ArticleJournal of medicinal chemistry2010
Assessment of chemoselective neoglycosylation methods using chlorambucil as a model.
Article in Journal of medicinal chemistry, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
What it found
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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
21 citing papers in PubMed, 55 citations in OpenAlex.
- Glycosylation modification: a trigger for obesity and its complications?Molecular medicine (Cambridge, Mass.) · 2026Review
- Glycosylation: mechanisms, biological functions and clinical implications.Signal transduction and targeted therapy · 2024Review
- A Small Sugar Molecule with Huge Potential in Targeted Cancer Therapy.Pharmaceutics · 2023Review
- Glycosylation and its research progress in endometrial cancer.Clinical & translational oncology : official publication of the Federation of Spanish Oncology Societies and of the National Cancer Institute of Mexico · 2022Review
- Altered glycosylation in cancer: A promising target for biomarkers and therapeutics.Biochimica et biophysica acta. Reviews on cancer · 2021Review
- Glycoconjugation: An approach to cancer therapeutics.World journal of clinical oncology · 2020Review
- Developments in Carbohydrate-Based Cancer Therapeutics.Pharmaceuticals (Basel, Switzerland) · 2019Review
- Principles in the design of ligand-targeted cancer therapeutics and imaging agents.Nature reviews. Drug discovery · 2015Review
- Ring-opening polymerization of prodrugs: a versatile approach to prepare well-defined drug-loaded nanoparticles.Angewandte Chemie (International ed. in English) · 2015Article
- The identification of perillyl alcohol glycosides with improved antiproliferative activity.Journal of medicinal chemistry · 2014Article
- Neoglycosylation and neoglycorandomization: Enabling tools for the discovery of novel glycosylated bioactive probes and early stage leads.MedChemComm · 2014Article
- Dual targeting of the Warburg effect with a glucose-conjugated lactate dehydrogenase inhibitor.Chembiochem : a European journal of chemical biology · 2013Article
- Synthesis and antibacterial activity of doxycycline neoglycosides.Journal of natural products · 2013Article
- A fused [3.3.0]-neoglycoside lactone derived from glucuronic acid.Acta crystallographica. Section C, Crystal structure communications · 2013Article
- Glucose conjugation for the specific targeting and treatment of cancer.Chemical science · 2013Article
- Natural product disaccharide engineering through tandem glycosyltransferase catalysis reversibility and neoglycosylation.Organic letters · 2012Article
- Enhancement of cyclopamine via conjugation with nonmetabolic sugars.Organic letters · 2012Article
- Warfarin glycosylation invokes a switch from anticoagulant to anticancer activity.ChemMedChem · 2011Article
- Glycosyloxyamine neoglycosylation: a model study using calicheamicin.ChemMedChem · 2011Article
- Tandem mass spectrometry for characterization of covalent adducts of DNA with anticancer therapeutics.Mass spectrometry reviewsReview
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
To systematically assess the impact of glycosylation and the corresponding chemoselective linker upon the anticancer activity/selectivity of the drug chlorambucil, herein we report the synthesis and anticancer activities of a 63-member library of chlorambucil-based neoglycosides. A comparison of N-alkoxyamine-, N-acylhydrazine-, and N-hydroxyamine-based chemoselective glycosylation of chlorambucil revealed sugar- and linker-dependent partitioning among open- and closed-ring neoglycosides and corresponding sugar-dependent variant biological activity. Cumulatively, this study represents the first neoglycorandomization of a synthetic drug and expands our understanding of the impact of sugar structure upon product distribution/equilibria in the context of N-alkoxyamino-, N-hydroxyamino-, and N-acylhydrazine-based chemoselective glycosylation. This study also revealed several analogues with increased in vitro anticancer activity, most notably D-threoside 60 (NSC 748747), which displayed much broader tumor specificity and notably increased potency over the parent drug.
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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.