메뉴 건너뛰기




Volumn 53, Issue 16, 2010, Pages 6040-6053

Improved syntheses of 5′- S -(2-Aminoethyl)-6- N -(4-nitrobenzyl)- 5′-thioadenosine (SAENTA), analogues, and fluorescent probe conjugates: Analysis of cell-surface human equilibrative nucleoside transporter 1 (hENT1) levels for prediction of the antitumor efficacy of gemcitabine

Author keywords

[No Author keywords available]

Indexed keywords

5' (2 AMINOETHYL) 6 N (4 NITROBENZYL) 5' THIOADENOSINE; 5' [2 (6 AMINOHEXANAMIDO)]ETHYL 6 N (4 NITROBENZYL) 5' THIOADENOSINE; ADENOSINE DERIVATIVE; EQUILIBRATIVE NUCLEOSIDE TRANSPORTER 1; FLUORESCEIN ISOTHIOCYANATE; FLUORESCENT DYE; FLUORIDE; GEMCITABINE; PURINE; RECOMBINANT PROTEIN; UNCLASSIFIED DRUG;

EID: 77955866444     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100432w     Document Type: Article
Times cited : (29)

References (38)
  • 3
    • 48749085061 scopus 로고    scopus 로고
    • Human Equilibrative Nucleoside Transporter (ENT) Family of Nucleoside and Nucleobase Transporter Proteins
    • Young, J. D.; Yao, S. Y.; Sun, L.; Cass, C. E.; Baldwin, S. A. Human Equilibrative Nucleoside Transporter (ENT) Family of Nucleoside and Nucleobase Transporter Proteins Xenobiotica 2008, 38, 995-1021
    • (2008) Xenobiotica , vol.38 , pp. 995-1021
    • Young, J.D.1    Yao, S.Y.2    Sun, L.3    Cass, C.E.4    Baldwin, S.A.5
  • 5
    • 0021953877 scopus 로고
    • Cytosine Arabinoside Transport and Metabolism in Acute Leukemias and T Cell Lymphoblastic Lymphoma
    • Wiley, J. S.; Taupin, J.; Jamieson, G. P.; Snook, M.; Sawyer, W. H.; Finch, L. R. Cytosine Arabinoside Transport and Metabolism in Acute Leukemias and T Cell Lymphoblastic Lymphoma J. Clin. Invest. 1985, 75, 632-642
    • (1985) J. Clin. Invest. , vol.75 , pp. 632-642
    • Wiley, J.S.1    Taupin, J.2    Jamieson, G.P.3    Snook, M.4    Sawyer, W.H.5    Finch, L.R.6
  • 6
    • 0026452169 scopus 로고
    • Comparison of the Abilities of Nitrobenzylthioinosine, Dilazep, and Dipyridamole to Protect Human Hematopoietic Cells from 7-Deazaadenosine (Tubercidin)
    • Cass, C. E.; King, K. M.; Montano, J. T.; Janowska-Wieczorek, A. A Comparison of the Abilities of Nitrobenzylthioinosine, Dilazep, and Dipyridamole to Protect Human Hematopoietic Cells from 7-Deazaadenosine (Tubercidin) Cancer Res. 1992, 52, 5879-5886
    • (1992) Cancer Res. , vol.52 , pp. 5879-5886
    • Cass, C.E.1    King, K.M.2    Montano, J.T.3    Janowska-Wieczorek, A.A.4
  • 7
    • 0026526266 scopus 로고
    • Nucleobase Transporter-Mediated Permeation of 2′,3′- Dideoxyguanosine in Human Erythrocytes and Human T-Lymphoblastoid CCRF-CEM Cells
    • Gati, W. P.; Paterson, A. R.; Tyrrell, D. L.; Cass, C. E.; Moravek, J.; Robins, M. J. Nucleobase Transporter-Mediated Permeation of 2′,3′- Dideoxyguanosine in Human Erythrocytes and Human T-Lymphoblastoid CCRF-CEM Cells J. Biol. Chem. 1992, 267, 22272-22276
    • (1992) J. Biol. Chem. , vol.267 , pp. 22272-22276
    • Gati, W.P.1    Paterson, A.R.2    Tyrrell, D.L.3    Cass, C.E.4    Moravek, J.5    Robins, M.J.6
  • 8
    • 0032188825 scopus 로고    scopus 로고
    • Functional Nucleoside Transporters Are Required for Gemcitabine Influx and Manifestation of Toxicity in Cancer Cell Lines
    • Mackey, J. R.; Mani, R. S.; Selner, M.; Mowles, D.; Young, J. D.; Belt, J. A.; Crawford, C. R.; Cass, C. E. Functional Nucleoside Transporters Are Required for Gemcitabine Influx and Manifestation of Toxicity in Cancer Cell Lines Cancer Res. 1998, 58, 4349-4357
    • (1998) Cancer Res. , vol.58 , pp. 4349-4357
    • MacKey, J.R.1    Mani, R.S.2    Selner, M.3    Mowles, D.4    Young, J.D.5    Belt, J.A.6    Crawford, C.R.7    Cass, C.E.8
  • 9
    • 0035702051 scopus 로고    scopus 로고
    • Cellular Abundance of es Nucleoside Transporters and Differential Drug Toxicity in Myelodysplastic Syndrome (MDS) Bone Marrow Cell Subpopulations
    • Gati, W. P.; Larratt, L. M.; Turner, A. R. Cellular Abundance of es Nucleoside Transporters and Differential Drug Toxicity in Myelodysplastic Syndrome (MDS) Bone Marrow Cell Subpopulations Proc. West. Pharmacol. Soc. 2001, 44, 93-96
    • (2001) Proc. West. Pharmacol. Soc. , vol.44 , pp. 93-96
    • Gati, W.P.1    Larratt, L.M.2    Turner, A.R.3
  • 10
    • 6044267987 scopus 로고    scopus 로고
    • The Absence of Human Equilibrative Nucleoside Transporter 1 Is Associated with Reduced Survival in Patients with Gemcitabine-Treated Pancreas Adenocarcinoma
    • Spratlin, J.; Sangha, R.; Glubrecht, D.; Dabbagh, L.; Young, J. D.; Dumontet, C.; Cass, C.; Lai, R.; Mackey, J. R. The Absence of Human Equilibrative Nucleoside Transporter 1 Is Associated with Reduced Survival in Patients with Gemcitabine-Treated Pancreas Adenocarcinoma Clin. Cancer Res. 2004, 10, 6956-6961
    • (2004) Clin. Cancer Res. , vol.10 , pp. 6956-6961
    • Spratlin, J.1    Sangha, R.2    Glubrecht, D.3    Dabbagh, L.4    Young, J.D.5    Dumontet, C.6    Cass, C.7    Lai, R.8    MacKey, J.R.9
  • 12
    • 65349163336 scopus 로고    scopus 로고
    • Human Equilibrative Nucleoside Transporter 1 and Human Concentrative Nucleoside Transporter 3 Predict Survival after Adjuvant Gemcitabine Therapy in Resected Pancreatic Adenocarcinoma
    • Marechal, R.; Mackey, J. R.; Lai, R.; Demetter, P.; Peeters, M.; Polus, M.; Cass, C. E.; Young, J.; Salmon, I.; Deviere, J.; Van Laethem, J.-L. Human Equilibrative Nucleoside Transporter 1 and Human Concentrative Nucleoside Transporter 3 Predict Survival After Adjuvant Gemcitabine Therapy in Resected Pancreatic Adenocarcinoma Clin. Cancer Res. 2009, 15, 2913-2919
    • (2009) Clin. Cancer Res. , vol.15 , pp. 2913-2919
    • Marechal, R.1    MacKey, J.R.2    Lai, R.3    Demetter, P.4    Peeters, M.5    Polus, M.6    Cass, C.E.7    Young, J.8    Salmon, I.9    Deviere, J.10    Van Laethem, J.-L.11
  • 13
    • 0035054188 scopus 로고    scopus 로고
    • Distinct Regional Distribution of Human Equilibrative Nucleoside Transporter Proteins 1 and 2 (hENT1 and hENT2) in the Central Nervous System
    • Jennings, L. L.; Hao, C.; Cabrita, M. A.; Vickers, M. F.; Baldwin, S. A.; Young, J. D.; Cass, C. E. Distinct Regional Distribution of Human Equilibrative Nucleoside Transporter Proteins 1 and 2 (hENT1 and hENT2) in the Central Nervous System Neuropharmacology 2001, 40, 722-731
    • (2001) Neuropharmacology , vol.40 , pp. 722-731
    • Jennings, L.L.1    Hao, C.2    Cabrita, M.A.3    Vickers, M.F.4    Baldwin, S.A.5    Young, J.D.6    Cass, C.E.7
  • 14
    • 0024514009 scopus 로고
    • Nucleoside Transport in Acute Leukaemia and Lymphoma: Close Relation to Proliferative Rate
    • Wiley, J. S.; Snook, M. B.; Jamieson, G. P. Nucleoside Transport in Acute Leukaemia and Lymphoma: Close Relation to Proliferative Rate Br. J. Haematol. 1989, 71, 203-207
    • (1989) Br. J. Haematol. , vol.71 , pp. 203-207
    • Wiley, J.S.1    Snook, M.B.2    Jamieson, G.P.3
  • 18
    • 0030971066 scopus 로고    scopus 로고
    • Sensitivity of Acute Leukemia Cells to Cytarabine Is a Correlate of Cellular es Nucleoside Transporter Site Content Measured by Flow Cytometry with SAENTA-fluorescein
    • Gati, W. P.; Paterson, A. R.; Larratt, L. M.; Turner, A. R.; Belch, A. R. Sensitivity of Acute Leukemia Cells to Cytarabine Is a Correlate of Cellular es Nucleoside Transporter Site Content Measured by Flow Cytometry with SAENTA-fluorescein Blood 1997, 90, 346-353
    • (1997) Blood , vol.90 , pp. 346-353
    • Gati, W.P.1    Paterson, A.R.2    Larratt, L.M.3    Turner, A.R.4    Belch, A.R.5
  • 20
    • 0016817706 scopus 로고
    • Inhibitors of Nucleoside Transport. Structure-Activity Study Using Human Erythrocytes
    • Paul, B.; Chen, M. F.; Paterson, A. R. P. Inhibitors of Nucleoside Transport. Structure-Activity Study Using Human Erythrocytes J. Med. Chem. 1975, 18, 968-973
    • (1975) J. Med. Chem. , vol.18 , pp. 968-973
    • Paul, B.1    Chen, M.F.2    Paterson, A.R.P.3
  • 21
    • 0026476060 scopus 로고
    • Photochemistry of Nucleoside Transport Inhibitor 6- S -Benzylated Thiopurine Ribonucleosides. Implications for a New Class of Photoaffinity Labels
    • Fleming, S. A.; Rawlins, D. B.; Samano, V.; Robins, M. J. Photochemistry of Nucleoside Transport Inhibitor 6- S -Benzylated Thiopurine Ribonucleosides. Implications for a New Class of Photoaffinity Labels J. Org. Chem. 1992, 57, 5968-5976
    • (1992) J. Org. Chem. , vol.57 , pp. 5968-5976
    • Fleming, S.A.1    Rawlins, D.B.2    Samano, V.3    Robins, M.J.4
  • 22
    • 0025708422 scopus 로고
    • 6-(4-nitrobenzyl)-5′- thioadenosine (SAENTA), a Novel Ligand with High Affinity for Polypeptides Associated with Nucleoside Transport. Partial Purification of the Nitrobenzylthioinosine-Binding Protein of Pig Erythrocytes by Affinity Chromatography
    • 6-(4-nitrobenzyl)-5′-thioadenosine (SAENTA), a Novel Ligand with High Affinity for Polypeptides Associated with Nucleoside Transport. Partial Purification of the Nitrobenzylthioinosine-Binding Protein of Pig Erythrocytes by Affinity Chromatography Biochem. J. 1990, 270, 605-614
    • (1990) Biochem. J. , vol.270 , pp. 605-614
    • Agbanyo, F.R.1    Vijayalakshmi, D.2    Craik, J.D.3    Gati, W.P.4    McAdam, D.P.5    Asakura, J.6    Robins, M.J.7    Paterson, A.R.P.8    Cass, C.E.9
  • 24
    • 0028363818 scopus 로고
    • Synthesis of Substituted-Benzyl and Sugar-Modified Analogs of 6- N -(4-Nitrobenzyl)adenosine and Their Interactions with " ES " Nucleoside Transport Systems
    • Robins, M. J.; Asakura, J.; Kaneko, M.; Shibuya, S.; Jacobs, E. S.; Agbanyo, F. R.; Cass, C. E.; Paterson, A. R. P. Synthesis of Substituted-Benzyl and Sugar-Modified Analogs of 6- N -(4-Nitrobenzyl)adenosine and Their Interactions with " ES " Nucleoside Transport Systems Nucleosides Nucleotides 1994, 13, 1627-1646
    • (1994) Nucleosides Nucleotides , vol.13 , pp. 1627-1646
    • Robins, M.J.1    Asakura, J.2    Kaneko, M.3    Shibuya, S.4    Jacobs, E.S.5    Agbanyo, F.R.6    Cass, C.E.7    Paterson, A.R.P.8
  • 25
    • 0019781093 scopus 로고
    • Nucleic Acid Related Compounds. 34. Nonaqueous Diazotization with tert -Butyl Nitrite. Introduction of Fluorine, Chlorine, and Bromine at C-2 of Purine Nucleosides
    • Robins, M. J.; Uznański, B. Nucleic Acid Related Compounds. 34. Nonaqueous Diazotization with tert -Butyl Nitrite. Introduction of Fluorine, Chlorine, and Bromine at C-2 of Purine Nucleosides Can. J. Chem. 1981, 59, 2608-2611
    • (1981) Can. J. Chem. , vol.59 , pp. 2608-2611
    • Robins, M.J.1    Uznański, B.2
  • 26
    • 18244380805 scopus 로고    scopus 로고
    • Fluoro, Alkylsulfanyl, and Alkylsulfonyl Leaving Groups in Suzuki Cross-Coupling Reactions of Purine 2′-Deoxynucleosides and Nucleosides
    • Liu, J.; Robins, M. J. Fluoro, Alkylsulfanyl, and Alkylsulfonyl Leaving Groups in Suzuki Cross-Coupling Reactions of Purine 2′-Deoxynucleosides and Nucleosides Org. Lett. 2005, 7, 1149-1151
    • (2005) Org. Lett. , vol.7 , pp. 1149-1151
    • Liu, J.1    Robins, M.J.2
  • 27
    • 34248550769 scopus 로고    scopus 로고
    • NAr Displacements with 6-(Fluoro, Chloro, Bromo, Iodo, and Alkylsulfonyl)purine Nucleosides: Synthesis, Kinetics, and Mechanism
    • NAr Displacements with 6-(Fluoro, Chloro, Bromo, Iodo, and Alkylsulfonyl)purine Nucleosides: Synthesis, Kinetics, and Mechanism J. Am. Chem. Soc. 2007, 129, 5962-5968
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 5962-5968
    • Liu, J.1    Robins, M.J.2
  • 28
    • 0025941446 scopus 로고
    • Nucleic Acid Related Compounds. 66. Improved Syntheses of 5′-Chloro-5′-deoxy- and 5′-S-Aryl(or Alkyl)-5′- thionucleosides
    • Robins, M. J.; Hansske, F.; Wnuk, S. F.; Kanai, T. Nucleic Acid Related Compounds. 66. Improved Syntheses of 5′-Chloro-5′-deoxy- and 5′-S-Aryl(or Alkyl)-5′-thionucleosides Can. J. Chem. 1991, 69, 1468-1474
    • (1991) Can. J. Chem. , vol.69 , pp. 1468-1474
    • Robins, M.J.1    Hansske, F.2    Wnuk, S.F.3    Kanai, T.4
  • 29
    • 0032515081 scopus 로고    scopus 로고
    • Demonstration of Equilibrative Nucleoside Transporters (hENT1, hENT2) in Nuclear Envelopes of Cultured Human Choriocarcinoma (BeWo) Cells by Functional Reconstitution in Proteoliposomes
    • Mani, R. S.; Hammond, J. R.; Marjan, J. M. J.; Graham, K. M.; Young, J. D.; Baldwin, S. A.; Cass, C. E. Demonstration of Equilibrative Nucleoside Transporters (hENT1, hENT2) in Nuclear Envelopes of Cultured Human Choriocarcinoma (BeWo) Cells by Functional Reconstitution in Proteoliposomes J. Biol. Chem. 1998, 273, 30818-30825
    • (1998) J. Biol. Chem. , vol.273 , pp. 30818-30825
    • Mani, R.S.1    Hammond, J.R.2    Marjan, J.M.J.3    Graham, K.M.4    Young, J.D.5    Baldwin, S.A.6    Cass, C.E.7
  • 30
    • 0025366065 scopus 로고
    • Identification and Reconstitution of the Nucleoside Transporter of CEM Human Leukemia Cells
    • Crawford, C. R.; Ng, C. Y.; Ullman, B.; Belt, J. A. Identification and Reconstitution of the Nucleoside Transporter of CEM Human Leukemia Cells Biochim. Biophys. Acta 1990, 1024, 289-297
    • (1990) Biochim. Biophys. Acta , vol.1024 , pp. 289-297
    • Crawford, C.R.1    Ng, C.Y.2    Ullman, B.3    Belt, J.A.4
  • 32
    • 71349084183 scopus 로고    scopus 로고
    • Predicting Gemcitabine Transport and Toxicity in Human Pancreatic Cancer Cell Lines with the Positron Emission Tomography Tracer 3′-Deoxy-3′- fluorothymidine
    • Paproski, R. J.; Young, J. D.; Cass, C. E. Predicting Gemcitabine Transport and Toxicity in Human Pancreatic Cancer Cell Lines with the Positron Emission Tomography Tracer 3′-Deoxy-3′-fluorothymidine Biochem. Pharmacol. 2010, 79, 587-595
    • (2010) Biochem. Pharmacol. , vol.79 , pp. 587-595
    • Paproski, R.J.1    Young, J.D.2    Cass, C.E.3
  • 33
    • 34347234554 scopus 로고    scopus 로고
    • Residues 334 and 338 in Transmembrane Segment 8 of Human Equilibrative Nucleoside Transporter 1 Are Important Determinants of Inhibitor Sensitivity, Protein Folding, and Catalytic Turnover
    • Visser, F.; Sun, L.; Damaraju, V.; Tackaberry, T.; Peng, Y.; Robins, M. J.; Baldwin, S. A.; Young, J. D.; Cass, C. E. Residues 334 and 338 in Transmembrane Segment 8 of Human Equilibrative Nucleoside Transporter 1 Are Important Determinants of Inhibitor Sensitivity, Protein Folding, and Catalytic Turnover J. Biol. Chem. 2007, 282, 14148-14157
    • (2007) J. Biol. Chem. , vol.282 , pp. 14148-14157
    • Visser, F.1    Sun, L.2    Damaraju, V.3    Tackaberry, T.4    Peng, Y.5    Robins, M.J.6    Baldwin, S.A.7    Young, J.D.8    Cass, C.E.9
  • 34
    • 42049091651 scopus 로고    scopus 로고
    • Two Distinct Molecular Mechanisms Underlying Cytarabine Resistance in Human Leukemic Cells
    • Cai, J.; Damaraju, V. L.; Groulx, N.; Mowles, D.; Peng, Y.; Robins, M. J.; Cass, C. E.; Gros, P. Two Distinct Molecular Mechanisms Underlying Cytarabine Resistance in Human Leukemic Cells Cancer Res. 2008, 68, 2349-2357
    • (2008) Cancer Res. , vol.68 , pp. 2349-2357
    • Cai, J.1    Damaraju, V.L.2    Groulx, N.3    Mowles, D.4    Peng, Y.5    Robins, M.J.6    Cass, C.E.7    Gros, P.8
  • 38
    • 0347997273 scopus 로고    scopus 로고
    • Comparison of the Interaction of Uridine, Cytidine, and Other Pyrimidine Nucleoside Analogues with Recombinant Human Equilibrative Nucleoside Transporter 2 (hENT2) Produced in Saccharomyces Cerevisiae
    • Vickers, M. F.; Kumar, R.; Visser, F.; Zhang, J.; Charania, J.; Raborn, R. T.; Baldwin, S. A.; Young, J. D.; Cass, C. E. Comparison of the Interaction of Uridine, Cytidine, and Other Pyrimidine Nucleoside Analogues with Recombinant Human Equilibrative Nucleoside Transporter 2 (hENT2) Produced in Saccharomyces Cerevisiae Biochem. Cell Biol. 2002, 80, 639-644
    • (2002) Biochem. Cell Biol. , vol.80 , pp. 639-644
    • Vickers, M.F.1    Kumar, R.2    Visser, F.3    Zhang, J.4    Charania, J.5    Raborn, R.T.6    Baldwin, S.A.7    Young, J.D.8    Cass, C.E.9


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.