메뉴 건너뛰기




Volumn 43, Issue 5, 2000, Pages 829-842

Synthesis, biological activity, and molecular modeling of ribose- modified deoxyadenosine bisphosphate analogues as P2Y1 receptor ligands

Author keywords

[No Author keywords available]

Indexed keywords

2' DEOXY 6 N METHYLADENOSINE 3',5' BISPHOSPHATE; DEOXYADENOSINE DERIVATIVE; PURINE P2Y RECEPTOR; PURINERGIC RECEPTOR BLOCKING AGENT; RIBOSE; UNCLASSIFIED DRUG;

EID: 0034624785     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990249v     Document Type: Article
Times cited : (124)

References (54)
  • 6
    • 0030958195 scopus 로고    scopus 로고
    • P2 purine and pyrimidine receptors: Emerging superfamilies of G protein and ligand-gated ion channel receptors
    • Bhagwhat, S. S.; Williams, M. P2 Purine and Pyrimidine Receptors: Emerging superfamilies of G protein and ligand-gated ion channel receptors. Eur. J. Med. Chem. 1997, 32, 183-193.
    • (1997) Eur. J. Med. Chem. , vol.32 , pp. 183-193
    • Bhagwhat, S.S.1    Williams, M.2
  • 7
    • 0032934111 scopus 로고    scopus 로고
    • Therapeutic applications of ATP-(P2) receptors agonists and antagonists
    • Fischer, B. Therapeutic applications of ATP-(P2) receptors agonists and antagonists. Exp. Opin. Ther. Patents 1999, 9, 385-399.
    • (1999) Exp. Opin. Ther. Patents , vol.9 , pp. 385-399
    • Fischer, B.1
  • 8
    • 0024022311 scopus 로고
    • Phosphoinositide hydrolysis by guanosine 5'-gamma-thio]triphosphate-activated phospholipase C of turkey erythrocyte membranes
    • Harden, T. K.; Hawkins, P. T.; Stephens, L.; Boyer, J. L.; Downes, P. Phosphoinositide hydrolysis by guanosine 5'-(gamma-thio]triphosphate-activated phospholipase C of turkey erythrocyte membranes. Biochem. J. 1988, 252, 583-593.
    • (1988) Biochem. J. , vol.252 , pp. 583-593
    • Harden, T.K.1    Hawkins, P.T.2    Stephens, L.3    Boyer, J.L.4    Downes, P.5
  • 9
    • 0031916728 scopus 로고    scopus 로고
    • 1 receptor mediates ADP-induced intracellular calcium mobilization and shape change in platelets
    • 1 receptor mediates ADP-induced intracellular calcium mobilization and shape change in platelets. J. Biol. Chem. 1998, 273, 2030-2034.
    • (1998) J. Biol. Chem. , vol.273 , pp. 2030-2034
    • Jin, J.1    Daniel, J.L.2    Kunapuli, S.P.3
  • 12
    • 0030691996 scopus 로고    scopus 로고
    • Oxygen-induced pulmonary vasodilation is mediated by adenosine triphosphate in newborn lambs
    • Crowley, M. R. Oxygen-induced pulmonary vasodilation is mediated by adenosine triphosphate in newborn lambs. J. Cardiovasc. Pharmacol. 1997, 30, 102-109.
    • (1997) J. Cardiovasc. Pharmacol. , vol.30 , pp. 102-109
    • Crowley, M.R.1
  • 23
    • 0027786906 scopus 로고
    • Identification of a P2Y-purinergic receptor that inhibits adenylyl cyclase but does not activate phospholipase C
    • Boyer, J. L.; Lazarowski, E.; Chen, X.-H.; Harden, T. K. Identification of a P2Y-purinergic receptor that inhibits adenylyl cyclase but does not activate phospholipase C. J. Pharmacol. Exp. Ther. 1993, 267, 1140-1146.
    • (1993) J. Pharmacol. Exp. Ther. , vol.267 , pp. 1140-1146
    • Boyer, J.L.1    Lazarowski, E.2    Chen, X.-H.3    Harden, T.K.4
  • 25
    • 0033942979 scopus 로고    scopus 로고
    • Activity of novel adenine nucleotide derivatives as agonists and antagonists at recombinant rat P2X receptors
    • in press
    • Brown, S.; King, B. F.; Kim, Y.-C.; Burnstock, G.; Jacobson, K. A. Activity of novel adenine nucleotide derivatives as agonists and antagonists at recombinant rat P2X receptors. Drug Dev. Res. 2000, in press.
    • (2000) Drug Dev. Res.
    • Brown, S.1    King, B.F.2    Kim, Y.-C.3    Burnstock, G.4    Jacobson, K.A.5
  • 26
    • 0343335008 scopus 로고
    • Carbocyclic analogues of 2'-Deoxyadenosine
    • Shealy, Y. F.; O'Dell, C. A. Carbocyclic Analogues of 2'-Deoxyadenosine. Tetrahedron Lett. 1969, 2231-2234.
    • (1969) Tetrahedron Lett. , pp. 2231-2234
    • Shealy, Y.F.1    O'Dell, C.A.2
  • 28
    • 33748590516 scopus 로고    scopus 로고
    • Conformationally locked carbocyclic nucleosides built on a bicyclo[3.1.0]hexane template with a fixed southern conformation. Synthesis and antiviral activity
    • Ezzitouni, A.; Marquez, V. E. Conformationally locked carbocyclic nucleosides built on a bicyclo[3.1.0]hexane template with a fixed southern conformation. Synthesis and antiviral activity. J. Chem. Soc., Perkin Trans. 1 1997, 1073-1078.
    • (1997) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 1073-1078
    • Ezzitouni, A.1    Marquez, V.E.2
  • 29
    • 0029815436 scopus 로고    scopus 로고
    • Nucleosides with a twist. Can fixed forms of sugar ring pucker influence biological activity in nucleosides and oligonucleotides?
    • Marquez, V. E.; Siddiqui, M. A.; Ezzitouni, A.; Russ, P.; Wang, J.; Wagner, R. W.; Matteucci, M. D. Nucleosides with a twist. Can fixed forms of sugar ring pucker influence biological activity in nucleosides and oligonucleotides? J. Med. Chem. 1996, 39, 3739-3747.
    • (1996) J. Med. Chem. , vol.39 , pp. 3739-3747
    • Marquez, V.E.1    Siddiqui, M.A.2    Ezzitouni, A.3    Russ, P.4    Wang, J.5    Wagner, R.W.6    Matteucci, M.D.7
  • 30
    • 0024382446 scopus 로고
    • Uncharged stereoregular nucleic acid analogues: 2. Morpholino nucleoside oligomers with carbamate internucleoside linkages
    • Stirchak, E. P.; Summerton, J. E.; Weller, D. D. Uncharged stereoregular nucleic acid analogues: 2. Morpholino nucleoside oligomers with carbamate internucleoside linkages. Nucleic Acids Res. 1989, 17, 6129-6141.
    • (1989) Nucleic Acids Res. , vol.17 , pp. 6129-6141
    • Stirchak, E.P.1    Summerton, J.E.2    Weller, D.D.3
  • 32
    • 0001614418 scopus 로고
    • Total synthesis of D-and L-myo-inositol 1,4,5-trisphosphate
    • Vacca, J. P.; deSolms, S. J.; Huff, J. R. Total synthesis of D-and L-myo-inositol 1,4,5-trisphosphate. J. Am. Chem. Soc. 1987, 109, 3478-3479.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 3478-3479
    • Vacca, J.P.1    DeSolms, S.J.2    Huff, J.R.3
  • 33
    • 0023871809 scopus 로고
    • A novel reagent for the synthesis of myo-inositol phospates: N,N-diisopropyl dibenzyl phosphoramidine
    • Yu, K.-L.; Fraser-Reid, B. A novel reagent for the synthesis of myo-inositol phospates: N,N-diisopropyl dibenzyl phosphoramidine. Tetrahedron Lett. 1988, 29, 979-982.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 979-982
    • Yu, K.-L.1    Fraser-Reid, B.2
  • 34
    • 0030749499 scopus 로고    scopus 로고
    • (1S,2R)-[(Benzyloxy)-methyl]cyclopent-3-enol. A versatile synthon for the preparation of 4',1'a-methano and 1',1'a-methano carbocyclic nucleosides
    • Ezzitouni, A.; Russ, P.; Marquez, V. E. (1S,2R)-[(Benzyloxy)-methyl]cyclopent-3-enol. A versatile synthon for the preparation of 4',1'a-methano and 1',1'a-methano carbocyclic nucleosides. J. Org. Chem. 1997, 62, 4870-4873.
    • (1997) J. Org. Chem. , vol.62 , pp. 4870-4873
    • Ezzitouni, A.1    Russ, P.2    Marquez, V.E.3
  • 35
    • 0029923673 scopus 로고    scopus 로고
    • Synthesis, conformational analysis, and biological activity of a rigid carbocyclic analogue of 2'-deoxyaristeromycin built on a bicyclo[3.1.0]hexane template
    • Siddiqui, M. A.; Ford, Jr. H.; George, C.; Marquez, V. E. Synthesis, conformational analysis, and biological activity of a rigid carbocyclic analogue of 2'-deoxyaristeromycin built on a bicyclo[3.1.0]hexane template. Nucleosides Nucleotides 1996, 15, 235-250.
    • (1996) Nucleosides Nucleotides , vol.15 , pp. 235-250
    • Siddiqui, M.A.1    Ford H., Jr.2    George, C.3    Marquez, V.E.4
  • 37
    • 0028167695 scopus 로고
    • Expression of a cloned P2Y purinergic receptor that couples to phospholipase C
    • Filtz, T. M.; Li, Q.; Boyer, J. L.; Nicholas, R. A.; Harden, T. K. Expression of a cloned P2Y purinergic receptor that couples to phospholipase C. Mol. Pharmacol. 1994, 46, 8-14.
    • (1994) Mol. Pharmacol. , vol.46 , pp. 8-14
    • Filtz, T.M.1    Li, Q.2    Boyer, J.L.3    Nicholas, R.A.4    Harden, T.K.5
  • 38
    • 0032559887 scopus 로고    scopus 로고
    • 1 receptor: Molecular modeling and site-directed mutagenesis as tools to identify agonist and antagonist recognition sites
    • 1 receptor: molecular modeling and site-directed mutagenesis as tools to identify agonist and antagonist recognition sites. J. Med. Chem. 1998, 41, 1456-1466.
    • (1998) J. Med. Chem. , vol.41 , pp. 1456-1466
    • Moro, S.1    Guo, D.2    Camaioni, E.3    Boyer, J.L.4    Harden, K.T.5    Jacobson, K.A.6
  • 40
    • 0023111788 scopus 로고
    • Conformational analysis of the deoxyribofuranose ring in DNA by means of sums of proton - Proton coupling constants: A graphical method
    • Rinkel, L. J.; Altona, C. Conformational analysis of the deoxyribofuranose ring in DNA by means of sums of proton - proton coupling constants: A graphical method. J. Biomol. Struct. Dyn. 1987, 4, 621-649.
    • (1987) J. Biomol. Struct. Dyn. , vol.4 , pp. 621-649
    • Rinkel, L.J.1    Altona, C.2
  • 43
    • 0018362115 scopus 로고
    • Synthetic studies on β-lactam antibiotics. VII. Mild removal of the Benzyl Ester protecting group with alumium trichloride
    • Tsuji, T.; Kataoka, T.; Yoshioka, M.; Sendo, Y.; Nishitani, Y.; Hirai, S.; Maeda, T.; Nagata, W. Synthetic Studies on β-Lactam Antibiotics. VII. Mild Removal of the Benzyl Ester Protecting Group with Alumium Trichloride. Tetrahedron Lett. 1979, 2793-2796.
    • (1979) Tetrahedron Lett. , pp. 2793-2796
    • Tsuji, T.1    Kataoka, T.2    Yoshioka, M.3    Sendo, Y.4    Nishitani, Y.5    Hirai, S.6    Maeda, T.7    Nagata, W.8
  • 44
    • 0001672498 scopus 로고
    • Synthesis of racemic fomannosin and illudol using a biosynthetically patterned common intermediate
    • Semmelhack, M. F.; Tomoda, S.; Nagaoka, H.; Boettger, S. D.; Hurst, K. M. Synthesis of Racemic Fomannosin and Illudol Using a Biosynthetically Patterned Common Intermediate. J. Am. Chem. Soc. 1982, 104, 747-759.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 747-759
    • Semmelhack, M.F.1    Tomoda, S.2    Nagaoka, H.3    Boettger, S.D.4    Hurst, K.M.5
  • 45
    • 0029658136 scopus 로고    scopus 로고
    • Identification of potent P2Y-purinoceptor agonists that are derivatives of adenosine 5'-monophosphate
    • Boyer, J. L.; Siddiqi, S.; Fischer, B.; Romero-Avila, T.; Jacobson, K. A.; Harden, T. K. Identification of potent P2Y-purinoceptor agonists that are derivatives of adenosine 5'-monophosphate. Br. J. Pharmacol. 1996, 118, 1959-1964.
    • (1996) Br. J. Pharmacol. , vol.118 , pp. 1959-1964
    • Boyer, J.L.1    Siddiqi, S.2    Fischer, B.3    Romero-Avila, T.4    Jacobson, K.A.5    Harden, T.K.6
  • 46
    • 0342899947 scopus 로고    scopus 로고
    • The program SYBYL 6.3 is available from TRIPOS Associates, St. Louis, MO; 1993
    • The program SYBYL 6.3 is available from TRIPOS Associates, St. Louis, MO; 1993.
  • 47
    • 0842341771 scopus 로고
    • AMI: A new general purpose quantum mechanical molecular model
    • Dewar, M. J. S. E.; Zoebisch, G.; Healy, E. F. AMI: A New General Purpose Quantum Mechanical Molecular Model. J. Am. Chem. Soc. 1985, 107, 3902-3909.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 3902-3909
    • Dewar, M.J.S.E.1    Zoebisch, G.2    Healy, E.F.3
  • 48
    • 0342899948 scopus 로고    scopus 로고
    • MOPAC 6.0 is available from Quantum Chemistry Program Exchange
    • MOPAC 6.0 is available from Quantum Chemistry Program Exchange.
  • 49
    • 0030782754 scopus 로고    scopus 로고
    • Conformational analysis of nucleosides constructed on a Bicyclo[3.1.0]hexane template. Structure-antiviral activity for the northern and southern hemispheres of the pseudorotational cycle
    • Marquez, V. E.; Ezzitouni, A.; Siddiqui, M. A.; Russ, P. Ikeda, H.; George, C. Conformational Analysis of Nucleosides Constructed on a Bicyclo[3.1.0]hexane Template. Structure-Antiviral Activity for the Northern and Southern Hemispheres of the Pseudorotational Cycle. Nucleosides Nucleotides 1997, 16, 1431-1434.
    • (1997) Nucleosides Nucleotides , vol.16 , pp. 1431-1434
    • Marquez, V.E.1    Ezzitouni, A.2    Siddiqui, M.A.3    Russ, P.4    Ikeda, H.5    George, C.6
  • 51
    • 0020475449 scopus 로고
    • A simple method for displaying the hydrophobic character of a protein
    • Kyte, J.; Doolittle, R. F. A simple method for displaying the hydrophobic character of a protein. J. Mol. Biol. 1982, 157, 105-132.
    • (1982) J. Mol. Biol. , vol.157 , pp. 105-132
    • Kyte, J.1    Doolittle, R.F.2
  • 52
    • 84988053694 scopus 로고
    • An all-atom force field for simulation of protein and nucleic acids
    • Weiner, S. J.; Kollman, P. A.; Nguyen, D. T.; Case, D. A. An all-atom force field for simulation of protein and nucleic acids. J. Comput. Chem. 1986, 7, 230-252.
    • (1986) J. Comput. Chem. , vol.7 , pp. 230-252
    • Weiner, S.J.1    Kollman, P.A.2    Nguyen, D.T.3    Case, D.A.4
  • 54
    • 0015511563 scopus 로고
    • Conformational analysis of the sugar ring in nucleosides and nucleotides. A new description using the concept of pseudorotation
    • Altona, C.; Sundaranlingam, M. Conformational Analysis of the Sugar Ring in Nucleosides and Nucleotides. A New Description Using the Concept of Pseudorotation. J. Am. Chem. Soc. 1972, 94, 8205-8212.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 8205-8212
    • Altona, C.1    Sundaranlingam, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.