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I7125

Sigma-Aldrich

5-Iodo-2′-deoxyuridine

≥99% (HPLC)

Synonym(s):

1-(2-Deoxy-β-D-ribofuranosyl)-5-iodouracil, 2′-Deoxy-5-iodouridine, 5-IUdR, IDU, IdUrd, Idoxuridine

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About This Item

Empirical Formula (Hill Notation):
C9H11IN2O5
CAS Number:
54-42-2
Molecular Weight:
354.10
Beilstein/REAXYS Number:
30397
EC Number:
200-207-8
MDL number:
MFCD00134656
UNSPSC Code:
41106305
PubChem Substance ID:
57654307
NACRES:
NA.51

biological source

synthetic (organic)

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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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Johan Neyts et al.
Antimicrobial agents and chemotherapy, 46(9), 2842-2847 (2002-08-17)
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
Julia Rousseau et al.
Journal of synchrotron radiation, 16(Pt 4), 573-581 (2009-06-19)
Iodine-enhanced synchrotron stereotactic radiotherapy takes advantage of the radiation dose-enhancement produced by high-Z elements when irradiated with mono-energetic beams of synchrotron X-rays. In this study it has been investigated whether therapeutic efficacy could be improved using a thymidine analogue, 5-iodo-2'-deoxyuridine
Esther G C Troost et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 51(5), 713-719 (2010-04-17)
Accelerated tumor cell repopulation is an important mechanism adversely affecting therapeutic outcome in head and neck cancer. The noninvasive assessment of the proliferative state of a tumor by PET may provide a selection tool for customized treatment. 3'-deoxy-3'-(18)F-fluorothymidine ((18)F-FLT) is
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)
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