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94330

Sigma-Aldrich

Uridine 5′-diphosphate disodium salt hydrate

≥96.0% (HPLC)

Synonym(s):

UDP, 5′-UDP-Na2

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About This Item

Empirical Formula (Hill Notation):
C9H12N2Na2O12P2 · xH2O
CAS Number:
27821-45-0
Molecular Weight:
448.12 (anhydrous basis)
Beilstein:
8817400
EC Number:
248-678-9
MDL number:
MFCD00149253
UNSPSC Code:
41106305
PubChem Substance ID:
57653599
NACRES:
NA.51

biological source

synthetic

Quality Level

100

Assay

≥96.0% (HPLC)

form

powder

impurities

≤15% water

storage temp.

−20°C

SMILES string

[Na+].[Na+].[H]O[H].O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP([O-])(=O)OP(O)([O-])=O)N2C=CC(=O)NC2=O

InChI

1S/C9H14N2O12P2.2Na.H2O/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18;;;/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,10,12,15)(H2,16,17,18);;;1H2/q;2*+1;/p-2/t4-,6-,7-,8-;;;/m1.../s1

InChI key

RHBXRWOXLRCWIZ-LLWADOMFSA-L

Related Categories

Application

Uridine 5′-diphosphate disodium salt hydrate has been used:
  • as a standard for quantification of metabolite levels in murine tumor interstitial fluid by liquid chromatography-mass spectrometry (LC/MS)
  • as a UDP standard for nucleotide analysis by liquid chromatography-high resolution mass spectrometry (LC-HRMS)
  • to treat E6.5 retina explants in vitro, to study its effect on the entry and elongation of microglial cells into the embryonic quail retina

Biochem/physiol Actions

Uridine 5′-diphosphate (UDP) is an endogenous signaling molecule produced by damaged cells to attract macrophages. In response to neuronal damage, UDP promotes chemotaxis and chemokinesis in microglial cells. UDP serves as a ligand for P2Y receptors. UDP and uridine 5′-triphosphate (UTP) may be used in studies on nucleic acid (RNA) biosynthesis and cell signaling. UDP is a nucleotide that upon phosphorylation to UTP becomes a substrate for enzymes such as RNA polymerase(s) and GTPases. These enzymes are involved in a wide range of applications from the synthesis of RNA to the regulation of G-coupled protein receptors (GPCR) and cell signaling molecules such as Rho-signaling via guanine nucleotide exchange factors (GEF).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

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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Kenneth A Jacobson et al.
Purinergic signalling, 5(1), 75-89 (2008-07-05)
Although elucidation of the medicinal chemistry of agonists and antagonists of the P2Y receptors has lagged behind that of many other members of group A G protein-coupled receptors, detailed qualitative and quantitative structure-activity relationships (SARs) were recently constructed for several
María Martín-Estebané et al.
PloS one, 12(8), e0182450-e0182450 (2017-08-02)
Microglial cell precursors located in the area of the base of the pecten and the optic nerve head (BP/ONH) start to enter the retina of quail embryos at the 7th day of incubation (E7), subsequently colonizing the entire retina by
Feng Ding et al.
Current topics in medicinal chemistry, 11(23), 2879-2887 (2011-08-10)
The Rho family small GTPases of the Ras superfamily play key roles in regulating diverse signaling pathways that control a myriad of fundamental cellular processes such as cytoskeletal dynamics, cell cycle progression, gene expression, cell polarity, migration and cell transformation.
Caroline Liot et al.
PloS one, 6(8), e23676-e23676 (2011-09-03)
Besides regulation of actin cytoskeleton-dependent functions, Rho GTPase pathways are essential to cell cycle progression and cell division. Rho, Rac and Cdc42 regulate G1 to S phase progression and are involved in cytokinesis. RhoA GDP/GTP cycling is required for normal
Sara J Wright et al.
Genetics, 189(1), 165-176 (2011-07-14)
Heterotrimeric (αβγ) G proteins are crucial components of eukaryotic signal transduction pathways. G-protein-coupled receptors (GPCRs) act as guanine nucleotide exchange factors (GEFs) for Gα subunits. Recently, facilitated GDP/GTP exchange by non-GPCR GEFs, such as RIC8, has emerged as an important
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