ArticlePurinergic signalling2009
Structure-activity relationships of anthraquinone derivatives derived from bromaminic acid as inhibitors of ectonucleoside triphosphate diphosphohydrolases (E-NTPDases).
Article in Purinergic signalling, 2009. 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, 78 citations in OpenAlex.
- Nucleotide-Derived Competitive Inhibitors of Ectonucleotidase CD39─A Promising Extracellular Target for Immunotherapy of Cancer.Journal of medicinal chemistry · 2026Article
- Development of CD73 Inhibitors in Tumor Immunotherapy and Opportunities in Imaging and Combination Therapy.Journal of medicinal chemistry · 2025Review
- Ectonucleotidase inhibitors: targeting signaling pathways for therapeutic advancement-an in-depth review.Purinergic signalling · 2025Review
- Elevated glucose levels increase vascular calcification risk by disrupting extracellular pyrophosphate metabolism.Cardiovascular diabetology · 2024Article
- Silencing NTPDase3 activity rehabilitates the osteogenic commitment of post-menopausal stem cell bone progenitors.Stem cell research & therapy · 2023Article
- Protein kinase inhibitor ceritinib blocks ectonucleotidase CD39 - a promising target for cancer immunotherapy.Journal for immunotherapy of cancer · 2022Article
- Mechanosensitive Hydrolysis of ATP and ADP in Lamina Propria of the Murine Bladder by Membrane-Bound and Soluble Nucleotidases.Frontiers in physiology · 2022Article
- Purinergic receptors in airway hydration.Biochemical pharmacology · 2021Review
- Sulfated Polysaccharides from Macroalgae Are Potent Dual Inhibitors of Human ATP-Hydrolyzing Ectonucleotidases NPP1 and CD39.Marine drugs · 2021Article
- Repurposing bioactive compounds for treating multidrug-resistant pathogens.Journal of medical microbiology · 2020Article
- Inhibition of ATP hydrolysis restores airway surface liquid production in cystic fibrosis airway epithelia.American journal of physiology. Lung cellular and molecular physiology · 2020Article
- Nucleotide Analog ARL67156 as a Lead Structure for the Development of CD39 and Dual CD39/CD73 Ectonucleotidase Inhibitors.Frontiers in pharmacology · 2020Article
- Development of Anthraquinone Derivatives as Ectonucleoside Triphosphate Diphosphohydrolase (NTPDase) Inhibitors With Selectivity for NTPDase2 and NTPDase3.Frontiers in pharmacology · 2020Article
- Trial Watch-Small molecules targeting the immunological tumor microenvironment for cancer therapy.Oncoimmunology · 2016Review
- Article
- Syntheses of 2-substituted 1-amino-4-bromoanthraquinones (bromaminic acid analogues) - precursors for dyes and drugs.Beilstein journal of organic chemistry · 2015Article
- Molecular Structure of P2Y Receptors: Mutagenesis, Modeling, and Chemical Probes.Wiley interdisciplinary reviews. Membrane transport and signaling · 2012Article
- Convergent synthesis of the potent P2Y receptor antagonist MG 50-3-1 based on a regioselective Ullmann coupling reaction.Molecules (Basel, Switzerland) · 2012Article
- Structural insights into the inhibition of cytosolic 5'-nucleotidase II (cN-II) by ribonucleoside 5'-monophosphate analogues.PLoS computational biology · 2011Article
- Synthesis of alkyl- and aryl-amino-substituted anthraquinone derivatives by microwave-assisted copper(0)-catalyzed Ullmann coupling reactions.Nature protocols · 2010Article
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Reactive blue 2 (RB-2) had been characterized as a relatively potent ectonucleoside triphosphate diphosphohydrolase (E-NTPDase) inhibitor with some selectivity for NTPDase3. In search for the pharmacophore and to analyze structure-activity relationships we synthesized a series of truncated derivatives and analogs of RB-2, including 1-amino-2-sulfo-4-ar(alk)ylaminoanthraquinones, 1-amino-2-methyl-4-arylaminoanthraquinones, 1-amino-4-bromoanthraquinone 2-sulfonic acid esters and sulfonamides, and bis-(1-amino-4-bromoanthraquinone) sulfonamides, and investigated them in preparations of rat NTPDase1, 2, and 3 using a capillary electrophoresis assay. Several 1-amino-2-sulfo-4-ar(alk)ylaminoanthraquinone derivatives inhibited E-NTPDases in a concentration-dependent manner. The 2-sulfonate group was found to be required for inhibitory activity, since 2-methyl-substituted derivatives were inactive. 1-Amino-2-sulfo-4-p-chloroanilinoanthraquinone (18) was identified as a nonselective competitive blocker of NTPDases1, 2, and 3 (K(i) 16-18 muM), while 1-amino-2-sulfo-4-(2-naphthylamino)anthraquinone (21) was a potent inhibitor with preference for NTPDase1 (K(i) 0.328 muM) and NTPDase3 (K(i) 2.22 muM). Its isomer, 1-amino-2-sulfo-4-(1-naphthylamino)anthraquinone (20), was a potent and selective inhibitor of rat NTPDase3 (K(i) 1.5 muM).
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Registered trials
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