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Merck

94330

Uridine 5′-diphosphate disodium salt hydrate

≥96.0% (HPLC), synthetic, powder

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)
NACRES:
NA.51
PubChem Substance ID:
57653599
UNSPSC Code:
41106305
EC Number:
248-678-9
MDL number:
MFCD00149253
Beilstein/REAXYS Number:
8817400
Assay:
≥96.0% (HPLC)
Biological source:
synthetic
Form:
powder
Storage temp.:
−20°C

Key Documents

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Product Name

Uridine 5′-diphosphate disodium salt hydrate, ≥96.0% (HPLC)

InChI key

RHBXRWOXLRCWIZ-LLWADOMFSA-L

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

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

biological source

synthetic

assay

≥96.0% (HPLC)

form

powder

impurities

≤15% water

storage temp.

−20°C

Quality Level

100

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

94330-VAR: + 94330-100MG: + 94330-500MG: + 94330-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM7093
BCCK4582
BCCG8814
BCCD6256
BCCB4639

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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
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
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
Raquel Buj et al.
Cell reports, 28(8), 1971-1980 (2019-08-23)
Reprogrammed metabolism and cell cycle dysregulation are two cancer hallmarks. p16 is a cell cycle inhibitor and tumor suppressor that is upregulated during oncogene-induced senescence (OIS). Loss of p16 allows for uninhibited cell cycle progression, bypass of OIS, and tumorigenesis.
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