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Glutathione-Mediated Conjugation of Anticancer Drugs: An Overview of Reaction Mechanisms and Biological Significance for Drug Detoxification and Bioactivation

https://doi.org/10.3390/molecules27165252
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Novel insights into the mechanism of cyclophosphamide-induced bladder toxicity: chloroacetaldehyde’s contribution to urothelial dysfunction in vitro
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Cytochrome P450 isozymes 3A4 and 2B6 are involved in the in vitro human metabolism of thiotepa to TEPA
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Metabolism of cisplatin in the organs of Rattus norvegicus: role of Glutathione S-transferase P1
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Glutathione conjugate mediated toxicities*1
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The carbonyl reactivity of 3-bromopyruvate and related compounds
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Studies on the mechanism of sulofenur and LY295501 toxicity: effect on the regulation of cytosolic calcium in relation to cytotoxicity in normal and tumorigenic rat kidney cell lines
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High-dose chemotherapy regimens for solid tumors
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Mitomycin C: small, fast and deadly (but very selective)
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Glutathione Transferases in the Bioactivation of Azathioprine
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Nucleophilic Substitution and Elimination Reactions
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Anticancer Drugs That Interact with the DNA Minor Groove
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Evaluation of the effect of oxygen exposure on human liver microsomal metabolism of mitomycin C in the presence of glutathioneusing liquid chromatography–quadrupole time of flight mass spectrometry
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The busulfan metabolite EdAG irreversibly glutathionylates glutaredoxins
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Glutathione catalysis and the reaction mechanisms of glutathione-dependent enzymes
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Comparative metabolism of cyclophosphamide and ifosfamide in the mouse using UPLC–ESI-QTOFMS-based metabolomics
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Ferroptosis: An Iron-Dependent Form of Nonapoptotic Cell Death
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Regulation of Ferroptotic Cancer Cell Death by GPX4
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A Genome-wide Haploid Genetic Screen Identifies Regulators of Glutathione Abundance and Ferroptosis Sensitivity
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Cabozantinib Versus Mitoxantrone-prednisone in Symptomatic Metastatic Castration-resistant Prostate Cancer: A Randomized Phase 3 Trial with a Primary Pain Endpoint
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The role of thiols in antioxidant systems
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Structural Determinants of Glutathione Transferases with Azathioprine Activity Identified by DNA Shuffling of Alpha Class Members
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The Anti-cancer Drug Chlorambucil as a Substrate for the Human Polymorphic Enzyme Glutathione Transferase P1-1: Kinetic Properties and Crystallographic Characterisation of Allelic Variants
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Novel insights into conjugation of antitumor-active unsymmetrical bisacridine C-2028 with glutathione: Characteristics of non-enzymatic and glutathione S-transferase-mediated reactions
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Regulation of glutathione synthesis
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The promising anticancer drug 3-bromopyruvate is metabolized through glutathione conjugation which affects chemoresistance and clinical practice: An evidence-based view
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Anticancer agent 3-bromopyruvic acid forms a conjugate with glutathione
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Glutathione conjugation as a bioactivation reaction
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Conjugation of chlorambucil with GSH by GST purified from human colon adenocarcinoma cells and its inhibition by plant polyphenols
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The Role of Glutathione and Glutathione S-Transferases in the Metabolism of Chemical Carcinogens and Other Electrophilic Agents
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Mechanism of azathioprine-induced injury to hepatocytes: roles of glutathione depletion and mitochondrial injury
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Cyclophosphamide and related anticancer drugs
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The importance of glutathione in human disease
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Glutathione and its role in cellular functions
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Covalent DNA–Protein Cross-Linking by Phosphoramide Mustard and Nornitrogen Mustard in Human Cells
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Stereoselectivity of isozyme C of glutathione S-transferase toward arene and azaarene oxides
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Platinum Drug Distribution in Cancer Cells and Tumors
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PABA/NO as an Anticancer Lead: Analogue Synthesis, Structure Revision, Solution Chemistry, Reactivity toward Glutathione, and in Vitro Activity
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Discovery of 3-(2,6-Dichloro-3,5-dimethoxy-phenyl)-1-{6-[4-(4-ethyl-piperazin-1-yl)-phenylamino]-pyrimidin-4-yl}-1-methyl-urea (NVP-BGJ398), A Potent and Selective Inhibitor of the Fibroblast Growth Factor Receptor Family of Receptor Tyrosine Kinase
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The Secondary Amine/Nitric Oxide Complex Ion R2N[N(O)NO]- as Nucleophile and Leaving Group in SNAr Reactions
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Comparison of metabolism and toxicity to the structure of the anticancer agent sulofenur and related sulfonylureas
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Conjugation of Glutathione and Other Thiols with Bioreductively Activated Mitomycin C. Effect of Thiols on the Reductive Activation Rate
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Glutathione Conjugation of the Cytostatic Drug Ifosfamide and the Role of Human Glutathione S-Transferases
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Glutathione-Dependent Metabolism of the Antitumor Agent Sulofenur. Evidence for the Formation of p-Chlorophenyl Isocyanate as a Reactive Intermediate
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Prediction of Michael-Type Acceptor Reactivity toward Glutathione
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Verification of the Structural Alerts for Michael Acceptors
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Glutathione Conjugation of Alkylating Cytostatic Drugs with a Nitrogen Mustard Group and the Role of Glutathione S-Transferases
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Structure, Catalytic Mechanism, and Evolution of the Glutathione Transferases
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Bioactivation of 6,7-Dimethyl-2,4-di-1-pyrrolidinyl-7H-pyrrolo[2,3-d]pyrimidine (U-89843) to Reactive Intermediates That Bind Covalently to Macromolecules and Produce Genotoxicity1
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Mechanisms of resistance to alkylating agents
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Glutathione disulfide induces neural cell death via a 12-lipoxygenase pathway
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Prodrugs: design and clinical applications
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Glutathione transferases: substrates, inihibitors and pro-drugs in cancer and neurodegenerative diseases
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Concerted nucleophilic aromatic substitutions
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The effect of busulphan on the pharmacokinetics of cyclophosphamide and its 4-hydroxy metabolite: time interval influence on therapeutic efficacy and therapy-related toxicity
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The role of glutathione-S-transferase in anti-cancer drug resistance
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Unbalanced Activation of Glutathione Metabolic Pathways Suggests Potential Involvement in Plant Defense against the Gall Midge Mayetiola destructor in Wheat
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Inhibition of transcription by platinum antitumor compounds
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Interactions of anticancer Pt compounds with proteins: an overlooked topic in medicinal inorganic chemistry?
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Phase I metabolic profiling and unexpected reactive metabolites in human liver microsome incubations of X-376 using LC-MS/MS: bioactivation pathway elucidation and in silico toxicity studies of its metabolites
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Identification and characterization of in silico , in vivo , in vitro , and reactive metabolites of infigratinib using LC-ITMS: bioactivation pathway elucidation and in silico toxicity studies of its metabolites
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Hexokinase II inhibition by 3-bromopyruvate sensitizes myeloid leukemic cells K-562 to anti-leukemic drug, daunorubicin
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Chemistry, pharmacology and pharmacokinetics of N,N′,N′′ -triethylenethiophosphoramide (ThioTEPA)
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Glutathione Adducts of Helenalin and 11α,13-Dihydrohelenalin Acetate Inhibit Glutathione S-Transferase from Horse Liver1
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Helenalin Acetate, a Natural Sesquiterpene Lactone with Anti-inflammatory and Anti-cancer Activity, Disrupts the Cooperation of CCAAT Box/Enhancer-binding Protein β (C/EBPβ) and Co-activator p300
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Glutathione and apoptosis
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N-Acetylcysteine as an antioxidant and disulphide breaking agent: the reasons why
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Glutathione metabolism in cancer progression and treatment resistance
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S-Glutathionylation: From Molecular Mechanisms to Health Outcomes
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Genetic and Environmental Factors Influencing Glutathione Homeostasis inSaccharomyces cerevisiae
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The high non-enzymatic conjugation rates of some glutathione S-transferase (GST) substrates at high glutathione concentrations
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Glutathione S-Transferase Activity, Sulfhydryl Group and Glutathione Levels, and DNA Cross-Linking Activity With Chlorambucil in Chronic Lymphocytic Leukemia
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Regulation of calcium signalling and gene expression by glutathione
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Mitomycin C
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Metabolism of Cisplatin to a Nephrotoxin in Proximal Tubule Cells
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Relations between polymorphisms in drug-metabolising enzymes and toxicity of chemotherapy with cyclophosphamide, thiotepa and carboplatin
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Azathioprine and 6‐mercaptopurine pharmacogenetics and metabolite monitoring in inflammatory bowel disease
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The Role of Extrahepatic Metabolism in the Pharmacokinetics of the Targeted Covalent Inhibitors Afatinib, Ibrutinib, and Neratinib
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ACETAMINOPHEN-INDUCED HEPATOTOXICITY
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Role of Cysteine S-Conjugate β-Lyase in the Metabolism of Cisplatin
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Dehydroalanine Analog of Glutathione: An Electrophilic Busulfan Metabolite That Binds to Human Glutathione S-Transferase A1-1
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Divergent Activities of Human Glutathione Transferases in the Bioactivation of Azathioprine
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Tumor Cell Responses to a Novel Glutathione S-Transferase–Activated Nitric Oxide-Releasing Prodrug
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The Nitrogen Mustards
inferredcites →https://doi.org/10.1146/annurev.pharmtox.45.120403.095857openalex-snapshot
GLUTATHIONE TRANSFERASES
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Glutathione Homeostasis and Functions: Potential Targets for Medical Interventions
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Spontaneous Production of Glutathione‐Conjugated Forms of 1,2‐Dichloropropane: Comparative Study on Metabolic Activation Processes of Dihaloalkanes Associated with Occupational Cholangiocarcinoma
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Glutathione Pathway Genetic Polymorphisms and Lung Cancer Survival After Platinum-Based Chemotherapy
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A Phase I/II Trial of MEC (Mitoxantrone, Etoposide, Cytarabine) in Combination with Ixazomib for Relapsed Refractory Acute Myeloid Leukemia
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Tyrosine kinase inhibitor NVP-BGJ398 functionally improves FGFR3-related dwarfism in mouse model
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NF-κB p65 repression by the sesquiterpene lactone, Helenalin, contributes to the induction of autophagy cell death
inferredcites →https://doi.org/10.1186/1756-8722-3-36openalex-snapshot
Pharmacokinetic targeting of intravenous busulfan reduces conditioning regimen related toxicity following allogeneic hematopoietic cell transplantation for acute myelogenous leukemia
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Targeting glycolysis by 3-bromopyruvate improves tamoxifen cytotoxicity of breast cancer cell lines
inferredcites →https://doi.org/10.1186/s12943-022-01530-yopenalex-snapshot
Ferroptosis in cancer therapy: a novel approach to reversing drug resistance
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Mitoxantrone, fluorouracil, and high-dose leucovorin: an effective, well-tolerated regimen for metastatic breast cancer.
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Results of a Randomized Trial of Chlorambucil Versus Fludarabine for Patients With Untreated Waldenström Macroglobulinemia, Marginal Zone Lymphoma, or Lymphoplasmacytic Lymphoma
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Phase II Study of BGJ398 in Patients With FGFR-Altered Advanced Cholangiocarcinoma
inferredcites →https://doi.org/10.1201/9781420028485openalex-snapshot
Drug Metabolizing Enzymes
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Conjugation Reactions In Drug Metabolism
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The Role of Glutathione in Detoxication
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Review on Pharmacology of Cisplatin: Clinical Use, Toxicity and Mechanism of Resistance of Cisplatin
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The Interaction of the Chemotherapeutic Drug Chlorambucil with Human Glutathione Transferase A1-1: Kinetic and Structural Analysis
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Glutathione dysregulation and the etiology and progression of human diseases
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Helenalin, an Anti-Inflammatory Sesquiterpene Lactone from Arnica, Selectively Inhibits Transcription Factor NF-κB
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Binding motifs of cisplatin interaction with simple biomolecules and aminoacid targets probed by IR ion spectroscopy
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Glutathione may have implications in the design of 3-bromopyruvate treatment protocols for both fungal and algal infections as well as multiple myeloma
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Structure-based design of anticancer prodrug PABA/NO
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Update of the Preclinical Situation of Anticancer Platinum Complexes: Novel Design Strategies and Innovative Analytical Approaches
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An Overview of Cyclophosphamide Development and Clinical Applications
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Role of Pharmacogenetics in Busulfan/Cyclophosphamide Conditioning Therapy Prior to Hematopoietic Stem Cell Transplantation
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Topics on Drug Metabolism

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