| Identification | More | [Name]
Broxuridine | [CAS]
59-14-3 | [Synonyms]
2'-DEOXY-5-BROMOROURIDINE
2'-DEOXY-5-BROMOURIDINE
5-BRDU
5-BROMO-1-(2-DEOXY-BETA-D-RIBOFURANOSYL)URACIL
(+)-5-BROMO-2'-DEOXYURIDINE
5-BROMO-2'-DEOXYURIDINE
5-BROMO-2'-DESOXYURIDINE
5-BROMO DEOXYURIDINE
BDU
BR-DU
BRDU LABELING REAGENT
BROMO-2'-DEOXYURIDINE,5-
BROXURIDINE
BRUDR
BUDR
CHEMPACIFIC 52436
5-bdu
5-bromodesoxyuridine
5-bromouracil-2-deoxyriboside
5-bromouracildeoxyriboside | [EINECS(EC#)]
200-415-9 | [Molecular Formula]
C7H11BN2O7 | [MDL Number]
MFCD00006529 | [Molecular Weight]
245.98 | [MOL File]
59-14-3.mol |
| Chemical Properties | Back Directory | [Appearance]
White crystalline powder | [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. ]
2-8°C
| [solubility ]
NH4OH: 0.1 M at 20 °C, clear, colorless
| [form ]
Crystals or Crystalline Powder | [pka]
7.73±0.10(Predicted) | [color ]
White to yellow | [Stability:]
Stable, but may be light sensitive. Incompatible with strong oxidizing agents. | [Water Solubility ]
1-5 g/100 mL at 22 ºC | [Usage]
A Thymidine analogue used as a mutagen in genetic research. Selectively incorporated into cellular DNA during S-phase | [Merck ]
14,1452 | [BRN ]
30395 | [InChIKey]
XMJRLEURHMTTRX-UHFFFAOYSA-N | [LogP]
-0.290 | [CAS DataBase Reference]
59-14-3(CAS DataBase Reference) | [EPA Substance Registry System]
59-14-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,T | [Risk Statements ]
R68:Possible risk of irreversible effects.
R36/37/38:Irritating to eyes, respiratory system and skin .
R63:Possible risk of harm to the unborn child.
R24:Toxic in contact with skin. | [Safety Statements ]
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36:Wear suitable protective clothing . | [WGK Germany ]
2
| [RTECS ]
YU7350000
| [F ]
10-23 | [TSCA ]
Yes | [HS Code ]
29349990 | [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 | [Hazardous Substances Data]
59-14-3(Hazardous Substances Data) |
| Hazard Information | Back Directory | [General Description]
White crystalline powder. | [Reactivity Profile]
5-BROMO-2'-DEOXYURIDINE(59-14-3) may be heat and light sensitive. . | [Air & Water Reactions]
Water soluble. | [Health Hazard]
ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits very toxic fumes of bromide ion and NOx. | [Fire Hazard]
Flash point data for this chemical are not available; however, 5-BROMO-2'-DEOXYURIDINE is probably combustible. | [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]
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. | [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. | [Definition]
ChEBI: A pyrimidine 2'-deoxyribonucleoside compound having 5-bromouracil as the nucleobase. | [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. | [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]
4°C, protect from light | [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. |
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