Broxuridine

Broxuridine Basic information
Product Name:Broxuridine
Synonyms:5-BROMO-1-(2-DEOXY-BETA-D-RIBOFURANOSYL)URACIL;5-BROMO DEOXYURIDINE;5-BROMO-2'-DESOXYURIDINE;(+)-5-BROMO-2'-DEOXYURIDINE;5-BROMO-2'-DEOXYURIDINE;5-budr;bromouracildeoxyriboside;5-Bromo-1-(2-deoxy-β-D-ribofuranosyl)uracil
CAS:59-14-3
MF:C9H11BrN2O5
MW:307.1
EINECS:200-415-9
Product Categories:Biochemistry;Chemical Reagents for Pharmacology Research;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents;Naphthyridine,Quinoline;Bases & Related Reagents;Drug Analogues;Nucleotides;inhibitor;Pharmaceutical Raw Materials
Mol File:59-14-3.mol
Broxuridine Structure
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
pka7.73±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.
InChIKeyXMJRLEURHMTTRX-UHFFFAOYSA-N
LogP-0.290
CAS DataBase Reference59-14-3(CAS DataBase Reference)
EPA Substance Registry SystemUridine, 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
10-23
TSCA Yes
HS Code 29349990
Hazardous Substances Data59-14-3(Hazardous Substances Data)
MSDS Information
ProviderLanguage
5-Bromo-2'-deoxyuridine English
SigmaAldrich English
ACROS English
Broxuridine Usage And Synthesis
Description5-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 PropertiesWhite crystalline powder
Uses5-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.
UsesA Thymidine analogue used as a mutagen in genetic research. Selectively incorporated into cellular DNA during S-phase
UsesResearch tool for measuring DNA synthesis.
DefinitionChEBI: A pyrimidine 2'-deoxyribonucleoside compound having 5-bromouracil as the nucleobase.
General DescriptionWhite crystalline powder.
Air & Water ReactionsWater soluble.
Reactivity ProfileBroxuridine may be heat and light sensitive. .
Health HazardACUTE/CHRONIC HAZARDS: When heated to decomposition Broxuridine emits very toxic fumes of bromide ion and NOx.
Fire HazardFlash point data for Broxuridine are not available; however, Broxuridine is probably combustible.
Biological Activity5-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 Actions5-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 ProfileModerately 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 vitrothe 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 vivoyoung 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 MethodsRecrystallise 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 Preparation Products And Raw materials
5-BROMO-2'-DEOXYURIDINE-5'-TRIPHOSPHATE LITHIUM SALT 5-BROMO-2',3',5'-TRI-O-ACETYLURIDINE DNA, SINGLE STRANDED, IMM. ON CELLULOSE, FROM CALF THYMUS* UMP 5-Bromouridine 5'-DMT-5-BROMO-DU PHOSPHORAMIDITE (CHIRAL) 5-BROMO-2'-DEOXYURIDINE 5'-TRIPHOSPHATE TRI(TRIETHYLAMMONIUM) SALT Deoxynucleotide 3',5'-DI-O-ACETYL-5-BROMO-2'-DEOXY-D-URIDINE 5-BROMO-2'-DEOXY-URIDINE-5'-DIPHOSPHATE, SODIUM SALT 5-BROMOURIDINE 5'-TRIPHOSPHATE SODIUM SALT 5-BROMO 2'-DEOXYURIDINE, [6-3H]- Deoxidizer 5-BROMOURIDINE, [2-14C]- TIMTEC-BB SBB005965 BrdU (Bromodeoxyuridine) 5-BROMODEOXYURIDINE 5'-MONOPHOSPHATE, DIAMMONIUM SALT, [6-3H]- 5-BROMO-2'-DEOXYURIDINE-2-14C

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