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C6891

Sigma-Aldrich

5-Chloro-2′-deoxyuridine

thymidine analog

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Synonym(s):
CldU
Empirical Formula (Hill Notation):
C9H11ClN2O5
CAS Number:
50-90-8
Molecular Weight:
262.65
MDL number:
MFCD00006531
PubChem Substance ID:
24892910
NACRES:
NA.51

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

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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).

Pictograms

Exclamation markHealth hazard
GHS07,GHS08

Signal Word

Warning

Hazard Statements

H302 + H312 + H332 - H351

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

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Masaya Kimoto et al.
The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society, 56(1), 15-24 (2007-09-19)
To identify stem cells in salivary glands, label-retaining cells (LRCs) were established in rat submandibular glands. Developing and regenerating glands were labeled with bromodeoxyuridine (BrdU). To cause gland regeneration, the glands were injured by duct obstruction. BrdU LRCs were observed
S M Ohline et al.
Brain structure & function, 223(7), 3213-3228 (2018-05-26)
Early during their maturation, adult-born dentate granule cells (aDGCs) are particularly excitable, but eventually develop the electrophysiologically quiet properties of mature cells. However, the stability versus plasticity of this quiet state across time and experience remains unresolved. By birthdating two
Beatrice Rondinelli et al.
Nature cell biology, 19(11), 1371-1378 (2017-10-17)
The emergence of resistance to poly-ADP-ribose polymerase inhibitors (PARPi) poses a threat to the treatment of BRCA1 and BRCA2 (BRCA1/2)-deficient tumours. Stabilization of stalled DNA replication forks is a recently identified PARPi-resistance mechanism that promotes genomic stability in BRCA1/2-deficient cancers.
Mary Youssef et al.
Scientific reports, 9(1), 4120-4120 (2019-03-13)
Early life stress predisposes to mental illness and behavioral dysfunction in adulthood, but the mechanisms underlying these persistent effects are poorly understood. Stress throughout life impairs the structure and function of the hippocampus, a brain system undergoing considerable development in
Olga A Mineyeva et al.
Frontiers in neuroscience, 12, 1013-1013 (2019-01-29)
While irradiation can effectively treat brain tumors, this therapy also causes cognitive impairments, some of which may stem from the disruption of hippocampal neurogenesis. To study how radiation affects neurogenesis, we combine phenotyping of subpopulations of hippocampal neural stem and
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