200,000+ products from a single source!

sales@angenechem.com

Home > Fluorides > 69123-98-4

69123-98-4

69123-98-4 | 1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodouracil

CAS No: 69123-98-4 Catalog No: AG0032ID MDL No:MFCD00866922

Product Description

Catalog Number:
AG0032ID
Chemical Name:
1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodouracil
CAS Number:
69123-98-4
Molecular Formula:
C9H10FIN2O5
Molecular Weight:
372.0890
MDL Number:
MFCD00866922
IUPAC Name:
1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione
InChI:
InChI=1S/C9H10FIN2O5/c10-5-6(15)4(2-14)18-8(5)13-1-3(11)7(16)12-9(13)17/h1,4-6,8,14-15H,2H2,(H,12,16,17)/t4-,5+,6-,8-/m1/s1
InChI Key:
IPVFGAYTKQKGBM-BYPJNBLXSA-N
SMILES:
OC[C@H]1O[C@H]([C@H]([C@@H]1O)F)n1cc(I)c(=O)[nH]c1=O
UNII:
53T7IN77LC

Properties

Complexity:
418  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
0
Exact Mass:
371.962g/mol
Formal Charge:
0
Heavy Atom Count:
18  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
372.091g/mol
Monoisotopic Mass:
371.962g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
99.1A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.9  

Literature

Title Journal
A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans. Toxicological sciences : an official journal of the Society of Toxicology 20140101
A multimodality reporter gene for monitoring transplanted stem cells. Nuclear medicine and biology 20120801
Development of a multiparametric cell-based protocol to screen and classify the hepatotoxicity potential of drugs. Toxicological sciences : an official journal of the Society of Toxicology 20120501
Imaging of a localized bacterial infection with endogenous thymidine kinase using radioisotope-labeled nucleosides. International journal of medical microbiology : IJMM 20120301
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps). PLoS computational biology 20111201
Evaluation of F-18-labeled 5-iodocytidine (18F-FIAC) as a new potential positron emission tomography probe for herpes simplex virus type 1 thymidine kinase imaging. Nuclear medicine and biology 20111001
The improved syntheses of 5-substituted 2'-[18F]fluoro-2'-deoxy-arabinofuranosyluracil derivatives ([18F]FAU, [18F]FEAU, [18F]FFAU, [18F]FCAU, [18F]FBAU and [18F]FIAU) using a multistep one-pot strategy. Nuclear medicine and biology 20110701
A predictive ligand-based Bayesian model for human drug-induced liver injury. Drug metabolism and disposition: the biological fate of chemicals 20101201
Effects of structural differences between radioiodine-labeled 1-(2'-fluoro-2'-deoxy-D-arabinofuranosyl)-5-iodouracil (FIAU) and 1-(2'-fluoro-2'-deoxy-d-ribofuranosyl)-5-iodouracil (FIRU) on HSV1-TK reporter gene imaging. Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20100601
Enhanced antitumor effects by combination gene therapy using MDR1 gene shRNA and HSV1-tk in a xenograft mouse model. Cancer letters 20100501
Improved synthesis of 2'-deoxy-2'-[18F]-fluoro-1-beta-D-arabinofuranosyl-5-iodouracil ([18F]-FIAU). Nuclear medicine and biology 20100501
In vivo trafficking and immunostimulatory potential of an intranasally-administered primary dendritic cell-based vaccine. BMC immunology 20100101
Herpes simplex virus thymidine kinase imaging in mice with (1-(2'-deoxy-2'-[18F]fluoro-1-β-D-arabinofuranosyl)-5-iodouracil) and metabolite (1-(2'-deoxy-2'-[18F]fluoro-1-β-D-arabinofuranosyl)-5-uracil). European journal of nuclear medicine and molecular imaging 20091201
Myopathy and neuropathy associated with nucleos(t)ide analog therapy for hepatitis B. Journal of hepatology 20091001
Letter to the editor. Seminars in nuclear medicine 20090901
Facilitated mitochondrial import of antiviral and anticancer nucleoside drugs by human equilibrative nucleoside transporter-3. American journal of physiology. Gastrointestinal and liver physiology 20090401
Comparative study of cellular kinetics of reporter probe [(131)I]FIAU in neonatal cardiac myocytes after transfer of HSV1-tk reporter gene with two vectors. Nuclear medicine and biology 20090201
5-[18F]Fluoroalkyl pyrimidine nucleosides: probes for positron emission tomography imaging of herpes simplex virus type 1 thymidine kinase gene expression. Nuclear medicine and biology 20090101
Bacterial thymidine kinase as a non-invasive imaging reporter for Mycobacterium tuberculosis in live animals. PloS one 20090101
Noninvasive molecular imaging of hypoxia in human xenografts: comparing hypoxia-induced gene expression with endogenous and exogenous hypoxia markers. Cancer research 20081015
Bortezomib-induced enzyme-targeted radiation therapy in herpesvirus-associated tumors. Nature medicine 20081001
Synthesis and in vitro evaluation of 5-[(18)f]fluoroalkyl pyrimidine nucleosides for molecular imaging of herpes simplex virus type 1 thymidine kinase reporter gene expression. Journal of medicinal chemistry 20080925
Biodistribution, cellular uptake and DNA-incorporation of the 2'-fluoro stabilized 5-iodo-2'-deoxyuridine analog 5-iodo-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)uracil (FIAU). The quarterly journal of nuclear medicine and molecular imaging : official publication of the Italian Association of Nuclear Medicine (AIMN) [and] the International Association of Radiopharmacology (IAR), [and] Section of the Society of... 20080901
Human breast tumor cells express multimodal imaging reporter genes. Molecular imaging and biology : MIB : the official publication of the Academy of Molecular Imaging 20080901
Expression and hepatobiliary transport characteristics of the concentrative and equilibrative nucleoside transporters in sandwich-cultured human hepatocytes. American journal of physiology. Gastrointestinal and liver physiology 20080901
Imaging of gene expression in live pancreatic islet cell lines using dual-isotope SPECT. Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20080101
In vivo evaluation of the uptake of [(123)I]FIAU, [(123)I]IVFRU and [(123)I]IVFAU by normal mouse brain: potential for noninvasive assessment of HSV-1 thymidine kinase gene expression in gliomas. Nucleosides, nucleotides & nucleic acids 20080101
Biodistribution, PET, and radiation dosimetry estimates of HSV-tk gene expression imaging agent 1-(2'-Deoxy-2'-18F-Fluoro-beta-D-arabinofuranosyl)-5-iodouracil in normal dogs. Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20070401
Virus-associated tumor imaging by induction of viral gene expression. Clinical cancer research : an official journal of the American Association for Cancer Research 20070301
Evaluation of herpes simplex virus 1 thymidine kinase-mediated trapping of (131)I FIAU and prodrug activation of ganciclovir as a synergistic cancer radio/chemotherapy. Molecular imaging and biology : MIB : the official publication of the Academy of Molecular Imaging 20070101
Imaging of musculoskeletal bacterial infections by [124I]FIAU-PET/CT. PloS one 20070101
[131I]FIAU labeling of genetically transduced, tumor-reactive lymphocytes: cell-level dosimetry and dose-dependent toxicity. European journal of nuclear medicine and molecular imaging 20060901
Assessment of 123I-FIAU imaging of herpes simplex viral gene expression in the treatment of glioma. Nuclear medicine communications 20060801
Molecular imaging with 123I-FIAU, 18F-FUdR, 18F-FET, and 18F-FDG for monitoring herpes simplex virus type 1 thymidine kinase and ganciclovir prodrug activation gene therapy of cancer. Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20060701
In vitro evaluation of herpes simplex virus type 1 thymidine kinase reporter system in dynamic studies of transcriptional gene regulation. Nuclear medicine and biology 20060701
Identification of the mitochondrial targeting signal of the human equilibrative nucleoside transporter 1 (hENT1): implications for interspecies differences in mitochondrial toxicity of fialuridine. The Journal of biological chemistry 20060616
Myocardial kinetics of reporter probe 124I-FIAU in isolated perfused rat hearts after in vivo adenoviral transfer of herpes simplex virus type 1 thymidine kinase reporter gene. Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20050101
Comparison of [14C]FMAU, [3H]FEAU, [14C]FIAU, and [3H]PCV for monitoring reporter gene expression of wild type and mutant herpes simplex virus type 1 thymidine kinase in cell culture. Molecular imaging and biology : MIB : the official publication of the Academy of Molecular Imaging 20050101
A preclinical model for noninvasive imaging of hypoxia-induced gene expression; comparison with an exogenous marker of tumor hypoxia. European journal of nuclear medicine and molecular imaging 20041101
PET of cardiac transgene expression: comparison of 2 approaches based on herpesviral thymidine kinase reporter gene. Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20041101
A novel triple-modality reporter gene for whole-body fluorescent, bioluminescent, and nuclear noninvasive imaging. European journal of nuclear medicine and molecular imaging 20040501
Mitochondrial expression of the human equilibrative nucleoside transporter 1 (hENT1) results in enhanced mitochondrial toxicity of antiviral drugs. The Journal of biological chemistry 20040206
Non-invasive in vivo imaging with radiolabelled FIAU for monitoring cancer gene therapy using herpes simplex virus type 1 thymidine kinase and ganciclovir. European journal of nuclear medicine and molecular imaging 20040101
Anti-cowpox virus activities of certain adenosine analogs, arabinofuranosyl nucleosides, and 2'-fluoro-arabinofuranosyl nucleosides. Nucleosides, nucleotides & nucleic acids 20040101
Comparison of [18F]FHBG and [14C]FIAU for imaging of HSV1-tk reporter gene expression: adenoviral infection vs stable transfection. European journal of nuclear medicine and molecular imaging 20031101
Noninvasive imaging of transgene expression by use of positron emission tomography in a pig model of myocardial gene transfer. Circulation 20031028
Oligodendrocyte ablation impairs cerebellum development. Development (Cambridge, England) 20031001
Development of radioiodinated nucleoside analogs for imaging tissue proliferation: comparisons of six 5-iodonucleosides. Nuclear medicine and biology 20031001
Imaging of dihydrofolate reductase fusion gene expression in xenografts of human liver metastases of colorectal cancer in living rats. European journal of nuclear medicine and molecular imaging 20030901
Serial in vivo imaging of the targeted migration of human HSV-TK-transduced antigen-specific lymphocytes. Nature biotechnology 20030401
Synthesis of 2'-deoxy-2'-[18F]fluoro-beta-D-arabinofuranosyl nucleosides, [18F]FAU, [18F]FMAU, [18F]FBAU and [18F]FIAU, as potential PET agents for imaging cellular proliferation. Synthesis of [18F]labelled FAU, FMAU, FBAU, FIAU. Nuclear medicine and biology 20030401
In vitro activity of potential anti-poxvirus agents. Antiviral research 20030101
Specific genetic modifications of domestic animals by gene targeting and animal cloning. Reproductive biology and endocrinology : RB&E 20030101
Comparison of radiolabeled nucleoside probes (FIAU, FHBG, and FHPG) for PET imaging of HSV1-tk gene expression. Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20020801
Imaging expression of adenoviral HSV1-tk suicide gene transfer using the nucleoside analogue FIRU. European journal of nuclear medicine and molecular imaging 20020701
Enhanced inhibition of orthopoxvirus replication in vitro by alkoxyalkyl esters of cidofovir and cyclic cidofovir. Antimicrobial agents and chemotherapy 20020401
Imaging expression of cytosine deaminase-herpes virus thymidine kinase fusion gene (CD/TK) expression with [124I]FIAU and PET. Molecular imaging 20020101
Positron-emission tomography of vector-mediated gene expression in gene therapy for gliomas. Lancet (London, England) 20010901
Salmonella-based tumor-targeted cancer therapy: tumor amplified protein expression therapy (TAPET) for diagnostic imaging. Journal of controlled release : official journal of the Controlled Release Society 20010706
Positron emission tomography imaging for herpes virus infection: Implications for oncolytic viral treatments of cancer. Nature medicine 20010701
Comparison of [18F]FHPG and [124/125I]FIAU for imaging herpes simplex virus type 1 thymidine kinase gene expression. European journal of nuclear medicine 20010601
Positron emission tomography-based imaging of transgene expression mediated by replication-conditional, oncolytic herpes simplex virus type 1 mutant vectors in vivo. Cancer research 20010401
Quantitative kinetics of [124I]FIAU in cat and man. Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20010301
Simultaneous evaluation of dual gene transfer to adherent cells by gamma-ray imaging. Nuclear medicine and biology 20010201
Anti-herpesvirus activity profile of 4'-thioarabinofuranosyl purine and uracil nucleosides and activity of 1-beta-D-2'-fluoro-4'-thioarabinofuranosyl guanine and 2,6-diaminopurine against clinical isolates of human cytomegalovirus. Antiviral research 19980801
Structure-activity relationship of the affinity of 5-substituted uracil nucleoside analogues for varicella-zoster virus thymidine kinase and their activity against varicella-zoster virus. Antiviral research 19970801
Identification of BMS-200475 as a potent and selective inhibitor of hepatitis B virus. Antimicrobial agents and chemotherapy 19970701
Falsely low calcium measurements after high volume plasma exchange in a patient with liver failure. Transfusion science 19940901
The in vitro anti-hepatitis B virus activity of FIAU [1-(2'-deoxy-2'-fluoro-1-beta-D-arabinofuranosyl-5-iodo)uracil] is selective, reversible, and determined, at least in part, by the host cell. Antiviral research 19940101
Multiple nuclear dots antinuclear antibodies are not specific for primary biliary cirrhosis. Hepatology (Baltimore, Md.) 19920701
Use of a standardized cell culture assay to assess activities of nucleoside analogs against hepatitis B virus replication. Antiviral research 19920701
2'-Fluorinated arabinonucleosides of 5-(2-haloalkyl)uracil: synthesis and antiviral activity. Journal of medicinal chemistry 19870701
In vitro and in vivo antiviral activity of 2'-fluorinated arabinosides of 5-(2-haloalkyl)uracil. Antiviral research 19870601
Nucleosides. 139. Synthesis and anticytomegalovirus and antiherpes simplex virus activity of 5'-modified analogues of 2'-fluoroarabinosylpyrimidine nucleosides. Journal of medicinal chemistry 19870101
Activities of 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-iodocytosine and its metabolites against herpes simplex virus types 1 and 2 in cell culture and in mice infected intracerebrally with herpes simplex virus type 2. Antimicrobial agents and chemotherapy 19860101
Activity of 1-(2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl)-5-iodouracil against simian varicella virus infections in African green monkeys. Antimicrobial agents and chemotherapy 19860101
Comparative efficacy and selectivity of some nucleoside analogs against Epstein-Barr virus. Antimicrobial agents and chemotherapy 19850601
Efficacy and selectivity of some nucleoside analogs as anti-human cytomegalovirus agents. Antimicrobial agents and chemotherapy 19831001
Differential activity of potential antiviral nucleoside analogs on herpes simplex virus-induced and human cellular thymidine kinases. Antimicrobial agents and chemotherapy 19810901
Nucleosides. 110. Synthesis and antiherpes virus activity of some 2'-fluoro-2'-deoxyarabinofuranosylpyrimidine nucleosides. Journal of medicinal chemistry 19790101

Related Products

© 2019 Angene International Limited. All rights Reserved.