ArticleACS medicinal chemistry letters2011
Stereochemical survey of digitoxin monosaccharides: new anticancer analogues with enhanced apoptotic activity and growth inhibitory effect on human non-small cell lung cancer cell.
Article in ACS medicinal chemistry letters, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 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
25 citing papers in PubMed, 77 citations in OpenAlex.
- De Novo Design and Asymmetric Synthesis of aOrganic letters · 2025Article
- Development of CPA-Catalyzed β-Selective Reductive Amination of Cardenolides for the Synthesis and Biological Evaluation of Hydrolytically Stable Analogs.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Review
- Article
- Cytotoxic effect of carbohydrate derivatives of digitoxigenin involves modulation of plasma membrane CaJournal of cellular biochemistry · 2021Article
- Implications of Synthetic Modifications of the Cardiotonic Steroid Lactone Ring on Cytotoxicity.The Journal of membrane biology · 2021Article
- Repurposing Cardiac Glycosides: Drugs for Heart Failure Surmounting Viruses.Molecules (Basel, Switzerland) · 2021Review
- Review
- Steroid Glycosides Hyrcanoside and Deglucohyrcanoside: On Isolation, Structural Identification, and Anticancer Activity.Foods (Basel, Switzerland) · 2021Article
- Potential antitumor activity of digitoxin and user-designed analog administered to human lung cancer cells.Biochimica et biophysica acta. General subjects · 2020Article
- Synthesis, cytotoxicity and anti-inflammatory activity of rhamnose-containing ursolic and betulinic acid saponins.RSC advances · 2019Article
- Stereochemical Structure Activity Relationship Studies (S-SAR) of Tetrahydrolipstatin.ACS medicinal chemistry letters · 2018Article
- Influence of Sugar Amine Regiochemistry on Digitoxigenin Neoglycoside Anticancer Activity.ACS medicinal chemistry letters · 2015Article
- Real-time analysis of the effects of toxic, therapeutic and sub-therapeutic concentrations of digitoxin on lung cancer cells.Biosensors & bioelectronics · 2014Article
- Digitoxin analogues with improved anticytomegalovirus activity.ACS medicinal chemistry letters · 2014Article
- Monosaccharide digitoxin derivative sensitize human non-small cell lung cancer cells to anoikis through Mcl-1 proteasomal degradation.Biochemical pharmacology · 2014Article
- Merremoside D: de novo synthesis of the purported structure, NMR analysis, and comparison of spectral data.Organic letters · 2014Article
- Olefin cross metathesis based de novo synthesis of a partially protected L-amicetose and a fully protected L-cinerulose derivative.Beilstein journal of organic chemistry · 2014Article
- Probing the regiospecificity of enzyme-catalyzed steroid glycosylation.Organic letters · 2012Article
- De novo asymmetric synthesis of all-D-, all-L-, and D-/L-oligosaccharides using atom-less protecting groups.Journal of the American Chemical Society · 2012Article
Corrections and comments
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
Abstract
A stereochemically diverse array of monosaccharide analogues of the trisaccharide based cardiac glycoside natural product digitoxin has been synthesized using a de novo asymmetric approach. The analogues were tested for cytotoxicity against the NCI panel of 60 human cancer cell lines and in more detail against non-small cell human lung cancer cells (NCI-H460). The results were compared with digitoxin and its aglycone digitoxigenin. Three novel digitoxin monosaccharide analogues with β-d-digitoxose, α-l-rhamnose, and α-l-amicetose sugar moieties showed excellent selectivity and activity. Further investigation revealed that digitoxin α-l-rhamnose and α-l-amicetose analogues displayed similar anti-proliferation effects, but with at least 5-fold greater potency in apoptosis induction than digitoxin against NCI-H460. This study demonstrates the ability to improve the digitoxin anti-cancer activity by modification of the stereochemistry and substitution of the carbohydrate moiety of this known cardiac drug.
Identifiers
What OpenQuestion holds
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.