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Merck
CN

57830

5-Iodo-2′-deoxyuridine

≥98.0% (NT)

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:
Molecular Weight:
354.10
EC Number:
200-207-8
UNSPSC Code:
41106305
MDL number:
Beilstein/REAXYS Number:
30397
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Product Name

5-Iodo-2′-deoxyuridine, ≥98.0% (NT)

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

SMILES string

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

assay

≥98.0% (NT)

optical activity

[α]20/D +29±2°, c = 1% in 1 M NaOH

mp

194 °C (lit.)

storage temp.

2-8°C

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Other Notes

An efficient inducing agent of oncornaviruses in mouse cells; Potent inhibitor of thymidine kinase and thymidylate synthetase; Incorporation into viral DNA

Regulatory Information

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J. Balzarini et al.
Biochemical Pharmacology, 31, 3673-3673 (1971)
D R Lowy et al.
Science (New York, N.Y.), 174(4005), 155-156 (1971-10-08)
Cells of embryos of the high leukemic mouse strain AKR can be grown in culture as virus-negative cell lines. However, these lines and clonal sublines uniformly have the capacity to initiate synthesis of murine leukemia virus. Exposure of the cells
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
Omar Mamlouk et al.
International journal of radiation biology, 88(12), 1019-1027 (2012-06-21)
To investigate the ability of human lymphocytes labeled with DNA-incorporated (125)I to exert an inhibitory (antiproliferative) bystander effect on co-cultured human colon adenocarcinoma LS174T cells in vitro. Human peripheral blood lymphocytes were stimulated to synthesize DNA in the presence of
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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