Uridine-5'-diphosphate disodium salt Chemical Properties

storage temp. 

-20°C

form 

Powder

color 

White to Off-white

Water Solubility 

Slightly soluble in water.

Sensitive 

Moisture Sensitive

BRN 

8817400

InChI

InChI=1/C9H14N2O12P2.Na.H/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);;/t4-,6-,7-,8-;;/s3

InChIKey

KWDGQJWFEYTPBN-IBOJMDDDSA-L

SMILES

O[C@@H]1[C@@H]([C@@H](COP(O)(=O)OP(O)(O)=O)O[C@H]1N1C=CC(=O)NC1=O)O.[NaH] |&1:1,2,3,15,r|

CAS DataBase Reference

27821-45-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

10-21

HS Code 

29349990

Uridine-5'-diphosphate disodium salt Usage And Synthesis

Description

Uridine-5'-diphosphate disodium salt (UDP-Na2) is a potent, selective P2Y6 receptor native agonist (EC50=300 nM; pEC50=6.52 for human P2Y6 receptor). It is an endogenous metabolite, catalyzes the glucuronidation of a wide array of substrates and is used in nucleic acid (RNA) biosynthesis. It has also been used as a purinergic agonist, in order to study its effect on the flux of absorbed cations in cochlear outer sulcus cells (OSC) and vestibular migratory cells (VTC). UDP-Na2 has also been used to determine the activity of nucleoside diphosphatase (NDPase) in the rabbit retina.

Uses

Uridine-5'-diphosphate disodium salt is mainly used in nucleic acid (RNA) biosynthesis and cell signalling studies. Uridine-5'-monophosphate disodium salt (UDP-MS) is a structural analogue of uridine and is used as a dietary supplement. It has been shown to inhibit phosphodiesterase and cyclic nucleotide phosphodiesterase, both of which are enzymes that degrade the secondary messenger cyclic adenosine monophosphate (cAMP).

Uses

Uridine-5'-diphosphate disodium salt (UDP-Na2) is an organometallic compound, It is a P2Y6 receptor agonist and GPR105 receptor inhibitor. It is 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).

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).

storage

Store at -20°C

Purification Methods

Crystallise it from MeOH. It may contain some Ba salt(s); hence stir it with Amberlite IR-120 cation exchanger (25mL, wet resin, 15-50 mesh in H+ form) in H2O (50mL) until the nucleotide dissolves. Filter, wash resin with H2O until the eluate is neutral. Combine the filtrate and washings, and adjust the pH to 8.0 with 2.0 M aqueous NaOH. Concentrate it in vacuo to a small volume (~ 20mL), and add Me2CO dropwise until crystallisation begins. Cool to 0o, and the shiny plates of di Na uridine-5’-phosphate dihydrate are filtered off and dried over P2O5 at 25o/0.1mm for 24hours (>76% recovery). UV: max at 262nm ( 10,000 M-1cm -1) in 0.1 M HCl. [Boon et al. J Chem Soc 408 1950, Smith Biochemical Preparations 8 130 1960.] [Beilstein 24 IV 1214.]

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