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I7125

Sigma-Aldrich

5-Iodo-2′-deoxyuridine

≥99% (HPLC)

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Synonym(s):
1-(2-Deoxy-β-D-ribofuranosyl)-5-iodouracil, 2′-Deoxy-5-iodouridine, 5-IUdR, IDU, IdUrd, Idoxuridine
Empirical Formula (Hill Notation):
C9H11IN2O5
CAS Number:
54-42-2
Molecular Weight:
354.10
Beilstein:
30397
EC Number:
200-207-8
MDL number:
MFCD00134656
UNSPSC Code:
41106305
PubChem Substance ID:
57654307
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

200

Assay

≥99% (HPLC)

form

powder or crystals

mp

194 °C (lit.)

solubility

1 N NH4OH: 50 mg/mL, clear to very slightly hazy, colorless to light yellow

storage temp.

2-8°C

SMILES string

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

InChI

1S/C9H11IN2O5/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

XQFRJNBWHJMXHO-RRKCRQDMSA-N

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Application

5-Iodo-2′-deoxyuridine (5-IUdR; IdUrd) is a pyrimidine analog (halogenated thymidine) that has antiviral activity agains vaccinia virus (orthopoxviruses). IdUrd is used as a radiosensitizer in human cancer studies.
5-Iodo-2′-deoxyuridine has been used in molecular combing assay or DNA fiber assay.

Biochem/physiol Actions

5-Iodo-2′-deoxyuridine prevents in vitro DNA viral replication. This is observed in herpesviruses and poxviruses It might possess teratogenic, tumor-promoting, mutagenic, and immunosuppressive properties. 5-Iodo-2′-deoxyuridine, used in topical applications, is effective against epithelial infections.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335,H341,H361

Hazard Classifications

Eye Irrit. 2 - Muta. 2 - Repr. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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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Mandell, Douglas, and Bennett's Principles and Practice of Infectious Diseases, 546-562 (2015)
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There is a concern that there may be unregistered stocks of smallpox that can be used for bioterrorism or biological warfare. According to the WHO Advisory Committee on Variola Research, there is a need to develop strategies to treat smallpox
Jan Kajstura et al.
Circulation research, 107(2), 305-315 (2010-06-05)
The ability of the human heart to regenerate large quantities of myocytes remains controversial, and the extent of myocyte renewal claimed by different laboratories varies from none to nearly 20% per year. To address this issue, we examined the percentage
Qiuwei Pan et al.
Gastroenterology, 144(4), 761-770 (2012-12-26)
The existence of slowly cycling, adult stem cells has been challenged by the identification of actively cycling cells. We investigated the existence of uncommitted, slowly cycling cells by tracking 5-iodo-2'-deoxyuridine (IdU) label-retaining cells (LRCs) in normal esophagus, Barrett's esophagus (BE)
Francisco Alén et al.
International journal of molecular sciences, 20(14) (2019-07-25)
Mutant mice with respect to the splicing factor Zrsr1 present altered spermatogenesis and infertility. To investigate whether Zrsr1 is involved in the homeostatic control that the hypothalamus exerts over reproductive functions, we first analyzed both differential gene and isoform expression
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