C6891

5-Chloro-2′-deoxyuridine

≥98% (HPLC), powder

• Synonym(s): CldU
• 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

Properties

• Product Name: 5-Chloro-2′-deoxyuridine, thymidine analog
• 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[1]
• analyze cell cycle length using an animal model[2]
• label HEK293T cells for molecular combing assay[3]

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.[4] CldU is a potent mutagen, clastogen, and toxicant.[5] It is used as a thymidine analog and is found to alter the dNTP pools and might lead to cell-cycle arrest.[4] CldU produces sister-chromatid exchange but has less response to ionizing radiation compared to other thymine analogs.[5] 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).

Safety Information

• pictograms: GHS08,GHS07
• signalword: Warning
• hcodes: H302 + H312 + H332,H351
• pcodes: P202 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 2
• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves