an adenosine receptor-independent mechanism in mice. Cell Death Dis. 2014 Jan 9;5:e985.

[Related Small Molecules]

Chemical & Physical Properties

[ Boiling Point ]:
798.5ºC at 760mmHg

[ Melting Point ]:
183-188 °C (dec.)(lit.)

[ Molecular Formula ]:
C₁₀H₁₆N₅O₈P

[ Molecular Weight ]:
365.237

[ Flash Point ]:
436.7ºC

[ Exact Mass ]:
365.073639

[ PSA ]:
205.11000

[ Vapour Pressure ]:
6.7E-27mmHg at 25°C

[ Storage condition ]:
-20 °C

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
AU7480500

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J. Chromatogr. A. 1360 , 240-7, (2014)

Glucaminium-based ionic liquids are a new class of recently developed ionic liquids and prepared by functionalizing the amine group of N-methyl-d-glucamine, which renders them good hydrophilicity due ...

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Dissecting the role of 5'-AMP for allosteric stimulation, activation, and deactivation of AMP-activated protein kinase.

J. Biol. Chem. 281(43) , 32207-16, (2006)

AMP-activated protein kinase (AMPK) is a heterotrimeric protein kinase that is crucial for cellular energy homeostasis of eukaryotic cells and organisms. Here we report on the activation of AMPK alpha...