2'-Fluoro-2'-deoxyuridine - CAS 784-71-4
Category:
Nucleosides
Product Name:
2'-Fluoro-2'-deoxyuridine
Catalog Number:
784-71-4
CAS Number:
784-71-4
Molecular Weight:
246.19
Molecular Formula:
C9H11FN2O5
COA:
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MSDS:
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Structure\Application:
2'-Deoxy-Nucleosides
Chemical Structure
CAS 784-71-4 2'-Fluoro-2'-deoxyuridine

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Reference Reading


1.In vivo comparison of IVDU and IVFRU in HSV1-TK gene expressing tumor bearing rats.
Choi TH1, Ahn SH, Kwon HC, Choi CW, Awh OD, Lim SM. Appl Radiat Isot. 2004 Jan;60(1):15-21.
(E)-5-(2-Iodovinyl)-2'-deoxyuridine (IVDU) and (E)-5-(2-iodovinyl)-2'-fluoro-2'-deoxyuridine (IVFRU) are potential substrates of Herpes Simplex Virus type 1 thymidine kinase (HSV-TK). In the present study, cellular uptake of radioiodinated substrates was found to be low in wild type MCA cells, but high in HSV-TK gene expressing cells. The carrier-free substrates, in particular, showed higher cellular uptake than carrier-added compounds. Biodistribution showed that the %ID/g of the MCA-TK/MCA tumor ratio of IVDU injected at 1, 4, and 24h were 1.1, 0.9 and 1.3, and those of IVFRU were 1.7, 1.7 and 1.8 respectively. Therefore, both IVDU and IVFRU could possibly be used as radiopharmaceuticals to evaluate reporter gene expression. However, IVFRU was more specific and stable than IVDU for selective non-invasive imaging of HSV-TK expression.
2.Binding of non-natural 3'-nucleotides to ribonuclease A.
Jenkins CL1, Thiyagarajan N, Sweeney RY, Guy MP, Kelemen BR, Acharya KR, Raines RT. FEBS J. 2005 Feb;272(3):744-55.
2'-Fluoro-2'-deoxyuridine 3'-phosphate (dU(F)MP) and arabinouridine 3'-phosphate (araUMP) have non-natural furanose rings. dU(F)MP and araUMP were prepared by chemical synthesis and found to have three- to sevenfold higher affinity than uridine 3'-phosphate (3'-UMP) or 2'-deoxyuridine 3'-phosphate (dUMP) for ribonuclease A (RNase A). These differences probably arise (in part) from the phosphoryl groups of 3'-UMP, dU(F)MP, and araUMP (pK(a) = 5.9) being more anionic than that of dUMP (pK(a) = 6.3). The three-dimensional structures of the crystalline complexes of RNase A with dUMP, dU(F)MP and araUMP were determined at < 1.7 A resolution by X-ray diffraction analysis. In these three structures, the uracil nucleobases and phosphoryl groups bind to the enzyme in a nearly identical position. Unlike 3'-UMP and dU(F)MP, dUMP and araUMP bind with their furanose rings in the preferred pucker. In the RNase A.araUMP complex, the 2'-hydroxyl group is exposed to the solvent.
3.A human osteosarcoma cell line expressing herpes simplex type-1 thymidine kinase: studies with radiolabeled (E)-5-(2-iodovinyl)-2'-fluoro-2'-deoxyuridine.
Morin KW1, Duan W, Knaus EE, McEwan AJ, Wiebe LI. Nucl Med Biol. 2005 Jul;32(5):459-64.
INTRODUCTION: (E)-5-(2-Iodovinyl)-2'-fluoro-2'-deoxyuridine (IVFRU) is a pyrimidine nucleoside analogue that accumulates selectively in murine cells expressing herpes simplex type-1 thymidine kinase (HSV-1 TK). The uptake of [(125)I]IVFRU in human 143B osteosarcoma cells transduced with a retroviral vector bearing the HSV-1 TK gene (143B-LTK cells) is now reported.
4.Evaluation of (76)Br-FBAU as a PET reporter probe for HSV1-tk gene expression imaging using mouse models of human glioma.
Cho SY1, Ravasi L, Szajek LP, Seidel J, Green MV, Fine HA, Eckelman WC. J Nucl Med. 2005 Nov;46(11):1923-30.
The utility of 5-(76)Br-bromo-2'-fluoro-2'-deoxyuridine ((76)Br-FBAU), a uracil analog, as a PET reporter probe for use with the herpes simplex virus type 1 thymidine kinase (HSV1-tk) reporter gene system for gene expression imaging was evaluated in vivo and in vitro using human and rat glioma cells.