| Identification | More | [Name]
5-CHLORO-2'-DEOXYURIDINE | [CAS]
50-90-8 | [Synonyms]
CldU
CLUDR
NSC-371331, CDC
Chlorodeoxyuridine
5-Chlorodeoxyuridin
5-CHLORODEOXYURIDINE
5-CHLORODESOXYURIDINE
5-CHLORO-2'-DEOXYURIDINE
5-chloro-2’-deoxy-uridin
2'-DEOXY-5-CHLOROURIDINE
Uridine,5-chloro-2'-deoxy-
5-Chloro-2'-deoxy-D-uridine
5-Chloro-2'-deoxyuridine ,98%
5-CHLORO-2'-DEOXYURIDINE USP/EP/BP
5-chloro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
5-CHLORO-1-[(2R,4S,5R)-4-HYDROXY-5-(HYDROXYMETHYL)OXOLAN-2-YL]-3H-PYRIMIDINE-2,4-DIONE
5-chloro-1-[(2R,4S,5R)-4-hydroxy-5-methylol-tetrahydrofuran-2-yl]pyrimidine-2,4-quinone
5-chloro-1-((2R,4S,5R)-4-hydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione | [Molecular Formula]
C9H11ClN2O5 | [MDL Number]
MFCD00006531 | [Molecular Weight]
262.65 | [MOL File]
50-90-8.mol |
| Chemical Properties | Back Directory | [Appearance]
White Needles | [Melting point ]
176-179°C | [density ]
1.5507 (rough estimate) | [refractive index ]
1.6500 (estimate) | [storage temp. ]
−20°C
| [solubility ]
DMSO (Slightly), Methanol (Slightly), Water (Slightly) | [form ]
Solid | [pka]
7.73±0.10(Predicted) | [color ]
White to Off-White | [Usage]
A halogenated uridine derivative used in pharmaceutical compositions. | [InChI]
InChI=1S/C9H11ClN2O5/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]
NJCXGFKPQSFZIB-RRKCRQDMSA-N | [SMILES]
OC[C@H]1O[C@@H](N2C=C(Cl)C(=O)NC2=O)C[C@@H]1O | [CAS DataBase Reference]
50-90-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS07,GHS08 | [Signal word ]
Warning | [Hazard statements ]
H302+H312+H332-H351 | [Precautionary statements ]
P202-P280-P301+P312-P302+P352+P312-P304+P340+P312-P308+P313 | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R40:Limited evidence of a carcinogenic effect. | [Safety Statements ]
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [WGK Germany ]
3
| [RTECS ]
YU7400000
| [HS Code ]
29349990 |
| Hazard Information | Back Directory | [Description]
5-Chloro-2''-deoxyuridine (CldU) is a thymidine analog that is readily incorporated, following phosphorylation, into newly synthesized DNA in place of thymidine.1 Like 5-bromo-2’-deoxyuridine (Item No. 15580) and 5-iodo-2’-deoxyuridine, CldU can be detected immunologically in cells and tissues.2,3 CldU can also be added to cells or tissues sequentially with another thymidine analog to label temporally distinct populations.4,5 The insertion of thymidine analogs, including CldU, can significantly alter DNA processing and replication, so these analogs have also been used as mutagens, clastogens, and antiviral compounds.1,6 | [Chemical Properties]
White Needles | [Uses]
5-Chloro-2′-deoxyuridine (CldU) is used as a thymidine analog to study the miscoding potential of hypochlorous acid damage to DNA and DNA precursors. When used with antibody based immunofluorescent imaging, 5-Chloro-2′-deoxyuridine incorporation may be used in protocols to identify sites of DNA replication. CldU may be used as a labeling substrate in conjunction with other halogenated uridine labeling substrates such as iododeoxyuridine (IdU). | [Uses]
5-Chloro-2'-deoxyuridine (CldU) is a thymidine analog that is readily incorporated, following phosphorylation, into newly synthesized DNA in place of thymidine. Like 5-bromo-2’-deoxyuridine and 5-iodo-2’-deoxyuridine, CldU can be detected immunologically in cells and tissues. CldU can also be added to cells or tissues sequentially with another thymidine analog to label temporally distinct populations. The insertion of thymidine analogs, including CldU, can significantly alter DNA processing and replication, so these analogs have also been used as mutagens, clastogens, and antiviral compounds.[Cayman Chemical] | [Uses]
A halogenated uridine derivative used in pharmaceutical compositions. | [Biochem/physiol Actions]
DNA labeled with 5-chloro-2′-deoxyuridine (CldU) serves as an effective tool to analyze and quantify DNA replication, repair, and recombination. CldU is a potent mutagen, clastogen, and toxicant. It is used as a thymidine analog and is found to alter the dNTP pools and might lead to cell-cycle arrest. CldU produces sister-chromatid exchange but has less response to ionizing radiation compared to other thymine analogs. 5-Chloro-2′-deoxyuridine (CldU) is used to study the miscoding potential of hypochlorous acid damage to DNA and DNA precursors. When used with antibody based immunofluorescent imaging, 5-Chloro-2′-deoxyuridine incorporation may be used in protocols to identify sites of DNA replication. CldU may be used as a labeling substrate in conjunction with other halogenated uridine labeling substrates such as iododeoxyuridine (IdU). | [storage]
Store at -20°C | [References]
[1] AMRITRAJ PATRA. Structure, stability and function of 5-chlorouracil modified A:U and G:U base pairs.[J]. Nucleic Acids Research, 2013: 2689-2697. DOI: 10.1093/nar/gks1316
[2] CLARA J. YUAN . Extended access methamphetamine decreases immature neurons in the hippocampus which results from loss and altered development of neural progenitors without altered dynamics of the S-phase of the cell cycle[J]. Pharmacology Biochemistry and Behavior, 2011, 100 1: Pages 98-108. DOI: 10.1016/j.pbb.2011.08.004
[3] SILJE ANDA Beata G Erik Boye. Cell-cycle analyses using thymidine analogues in fission yeast.[J]. PLoS ONE, 2014: e88629. DOI: 10.1371/journal.pone.0088629
[4] MARíA LLORENS-MARTíN José L T Gonzalo S Tejeda. Differential regulation of the variations induced by environmental richness in adult neurogenesis as a function of time: a dual birthdating analysis.[J]. PLoS ONE, 2010: e12188. DOI: 10.1371/journal.pone.0012188
[5] ALEX H TUTTLE. Immunofluorescent detection of two thymidine analogues (CldU and IdU) in primary tissue.[J]. Jove-Journal of Visualized Experiments, 2010, 46. DOI: 10.3791/2166
[6] L M FOX. Capacity of deoxycytidine to selectively antagonize cytotoxicity of 5-halogenated analogs of deoxycytidine without loss of antiherpetic activity.[J]. Antimicrobial Agents and Chemotherapy, 1982, 22 3: 431-441. DOI: 10.1128/aac.22.3.431 |
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Sigma-Aldrich
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