Broxuridine CAS 59-14-3
Introduction：Basic information about Broxuridine CAS 59-14-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Broxuridine Basic information
| Product Name: | Broxuridine |
| Synonyms: | 5-BROMO-1-(2-DEOXY-BETA-D-RIBOFURANOSYL)URACIL;5-BRDU;5-BROMO DEOXYURIDINE;5-BROMO-2'-DESOXYURIDINE;(+)-5-BROMO-2'-DEOXYURIDINE;5-budr;bromodeoxyuridine;bromouracildeoxyriboside |
| 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 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 |
| Appearance | white crystals |
| biological source | synthetic (organic) |
| 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. |
| InChI | 1S/C9H11BrN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1 |
| InChIKey | XMJRLEURHMTTRX-UHFFFAOYSA-N |
| SMILES | OC[C@H]1O[C@H](C[C@@H]1O)N2C=C(Br)C(=O)NC2=O |
| 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 | TSCA listed |
| HS Code | 29349990 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Muta. 1B Repr. 2 |
| Hazardous Substances Data | 59-14-3(Hazardous Substances Data) |
| 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 |
| Synthesis | 951-78-0 59-14-3 The general procedure for the synthesis of 5-bromo-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-diones from 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-diones was carried out under stirring conditions as follows. 2'-O-methyluridine (5, 0.103 g, 0.4 mmol) was dissolved in aqueous acetonitrile (H2O:CH3CN = 1:9, 5 mL). Subsequently, NaN3 (0.104 g, 1.6 mmol) was added followed by SMBI (0.101 g, 0.44 mmol) at room temperature. The reaction mixture was continuously stirred and the progress of the reaction was monitored by thin layer chromatography (TLC). The reaction was completed after about 1.5 h. The reaction mixture was filtered, concentrated under reduced pressure and co-evaporated with acetonitrile (2 x 2 mL) to remove residual water. The crude product was purified by column chromatography using a mixture of dichloromethane (DCM) and methanol (MeOH) (4%-6% MeOH in DCM, v/v) as eluent, resulting in purified bromonucleoside 6 (0.117 g, 93% yield) as a white solid. |
| 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 Preparation Products And Raw materials
| Raw materials | 5-Bromouracil-->2'-Deoxyuridine-->Thymidine-->Acetonitrile-->Sodium azide-->N-Bromoisocyanuric acid monosodium salt |
