ArticleDrug development research1998
Synthesis and Structure-Activity Relationships of Pyridoxal-6-arylazo-5'-phosphate and Phosphonate Derivatives as P2 Receptor Antagonists.
Article in Drug development research, 1998. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
What it found
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Who cites it
19 citing papers in PubMed, 39 citations in OpenAlex.
- Usnic Acid Targets 14-3-3 Proteins and Suppresses Cancer Progression by Blocking Substrate Interaction.JACS Au · 2024Article
- Mapping the binding site of the P2X receptor antagonist PPADS reveals the importance of orthosteric site charge and the cysteine-rich head region.The Journal of biological chemistry · 2018Article
- Modulators of 14-3-3 Protein-Protein Interactions.Journal of medicinal chemistry · 2018Review
- Purinergic signalling in the gastrointestinal tract and related organs in health and disease.Purinergic signalling · 2014Review
- Development of a comprehensive set of P2 receptor pharmacological research compounds.Purinergic signalling · 2012Article
- Discovery and structural characterization of a small molecule 14-3-3 protein-protein interaction inhibitor.Proceedings of the National Academy of Sciences of the United States of America · 2011Article
- Agonist and antagonist effects of diadenosine tetraphosphate, a platelet dense granule constituent, on platelet P2Y1, P2Y12 and P2X1 receptors.Thrombosis research · 2010Article
- Identification of atropine- and P2X1 receptor antagonist-resistant, neurogenic contractions of the urinary bladder.The Journal of neuroscience : the official journal of the Society for Neuroscience · 2007Article
- Synthesis of pyridoxal phosphate derivatives with antagonist activity at the P2Y13 receptor.Biochemical pharmacology · 2005Article
- Evidence for the Recognition of Non-Nucleotide Antagonists Within the Transmembrane Domains of the Human P2Y(1) Receptor.Drug development research · 2002Article
- Purine and pyrimidine (P2) receptors as drug targets.Journal of medicinal chemistry · 2002Review
- Actions of a Series of PPADS Analogs at P2XDrug development research · 2001Article
- Structure-activity relationships of pyridoxal phosphate derivatives as potent and selective antagonists of P2X1 receptors.Journal of medicinal chemistry · 2001Article
- Inhibition of Ecto-Apyrase and Ecto-ATPase by Pyridoxal Phosphate-Related Compounds.Drug development research · 2000Article
- EFFECT OF NEW PYRIDOXAL PHOSPHATE ARYLAZO DERIVATIVES ON THE ECTO-ATPase ACTIVITY IN GUINEA PIG TISSUES.Pharmaceutical chemistry journal · 2000Article
- Synthesis, biological activity, and molecular modeling of ribose-modified deoxyadenosine bisphosphate analogues as P2Y(1) receptor ligands.Journal of medicinal chemistry · 2000Article
- Article
- Structure-activity relationships of bisphosphate nucleotide derivatives as P2Y1 receptor antagonists and partial agonists.Journal of medicinal chemistry · 1999Article
- Molecular recognition in P2 receptors: ligand development aided by molecular modeling and mutagenesis.Progress in brain research · 1999Review
Corrections and comments
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Authors and funding
14 authors at 5 institutions in 2 countries.
Funding
Abstract
Novel analogs of the P2 receptor antagonist pyridoxal-5'-phosphate-6-phenylazo-2',4'-disulfonate (PPADS) were synthesized. Modifications were made through functional group substitution on the sulfophenyl ring and at the phosphate moiety through the inclusion of phosphonates, demonstrating that a phosphate linkage is not required for P2 receptor antagonism. Substituted 6-phenylazo and 6-naphthylazo derivatives were also evaluated. Among the 6-phenylazo derivatives, 5'-methyl, ethyl, propyl, vinyl, and allyl phosphonates were included. The compounds were tested as antagonists at turkey erythrocyte and guinea-pig taenia coli P2Y(1) receptors, in guinea-pig vas deferens and bladder P2X(1) receptors, and in ion flux experiments by using recombinant rat P2X(2) receptors expressed in Xenopus oocytes. Competitive binding assay at human P2X(1) receptors in differentiated HL-60 cell membranes was carried out by using [(35)S]ATP-γ-S. A 2'-chloro-5'-sulfo analog of PPADS (C(14)H(12)O(9)N(3)ClPSNa), a vinyl phosphonate derivative (C(15)H(12)O(11)N(3)PS(2)Na(3)), and a naphthylazo derivative (C(18)H(14)O(12)N(3)PS(2)Na(2)), were particularly potent in binding to human P2X(1) receptors. The potencies of phosphate derivatives at P2Y(1) receptors were generally similar to PPADS itself, except for the p-carboxyphenylazo phosphate derivative C(15)H(13)O(8)N(3)PNa and its m-chloro analog C(15)H(12)O(8)N(3)ClPNa, which were selective for P2X vs. P2Y(1) receptors. C(15)H(12)O(8)N(3)ClPNa was very potent at rat P2X(2) receptors with an IC(50) value of 0.82 μM. Among the phosphonate derivatives, [4-formyl-3-hydroxy-2-methyl-6-(2-chloro-5-sulfonylphenylazo)-pyrid-5-yl]methylphosphonic acid (C(14)H(12)-O(8)N(3)ClPSNa) showed high potency at P2Y(1) receptors with an IC(50) of 7.23 μM. The corresponding 2,5-disulfonylphenyl derivative was nearly inactive at turkey erythrocyte P2Y(1) receptors, whereas at recombinant P2X(2) receptors had an IC(50) value of 1.1 μM. An ethyl phosphonate derivative (C(15)H(15)O(11)N(3)PS(2)Na(3)), whereas inactive at turkey erythrocyte P2Y(1) receptors, was particularly potent at recombinant P2X(2) receptors.
Identifiers
22922976PMC3424000W2014680256What 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.