메뉴 건너뛰기




Volumn 53, Issue 9, 2010, Pages 3454-3464

Synthesis, chiral high performance liquid chromatographic resolution and enantiospecific activity of a potent new geranylgeranyl transferase inhibitor, 2-hydroxy-3-imidazo[1,2-a]pyridin-3-yl-2-phosphonopropionic Acid

Author keywords

[No Author keywords available]

Indexed keywords

2 (3 PYRIDYL) 1 HYDROXYETHYLIDENEBIS(PHOSPHONIC ACID); 2 (DIETHOXYPHOSPHORYL) 2 HYDROXY 3 IMIDAZO[1,2 A]PYRIDIN 3 YL PROPIONIC ACID ETHYL ESTER; 2 AMINO 3 IMIDAZO[1,2 A]PYRIDIN 3 YL ACRYLIC ACID ETHYL ESTER; 2 AZIDO 3 IMIDAZO[1,2 A]PYRIDIN 3 YL ACRYLIC ACID ETHYL ESTER; 2 HYDROXY 3 IMIDAZO[1,2 A]PYRIDIN 3 YL 2 PHOSPHONOPROPIONIC ACID; 2 HYDROXY 3 IMIDAZO[1,2 A]PYRIDIN 3 YL ACRYLIC ACID ETHYL ESTER; 3 (3 PYRIDYL) 2-HYDROXY 2 PHOSPHONOPROPANOIC ACID; ETHYL AZIDOACETATE; GERANYLTRANSFERASE; IMIDAZO[1,2 A]PYRIDIN 3 CARBALDEHYDE; MINODRONIC ACID; RAB PROTEIN; RISEDRONIC ACID; TRANSFERASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 77952025403     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm900232u     Document Type: Article
Times cited : (56)

References (60)
  • 1
    • 18244410156 scopus 로고    scopus 로고
    • Bisphosphonate inhibitors of Toxoplasma gondi growth: In vitro, QSAR, and in vivo investigations
    • Ling, Y.; Sahota, G.; Odeh, S.; Chan, J. M. W.; Araujo, F. G.; Moreno, S. N. J.; Oldfield, E. Bisphosphonate inhibitors of Toxoplasma gondi growth: In vitro, QSAR, and in vivo investigations J. Med. Chem. 2005, 48, 3130-3140
    • (2005) J. Med. Chem. , vol.48 , pp. 3130-3140
    • Ling, Y.1    Sahota, G.2    Odeh, S.3    Chan, J.M.W.4    Araujo, F.G.5    Moreno, S.N.J.6    Oldfield, E.7
  • 2
    • 33646079633 scopus 로고    scopus 로고
    • Bisphosphonate actions: Physical chemistry revisited
    • Papapoulos, S. E. Bisphosphonate actions: physical chemistry revisited Bone 2006, 38, 613-616
    • (2006) Bone , vol.38 , pp. 613-616
    • Papapoulos, S.E.1
  • 3
    • 35648981004 scopus 로고    scopus 로고
    • The farnesyl-diphosphate/geranylgeranyl-diphosphate synthase of Toxoplasma gondii is a bifunctional enzyme and a molecular target of bisphosphonates
    • Ling, Y.; Li, Z. H.; Miranda, K.; Oldfield, E.; Moreno, S. N. J. The farnesyl-diphosphate/geranylgeranyl-diphosphate synthase of Toxoplasma gondii is a bifunctional enzyme and a molecular target of bisphosphonates J. Biol. Chem. 2007, 282, 30804-30816
    • (2007) J. Biol. Chem. , vol.282 , pp. 30804-30816
    • Ling, Y.1    Li, Z.H.2    Miranda, K.3    Oldfield, E.4    Moreno, S.N.J.5
  • 5
    • 33748861780 scopus 로고    scopus 로고
    • Activity of nitrogen-containing and non-nitrogen-containing bisphosphonates on tumor cell lines
    • Zhang, Y.; Leon, A.; Song, Y.; Studer, D.; Haase, C.; Koscielski, L. A.; Oldfield, E. Activity of nitrogen-containing and non-nitrogen-containing bisphosphonates on tumor cell lines J. Med. Chem. 2006, 49, 5804-5814
    • (2006) J. Med. Chem. , vol.49 , pp. 5804-5814
    • Zhang, Y.1    Leon, A.2    Song, Y.3    Studer, D.4    Haase, C.5    Koscielski, L.A.6    Oldfield, E.7
  • 6
    • 33750733277 scopus 로고    scopus 로고
    • Molecular mechanisms of action of bisphosphonates: Current status
    • Roelofs, A. J.; Thompson, K.; Gordon, S.; Rogers, M. J. Molecular mechanisms of action of bisphosphonates: current status Clin. Cancer Res. 2006, 12, 6222S-6230S
    • (2006) Clin. Cancer Res. , vol.12
    • Roelofs, A.J.1    Thompson, K.2    Gordon, S.3    Rogers, M.J.4
  • 7
    • 43049109229 scopus 로고    scopus 로고
    • Mechanisms of action of bisphosphonates: Similarities and differences and their potential influence on clinical efficacy
    • Russell, R. G. G.; Watts, N. B.; Ebetino, F. H.; Rogers, M. J. Mechanisms of action of bisphosphonates: similarities and differences and their potential influence on clinical efficacy Osteoporosis Int. 2008, 19, 733-759
    • (2008) Osteoporosis Int. , vol.19 , pp. 733-759
    • Russell, R.G.G.1    Watts, N.B.2    Ebetino, F.H.3    Rogers, M.J.4
  • 8
    • 41849123834 scopus 로고    scopus 로고
    • Structure-activity relationships among the nitrogen containing bisphosphonates in clinical use and other analogues: Time-dependent inhibition of human farnesyl pyrophosphate synthase
    • Dunford, J. E.; Kwaasi, A. A.; Rogers, M. J.; Barnett, B. L.; Ebetino, F. H.; Russell, R. G. G.; Oppermann, U.; Kavanagh, K. L. Structure-activity relationships among the nitrogen containing bisphosphonates in clinical use and other analogues: time-dependent inhibition of human farnesyl pyrophosphate synthase J. Med. Chem. 2008, 51, 2187-2195
    • (2008) J. Med. Chem. , vol.51 , pp. 2187-2195
    • Dunford, J.E.1    Kwaasi, A.A.2    Rogers, M.J.3    Barnett, B.L.4    Ebetino, F.H.5    Russell, R.G.G.6    Oppermann, U.7    Kavanagh, K.L.8
  • 10
    • 0028796338 scopus 로고
    • Some phosphonic acid analogs as inhibitors of pyrophosphate-dependent phosphofructokinase, a novel target in Toxoplasma gondii
    • Peng, Z.-Y.; Mansour, J. M.; Araujo, F.; Ju, J.-Y.; McKenna, C. E.; Mansour, T. E. Some phosphonic acid analogs as inhibitors of pyrophosphate-dependent phosphofructokinase, a novel target in Toxoplasma gondii Biochem. Pharm. 1995, 49, 105-113
    • (1995) Biochem. Pharm. , vol.49 , pp. 105-113
    • Peng, Z.-Y.1    Mansour, J.M.2    Araujo, F.3    Ju, J.-Y.4    McKenna, C.E.5    Mansour, T.E.6
  • 13
    • 33747493778 scopus 로고    scopus 로고
    • Selective inhibition of Rab prenylation by a phosphonocarboxylate analogue of risedronate induces apoptosis, but not S-phase arrest, in human myeloma cells
    • Roelofs, A. J.; Hulley, P. A.; Meijer, A.; Ebetino, F. H.; Graham, R.; Russell, G.; Shipman, C. M. Selective inhibition of Rab prenylation by a phosphonocarboxylate analogue of risedronate induces apoptosis, but not S-phase arrest, in human myeloma cells Int. J. Cancer 2006, 119, 1254-1261
    • (2006) Int. J. Cancer , vol.119 , pp. 1254-1261
    • Roelofs, A.J.1    Hulley, P.A.2    Meijer, A.3    Ebetino, F.H.4    Graham, R.5    Russell, G.6    Shipman, C.M.7
  • 14
    • 23844443254 scopus 로고    scopus 로고
    • Phosphonocarboxylate inhibitors of Rab geranylgeranyl transferase disrupt the prenylation and membrane localization of Rab proteins in osteoclasts in vitro and in vivo
    • Coxon, F. P.; Ebetino, F. H.; Mules, E. H.; Seabra, M. C.; McKenna, C. E.; Rogers, M. J. Phosphonocarboxylate inhibitors of Rab geranylgeranyl transferase disrupt the prenylation and membrane localization of Rab proteins in osteoclasts in vitro and in vivo Bone 2005, 37, 349-358
    • (2005) Bone , vol.37 , pp. 349-358
    • Coxon, F.P.1    Ebetino, F.H.2    Mules, E.H.3    Seabra, M.C.4    McKenna, C.E.5    Rogers, M.J.6
  • 15
    • 16844384058 scopus 로고    scopus 로고
    • Emerging role of RAB GTPases in cancer and human disease
    • Cheng, K. W.; Lahad, J. P.; Gray, J. W.; Mills, G. B. Emerging role of RAB GTPases in cancer and human disease Cancer Res. 2005, 65, 2516-2519
    • (2005) Cancer Res. , vol.65 , pp. 2516-2519
    • Cheng, K.W.1    Lahad, J.P.2    Gray, J.W.3    Mills, G.B.4
  • 16
    • 0034714098 scopus 로고    scopus 로고
    • The mammalian Rab family of small GTPases: Definition of family and subfamily sequence motifs suggests a mechanism for functional specificity in the Ras superfamily
    • Pereira-Leal, J. B.; Seabra, M. C. The mammalian Rab family of small GTPases: definition of family and subfamily sequence motifs suggests a mechanism for functional specificity in the Ras superfamily J. Mol. Biol. 2000, 301, 1077-1087
    • (2000) J. Mol. Biol. , vol.301 , pp. 1077-1087
    • Pereira-Leal, J.B.1    Seabra, M.C.2
  • 17
    • 33644748150 scopus 로고    scopus 로고
    • Geranylgeranylation of rab GTPases
    • Leung, K. F.; Baron, R.; Seabra, M. C. Geranylgeranylation of Rab GTPases J. Lipid Res. 2006, 47, 467-475
    • (2006) J. Lipid Res. , vol.47 , pp. 467-475
    • Leung, K.F.1    Baron, R.2    Seabra, M.C.3
  • 23
    • 44349178715 scopus 로고    scopus 로고
    • Inhibitors of protein geranylgeranyltransferase i and Rab geranylgeranyltransferase identified from a library of allenoate-derived compounds
    • Watanabe, M.; Fiji, H. D. G.; Guo, L.; Chan, L.; Kinderman, S. S.; Slamon, D. J.; Kwon, O.; Tamanoi, F. Inhibitors of protein geranylgeranyltransferase I and Rab geranylgeranyltransferase identified from a library of allenoate-derived compounds J. Biol. Chem. 2008, 283, 9571-9579
    • (2008) J. Biol. Chem. , vol.283 , pp. 9571-9579
    • Watanabe, M.1    Fiji, H.D.G.2    Guo, L.3    Chan, L.4    Kinderman, S.S.5    Slamon, D.J.6    Kwon, O.7    Tamanoi, F.8
  • 26
    • 55349135188 scopus 로고    scopus 로고
    • Lowering Bone Mineral Affinity of Bisphosphonates as a Therapeutic Strategy to Optimize Skeletal Tumor Growth Inhibition in Vivo
    • Fournier, P. G. J.; Dauhine, F.; Lundy, M. W.; Rogers, M. J.; Ebetino, F. H.; ClezardP. Lowering Bone Mineral Affinity of Bisphosphonates as a Therapeutic Strategy to Optimize Skeletal Tumor Growth Inhibition In Vivo Cancer Res. 2008, 68, 8945-8953
    • (2008) Cancer Res. , vol.68 , pp. 8945-8953
    • Fournier, P.G.J.1    Dauhine, F.2    Lundy, M.W.3    Rogers, M.J.4    Ebetino, F.H.5    Clezardin, P.6
  • 27
    • 0031760512 scopus 로고    scopus 로고
    • Studies on novel bone resorption inhibitors. II. Synthesis and pharmacological activities of fused aza-heteroarylbisphosphonate derivatives
    • Takeuchi, M.; Sakamoto, S.; Kawamuki, K.; Kurihara, H.; Nakahara, H.; Isomura, Y. Studies on novel bone resorption inhibitors. II. Synthesis and pharmacological activities of fused aza-heteroarylbisphosphonate derivatives Chem. Pharm. Bull. 1998, 46, 1703-1709
    • (1998) Chem. Pharm. Bull. , vol.46 , pp. 1703-1709
    • Takeuchi, M.1    Sakamoto, S.2    Kawamuki, K.3    Kurihara, H.4    Nakahara, H.5    Isomura, Y.6
  • 32
    • 0014876454 scopus 로고
    • Imidazole Derivatives. 4. Synthesis and Pharmacologic Activity of Oxygenated Derivatives of Imidazo [1,2- a ]Pyridine
    • Almirante, L; Mugnaini, A.; Detoma, N.; Gamba, A.; Murmann, W.; Hidalgo, J. Imidazole Derivatives. 4. Synthesis and Pharmacologic Activity of Oxygenated Derivatives of Imidazo [1,2- a ]Pyridine J. Med. Chem. 1970, 13, 1048-1051
    • (1970) J. Med. Chem. , vol.13 , pp. 1048-1051
    • Almirante, L.1    Mugnaini, A.2    Detoma, N.3    Gamba, A.4    Murmann, W.5    Hidalgo, J.6
  • 34
    • 0037167884 scopus 로고    scopus 로고
    • A study of the thermal decomposition of 2-azidoethanol and 2-azidoethyl acetate by ultraviolet photoelectron spectroscopy and matrix isolation infrared spectroscopy
    • Hooper, N.; Beeching, L. J.; Dyke, J. M.; Morris, A.; Ogden, J. S.; Dias, A. A.; Costa, M. L.; Barros, M. T.; Cabral, M. H.; Moutinho, A. M. C. A study of the thermal decomposition of 2-azidoethanol and 2-azidoethyl acetate by ultraviolet photoelectron spectroscopy and matrix isolation infrared spectroscopy J. Phys. Chem. A 2002, 106, 9968-9975
    • (2002) J. Phys. Chem. A , vol.106 , pp. 9968-9975
    • Hooper, N.1    Beeching, L.J.2    Dyke, J.M.3    Morris, A.4    Ogden, J.S.5    Dias, A.A.6    Costa, M.L.7    Barros, M.T.8    Cabral, M.H.9    Moutinho, A.M.C.10
  • 36
    • 0032844288 scopus 로고    scopus 로고
    • Synthetic utility of tert -butyl azidoacetate on the Hemetsberger-Knittel reaction (synthetic studies of indoles and related compounds part 47)
    • Kondo, K.; Morohoshi, S.; Mitsuhashi, M.; Murakami, Y. Synthetic utility of tert -butyl azidoacetate on the Hemetsberger-Knittel reaction (synthetic studies of indoles and related compounds part 47) Chem. Pharm. Bull. 1999, 47, 1227-1231
    • (1999) Chem. Pharm. Bull. , vol.47 , pp. 1227-1231
    • Kondo, K.1    Morohoshi, S.2    Mitsuhashi, M.3    Murakami, Y.4
  • 38
    • 0000936298 scopus 로고
    • Dehydrooligopeptides. 8. Convenient Syntheses of Various Dehydrotyrosine Derivatives Protected with Useful N,O-Protecting Groups Via N -Carboxy Dehydrotyrosine Anhydrides
    • ShC.; Yonezawa, Y.; Obara, T.; Nishio, H. Dehydrooligopeptides. 8. Convenient Syntheses of Various Dehydrotyrosine Derivatives Protected with Useful N,O-Protecting Groups Via N -Carboxy Dehydrotyrosine Anhydrides Bull. Chem. Soc. Jpn. 1988, 61, 885-891
    • (1988) Bull. Chem. Soc. Jpn. , vol.61 , pp. 885-891
    • Shin, C.1    Yonezawa, Y.2    Obara, T.3    Nishio, H.4
  • 39
    • 77952052181 scopus 로고
    • Phosphonate-phosphate rearrangement of esters of alpha- hydroxyalkylphosphonic acids
    • Pudovik, A. N.; Guryanov, I. V.; Banderov, Lv.; Romanov, G. V. Phosphonate-Phosphate Rearrangement of Esters of Alpha-Hydroxyalkylphosphonic Acids J. Gen. Chem. U.S.S.R. 1968, 38, 142-149
    • (1968) J. Gen. Chem. U.S.S.R. , vol.38 , pp. 142-149
    • Pudovik, A.N.1    Guryanov, I.V.2    Banderov, Lv.3    Romanov, G.V.4
  • 40
    • 0342516044 scopus 로고
    • Novel Synthetic Aspects of the Phosphonate-Phosphate Rearrangement. 2. Synthesis of Enolphosphates from 1-Oxoalkanphosphonates and Sulfur-Ylides
    • Hammerschmidt, F.; Zbiral, E. Novel Synthetic Aspects of the Phosphonate-Phosphate Rearrangement. 2. Synthesis of Enolphosphates from 1-Oxoalkanphosphonates and Sulfur-Ylides Monatsh. Chem. 1980, 111, 1015-1023
    • (1980) Monatsh. Chem. , vol.111 , pp. 1015-1023
    • Hammerschmidt, F.1    Zbiral, E.2
  • 41
    • 21344494716 scopus 로고
    • Phosphonate-Phosphate Rearrangement and Phosphate-Phosphonate Rearrangement and Its Application. 2. Stereochemistry of Phosphonate-Phosphate Rearrangement at Carbon as Exemplified by the Isomerization of (R)-(+)-(1-Hydroxy-1-phenylethyl)phosphonic and (S)-(-)-(1-Hydroxy-1- phenylethyl)phosphonic acid diethyl ester
    • Hammerschmidt, F. Phosphonate-Phosphate Rearrangement and Phosphate-Phosphonate Rearrangement and Its Application. 2. Stereochemistry of Phosphonate-Phosphate Rearrangement at Carbon as Exemplified by the Isomerization of (R)-(+)-(1-Hydroxy-1-phenylethyl)phosphonic and (S)-(-)-(1-Hydroxy-1-phenylethyl)phosphonic acid diethyl ester Monatsh. Chem. 1993, 124, 1063-1069
    • (1993) Monatsh. Chem. , vol.124 , pp. 1063-1069
    • Hammerschmidt, F.1
  • 42
    • 0012130558 scopus 로고    scopus 로고
    • Recent progress in carbonylphosphonate chemistry
    • Springer: Heidelberg, Germany
    • McKenna, C. E.; Kashemirov, B. A. Recent progress in carbonylphosphonate chemistry. In New Aspects in Phosphorus Chem. I; Springer: Heidelberg, Germany, 2002; Vol. 220, pp 201-238.
    • (2002) New Aspects in Phosphorus Chem. i , vol.220 , pp. 201-238
    • McKenna, C.E.1    Kashemirov, B.A.2
  • 44
    • 42949143745 scopus 로고    scopus 로고
    • Farnesyl pyrophosphate synthase enantiospecificity with a chiral risedronate analog, [6,7-dihydro-5 H -cyclopenta[ c ]pyridin-7yl(hydroxy) methylene]bis(phosphonic acid) (NE-10501): Synthetic, structural, and modeling studies
    • Deprele, S.; Kashemirov, B. A.; Hogan, J. M.; Ebetino, F. H.; Barnett, B. L.; Evdokimov, A.; McKenna, C. E. Farnesyl pyrophosphate synthase enantiospecificity with a chiral risedronate analog, [6,7-dihydro-5 H -cyclopenta[ c ]pyridin-7yl(hydroxy)methylene]bis(phosphonic acid) (NE-10501): synthetic, structural, and modeling studies Bioorg. Med. Chem. Lett. 2008, 18, 2878-2882
    • (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 2878-2882
    • Deprele, S.1    Kashemirov, B.A.2    Hogan, J.M.3    Ebetino, F.H.4    Barnett, B.L.5    Evdokimov, A.6    McKenna, C.E.7
  • 45
    • 0030576524 scopus 로고    scopus 로고
    • Quinine and quinidine derivatives as chiral selectors. 1. Brush type chiral stationary phases for high-performance liquid chromatography based on cinchonan carbamates and their application as chiral anion exchangers
    • Lammerhofer, M.; Lindner, W. Quinine and quinidine derivatives as chiral selectors. 1. Brush type chiral stationary phases for high-performance liquid chromatography based on cinchonan carbamates and their application as chiral anion exchangers J. Chromatogr., A 1996, 741, 33-48
    • (1996) J. Chromatogr., A , vol.741 , pp. 33-48
    • Lammerhofer, M.1    Lindner, W.2
  • 46
    • 0032808073 scopus 로고    scopus 로고
    • Enantioselective anion exchangers based on cinchona alkaloid-derived carbamates: Influence of C-8/C-9 stereochemistry on chiral recognition
    • Maier, N. M.; Nicoletti, L.; Lammerhofer, M.; Lindner, W. Enantioselective anion exchangers based on cinchona alkaloid-derived carbamates: influence of C-8/C-9 stereochemistry on chiral recognition Chirality 1999, 11, 522-528
    • (1999) Chirality , vol.11 , pp. 522-528
    • Maier, N.M.1    Nicoletti, L.2    Lammerhofer, M.3    Lindner, W.4
  • 47
    • 0035146537 scopus 로고    scopus 로고
    • Structure-activity relationships for inhibition of farnesyl diphosphate synthase in vitro and inhibition of bone resorption in vivo by nitrogen-containing bisphosphonates
    • Dunford, J. E.; Thompson, K.; Coxon, F. P.; Luckman, S. P.; Hahn, F. M.; Poulter, C. D.; Ebetino, F. H.; Rogers, M. J. Structure-activity relationships for inhibition of farnesyl diphosphate synthase in vitro and inhibition of bone resorption in vivo by nitrogen-containing bisphosphonates J. Pharmacol. Exp. Ther. 2001, 296, 235-242
    • (2001) J. Pharmacol. Exp. Ther. , vol.296 , pp. 235-242
    • Dunford, J.E.1    Thompson, K.2    Coxon, F.P.3    Luckman, S.P.4    Hahn, F.M.5    Poulter, C.D.6    Ebetino, F.H.7    Rogers, M.J.8
  • 48
    • 0028810275 scopus 로고
    • Disruption of Oncogenic K-RAS4B Processing and Signaling by a Potent Geranylgeranyltransferase-I Inhibitor
    • Lerner, E. C.; Qian, Y. M.; Hamilton, A. D.; Sebit, S. M. Disruption of Oncogenic K-RAS4B Processing and Signaling by a Potent Geranylgeranyltransferase-I Inhibitor J. Biol. Chem. 1995, 270, 26770-26773
    • (1995) J. Biol. Chem. , vol.270 , pp. 26770-26773
    • Lerner, E.C.1    Qian, Y.M.2    Hamilton, A.D.3    Sebit, S.M.4
  • 49
    • 0029926493 scopus 로고    scopus 로고
    • Platelet-derived growth factor receptor tyrosine phosphorylation requires protein geranylgeranylation but not farnesylation
    • McGuire, T. F.; Qian, Y. M.; Vogt, A.; Hamilton, A. D.; Sebti, S. M. Platelet-Derived Growth Factor Receptor Tyrosine Phosphorylation Requires Protein Geranylgeranylation But Not Farnesylation J. Biol. Chem. 1996, 271, 27402-27407
    • (1996) J. Biol. Chem. , vol.271 , pp. 27402-27407
    • McGuire, T.F.1    Qian, Y.M.2    Vogt, A.3    Hamilton, A.D.4    Sebti, S.M.5
  • 52
    • 49649084975 scopus 로고    scopus 로고
    • Biphasic requirement for geranylgeraniol in hippocampal long-term potentiation
    • Kotti, T.; Head, D. D.; McKenna, C. E.; Russell, D. W. Biphasic requirement for geranylgeraniol in hippocampal long-term potentiation Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 11394-11399
    • (2008) Proc. Natl. Acad. Sci. U.S.A. , vol.105 , pp. 11394-11399
    • Kotti, T.1    Head, D.D.2    McKenna, C.E.3    Russell, D.W.4
  • 54
    • 0001373381 scopus 로고
    • NMR spectra and Pi-electron densities of some imidazo(1,2-a) pyridines
    • Paudler, W. W.; Blewitt, H. L. NMR Spectra and Pi-Electron Densities of Some Imidazo(1,2- a) Pyridines Tetrahedron 1965, 21, 353-361
    • (1965) Tetrahedron , vol.21 , pp. 353-361
    • Paudler, W.W.1    Blewitt, H.L.2
  • 57
    • 33746836518 scopus 로고    scopus 로고
    • The crystal structure of human geranylgeranyl pyrophosphate synthase reveals a novel hexameric arrangement and inhibitory product binding
    • Kavanagh, K. L.; Dunford, J. E.; Bunkoczi, G.; Russell, R. G. G.; Oppermann, U. The crystal structure of human geranylgeranyl pyrophosphate synthase reveals a novel hexameric arrangement and inhibitory product binding J. Biol. Chem. 2006, 281, 22004-22012
    • (2006) J. Biol. Chem. , vol.281 , pp. 22004-22012
    • Kavanagh, K.L.1    Dunford, J.E.2    Bunkoczi, G.3    Russell, R.G.G.4    Oppermann, U.5
  • 58
    • 0037302856 scopus 로고    scopus 로고
    • Antagonistic effects of different classes of bisphosphonates in osteoclasts and macrophages in vitro
    • Frith, J. C.; Rogers, M. J. Antagonistic effects of different classes of bisphosphonates in osteoclasts and macrophages in vitro J. Bone Miner. Res. 2003, 18, 204-212
    • (2003) J. Bone Miner. Res. , vol.18 , pp. 204-212
    • Frith, J.C.1    Rogers, M.J.2
  • 59
    • 0033930168 scopus 로고    scopus 로고
    • Protein geranylgeranylation is required for osteoclast formation, function, and survival: Inhibition by bisphosphonates and GGTI-298
    • Coxon, F. P.; Helfrich, M. H.; Van't Hof, R.; Sebti, S.; Ralston, S. H.; Hamilton, A.; Rogers, M. J. Protein geranylgeranylation is required for osteoclast formation, function, and survival: inhibition by bisphosphonates and GGTI-298 J. Bone Miner. Res. 2000, 15, 1467-1476
    • (2000) J. Bone Miner. Res. , vol.15 , pp. 1467-1476
    • Coxon, F.P.1    Helfrich, M.H.2    Van't Hof, R.3    Sebti, S.4    Ralston, S.H.5    Hamilton, A.6    Rogers, M.J.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.