ArticleJournal of the American Chemical Society2014
The disaccharide moiety of bleomycin facilitates uptake by cancer cells.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 29 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
29 citing papers in PubMed, 112 citations in OpenAlex.
- Carbamate-Bearing Carbohydrates: Natural Occurrence, Pharmacological Relevance, and Chemical Synthesis.ACS omega · 2026Review
- Formation and cellular uptake of Bleomycin saccharide decorated molecular spherical nucleic acids evaluated by time-resolved fluorescence spectroscopy.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2026Article
- Hybrid Molecules as Efficient Drugs against Multidrug-Resistant Malaria Parasites.ChemMedChem · 2025Review
- Stereoselective chemical N-glycoconjugation of amines via CONature communications · 2024Article
- A Simple Colorimetric Assay of Bleomycin-Mediated DNA Cleavage Utilizing Double-Stranded DNA-Modified Gold Nanoparticles.Chembiochem : a European journal of chemical biology · 2023Article
- Assembly of Bleomycin Saccharide-Decorated Spherical Nucleic Acids.Bioconjugate chemistry · 2022Article
- GDP-Mannose 3,5-Epimerase: A View on Structure, Mechanism, and Industrial Potential.Frontiers in molecular biosciences · 2021Review
- Precise Targeted Cleavage of a r(CUG) Repeat Expansion in Cells by Using a Small-Molecule-Deglycobleomycin Conjugate.ACS chemical biology · 2020Article
- Characterization of the First Bacterial and Thermostable GDP-Mannose 3,5-Epimerase.International journal of molecular sciences · 2019Article
- Vitamin C increases DNA breaks and suppresses DNA damage-independent activation of ATM by bleomycin.Free radical biology & medicine · 2019Article
- Vitamin C as a Modulator of the Response to Cancer Therapy.Molecules (Basel, Switzerland) · 2019Review
- The Interaction of the Metallo-Glycopeptide Anti-Tumour Drug Bleomycin with DNA.International journal of molecular sciences · 2018Review
- Structural changes of Zn(II)bleomycin complexes when bound to DNA hairpins containing the 5'-GT-3' and 5'-GC-3' binding sites studied through NMR spectroscopy.Magnetochemistry (Basel, Switzerland) · 2018Article
- Article
- The DNA sequence specificity of bleomycin cleavage in a systematically altered DNA sequence.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2017Article
- NMR study of the effects of some bleomycin C-termini on the structure of a DNA hairpin with the 5'-GC-3' binding site.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2017Article
- Rapamycin-loaded Immunoliposomes Functionalized with Trastuzumab: A Strategy to Enhance Cytotoxicity to HER2-positive Breast Cancer Cells.Anti-cancer agents in medicinal chemistry · 2017Article
- SLC2A8 (GLUT8) is a mammalian trehalose transporter required for trehalose-induced autophagy.Scientific reports · 2016Article
- The genome-wide DNA sequence specificity of the anti-tumour drug bleomycin in human cells.Molecular biology reports · 2016Article
- The use of fluorescently-tagged apoptolidins in cellular uptake and response studies.The Journal of antibiotics · 2016Article
Corrections and comments
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Authors and funding
9 authors at 4 institutions in 1 country.
Funding
Abstract
The disaccharide moiety is responsible for the tumor cell targeting properties of bleomycin (BLM). While the aglycon (deglycobleomycin) mediates DNA cleavage in much the same fashion as bleomycin, it exhibits diminished cytotoxicity in comparison to BLM. These findings suggested that BLM might be modular in nature, composed of tumor-seeking and tumoricidal domains. To explore this possibility, BLM analogues were prepared in which the disaccharide moiety was attached to deglycobleomycin at novel positions, namely, via the threonine moiety or C-terminal substituent. The analogues were compared with BLM and deglycoBLM for DNA cleavage, cancer cell uptake, and cytotoxic activity. BLM is more potent than deglycoBLM in supercoiled plasmid DNA relaxation, while the analogue having the disaccharide on threonine was less active than deglycoBLM and the analogue containing the C-terminal disaccharide was slightly more potent. While having unexceptional DNA cleavage potencies, both glycosylated analogues were more cytotoxic to cultured DU145 prostate cancer cells than deglycoBLM. Dye-labeled conjugates of the cytotoxic BLM aglycons were used in imaging experiments to determine the extent of cell uptake. The rank order of internalization efficiencies was the same as their order of cytotoxicities toward DU145 cells. These findings establish a role for the BLM disaccharide in tumor targeting/uptake and suggest that the disaccharide moiety may be capable of delivering other cytotoxins to cancer cells. While the mechanism responsible for uptake of the BLM disaccharide selectively by tumor cells has not yet been established, data are presented which suggest that the metabolic shift to glycolysis in cancer cells may provide the vehicle for selective internalization.
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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.