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Key Documents

U6875

Sigma-Aldrich

Uridine 5′-triphosphate tris salt

Type VI, ≥90%

Synonym(s):

UTP

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About This Item

Empirical Formula (Hill Notation):
C9H15N2O15P3
CAS Number:
Molecular Weight:
484.14
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

type

Type VI

Quality Level

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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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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


Certificates of Analysis (COA)

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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)
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)
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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