Uridine triphosphate

Names

[ CAS No. ]:
63-39-8

[ Name ]:
Uridine triphosphate

[Synonym ]:
uridine-triphosphate
Uteplex
[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
Uridine 5'-triphosphoric acid
uridine 5'-O-triphosphate
MFCD00274571
5'-UTP
uridine 5'-triphosphate
EINECS 243-347-5
Uridine triphosphate
Uridine 5'-(tetrahydrogen triphosphate)

Biological Activity

[Description]:

Uridine triphosphate (UTP;Uridine 5'-triphosphate) is a pyrimidine nucleoside triphosphate that participates in glycogen metabolism and synthesis of RNA during transcription.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

Research Areas >> Cardiovascular Disease

Research Areas >> Inflammation/Immunology

[In Vitro]

Uridine triphosphate treatment induces Schwannoma cell migration through activation of P2Y2 receptors and through the increase of extracellular matrix metalloproteinase-2 (MMP-2) activation and expression[1]. Uridine triphosphate-induced proliferation is mediated by protein kinase D, Src-family tyrosine kinase, Ca/calmodulin-dependent protein kinase II, phosphatidylinositol 3-kinase (PI3K), Akt, and phospholipase D. Uridine triphosphate increases phosphorylation of Akt through protein kinase C, Src-family tyrosine kinase, Ca/calmodulin-dependent protein kinase II, and PI3K[2].

[In Vivo]

Uridine triphosphate reduces mitochondrial calcium levels following hypoxia. Early or late uridine triphosphate preconditioning is effective to reduce infarct size and superior myocardial function[3]. Uridine triphosphate treatment increases the number of monocytes and macrophages infiltrating the pouch and up-regulates the gene expression of IL-4 and IL-13 in the regional lymph nodes[4].

[Cell Assay]

Pancreatic duct epithelial cells are treated with (0.1 μM-1 mM) uridine triphosphate. BrdU is added after different time points (12-24 hours). Proliferation is measured using the BrdU incorporation assay in triplicate[2].

[Animal admin]

Rats: Four main groups are tested: (1) sham without LAD ligation, (2) LAD ligation, (3) injected with UTP (0.44 µg/kg i.v.) 30 min before MI, (4) UTP injection (4.4 µg/kg i.v.) 24 h prior to MI. Several different concentrations of UTP are tested (0.044–44.4 µg/kg). Left ventricular systolic pressure (LVSP), end-diastolic pressure (LVEDP) and heart rates are monitored before, after UTP treatment and post MI[3].

[References]

[1]. Lamarca A, et al. Uridine 5'-triphosphate promotes in vitro Schwannoma cell migration through matrix metalloproteinase-2 activation. PLoS One. 2014 Jun 6;9(6):e98998.

[2]. Choi JH, et al. Uridine triphosphate increases proliferation of human cancerous pancreatic duct epithelial cells by activating P2Y2 receptor. Pancreas. 2013 May;42(4):680-6.

[3]. Yitzhaki S, et al. Uridine-5'-triphosphate (UTP) reduces infarct size and improves rat heart function aftermyocardial infarct. Biochem Pharmacol. 2006 Oct 16;72(8):949-55.

[4]. Iwaki Y, et al. Enhancement of antibody production against rabies virus by uridine 5'-triphosphate in mice. Microbes Infect. 2014 Mar;16(3):196-202.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
2.106 g/cm3

[ Molecular Formula ]:
C₉H₁₅N₂O₁₅P₃

[ Molecular Weight ]:
484.14100

[ Flash Point ]:
113ºC

[ Exact Mass ]:
483.96900

[ PSA ]:
293.80000

[ Storage condition ]:
−20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YU8083000

CHEMICAL NAME :: Uridine, 5'-(tetrahydrogen triphosphate)

CAS REGISTRY NUMBER :: 63-39-8

BEILSTEIN REFERENCE NO. :: 0071520

LAST UPDATED :: 199701

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C9-H15-N2-O15-P3

MOLECULAR WEIGHT :: 484.17

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Human Cells - not otherwise specified

DOSE/DURATION :: 1 mmol/L

REFERENCE :: JIDEAE Journal of Investigative Dermatology. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1938- Volume(issue)/page/year: 65,52,1975

Uridine triphosphate

Names

Biological Activity

Chemical & Physical Properties

Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

Safety Information

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds