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C6891

5-Chloro-2′-deoxyuridine

Name: 5-Chloro-2&#8242;-deoxyuridine
Brand: SIGMA

≥98% (HPLC), powder

Synonym(s):

CldU

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About This Item

Empirical Formula (Hill Notation):

C₉H₁₁ClN₂O₅

CAS Number:

50-90-8

Molecular Weight:

262.65

UNSPSC Code:

41106305

PubChem Substance ID:

24892910

NACRES:

NA.51

MDL number:

MFCD00006531

Assay:

≥98% (HPLC)

Form:

powder

Solubility:

1 M NH4OH: 20 mg/mL, clear, colorless to faintly yellow

Storage temp.:

−20°C

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Properties

Product Name

5-Chloro-2′-deoxyuridine, thymidine analog

Quality Level

100

assay

≥98% (HPLC)

form

powder

solubility

1 M NH4OH: 20 mg/mL, clear, colorless to faintly yellow

storage temp.

−20°C

SMILES string

OC[C@H]1O[C@H](C[C@@H]1O)N2C=C(Cl)C(=O)NC2=O

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

InChI key

NJCXGFKPQSFZIB-RRKCRQDMSA-N

Description

Application

5-Chloro-2′-deoxyuridine has been used to:

study cell cycle dynamics by immunohistochemical analysis and double S-phase labeling using animal models
analyze cell cycle length using an animal model
label HEK293T cells for molecular combing assay

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).