Relevant bibliographies by topics / Zidovudine (ZDV) [Azidothymidine (AZT)]

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Academic literature on the topic 'Zidovudine (ZDV) [Azidothymidine (AZT)]'

Author: Grafiati
Published: 4 June 2025
Last updated: 6 July 2025

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Journal articles on the topic "Zidovudine (ZDV) [Azidothymidine (AZT)]"

1

Tucci, Amanda Resende, Raquel Mello da Rosa, Alice Santos Rosa, et al. "Antiviral Effect of 5′-Arylchalcogeno-3-aminothymidine Derivatives in SARS-CoV-2 Infection." Molecules 28, no. 18 (2023): 6696. http://dx.doi.org/10.3390/molecules28186696.

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The understanding that zidovudine (ZDV or azidothymidine, AZT) inhibits the RNA-dependent RNA polymerase (RdRp) of SARS-CoV-2 and that chalcogen atoms can increase the bioactivity and reduce the toxicity of AZT has directed our search for the discovery of novel potential anti-coronavirus compounds. Here, the antiviral activity of selenium and tellurium containing AZT derivatives in human type II pneumocytes cell model (Calu-3) and monkey kidney cells (Vero E6) infected with SARS-CoV-2, and their toxic effects on these cells, was evaluated. Cell viability analysis revealed that organoselenium (R3a–R3e) showed lower cytotoxicity than organotellurium (R3f, R3n–R3q), with CC50 ≥ 100 µM. The R3b and R3e were particularly noteworthy for inhibiting viral replication in both cell models and showed better selectivity index. In Vero E6, the EC50 values for R3b and R3e were 2.97 ± 0.62 µM and 1.99 ± 0.42 µM, respectively, while in Calu-3, concentrations of 3.82 ± 1.42 µM and 1.92 ± 0.43 µM (24 h treatment) and 1.33 ± 0.35 µM and 2.31 ± 0.54 µM (48 h) were observed, respectively. The molecular docking calculations were carried out to main protease (Mpro), papain-like protease (PLpro), and RdRp following non-competitive, competitive, and allosteric inhibitory approaches. The in silico results suggested that the organoselenium is a potential non-competitive inhibitor of RdRp, interacting in the allosteric cavity located in the palm region. Overall, the cell-based results indicated that the chalcogen-zidovudine derivatives were more potent than AZT in inhibiting SARS-CoV-2 replication and that the compounds R3b and R3e play an important inhibitory role, expanding the knowledge about the promising therapeutic capacity of organoselenium against COVID-19.
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2

Mariano, DOC, D. de Souza, DF Meinerz, et al. "The potential toxicological insights about the anti-HIV drug azidothymidine-derived monoselenides in human leukocytes: Toxicological insights of new selenium-azidothymidine analogs." Human & Experimental Toxicology 36, no. 9 (2016): 910–18. http://dx.doi.org/10.1177/0960327116674529.

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Acquired immunodeficiency syndrome (AIDS) is a worldwide disease characterized by impairments of immune function. AIDS can be associated with oxidative stress (OS) that can be linked to selenium (Se) deficiency. Se is fundamental for the synthesis of selenoproteins, such as glutathione peroxidase and thioredoxin reductase. These enzymes catalyze the decomposition of reactive oxygen species and contribute to maintain equilibrium in cell redox status. Literature data indicate that organoselenium compounds, such as ebselen and diphenyl diselenide, have antioxidant properties in vitro and in vivo models associated with OS. Nevertheless, selenocompounds can also react and oxidize thiols groups, inducing toxicity in mammals. Here, we tested the potential cytotoxic and genotoxic properties of six analogs of the prototypal anti-HIV drug azidothymidine (AZT) containing Se (5′-Se-(phenyl)zidovudine; 5′-Se-(1,3,5-trimethylphenyl)zidovudine; 5′-Se-(1-naphtyl)zidovudine; 5′-Se-(4-chlorophenyl)zidovudine) (C4); 5′-Se-(4-methylphenyl)zidovudine (C5); and 5′-(4-methylbenzoselenoate)zidovudine). C5 increased the rate of dithiothreitol oxidation (thiol oxidase activity) and C2-C4 and C6 (at 100 µM) increased DNA damage index (DI) in human leukocytes. Moreover, C5 (200 µM) decreased human leukocyte viability to about 50%. Taken together, these results indicated the low in vitro toxicity in human leukocytes of some Se-containing analogs of AZT.
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3

Tadepalli, S. M., L. Puckett, S. Jeal, L. Kanics, and R. P. Quinn. "Differential assay of zidovudine and its glucuronide metabolite in serum and urine with a radioimmunoassay kit." Clinical Chemistry 36, no. 6 (1990): 897–900. http://dx.doi.org/10.1093/clinchem/36.6.897.

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Abstract We developed an ancillary procedure for the ZDV-Trac RIA (Incstar) to allow simultaneous determination of both zidovudine (3'-azido-3'-deoxythymidine, ZDV, AZT, Retrovir) and its metabolite, the glucuronide of ZDV (3'-azido-3'-deoxy-5'-O-beta-D-glucopyranuronosylthymidine, ZDVG, GAZT), in human serum and urine. Using the ZDV-Trac RIA, we measured ZDV concentrations before and after ZDVG in samples was hydrolyzed to ZDV by beta-glucuronidase (EC 3.2.1.31); ZDVG concentration was calculated as the difference between the two results. This method enables rapid evaluation of a large number of samples with a total turn-around time of 6 h. The lower detection limit of the RIA was 0.27 micrograms/L; the measurements varied linearly with ZDV concentrations from 0.27 to 217 micrograms/L, with the 50% inhibitory concentration being approximately 10 micrograms/L. Analytical recoveries of inhouse serum and urine controls for both ZDV and ZDVG exceeded 90%. Coefficients of variation (CVs) of serum controls were less than 6% for ZDV and less than 11% for ZDVG; for urine controls, CVs for both ZDV and ZDVG were less than 6%. Results for ZDVG concentrations obtained by HPLC and by the ZDV-Trac RIA system compared well: r = 0.978, slope 1.0, for serum samples, and r = 0.993, slope 1.09, for urine samples.
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4

Song, Heng, George W. Griesgraber, Carston R. Wagner, and Cheryl L. Zimmerman. "Pharmacokinetics of Amino Acid Phosphoramidate Monoesters of Zidovudine in Rats." Antimicrobial Agents and Chemotherapy 46, no. 5 (2002): 1357–63. http://dx.doi.org/10.1128/aac.46.5.1357-1363.2002.

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ABSTRACT In vitro studies have demonstrated that water-soluble, nontoxic phosphoramidates of azidothymidine (zidovudine [AZT]) have significant and specific anti-human immunodeficiency virus and anticancer activity. Although polar, these compounds are internalized and processed to the corresponding nucleoside monophosphates. Eight methyl amide and methyl ester phosphoramidate monoesters composed of d- or l-phenylalanine or tryptophan and AZT were synthesized. The plasma stability and protein binding studies were carried out in vitro. Then in vivo pharmacokinetic evaluations of six of the compounds were conducted. Sprague-Dawley rats received each compound by intravenous bolus dose, and serial blood and urine samples were collected. AZT and phosphoramidate concentrations in plasma and urine were quantitated by high-performance liquid chromatography with UV or fluorescence detection. Pharmacokinetic parameters were calculated by standard noncompartmental means. The plasma half-lives of the phosphoramidates were 10- to 20-fold longer than the half-life of AZT. Although the renal clearances of the phosphoramidates were similar to AZT, their total body clearances were significantly greater than that of AZT. The 3- to 15-fold-larger volume of distribution (V ss) for the phosphoramidates relative to AZT appeared to be dependent on the stereochemistry of the amino acid, with the largest values being associated with the l-amino acids. The increased V ss indicates a much greater tissue distribution of the phosphoramidate prodrugs than of AZT. Amino acid phosphoramidate monoesters of AZT have improved pharmacokinetic properties over AZT and significant potential as in vivo pronucleotides.
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Cho, Hyejin, and Kwang-sun Kim. "Repurposing of Ciclopirox to Overcome the Limitations of Zidovudine (Azidothymidine) against Multidrug-Resistant Gram-Negative Bacteria." Pharmaceutics 14, no. 3 (2022): 552. http://dx.doi.org/10.3390/pharmaceutics14030552.

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Multidrug-resistant (MDR) Gram-negative bacteria are the top-priority pathogens to be eradicated. Drug repurposing (e.g., the use of non-antibiotics to treat bacterial infections) may be helpful to overcome the limitations of current antibiotics. Zidovudine (azidothymidine, AZT), a licensed oral antiviral agent, is a leading repurposed drug against MDR Gram-negative bacterial infections. However, the rapid emergence of bacterial resistance due to long-term exposure, overuse, or misuse limits its application, making it necessary to develop new alternatives. In this study, we investigated the efficacy of ciclopirox (CPX) as an alternative to AZT. The minimum inhibitory concentrations of AZT and CPX against MDR Gram-negative bacteria were determined; CPX appeared more active against β-lactamase-producing Escherichia coli, whereas AZT displayed no selectivity for any antibiotic-resistant strain. Motility assays revealed that β-lactamase-producing Escherichia coli strains were less motile in nature and more strongly affected by CPX than a parental strain. Resistance against CPX was not observed in E. coli even after 25 days of growth, whereas AZT resistance was observed in less than 2 days. Moreover, CPX effectively killed AZT-resistant strains with different resistance mechanisms. Our findings indicate that CPX may be utilized as an alternative or supplement to AZT-based medications to treat opportunistic Gram-negative bacterial infections.
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Bradshaw, Patrick C., Jiaxin Li, and David C. Samuels. "A computational model of mitochondrial AZT metabolism." Biochemical Journal 392, no. 2 (2005): 363–73. http://dx.doi.org/10.1042/bj20050749.

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The mechanisms of the mitochondrial toxicity of AZT (azidothymidine; zidovudine) are not clear. The two main contenders are the incorporation of phosphorylated AZT into the mtDNA (mitochondrial DNA) and the competitive inhibition of natural deoxynucleotide metabolism. We have built a computational model of AZT metabolism in mitochondria in order to better understand these toxicity mechanisms. The model includes the transport of non-phosphorylated and phosphorylated forms of AZT into mitochondria, phosphorylation, and incorporation into mtDNA. The model also includes the mitochondrial metabolism of the natural deoxynucleotides. We define three simulated cell types, i.e. rapidly dividing, slowly dividing and postmitotic cells. Our standard simulation indicates that incorporation of AZT into mtDNA is highest in rapidly dividing cells because of the higher mitochondrial AZTTP (3′-azidothymidine-5′-triphosphate)/dTTP ratio in this cell type. However, under these standard conditions the rate of incorporation into mtDNA is too low to be a major cause of toxicity. These simulations relied on the assumption that phosphorylated AZT is transported with the same kinetics as phosphorylated thymidine. In simulations with mitochondria set to have a limited ability to transport phosphorylated AZT, AZTTP accumulates to toxic levels in the mitochondria of postmitotic cells, while low levels are maintained in mitochondria from rapidly dividing cells. This result is more consistent with the tissue toxicities observed in patients. Our model also predicts that inhibition by AZT of mitochondrial deoxycytidine phosphorylation by thymidine kinase 2 may contribute to the mitochondrial toxicity, since in simulations using a typical peak plasma AZT level the mtDNA replication rate is decreased by 30% in postmitotic cell simulations.
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7

Di Bella, Stefano, Roberto Luzzati, and Cristina Lagatolla. "Zidovudine (azidothymidine, AZT) unexpressed clinical potential against multidrug-resistant Gram-negative isolates." International Journal of Antimicrobial Agents 59, no. 1 (2022): 106500. http://dx.doi.org/10.1016/j.ijantimicag.2021.106500.

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8

Bianco, Maria da Conceição Avelino Dias, Debora Inacio Leite, Frederico Silva Castelo Branco, et al. "The Use of Zidovudine Pharmacophore in Multi-Target-Directed Ligands for AIDS Therapy." Molecules 27, no. 23 (2022): 8502. http://dx.doi.org/10.3390/molecules27238502.

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The concept of polypharmacology embraces multiple drugs combined in a therapeutic regimen (drug combination or cocktail), fixed dose combinations (FDCs), and a single drug that binds to different targets (multi-target drug). A polypharmacology approach is widely applied in the treatment of acquired immunodeficiency syndrome (AIDS), providing life-saving therapies for millions of people living with HIV. Despite the success in viral load suppression and patient survival of combined antiretroviral therapy (cART), the development of new drugs has become imperative, owing to the emergence of resistant strains and poor adherence to cART. 3′-azido-2′,3′-dideoxythymidine, also known as azidothymidine or zidovudine (AZT), is a widely applied starting scaffold in the search for new compounds, due to its good antiretroviral activity. Through the medicinal chemistry tool of molecular hybridization, AZT has been included in the structure of several compounds allowing for the development of multi-target-directed ligands (MTDLs) as antiretrovirals. This review aims to systematically explore and critically discuss AZT-based compounds as potential MTDLs for the treatment of AIDS. The review findings allowed us to conclude that: (i) AZT hybrids are still worth exploring, as they may provide highly active compounds targeting different steps of the HIV-1 replication cycle; (ii) AZT is a good starting point for the preparation of co-drugs with enhanced cell permeability.
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9

Szafrański, Przemysław W., Patryk Kasza, Mariusz Kępczyński, and Marek T. Cegła. "Fluorescent 1,2,3-triazole derivative of 3′-deoxy-3-azidothymidine: synthesis and absorption/emission spectra." Heterocyclic Communications 21, no. 5 (2015): 263–67. http://dx.doi.org/10.1515/hc-2015-0195.

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Abstract3′-Deoxy-3-azidothymidine (AZT, zidovudine) is a nucleoside-analog reverse transcriptase inhibitor, successfully used against the human immunodeficiency virus (HIV). Its structure contains an azide function, which makes it a useful substrate for 1,2,3-triazole synthesis, using the copper-catalyzed azide-alkyne cycloaddition, the flagship reaction of ‘click chemistry’. Herein we present the synthesis and spectral characterization of its 1,2,3-triazole derivative containing a fluorenylmethyloxycarbonyl (fmoc) fluorescent fragment. The preparation and characteristics of a novel fluorescent probe, 9H-fluoren-9-ylmethyl prop-2-yn-1-yl carbonate (propargyl-fmoc) is also presented.
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10

Kovalev, I. E., and N. V. Shipulina. "Interaction of the anti-HIV drug azidothymidine (zidovudine, AZT) with cytochrome P-450." Pharmaceutical Chemistry Journal 28, no. 5 (1994): 303–6. http://dx.doi.org/10.1007/bf02218423.

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Dissertations / Theses on the topic "Zidovudine (ZDV) [Azidothymidine (AZT)]"

1

MALET, CORINNE. "A propos d'un cas d'infection a vih suivi a l'hopital d'aurillac : discussion clinique et therapeutique (azt)." Clermont-Ferrand 1, 1989. http://www.theses.fr/1989CLF13080.

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Books on the topic "Zidovudine (ZDV) [Azidothymidine (AZT)]"

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Program advisory: Use of zidovudine (ZDV) to reduce perinatal HIV transmission in HRSA-funded programs. U.S. Department of Health & Human Services, Public Health Service, Health Resources & Services Administration, 1995.

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Book chapters on the topic "Zidovudine (ZDV) [Azidothymidine (AZT)]"

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Mondal, D. "Zidovudine (azidothymidine AZT)☆." In Reference Module in Biomedical Sciences. Elsevier, 2016. http://dx.doi.org/10.1016/b978-0-12-801238-3.99390-5.

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