5-CHLORO-2'-DEOXYURIDINE Chemical Properties

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

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 Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-40

Safety Statements 

36/37/39-45

WGK Germany 

3

RTECS 

YU7400000

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich

5-CHLORO-2'-DEOXYURIDINE Usage And Synthesis

Description

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.

Chemical Properties

White Needles

Uses

A halogenated uridine derivative used in pharmaceutical compositions.

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

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).

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).

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

5-CHLORO-2'-DEOXYURIDINE(50-90-8)Related Product Information

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