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C6891

Sigma-Aldrich

5-Chloro-2′-deoxyuridine

thymidine analog

Synonym(s):

CldU

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About This Item

Empirical Formula (Hill Notation):
C9H11ClN2O5
CAS Number:
50-90-8
Molecular Weight:
262.65
MDL number:
MFCD00006531
UNSPSC Code:
41106305
PubChem Substance ID:
24892910
NACRES:
NA.51

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

Health hazardExclamation mark
GHS08,GHS07

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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S M Ohline et al.
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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
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.
Fan Xuan et al.
Cell death & disease, 9(11), 1062-1062 (2018-10-20)
MYC-induced nuclear antigen (MINA53) is a JmjC (jumonji C domain)-containing protein, which is highly expressed in many cancers including glioblastoma. We have revealed in our previous report that MINA53 is a poor prognostic indicator for glioblastoma patients, and knockdown of
Eyal Ben-David et al.
Cancer research, 74(19), 5532-5540 (2014-08-16)
Colorectal cancer develops in a sequential, evolutionary process, leading to a heterogenic tumor. Comprehensive molecular studies of colorectal cancer have been previously performed; still, the process of carcinogenesis is not fully understood. We utilized gene expression patterns from 94 samples
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