ArticleBioorganic & medicinal chemistry2009
Molecular recognition in the P2Y(14) receptor: Probing the structurally permissive terminal sugar moiety of uridine-5'-diphosphoglucose.
Article in Bioorganic & medicinal chemistry, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 35 citations in OpenAlex.
- UDP-glucose and MRS2905 agonist-bound states of the purinergic P2YCommunications biology · 2025Article
- Article
- Alicyclic Ring Size Variation of 4-Phenyl-2-naphthoic Acid Derivatives as P2YJournal of medicinal chemistry · 2023Article
- Expanding the repertoire of methanocarba nucleosides from purinergic signaling to diverse targets.RSC medicinal chemistry · 2021Review
- Synthesis of Terminal Ribose Analogues of Adenosine 5'-Diphosphate Ribose as Probes for the Transient Receptor Potential Cation Channel TRPM2.The Journal of organic chemistry · 2019Article
- UDP-sugars activate P2YVascular pharmacology · 2018Article
- Pyrimidine Nucleotides Containing a (S)-Methanocarba Ring as P2YMedChemComm · 2017Article
- Design, synthesis, pharmacological characterization of a fluorescent agonist of the P2Y₁₄ receptor.Bioorganic & medicinal chemistry letters · 2015Article
- Nucleotides Acting at P2Y Receptors: Connecting Structure and Function.Molecular pharmacology · 2015Review
- Molecular modeling of the human P2Y14 receptor: A template for structure-based design of selective agonist ligands.Bioorganic & medicinal chemistry · 2015Article
- UDP-Sugars as Extracellular Signaling Molecules: Cellular and Physiologic Consequences of P2Y14 Receptor Activation.Molecular pharmacology · 2015Review
- Exploring a 2-naphthoic acid template for the structure-based design of P2Y14 receptor antagonist molecular probes.ACS chemical biology · 2014Article
- Novel vasocontractile role of the P2Y₁₄ receptor: characterization of its signalling in porcine isolated pancreatic arteries.British journal of pharmacology · 2014Article
- Using simple donors to drive the equilibria of glycosyltransferase-catalyzed reactions.Nature chemical biology · 2011Article
- Pyrimidine ribonucleotides with enhanced selectivity as P2Y(6) receptor agonists: novel 4-alkyloxyimino, (S)-methanocarba, and 5'-triphosphate gamma-ester modifications.Journal of medicinal chemistry · 2010Article
- Signalling and pharmacological properties of the P2Y receptor.Acta physiologica (Oxford, England) · 2010Review
- UDP-glucose acting at P2Y14 receptors is a mediator of mast cell degranulation.Biochemical pharmacology · 2010Article
- Polyamidoamine (PAMAM) dendrimer conjugates of "clickable" agonists of the A3 adenosine receptor and coactivation of the P2Y14 receptor by a tethered nucleotide.Bioconjugate chemistry · 2010Article
- Human P2Y(14) receptor agonists: truncation of the hexose moiety of uridine-5'-diphosphoglucose and its replacement with alkyl and aryl groups.Journal of medicinal chemistry · 2010Article
- Enhanced potency of nucleotide-dendrimer conjugates as agonists of the P2Y14 receptor: multivalent effect in G protein-coupled receptor recognition.Bioconjugate chemistry · 2009Article
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Authors and funding
13 authors at 3 institutions in 1 country.
Funding
Abstract
The P2Y(14) receptor, a nucleotide signaling protein, is activated by uridine-5'-diphosphoglucose 1 and other uracil nucleotides. We have determined that the glucose moiety of 1 is the most structurally permissive region for designing analogues of this P2Y(14) agonist. For example, the carboxylate group of uridine-5'-diphosphoglucuronic acid proved to be suitable for flexible substitution by chain extension through an amide linkage. Functionalized congeners containing terminal 2-acylaminoethylamides prepared by this strategy retained P2Y(14) activity, and molecular modeling predicted close proximity of this chain to the second extracellular loop of the receptor. In addition, replacement of glucose with other sugars did not diminish P2Y(14) potency. For example, the [5'']ribose derivative had an EC(50) of 0.24muM. Selective monofluorination of the glucose moiety indicated a role for the 2''- and 6''-hydroxyl groups of 1 in receptor recognition. The beta-glucoside was twofold less potent than the native alpha-isomer, but methylene replacement of the 1''-oxygen abolished activity. Replacement of the ribose ring system with cyclopentyl or rigid bicyclo[3.1.0]hexane groups abolished activity. Uridine-5'-diphosphoglucose also activates the P2Y(2) receptor, but the 2-thio analogue and several of the potent modified-glucose analogues were P2Y(14)-selective.
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