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U6875

Uridine 5′-triphosphate tris salt

Name: Uridine 5′-triphosphate tris salt
Brand: SIGMA

Type VI, ≥90%

Synonym(s):

UTP

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About This Item

Empirical Formula (Hill Notation):

C₉H₁₅N₂O₁₅P₃

CAS Number:

108321-53-5

Molecular Weight:

484.14

MDL number:

MFCD00058360

UNSPSC Code:

12352200

PubChem Substance ID:

329827645

NACRES:

NA.77

type

Type VI

Quality Level

200

Assay

≥90%

solubility

H₂O: soluble 50 mg/mL, clear, colorless

shipped in

dry ice

storage temp.

−20°C

SMILES string

NC(CO)(CO)CO.O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N2C=CC(=O)NC2=O

InChI

1S/C9H15N2O15P3.C4H11NO3/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18;5-4(1-6,2-7)3-8/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H,10,12,15)(H2,16,17,18);6-8H,1-3,5H2/t4-,6-,7-,8-;/m1./s1

InChI key

NHMNWWVJZZPKSL-IAIGYFSYSA-N

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Related Categories

Phosphates

Application

UTP has been used to study intracellular Ca²⁺ concentration in alveolar type II (AT2) cells. UTP has also been used as a phosphate donor for in vitro kinase assays using deoxycytidine kinase (DCK) or whole cell lysates.

Uridine 5′-triphosphate tris salt has been used:

to investigate its activation potential on the purinergic P2Y2 Receptor in THP1 monocytes
as a component of non-radioactive nucleoside triphosphate solution used in in vitro RNA polymerase assay
as a P2Y2 agonist in human embryonic kidney cells (HEK293T) in dynamic mass redistribution (DMR) assays

Biochem/physiol Actions

Uridine 5′-triphosphate (UTP) is synthesized from uridine 5′-diphosphate (UDP) in the presence of the enzyme nucleoside diphosphate kinase (NDPK). Plant cells have high uridine as UTP. UTP on amination results in the generation of CTP and is catalysed by enzyme CTP synthetase. UTP acts on the purinergic (P2Y2) receptor and mediates smooth muscle cells (SMCs) mitogenic activation. It also modulates osteopontin expression in SMCs. UTP is a sputum inducer and a promising candidate for assessing the inflammation in respiratory airway.

P2Y receptor agonist.

Preparation Note

Uridine 5′-triphosphate (UTP) tris salt is soluble in water at 50 mg/ml and yields a clear, colorless solution.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Validity and safety of sputum induction by inhaled uridine 5?-triphosphate

Tamaoki JUN, et al.

American Journal of Respiratory and Critical Care Medicine, 164(3), 378-381 (2001)

Dynamic mass redistribution reveals diverging importance of PDZ-ligands for G protein-coupled receptor pharmacodynamics

Camp ND, et al.

Pharmacological Research, 105(3), 13-21 (2016)

Modulation of pulmonary alveolar type II cell phenotype and communication by extracellular matrix and KGF.

B E Isakson et al.

American journal of physiology. Cell physiology, 281(4), C1291-C1299 (2001-09-08)

The alveolar epithelium consists of two cell types, alveolar type I (AT1) and alveolar type II (AT2) cells. We have recently shown that 7-day-old cultures of AT2 cells grown on a type I collagen/fibronectin matrix develop phenotypic characteristics of AT1

HIV-1 Envelope Overcomes NLRP3-Mediated Inhibition of F-Actin Polymerization for Viral Entry

Paoletti A, et al.

Testing, 28(13), 3381-3394 (2019)

Noninvasive prediction of tumor responses to gemcitabine using positron emission tomography.

Rachel E Laing et al.

Proceedings of the National Academy of Sciences of the United States of America, 106(8), 2847-2852 (2009-02-07)

Gemcitabine (2',2'-difluorodeoxycytidine, dFdC) and cytosine arabinoside (cytarabine, ara-C) represent a class of nucleoside analogs used in cancer chemotherapy. Administered as prodrugs, dFdC and ara-C are transported across cell membranes and are converted to cytotoxic derivatives through consecutive phosphorylation steps catalyzed

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