Architecture of P2Y nucleotide receptors: structural comparison based on sequence analysis, mutagenesis, and homology modeling.

Human P2Y receptors encompass at least eight subtypes of Class A G protein-coupled receptors (GPCRs), responding to adenine and/or uracil nucleotides. Using a BLAST search against the Homo sapiens subset of the SWISS-PROT and TrEMBL databases, we identified 68 proteins showing high similarity to P2Y receptors. To address the problem of low sequence identity between rhodopsin and the P2Y receptors, we performed a multiple-sequence alignment of the retrieved proteins and the template bovine rhodopsin, combining manual identification of the transmembrane domains (TMs) with automatic techniques. The resulting phylogenetic tree delineated two distinct subgroups of P2Y receptors: Gq-coupled subtypes (e.g., P2Y1) and those coupled to Gi (e.g., P2Y12). On the basis of sequence comparison we mutated three Tyr residues of the putative P2Y1 binding pocket to Ala and Phe and characterized pharmacologically the mutant receptors expressed in COS-7 cells. The mutation of Y306 (7.35, site of a cationic residue in P2Y12) or Y203 in the second extracellular loop selectively decreased the affinity of the agonist 2-MeSADP, and the Y306F mutation also reduced antagonist (MRS2179) affinity by 5-fold. The Y273A (6.48) mutation precluded the receptor activation without a major effect on the ligand-binding affinities, but the Y273F mutant receptor still activated G proteins with full agonist affinity. Thus, we have identified new recognition elements to further define the P2Y1 binding site and related these to other P2Y receptor subtypes. Following sequence-based secondary-structure prediction, we constructed complete models of all the human P2Y receptors by homology to rhodopsin. Ligand docking on P2Y1 and P2Y12 receptor models was guided by mutagenesis results, to identify the residues implicated in the binding process. Different sets of cationic residues in the two subgroups appeared to coordinate phosphate-bearing ligands. Within the P2Y1 subgroup these residues are R3.29, K/R6.55, and R7.39. Within the P2Y12 subgroup, the only residue in common with P2Y1 is R6.55, and the role of R3.29 in TM3 seems to be fulfilled by a Lys residue in EL2, whereas the R7.39 in TM7 seems to be substituted by K7.35. Thus, we have identified common and distinguishing features of P2Y receptor structure and have proposed modes of ligand binding for the two representative subtypes that already have well-developed ligands.

[1]  Jinhai Gao,et al.  Citric acid cycle intermediates as ligands for orphan G-protein-coupled receptors , 2004, Nature.

[2]  Takao Shimizu,et al.  Identification of p2y9/GPR23 as a Novel G Protein-coupled Receptor for Lysophosphatidic Acid, Structurally Distant from the Edg Family* , 2003, Journal of Biological Chemistry.

[3]  P. White,et al.  Characterization of a Ca2+ response to both UTP and ATP at human P2Y11 receptors: evidence for agonist-specific signaling. , 2003, Molecular pharmacology.

[4]  H. Schiöth,et al.  The G-protein-coupled receptors in the human genome form five main families. Phylogenetic analysis, paralogon groups, and fingerprints. , 2003, Molecular pharmacology.

[5]  S. Kunapuli,et al.  Inactivation of the human P2Y12 receptor by thiol reagents requires interaction with both extracellular cysteine residues, Cys17 and Cys270. , 2003, Blood.

[6]  M. Mortrud,et al.  The G protein-coupled receptor repertoires of human and mouse , 2003, Proceedings of the National Academy of Sciences of the United States of America.

[7]  S. Dowell,et al.  Molecular Identification of High and Low Affinity Receptors for Nicotinic Acid* , 2003, The Journal of Biological Chemistry.

[8]  Krzysztof Palczewski,et al.  Role of the conserved NPxxY(x)5,6F motif in the rhodopsin ground state and during activation , 2003, Proceedings of the National Academy of Sciences of the United States of America.

[9]  J. Ware,et al.  Molecular bases of defective signal transduction in the platelet P2Y12 receptor of a patient with congenital bleeding , 2003, Proceedings of the National Academy of Sciences of the United States of America.

[10]  G. Burnstock,et al.  Characterization of the UDP-glucose receptor (re-named here the P2Y14 receptor) adds diversity to the P2Y receptor family. , 2003, Trends in pharmacological sciences.

[11]  Stefano Costanzi,et al.  2- and 8-alkynyladenosines: conformational studies and docking to human adenosine A3 receptor can explain their different biological behavior. , 2003, Journal of molecular graphics & modelling.

[12]  S. Moro,et al.  Evidence for the recognition of non‐nucleotide antagonists within the transmembrane domains of the human P2Y1 receptor , 2002, Drug development research.

[13]  K. Jacobson,et al.  Quantitation of the P2Y(1) receptor with a high affinity radiolabeled antagonist. , 2002, Molecular pharmacology.

[14]  Kenneth A. Jacobson,et al.  Structural Determinants of A3 Adenosine Receptor Activation: Nucleoside Ligands at the Agonist/Antagonist Boundary , 2002 .

[15]  K. Jacobson,et al.  Purine and pyrimidine (P2) receptors as drug targets. , 2002, Journal of medicinal chemistry.

[16]  Yan Xu,et al.  Sphingosylphosphorylcholine and lysophosphatidylcholine: G protein-coupled receptors and receptor-mediated signal transduction. , 2002, Biochimica et Biophysica Acta.

[17]  Yoshinori Shichida,et al.  Functional role of internal water molecules in rhodopsin revealed by x-ray crystallography , 2002, Proceedings of the National Academy of Sciences of the United States of America.

[18]  K. Jacobson,et al.  Acyclic and cyclopropyl analogues of adenosine bisphosphate antagonists of the P2Y1 receptor: structure-activity relationships and receptor docking. , 2001, Journal of medicinal chemistry.

[19]  J. Ballesteros,et al.  Structural mimicry in G protein-coupled receptors: implications of the high-resolution structure of rhodopsin for structure-function analysis of rhodopsin-like receptors. , 2001, Molecular pharmacology.

[20]  Krzysztof Palczewski,et al.  Crystal Structure of Rhodopsin: A G‐Protein‐Coupled Receptor , 2002, Science.

[21]  K. Jacobson Synthesis, Biological Activity, and Molecular Modeling of Ribose-Modified Deoxyadenosine Bisphosphate Analogues as P2Y1 Receptor Ligands. , 2000 .

[22]  J. Chambers,et al.  A G Protein-coupled Receptor for UDP-glucose* , 2000, The Journal of Biological Chemistry.

[23]  C Combet,et al.  NPS@: network protein sequence analysis. , 2000, Trends in biochemical sciences.

[24]  S. Coughlin,et al.  How the protease thrombin talks to cells. , 1999, Proceedings of the National Academy of Sciences of the United States of America.

[25]  Kenneth A. Jacobson,et al.  The Role of Amino Acids in Extracellular Loops of the Human P2Y1 Receptor in Surface Expression and Activation Processes* , 1999, The Journal of Biological Chemistry.

[26]  Christophe Geourjon,et al.  Improved performance in protein secondary structure prediction by inhomogeneous score combination , 1999, Bioinform..

[27]  S. Moro,et al.  Role of the extracellular loops of G protein-coupled receptors in ligand recognition: a molecular modeling study of the human P2Y1 receptor. , 1999, Biochemistry.

[28]  S. Moro,et al.  Human P2Y1 receptor: molecular modeling and site-directed mutagenesis as tools to identify agonist and antagonist recognition sites. , 1998, Journal of medicinal chemistry.

[29]  J. Thompson,et al.  The CLUSTAL_X windows interface: flexible strategies for multiple sequence alignment aided by quality analysis tools. , 1997, Nucleic acids research.

[30]  K. Jacobson,et al.  A mutational analysis of residues essential for ligand recognition at the human P2Y1 receptor. , 1997, Molecular pharmacology.

[31]  Kenneth A Jacobson,et al.  Molecular architecture of G protein‐coupled receptors , 1996, Drug development research.

[32]  J. Gibrat,et al.  GOR method for predicting protein secondary structure from amino acid sequence. , 1996, Methods in enzymology.

[33]  Christophe Geourjon,et al.  SOPMA: significant improvements in protein secondary structure prediction by consensus prediction from multiple alignments , 1995, Comput. Appl. Biosci..

[34]  K. Jacobson,et al.  Modelling the P2Y purinoceptor using rhodopsin as template. , 1995, Drug design and discovery.

[35]  J. Thompson,et al.  CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. , 1994, Nucleic acids research.

[36]  John P. Overington,et al.  Derivation of rules for comparative protein modeling from a database of protein structure alignments , 1994, Protein science : a publication of the Protein Society.

[37]  Ming-Jing Hwang,et al.  Derivation of Class II Force Fields. 2. Derivation and Characterization of a Class II Force Field, CFF93, for the Alkyl Functional Group and Alkane Molecules , 1994 .

[38]  Ming-Jing Hwang,et al.  Derivation of class II force fields. I. Methodology and quantum force field for the alkyl functional group and alkane molecules , 1994, J. Comput. Chem..

[39]  T. Blundell,et al.  Comparative protein modelling by satisfaction of spatial restraints. , 1993, Journal of molecular biology.

[40]  J. Thornton,et al.  PROCHECK: a program to check the stereochemical quality of protein structures , 1993 .

[41]  J. Thornton,et al.  Stereochemical quality of protein structure coordinates , 1992, Proteins.

[42]  N. Saitou,et al.  The neighbor-joining method: a new method for reconstructing phylogenetic trees. , 1987, Molecular biology and evolution.

[43]  Barry Robson,et al.  An algorithm for secondary structure determination in proteins based on sequence similarity , 1986, FEBS letters.

[44]  U. Singh,et al.  A NEW FORCE FIELD FOR MOLECULAR MECHANICAL SIMULATION OF NUCLEIC ACIDS AND PROTEINS , 1984 .

[45]  M. O. Dayhoff,et al.  Atlas of protein sequence and structure , 1965 .