C6891
5-Chloro-2′-deoxyuridine
thymidine analog
Synonym(s):
CldU
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About This Item
Empirical Formula (Hill Notation):
C9H11ClN2O5
CAS Number:
Molecular Weight:
262.65
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51
Recommended Products
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
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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).
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 2
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Inflammation-mediated hypochlorous acid (HOCl) can damage DNA, DNA precursors, and other biological molecules, thereby producing an array of damage products such as 5-chlorouracil (ClU). In this study, we prepared and studied 5-chloro-2'-deoxyuridine (CldU) and ClU-containing oligonucleotide templates. We demonstrate that
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