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29706-85-2,MFCD02091759
Catalog No.:AA00C2OU

29706-85-2 | 3'-AZIDO-2',3'-DIDEOXY-THYMIDINE-5'-MONOPHOSPHATE, SODIUM SALT

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10mg
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  • Technical Information
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Technical Information
Catalog Number:
AA00C2OU
Chemical Name:
3'-AZIDO-2',3'-DIDEOXY-THYMIDINE-5'-MONOPHOSPHATE, SODIUM SALT
CAS Number:
29706-85-2
Molecular Formula:
C10H14N5O7P
Molecular Weight:
347.2212
MDL Number:
MFCD02091759
SMILES:
CC1=CN(C(=O)NC1=O)C2CC(C(O2)COP(=O)(O)O)N=[N+]=[N-]
Properties
Computed Properties
 
Complexity:
640  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
9  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
5  
XLogP3:
-1  

Literature

Title: Azidothymidine-triphosphate impairs mitochondrial dynamics by disrupting the quality control system.

Journal: Redox biology 20171001

Title: Synthesis and anti-HIV properties of new carbamate prodrugs of AZT.

Journal: Chemical biology & drug design 20121201

Title: Synthesis and inhibitory activity of thymidine analogues targeting Mycobacterium tuberculosis thymidine monophosphate kinase.

Journal: Bioorganic & medicinal chemistry 20111215

Title: Aryl H-phosphonates 17: (N-aryl)phosphoramidates of pyrimidine nucleoside analogues and their synthesis, selected properties, and anti-HIV activity.

Journal: Journal of medicinal chemistry 20111013

Title: Novel antiviral C5-substituted pyrimidine acyclic nucleoside phosphonates selected as human thymidylate kinase substrates.

Journal: Journal of medicinal chemistry 20110113

Title: Structural basis for the efficient phosphorylation of AZT-MP (3'-azido-3'-deoxythymidine monophosphate) and dGMP by Plasmodium falciparum type I thymidylate kinase.

Journal: The Biochemical journal 20100527

Title: Decomposition of 3'-azido-2',3'-dideoxythymidine 5'-monophosphate (AZTMP) prodrugs in biological media studied by on-line solid-phase extraction coupled to liquid chromatography mass spectrometry.

Journal: Biomedical chromatography : BMC 20091101

Title: Monitoring therapy in canine malignant lymphoma and leukemia with serum thymidine kinase 1 activity--evaluation of a new, fully automated non-radiometric assay.

Journal: International journal of oncology 20090201

Title: Bisphosphonate inhibitors of ATP-mediated HIV-1 reverse transcriptase catalyzed excision of chain-terminating 3'-azido, 3'-deoxythymidine: a QSAR investigation.

Journal: Bioorganic & medicinal chemistry 20081001

Title: Quantification of zidovudine and its monophosphate in cell extracts by on-line solid-phase extraction coupled to liquid chromatography.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20071015

Title: Comparison of the phosphorylation of 4'-ethynyl 2',3'-dihydro-3'-deoxythymidine with that of other anti-human immunodeficiency virus thymidine analogs.

Journal: Antimicrobial agents and chemotherapy 20070501

Title: Improved method to quantify intracellular zidovudine mono- and triphosphate in peripheral blood mononuclear cells by liquid chromatography-tandem mass spectrometry.

Journal: Journal of mass spectrometry : JMS 20070301

Title: 3'-Azido-3'-deoxythymidine-(5')-tetraphospho-(5')-adenosine, the product of ATP-mediated excision of chain-terminating AZTMP, is a potent chain-terminating substrate for HIV-1 reverse transcriptase.

Journal: Biochemistry 20070123

Title: Antiretroviral agents during pregnancy: consequences on hematologic parameters in HIV-exposed, uninfected newborn infant.

Journal: European journal of obstetrics, gynecology, and reproductive biology 20060101

Title: AZT and AZT-monophosphate prodrugs incorporating HIV-protease substrate fragment: synthesis and evaluation as specific drug delivery systems.

Journal: Antiviral chemistry & chemotherapy 20060101

Title: Suppression of multidrug-resistant HIV-1 reverse transcriptase primer unblocking activity by alpha-phosphate-modified thymidine analogues.

Journal: Journal of molecular biology 20050610

Title: The crystal structure of Mycobacterium tuberculosis thymidylate kinase in complex with 3'-azidodeoxythymidine monophosphate suggests a mechanism for competitive inhibition.

Journal: Biochemistry 20050111

Title: A method for quantitating the intracellular metabolism of AZT amino acid phosphoramidate pronucleotides by capillary high-performance liquid chromatography-electrospray ionization mass spectrometry.

Journal: Molecular pharmaceutics 20050101

Title: [The study of coupling agents for the phosphorylation of 3'-azido-3'-deoxythymidine with (P32)orthophosphoric acid].

Journal: Bioorganicheskaia khimiia 20050101

Title: Synthesis of carbocyclic nucleotides as potential substrates for thymidylate kinase.

Journal: Nucleosides, nucleotides & nucleic acids 20050101

Title: Simultaneous quantitation of zidovudine and zidovudine monophosphate from plasma, amniotic fluid and tissues by micellar capillary electrophoresis.

Journal: Biomedical chromatography : BMC 20041001

Title: Sensitive nonradiometric method for determining thymidine kinase 1 activity.

Journal: Clinical chemistry 20040901

Title: L-chicoric acid inhibits human immunodeficiency virus type 1 integration in vivo and is a noncompetitive but reversible inhibitor of HIV-1 integrase in vitro.

Journal: Virology 20040901

Title: Intracellular metabolism and pharmacokinetics of 5'-hydrogenphosphonate of 3'-azido-2',3'-dideoxythymidine, a prodrug of 3'-azido-2',3'-dideoxythymidine.

Journal: Antiviral research 20040801

Title: Structural requirements for efficient phosphorylation of nucleotide analogs by human thymidylate kinase.

Journal: Mini reviews in medicinal chemistry 20040501

Title: Pro-oxidant properties and cytotoxicity of AZT-monophosphate and AZT.

Journal: Cardiovascular toxicology 20040101

Title: Phosphorylation of thymidine and AZT in heart mitochondria: elucidation of a novel mechanism of AZT cardiotoxicity.

Journal: Cardiovascular toxicology 20040101

Title: Direct measurement of nucleoside monophosphate delivery from a phosphoramidate pronucleotide by stable isotope labeling and LC-ESI(-)-MS/MS.

Journal: Molecular pharmaceutics 20040101

Title: Non-nucleoside inhibitors of HIV-1 reverse transcriptase inhibit phosphorolysis and resensitize the 3'-azido-3'-deoxythymidine (AZT)-resistant polymerase to AZT-5'-triphosphate.

Journal: The Journal of biological chemistry 20031024

Title: The Y181C substitution in 3'-azido-3'-deoxythymidine-resistant human immunodeficiency virus, type 1, reverse transcriptase suppresses the ATP-mediated repair of the 3'-azido-3'-deoxythymidine 5'-monophosphate-terminated primer.

Journal: The Journal of biological chemistry 20031017

Title: Thymidine and thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.

Journal: Bioorganic & medicinal chemistry letters 20030915

Title: 3'-C-branched-chain-substituted nucleosides and nucleotides as potent inhibitors of Mycobacterium tuberculosis thymidine monophosphate kinase.

Journal: Journal of medicinal chemistry 20030828

Title: Relationship between 3'-azido-3'-deoxythymidine resistance and primer unblocking activity in foscarnet-resistant mutants of human immunodeficiency virus type 1 reverse transcriptase.

Journal: Journal of virology 20030601

Title: Potentiation of TRAIL-induced apoptosis in primary effusion lymphoma through azidothymidine-mediated inhibition of NF-kappa B.

Journal: Blood 20030315

Title: Enzymatic and structural analysis of inhibitors designed against Mycobacterium tuberculosis thymidylate kinase. New insights into the phosphoryl transfer mechanism.

Journal: The Journal of biological chemistry 20030214

Title: Assessment of the effect of phosphorylated metabolites of anti-human immunodeficiency virus and anti-hepatitis B virus pyrimidine analogs on the behavior of human deoxycytidylate deaminase.

Journal: Molecular pharmacology 20030101

Title: Novel nucleotide analogues as potential substrates for TMPK, a key enzyme in the metabolism of AZT.

Journal: Nucleosides, nucleotides & nucleic acids 20030101

Title: SATE (aryl) phosphotriester series. II. Stability studies and physicochemical parameters.

Journal: Nucleosides, nucleotides & nucleic acids 20030101

Title: Structures of HIV-1 reverse transcriptase with pre- and post-translocation AZTMP-terminated DNA.

Journal: The EMBO journal 20021202

Title: Synthesis and evaluation of thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.

Journal: Bioorganic & medicinal chemistry letters 20021007

Title: Database searching for thymidine and thymidylate kinase inhibitors using three-dimensional structure-based methods.

Journal: Journal of enzyme inhibition and medicinal chemistry 20020601

Title: Synthesis, anti-HIV activity, and stability studies of 5'-phosphorofluoridate derivatives of AZT.

Journal: Bioorganic chemistry 20011201

Title: Low-dose, sublingual AZT-monophosphate therapy for HIV+ patients?

Journal: Medical hypotheses 20010301

Title: Recognition and inhibition of HIV integrase by a novel dinucleotide.

Journal: Bioorganic & medicinal chemistry letters 20000207

Title: Characterization of the activation pathway of phosphoramidate triester prodrugs of stavudine and zidovudine.

Journal: Molecular pharmacology 19991001

Title: A mechanism of AZT resistance: an increase in nucleotide-dependent primer unblocking by mutant HIV-1 reverse transcriptase.

Journal: Molecular cell 19990701

Title: Synthesis, anti-HIV activity and stability studies of 3'-azido-2',3'-dideoxythymidine 5'-fluorophosphate.

Journal: Nucleosides & nucleotides 19990101

Title: Identification of a nucleotide binding site in HIV-1 integrase.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19980414

Title: Differential inhibition of HIV-1 preintegration complexes and purified integrase protein by small molecules.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19960903

Title: Mononucleoside phosphotriester derivatives with S-acyl-2-thioethyl bioreversible phosphate-protecting groups: intracellular delivery of 3'-azido-2',3'-dideoxythymidine 5'-monophosphate.

Journal: Journal of medicinal chemistry 19950929

Title: Inhibition of human immunodeficiency virus type 1 integrase by 3'-azido-3'-deoxythymidylate.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19940621

Title: 5'-Hydrogenphosphonates of anti-HIV nucleoside analogues revisited: controversial mode of action.

Journal: Antiviral research 19931001

Title: Targeting of antiviral drugs to T4-lymphocytes. Anti-HIV activity of neoglycoprotein-AZTMP conjugates in vitro.

Journal: Biochemical pharmacology 19901215

Title: Alpha, beta- and beta, gamma-methylene 5'-phosphonate derivatives of 3'-azido-2',3'-dideoxythymidine-5'-triphosphate. Correlation between affinity for reverse transcriptase, susceptibility to hydrolysis by phosphodiesterases and anti-retrovirus activity.

Journal: Biochemical pharmacology 19880615

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