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Volumn 57, Issue 1, 2014, Pages 191-203

Synthesis and cytostatic evaluation of 4-N-alkanoyl and 4-N-alkyl gemcitabine analogues

Author keywords

[No Author keywords available]

Indexed keywords

2 DEOXYCYTIDINE KINASE; 4 N (10 FLUOROUNDECANOYL) 2' DEOXY 2',2' DIFLUOROCYTIDINE; 4 N (10 UNDECANOYL) 2' DEOXY 2',2' DIFLUOROCYTIDINE; 4 N (10 UNDECENYL) 2' DEOXY 2',2' DIFLUOROCYTIDINE; 4 N (11 BENZLOXYUNDECANYL) 2' DEOXY 2',2' DIFLUOROCYTIDINE; 4 N (11 BROMOUNDECANOYL) 2' DEOXY 2',2' DIFLUOROCYTIDINE; 4 N (11 CHLOROUNDECANOYL) 2' DEOXY 2',2' DIFLUOROCYTIDINE; 4 N (11 FLUOROUNDECANOYL) 2' DEOXY 2',2' DIFLUOROCYTIDINE; 4 N (11 HYDROXYUNDECANOYL) 2' DEOXY 2',2' DIFLUOROCYTIDINE; 4 N (11 HYDROXYUNDECANYL) 2' DEOXY 2',2' DIFLUOROCYTIDINE; 4 N (8 NONENOYL) 2' DEOXY 2',2' DIFLUOROCYTIDINE; 4 N (TRIDECENOYL) 2' DEOXY 2',2' DIFLUOROCYTIDINE; 4 N (UNDECANOYL) 2' DEOXY 2',2' DIFLUOROCYTIDINE; 4 N [11 (1H BENZOTRIAZOL 1 YLOXY) UNDECANOYL] 2' DEOXY 2',2' DIFLUOROCYTIDINE; 4 TOSYLGEMCITABINE; AMINE; CARBOXYLIC ACID DERIVATIVE; CYTOSTATIC AGENT; DEOXYCYTIDINE KINASE; GEMCITABINE; GEMCITABINE DERIVATIVE; HYDROXYL GROUP; UNCLASSIFIED DRUG;

EID: 84892608365     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm401586a     Document Type: Article
Times cited : (21)

References (56)
  • 3
    • 0023935362 scopus 로고
    • Synthesis of 2-deoxy-2,2-difluoro- d -ribose and 2-deoxy-2,2′- difluoro- d -ribofuranosyl nucleosides
    • Hertel, L. W.; Kroin, J. S.; Misner, J. W.; Tustin, J. M. Synthesis of 2-deoxy-2,2-difluoro- d -ribose and 2-deoxy-2,2′-difluoro- d -ribofuranosyl nucleosides J. Org. Chem. 1988, 53, 2406-2409
    • (1988) J. Org. Chem. , vol.53 , pp. 2406-2409
    • Hertel, L.W.1    Kroin, J.S.2    Misner, J.W.3    Tustin, J.M.4
  • 4
    • 84860743457 scopus 로고    scopus 로고
    • Molecular predictors of gemcitabine response in pancreatic cancer
    • Voutsadakis, I. A. Molecular predictors of gemcitabine response in pancreatic cancer World J. Gastrointest. Oncol. 2011, 3, 153-164
    • (2011) World J. Gastrointest. Oncol. , vol.3 , pp. 153-164
    • Voutsadakis, I.A.1
  • 5
    • 42049099094 scopus 로고    scopus 로고
    • Systemic chemotherapy for advanced non-small cell lung cancer: Recent advances and future directions
    • Ramalingam, S.; Belani, C. Systemic chemotherapy for advanced non-small cell lung cancer: Recent advances and future directions Oncologist 2008, 13, 5-13
    • (2008) Oncologist , vol.13 , pp. 5-13
    • Ramalingam, S.1    Belani, C.2
  • 7
    • 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
  • 8
    • 0023783698 scopus 로고
    • Comparison of the cellular pharmacokinetics and toxicity of 2′,2′-difluorodeoxycytidine and 1-β- d - arabinofuranosylcytosine
    • Heinemann, V.; Hertel, L. W.; Grindey, G. B.; Plunkett, W. Comparison of the cellular pharmacokinetics and toxicity of 2′,2′- difluorodeoxycytidine and 1-β- d -arabinofuranosylcytosine Cancer Res. 1988, 48, 4024-4031
    • (1988) Cancer Res. , vol.48 , pp. 4024-4031
    • Heinemann, V.1    Hertel, L.W.2    Grindey, G.B.3    Plunkett, W.4
  • 10
    • 0025295958 scopus 로고
    • Modulatory activity of 2′,2′-difluorodeoxycytidine on the phosphorylation and cytotoxicity of arabinosyl nucleosides
    • Gandhi, V.; Plunkett, W. Modulatory activity of 2′,2′- difluorodeoxycytidine on the phosphorylation and cytotoxicity of arabinosyl nucleosides Cancer Res. 1990, 50, 3675-3680
    • (1990) Cancer Res. , vol.50 , pp. 3675-3680
    • Gandhi, V.1    Plunkett, W.2
  • 11
  • 12
    • 0027180521 scopus 로고
    • 2′,2′-Difluoro-deoxycytidine (gemcitabine) incorporation into RNA and DNA of tumour cell lines
    • Ruiz van Haperen, V. W. T.; Veerman, G.; Vermorken, J. B.; Peters, G. J. 2′,2′-Difluoro-deoxycytidine (gemcitabine) incorporation into RNA and DNA of tumour cell lines Biochem. Pharmacol. 1993, 46, 762-766
    • (1993) Biochem. Pharmacol. , vol.46 , pp. 762-766
    • Ruiz Van Haperen, V.W.T.1    Veerman, G.2    Vermorken, J.B.3    Peters, G.J.4
  • 13
    • 0028832342 scopus 로고
    • Gemcitabine: A modulator of intracellular nucleotide and deoxynucleotide metabolism
    • Heinemann, V.; Schulz, L.; Issels, R. D.; Plunkett, W. Gemcitabine: A modulator of intracellular nucleotide and deoxynucleotide metabolism Semin. Oncol. 1995, 22, 11-18
    • (1995) Semin. Oncol. , vol.22 , pp. 11-18
    • Heinemann, V.1    Schulz, L.2    Issels, R.D.3    Plunkett, W.4
  • 14
  • 16
    • 0025737572 scopus 로고
    • 2′-Deoxy-2′-methylenecytidine and 2′-deoxy-2′, 2′-difluorocytidine 5′-diphosphates: Potent mechanism-based inhibitors of ribonucleotide reductase
    • Baker, C. H.; Banzon, J.; Bollinger, J. M.; Stubbe, J.; Samano, V.; Robins, M. J.; Lippert, B.; Jarvi, E.; Resvick, R. 2′-Deoxy-2′- methylenecytidine and 2′-deoxy-2′,2′-difluorocytidine 5′-diphosphates: Potent mechanism-based inhibitors of ribonucleotide reductase J. Med. Chem. 1991, 34, 1879-1884
    • (1991) J. Med. Chem. , vol.34 , pp. 1879-1884
    • Baker, C.H.1    Banzon, J.2    Bollinger, J.M.3    Stubbe, J.4    Samano, V.5    Robins, M.J.6    Lippert, B.7    Jarvi, E.8    Resvick, R.9
  • 17
    • 0032554617 scopus 로고    scopus 로고
    • Gemcitabine 5′-triphosphate is a stoichiometric mechanism-based inhibitor of Lactobacillus leichmannii ribonucleoside triphosphate reductase: Evidence for thiyl radical-mediated nucleotide radical formation
    • Silva, D. J.; Stubbe, J.; Samano, V.; Robins, M. J. Gemcitabine 5′-triphosphate is a stoichiometric mechanism-based inhibitor of Lactobacillus leichmannii ribonucleoside triphosphate reductase: Evidence for thiyl radical-mediated nucleotide radical formation Biochemistry 1998, 37, 5528-5535
    • (1998) Biochemistry , vol.37 , pp. 5528-5535
    • Silva, D.J.1    Stubbe, J.2    Samano, V.3    Robins, M.J.4
  • 18
    • 0032485857 scopus 로고    scopus 로고
    • Detection of a new substrate-derived radical during inactivation of ribonucleotide reductase from Escherichia coli by gemcitabine 5′-diphosphate
    • van der Donk, W. A.; Yu, G. X.; Perez, L.; Sanchez, R. J.; Stubbe, J.; Samano, V.; Robins, M. J. Detection of a new substrate-derived radical during inactivation of ribonucleotide reductase from Escherichia coli by gemcitabine 5′-diphosphate Biochemistry 1998, 37, 6419-6426
    • (1998) Biochemistry , vol.37 , pp. 6419-6426
    • Van Der Donk, W.A.1    Yu, G.X.2    Perez, L.3    Sanchez, R.J.4    Stubbe, J.5    Samano, V.6    Robins, M.J.7
  • 19
    • 71549129302 scopus 로고    scopus 로고
    • Insight into the mechanism of inactivation of ribonucleotide reductase by gemcitabine 5′-diphosphate in the presence or absence of reductant
    • Artin, E.; Wang, J.; Lohman, G. J. S.; Yokoyama, K.; Yu, G. X.; Griffin, R. G.; Bar, G.; Stubbe, J. Insight into the mechanism of inactivation of ribonucleotide reductase by gemcitabine 5′-diphosphate in the presence or absence of reductant Biochemistry 2009, 48, 11622-11629
    • (2009) Biochemistry , vol.48 , pp. 11622-11629
    • Artin, E.1    Wang, J.2    Lohman, G.J.S.3    Yokoyama, K.4    Yu, G.X.5    Griffin, R.G.6    Bar, G.7    Stubbe, J.8
  • 20
    • 71549157751 scopus 로고    scopus 로고
    • Mechanism of inactivation of human ribonucleotide reductase with p53R2 by gemcitabine 5′-diphosphate
    • Wang, J.; Lohman, G. J. S.; Stubbe, J. Mechanism of inactivation of human ribonucleotide reductase with p53R2 by gemcitabine 5′-diphosphate Biochemistry 2009, 48, 11612-11621
    • (2009) Biochemistry , vol.48 , pp. 11612-11621
    • Wang, J.1    Lohman, G.J.S.2    Stubbe, J.3
  • 21
    • 0026465478 scopus 로고
    • Metabolism and disposition of gemcitabine, and oncolytic deoxycytidine analog, in mice, rats, and dogs
    • Shipley, L. A.; Brown, T. J.; Cornpropst, J. D.; Hamilton, M.; Daniels, W. D.; Culp, H. W. Metabolism and disposition of gemcitabine, and oncolytic deoxycytidine analog, in mice, rats, and dogs Drug Metab. Dispos. 1992, 20, 849-855
    • (1992) Drug Metab. Dispos. , vol.20 , pp. 849-855
    • Shipley, L.A.1    Brown, T.J.2    Cornpropst, J.D.3    Hamilton, M.4    Daniels, W.D.5    Culp, H.W.6
  • 22
    • 0035424877 scopus 로고    scopus 로고
    • Phase II clinical investigation of gemcitabine in advanced soft tissue sarcomas and window evaluation of dose rate on gemcitabine triphosphate accumulation
    • Patel, S. R.; Gandhi, V.; Jenkins, J.; Papadopolous, N.; Burgess, M. A.; Plager, C.; Plunkett, W.; Benjamin, R. S. Phase II clinical investigation of gemcitabine in advanced soft tissue sarcomas and window evaluation of dose rate on gemcitabine triphosphate accumulation J. Clin. Oncol. 2001, 19, 3483-3489
    • (2001) J. Clin. Oncol. , vol.19 , pp. 3483-3489
    • Patel, S.R.1    Gandhi, V.2    Jenkins, J.3    Papadopolous, N.4    Burgess, M.A.5    Plager, C.6    Plunkett, W.7    Benjamin, R.S.8
  • 23
    • 0036467995 scopus 로고    scopus 로고
    • Prolonged infusion of gemcitabine: Clinical and pharmacodynamic studies during a phase i trial in relapsed acute myelogenous leukemia
    • Gandhi, V.; Plunkett, W.; Du, M.; Ayres, M.; Estey, E. H. Prolonged infusion of gemcitabine: Clinical and pharmacodynamic studies during a phase I trial in relapsed acute myelogenous leukemia J. Clin. Oncol. 2002, 20, 665-673
    • (2002) J. Clin. Oncol. , vol.20 , pp. 665-673
    • Gandhi, V.1    Plunkett, W.2    Du, M.3    Ayres, M.4    Estey, E.H.5
  • 24
    • 84880648722 scopus 로고    scopus 로고
    • Advances in the development of nucleoside and nucleotide analogues for cancer and viral diseases
    • Jordheim, L. P.; Durantel, D.; Zoulim, F.; Dumontet, C. Advances in the development of nucleoside and nucleotide analogues for cancer and viral diseases Nat. Rev. Drug Discovery 2013, 12, 447-464
    • (2013) Nat. Rev. Drug Discovery , vol.12 , pp. 447-464
    • Jordheim, L.P.1    Durantel, D.2    Zoulim, F.3    Dumontet, C.4
  • 28
    • 9644302465 scopus 로고    scopus 로고
    • Preparation, characterization, cytotoxicity and pharmacokinetics of liposomes containing lipophilic gemcitabine prodrugs
    • Immordino, M. L.; Brusa, P.; Rocco, F.; Arpicco, S.; Ceruti, M.; Cattel, L. Preparation, characterization, cytotoxicity and pharmacokinetics of liposomes containing lipophilic gemcitabine prodrugs J. Controlled Release 2004, 100, 331-346
    • (2004) J. Controlled Release , vol.100 , pp. 331-346
    • Immordino, M.L.1    Brusa, P.2    Rocco, F.3    Arpicco, S.4    Ceruti, M.5    Cattel, L.6
  • 30
    • 84874865201 scopus 로고    scopus 로고
    • Human carboxylesterase-2 hydrolyzes the prodrug of gemcitabine (LY2334737) and confers prodrug sensitivity to cancer cells
    • Pratt, S. E.; Durland-Busbice, S.; Shepard, R. L.; Heinz-Taheny, K.; Iversen, P. W.; Dantzig, A. H. Human carboxylesterase-2 hydrolyzes the prodrug of gemcitabine (LY2334737) and confers prodrug sensitivity to cancer cells Clin. Cancer Res. 2013, 19, 1159-1168
    • (2013) Clin. Cancer Res. , vol.19 , pp. 1159-1168
    • Pratt, S.E.1    Durland-Busbice, S.2    Shepard, R.L.3    Heinz-Taheny, K.4    Iversen, P.W.5    Dantzig, A.H.6
  • 31
    • 82255175232 scopus 로고    scopus 로고
    • Squalenoyl gemcitabine nanomedicine overcomes the low efficacy of gemcitabine therapy in pancreatic cancer
    • Rejiba, S.; Reddy, L. H.; Bigand, C.; Parmentier, C.; Couvreur, P.; Hajri, A. Squalenoyl gemcitabine nanomedicine overcomes the low efficacy of gemcitabine therapy in pancreatic cancer Nanomedicine 2011, 7, 841-849
    • (2011) Nanomedicine , vol.7 , pp. 841-849
    • Rejiba, S.1    Reddy, L.H.2    Bigand, C.3    Parmentier, C.4    Couvreur, P.5    Hajri, A.6
  • 32
    • 84877745217 scopus 로고    scopus 로고
    • Preclinical absorption, distribution, metabolism, and excretion of an oral amide prodrug of gemcitabine designed to deliver prolonged systemic exposure
    • Wickremsinhe, E.; Bao, J.; Smith, R.; Burton, R.; Dow, S.; Perkins, E. Preclinical absorption, distribution, metabolism, and excretion of an oral amide prodrug of gemcitabine designed to deliver prolonged systemic exposure Pharmaceutics 2013, 5, 261-276
    • (2013) Pharmaceutics , vol.5 , pp. 261-276
    • Wickremsinhe, E.1    Bao, J.2    Smith, R.3    Burton, R.4    Dow, S.5    Perkins, E.6
  • 35
    • 84875480413 scopus 로고    scopus 로고
    • Gemcitabine-coumarin-biotin conjugates: A target specific theranostic anticancer prodrug
    • Maiti, S.; Park, N.; Han, J. H.; Jeon, H. M.; Lee, J. H.; Bhuniya, S.; Kang, C.; Kim, J. S. Gemcitabine-coumarin-biotin conjugates: A target specific theranostic anticancer prodrug J. Am. Chem. Soc. 2013, 135, 4567-4572
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 4567-4572
    • Maiti, S.1    Park, N.2    Han, J.H.3    Jeon, H.M.4    Lee, J.H.5    Bhuniya, S.6    Kang, C.7    Kim, J.S.8
  • 36
    • 84880340647 scopus 로고    scopus 로고
    • A fluorescence off-on reporter for real time monitoring of gemcitabine delivery to the cancer cells
    • Bhuniya, S.; Lee, M. H.; Jeon, H. M.; Han, J. H.; Lee, J. H.; Park, N.; Maiti, S.; Kang, C.; Kim, J. S. A fluorescence off-on reporter for real time monitoring of gemcitabine delivery to the cancer cells Chem. Commun. 2013, 49, 7141-7143
    • (2013) Chem. Commun. , vol.49 , pp. 7141-7143
    • Bhuniya, S.1    Lee, M.H.2    Jeon, H.M.3    Han, J.H.4    Lee, J.H.5    Park, N.6    Maiti, S.7    Kang, C.8    Kim, J.S.9
  • 40
    • 46749110051 scopus 로고    scopus 로고
    • Molecular imaging of lymphoid organs and immune activation by positron emission tomography with a new [(18)F]-labeled 2′-deoxycytidine analog
    • Radu, C. G.; Shu, C. J.; Nair-Gill, E.; Shelly, S. M.; Barrio, J. R.; Satyamurthy, N.; Phelps, M. E.; Witte, O. N. Molecular imaging of lymphoid organs and immune activation by positron emission tomography with a new [(18)F]-labeled 2′-deoxycytidine analog Nature Med. 2008, 14, 783-788
    • (2008) Nature Med. , vol.14 , pp. 783-788
    • Radu, C.G.1    Shu, C.J.2    Nair-Gill, E.3    Shelly, S.M.4    Barrio, J.R.5    Satyamurthy, N.6    Phelps, M.E.7    Witte, O.N.8
  • 42
    • 84863054683 scopus 로고    scopus 로고
    • Stratification of nucleoside analog chemotherapy using 1-(2′-deoxy-2′-F-18-fluoro-beta- d -arabinofuranosyl)cytosine and 1-(2′-deoxy-2′-F-18-fluoro-beta- l -arabinofuranosyl)-5- methylcytosine PET
    • Lee, J. T.; Campbell, D. O.; Satyamurthy, N.; Czernin, J.; Radu, C. G. Stratification of nucleoside analog chemotherapy using 1-(2′-deoxy- 2′-F-18-fluoro-beta- d -arabinofuranosyl)cytosine and 1-(2′-deoxy- 2′-F-18-fluoro-beta- l -arabinofuranosyl)-5-methylcytosine PET J. Nucl. Med. 2012, 53, 275-280
    • (2012) J. Nucl. Med. , vol.53 , pp. 275-280
    • Lee, J.T.1    Campbell, D.O.2    Satyamurthy, N.3    Czernin, J.4    Radu, C.G.5
  • 43
  • 44
    • 0028818648 scopus 로고
    • A simple method for N-acylation of adenosine and cytidine nucleosides using carboxylic acids activated in-situ with carbonyldiimidazole
    • Sinha, N. D.; Davis, P.; Schultze, L. M.; Upadhya, K. A simple method for N-acylation of adenosine and cytidine nucleosides using carboxylic acids activated in-situ with carbonyldiimidazole Tetrahedron Lett. 1995, 36, 9277-9280
    • (1995) Tetrahedron Lett. , vol.36 , pp. 9277-9280
    • Sinha, N.D.1    Davis, P.2    Schultze, L.M.3    Upadhya, K.4
  • 45
    • 0038330762 scopus 로고    scopus 로고
    • An improved transient method for the synthesis of N-benzoylated nucleosides
    • Zhu, X. F.; Williams, H. J.; Scott, A. I. An improved transient method for the synthesis of N-benzoylated nucleosides Synth. Commun. 2003, 33, 1233-1243
    • (2003) Synth. Commun. , vol.33 , pp. 1233-1243
    • Zhu, X.F.1    Williams, H.J.2    Scott, A.I.3
  • 46
    • 0033615679 scopus 로고    scopus 로고
    • Selective protection of 2′,2′-difluorodeoxycytidine (gemcitabine)
    • Guo, Z. W.; Gallo, J. M. Selective protection of 2′,2′- difluorodeoxycytidine (gemcitabine) J. Org. Chem. 1999, 64, 8319-8322
    • (1999) J. Org. Chem. , vol.64 , pp. 8319-8322
    • Guo, Z.W.1    Gallo, J.M.2
  • 47
    • 77956556566 scopus 로고    scopus 로고
    • Synthesis of geminal difluorides by oxidative desulfurization- difluorination of alkyl aryl thioethers with halonium electrophiles in the presence of fluorinating reagents and its application for 18F-radiolabeling
    • Hugenberg, V.; Wagner, S.; Kopka, K.; Schober, O.; Schafers, M.; Haufe, G. Synthesis of geminal difluorides by oxidative desulfurization-difluorination of alkyl aryl thioethers with halonium electrophiles in the presence of fluorinating reagents and its application for 18F-radiolabeling J. Org. Chem. 2010, 75, 6086-6095
    • (2010) J. Org. Chem. , vol.75 , pp. 6086-6095
    • Hugenberg, V.1    Wagner, S.2    Kopka, K.3    Schober, O.4    Schafers, M.5    Haufe, G.6
  • 48
    • 0037014698 scopus 로고    scopus 로고
    • Stable dialkyl ether/poly(hydrogen fluoride) complexes: Dimethyl ether/poly(hydrogen fluoride), a new, convenient, and effective fluorinating agent
    • Bucsi, I.; Torok, B.; Marco, A. I.; Rasul, G.; Prakash, G. K.; Olah, G. A. Stable dialkyl ether/poly(hydrogen fluoride) complexes: Dimethyl ether/poly(hydrogen fluoride), a new, convenient, and effective fluorinating agent J. Am. Chem. Soc. 2002, 124, 7728-7736
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 7728-7736
    • Bucsi, I.1    Torok, B.2    Marco, A.I.3    Rasul, G.4    Prakash, G.K.5    Olah, G.A.6
  • 49
    • 84882268052 scopus 로고    scopus 로고
    • Introduction of fluorine and fluorine-containing functional groups
    • Liang, T.; Neumann, C. N.; Ritter, T. Introduction of fluorine and fluorine-containing functional groups Angew. Chem., Int. Ed. 2013, 52, 8214-8264
    • (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 8214-8264
    • Liang, T.1    Neumann, C.N.2    Ritter, T.3
  • 51
    • 0016687175 scopus 로고
    • Alkylated cytosine nucleosides: Substrate and inhibitor properties in enzymatic deamination
    • Krajewska, E.; Shugar, D. Alkylated cytosine nucleosides: Substrate and inhibitor properties in enzymatic deamination Acta Biochim. Pol. 1975, 22, 185-194
    • (1975) Acta Biochim. Pol. , vol.22 , pp. 185-194
    • Krajewska, E.1    Shugar, D.2
  • 53
    • 13444283619 scopus 로고    scopus 로고
    • Phototriggering of caged fluorescent oligodeoxynucleotides
    • Tang, X. J.; Dmochowski, I. J. Phototriggering of caged fluorescent oligodeoxynucleotides Org. Lett. 2005, 7, 279-282
    • (2005) Org. Lett. , vol.7 , pp. 279-282
    • Tang, X.J.1    Dmochowski, I.J.2
  • 55
    • 0022655279 scopus 로고
    • Synthesis of 4-mono- and dialkyl-2′-deoxycytidines and their insertion into an oligonucleotide
    • Kraszewski, A.; Delort, A. M.; Teoule, R. Synthesis of 4-mono- and dialkyl-2′-deoxycytidines and their insertion into an oligonucleotide Tetrahedron Lett. 1986, 27, 861-864
    • (1986) Tetrahedron Lett. , vol.27 , pp. 861-864
    • Kraszewski, A.1    Delort, A.M.2    Teoule, R.3
  • 56
    • 77956196117 scopus 로고    scopus 로고
    • Synthesis and preliminary evaluation of 18-F-18-fluoro-4-thia-oleate as a PET probe of fatty acid oxidation
    • DeGrado, T. R.; Bhattacharyya, F.; Pandey, M. K.; Belanger, A. P.; Wang, S. Y. Synthesis and preliminary evaluation of 18-F-18-fluoro-4-thia-oleate as a PET probe of fatty acid oxidation J. Nucl. Med. 2010, 51, 1310-1317
    • (2010) J. Nucl. Med. , vol.51 , pp. 1310-1317
    • Degrado, T.R.1    Bhattacharyya, F.2    Pandey, M.K.3    Belanger, A.P.4    Wang, S.Y.5


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