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I7125

Sigma-Aldrich

5-Iodo-2′-deoxyuridine

≥99% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C9H11IN2O5
Numéro CAS:
54-42-2
Poids moléculaire :
354.10
Numéro Beilstein :
30397
Numéro CE :
200-207-8
Numéro MDL:
MFCD00134656
Code UNSPSC :
41106305
ID de substance PubChem :
57654307
Nomenclature NACRES :
NA.51

Source biologique

synthetic (organic)

Niveau de qualité

200

Pureté

≥99% (HPLC)

Forme

powder or crystals

Pf

194 °C (lit.)

Solubilité

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

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

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.

Actions biochimiques/physiologiques

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.

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335,H341,H361

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "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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