Broxuridine Chemical Properties

Melting point:

191-194 °C (dec.)(lit.)

alpha 

31 º (c=1, 0.1N NaOH)

Density 

1.8573 (rough estimate)

refractive index 

22 ° (C=1, H2O)

storage temp. 

-20°C

solubility 

NH₄OH: 0.1 M at 20 °C, clear, colorless

pka

7.73±0.10(Predicted)

form 

Crystals or Crystalline Powder

color 

White to yellow

Water Solubility 

1-5 g/100 mL at 22 ºC

Merck 

14,1452

BRN 

30395

Stability:

Stable, but may be light sensitive. Incompatible with strong oxidizing agents.

InChIKey

XMJRLEURHMTTRX-UHFFFAOYSA-N

LogP

-0.290

CAS DataBase Reference

59-14-3(CAS DataBase Reference)

EPA Substance Registry System

Uridine, 5-bromo-2'-deoxy- (59-14-3)

Safety Information

Hazard Codes 

Xn,T

Risk Statements 

68-36/37/38-63-46-24-61

Safety Statements 

36/37/39-26-53-45-36

WGK Germany 

2

RTECS 

YU7350000

F 

10-23

TSCA 

Yes

HS Code 

29349990

Hazardous Substances Data

59-14-3(Hazardous Substances Data)

MSDS

• Language:English Provider:5-Bromo-2'-deoxyuridine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Broxuridine Usage And Synthesis

Description

5-Bromo-2'-deoxyuridine is a nitrate reductase inhibitor that prevents the reduction of nitrate to nitrite by inhibiting the enzyme nitrate reductase. 5-Bromo-2'-deoxyuridine is a genotoxic agent that has been shown to cause DNA damage and cell death in vitro. 5-Bromo-2'-deoxyuridine also binds to NMDA receptors and may be useful as a model system for studying neurodegenerative diseases.

Chemical Properties

White crystalline powder

Uses

A Thymidine analogue used as a mutagen in genetic research. Selectively incorporated into cellular DNA during S-phase

Uses

Research tool for measuring DNA synthesis.

Uses

5-Bromo-2'-deoxyuridine (BrdU) is a thymidine analog used to label DNA. It is incorporated into newly synthesized DNA in place of thymidine during the S phase of the cell cycle. Cells that were actively proliferating can then be detected by denaturing the DNA and allowing specific antibodies to target the BrdU incorporation. Consequently 5-BrdU is used to study cell signaling and other processes that induce cell proliferation.

Definition

ChEBI: A pyrimidine 2'-deoxyribonucleoside compound having 5-bromouracil as the nucleobase.

General Description

White crystalline powder.

Air & Water Reactions

Water soluble.

Reactivity Profile

Broxuridine may be heat and light sensitive. .

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition Broxuridine emits very toxic fumes of bromide ion and NOx.

Fire Hazard

Flash point data for Broxuridine are not available; however, Broxuridine is probably combustible.

Biological Activity

5-bromodeoxyuridine (5-brdu) is an analog of thy that is incorporated into the dna of cells undergoing the s-phase and can be detected by monoclonal antibodies or polyclona111.

Biochem/physiol Actions

5-Bromo-2′-deoxyuridine (BrdU) is used to analyze cell proliferation, because of its facile incorporation into DNA during the S phase of the cell cycle. BrdU stimulates cellular differentiation and maturation in leukemia cell lines, while it inhibits differentiation of friend erythroleukemia cells. Studies of BrdU incorporation often subsequently use BrdU-specific antibodies with fluorescent tags, for detection of the incorporated BrdU, via such methods as flow cytometry or fluorescence microscopy.

Safety Profile

Moderately toxic by subcutaneous, intravenous, intraperitoneal, and possibly other routes. Mildly toxic by ingestion. Experimental teratogenic and reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of Brand NOx

in vitro

the effect of 5-brdu on the proliferation was studied in the early phases of dedifferentiation of nicotiana glauca pith explants grown. it was found to be wholly inhibitory only when given during the first 72 h of culture, this inhibition being reversed by simultaneous addition of either deoxyeytidine or thymidine [1].

in vivo

young adult offspring mice were stained for 5-brdu using a monoclonal antibody and the peroxidase-antiperoxidase method. the distribution of immunoreactive nuclei was very similar to the previous [3h] thymidine data. the pattern of labelled nuclei at different embryonic ages followed the spatiotemporal gradients described for cortical and hippocampal neurogenesis. these data indicate that brdu can be used to map neuronal birthdates [2].

storage

-20°C

Purification Methods

Recrystallise the uridine from EtOH or 96% EtOH. It has max 279 nm at pH 7.0, and 279 nm (log  3.95) at pH 1.9. Its RF values are 0.49, 0.46 and 0.53 in n-BuOH/AcOH/H2O (4:1:1), n-BuOH/EtOH/H2O (40:11:19) and i-PrOH-25% aqueous NH3-H2O (7:1:1), respectively. [Nature 209 230 1966, Pryst.s & Sorm Collect Czech Chem Comm 29 2956 1964, Beilstein 24 III/IV 1234.]

References

[1] m. durante, c. geri, v. nuti-ronchi, g. martini, e. guillé, j. grisvard, l. giorgi, r. parenti, m. bulatti. inhibition of nicotiana glauca pich tissue proliferation through incorporation of 5-brdu into sna. cell differentiation, volume 6, issue 1, june 1977, pages 53-63
[2] del rio ja, soriano e. immunocytochemical detection of 5'-bromodeoxyuridine incorporation in the central nervous system of the mouse. brain res dev brain res. 1989 oct 1; 49 (2): 311-7.

Broxuridine(59-14-3)Related Product Information

• Trifluridine
• UMP
• 1-beta-D-Arabinofuranosyluracil
• Doxifluridine
• 2'-Deoxyuridine
• Bromocresol Purple
• Dimidium bromide
• Ethidium bromide
• Bromocresol green
• 1-Bromohexane
• Cyanogen bromide
• 5-Bromouridine
• 5-Bromo-2'-deoxy-5'-uridylic acid disodium salt
• 5-Bromouracil
• Uridine
• Uracil
• Bromine
• BrdU (Bromodeoxyuridine)