ArticleBioconjugate chemistry2016
Targeting Iron in Colon Cancer via Glycoconjugation of Thiosemicarbazone Prochelators.
Article in Bioconjugate chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed, 48 citations in OpenAlex.
- Glyco-Conjugation of Thiosemicarbazone Copper(II) Complexes Enhances Selectivity toward Cancer Cells Overexpressing GLUT1.ACS omega · 2026Article
- Recent Advances in the Development of Metal-Glycoconjugates for Medicinal Applications.Molecules (Basel, Switzerland) · 2025Review
- Disulfide-based 2-pyridyl-hydrazone prochelators induce iron deprivation and oxidative stress in ovarian cancer cells.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2025Article
- Review
- Functionalizing Thiosemicarbazones for Covalent Conjugation.Molecules (Basel, Switzerland) · 2024Article
- Design of Tetrazolium Cations for the Release of Antiproliferative Formazan Chelators in Mammalian Cells.Journal of the American Chemical Society · 2023Article
- Targeting iron to contrast cancer progression.Current opinion in chemical biology · 2023Review
- Thiol-Reactive Arylsulfonate Masks for Phenolate Donors in Antiproliferative Iron Prochelators.Inorganic chemistry · 2022Article
- Glycoconjugation of Quinoline Derivatives Using the C-6 Position in Sugars as a Strategy for Improving the Selectivity and Cytotoxicity of Functionalized Compounds.Molecules (Basel, Switzerland) · 2022Article
- Aroylhydrazone Glycoconjugate Prochelators Exploit Glucose Transporter 1 (GLUT1) to Target Iron in Cancer Cells.ACS medicinal chemistry letters · 2022Article
- Albumin Conjugates of Thiosemicarbazone and Imidazole-2-thione Prochelators: Iron Coordination and Antiproliferative Activity.ChemMedChem · 2021Article
- Iron Complexes of an Antiproliferative Aroyl Hydrazone: Characterization of Three Protonation States by Electron Paramagnetic Resonance Methods.Inorganic chemistry · 2020Article
- Novel pyridinecarboxaldehyde thiosemicarbazone conjugated magnetite nanoparticulates (MNPs) promote apoptosis in human lung cancer A549 cells.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2020Article
- Bifunctional ligand design for modulating mutant p53 aggregation in cancer.Chemical science · 2019Article
- Review
- Strategies to Interfere with Tumor Metabolism through the Interplay of Innate and Adaptive Immunity.Cells · 2019Review
- Iron as a Central Player and Promising Target in Cancer Progression.International journal of molecular sciences · 2019Review
- Modifying aroylhydrazone prochelators for hydrolytic stability and improved cytoprotection against oxidative stress.Bioorganic & medicinal chemistry · 2018Article
- Disulfide-masked iron prochelators: Effects on cell death, proliferation, and hemoglobin production.Journal of inorganic biochemistry · 2018Article
- Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
The implication of iron in the pathophysiology of colorectal cancer is documented at both the biochemical and epidemiological levels. Iron chelators are therefore useful molecular tools for the study and potential treatment of this type of cancer characterized by high incidence and mortality rates. We report a novel prochelation strategy that utilizes a disulfide redox switch to connect a thiosemicarbazone iron-binding unit with carbohydrate moieties targeting the increased expression of glucose transporters in colorectal cancer cells. We synthesized three glycoconjugates (GA2TC4, G6TC4, and M6TC4) with different connectivity and/or carbohydrate moieties, as well as an aglycone analog (ATC4). The sugar conjugates present increased solubility in neutral aqueous solutions, and the ester-linked conjugates M6TC4 and G6TC4 compete as effectively as d-glucose for transporter-mediated cellular uptake. The glycoconjugates show improved selectivity compared to the aglycone analog and are 6-11 times more toxic in Caco-2 colorectal adenocarcinoma cells than in normal CCD18-co colon fibroblasts.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.