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Volumn 100, Issue , 2015, Pages 197-209

Synthesis and evaluation of thymidine kinase 1-targeting carboranyl pyrimidine nucleoside analogs for boron neutron capture therapy of cancer

Author keywords

Boron neutron capture therapy (BNCT); Carborane; Carboranyl pyrimidine nucleoside analog; Thymidine kinase 1 (TK1)

Indexed keywords

3 (2 AMINOETHYL)THYMIDINE; 3 (2 CYANOETHYL)THYMIDINE; 3 (3 AMINOPROPYL)THYMIDINE; 3 (3 CYANOPROPYL)THYMIDINE; 3 (4 AMINOBUTYL)THYMIDINE; 3 AMINO 3',5' BIS O (TERT BUTYLDIMETHYLSILYL)THYMIDINE; 3 AMINOTHYMIDINE; 3 [[2 [2 (CLOSO 1,7 CARBORANYL)ETHYL]AMINO] 2 OXOETHYL]THYMIDINE; 3 [[2 [2 (CLOSO 1,7 CARBORANYL)ETHYL]AMINO]ETHYL]THYMIDINE; 3 [[2 [3 (CLOSO 1,7 CARBORANYL)PROPYL]AMINO] 2 OXOETHYL]THYMIDINE; 3 [[2 [3 (CLOSO 1,7 CARBORANYL)PROPYL]AMINO]ETHYL]THYMIDINE; 3 [[2 [4 (CLOSO 1,7 CARBORANYL)BUTYL]AMINO] 2 OXOETHYL]THYMIDINE; 3 [[2 [4 (CLOSO 1,7 CARBORANYL)BUTYL]AMINO]ETHYL]THYMIDINE; 3 [[3 (CLOSO 1,7 CARBORANYL)PROPYL]AMINO]THYMIDINE; 3 [[3 [3 (CLOSO 1,7 CARBORANYL)PROPYL]AMINO]PROPYL]THYMIDINE; 3 [[3 [4 (CLOSO 1,7 CARBORANYL)BUTYL]AMINO]PROPYL]THYMIDINE; 3 [[4 [3 (CLOSO 1,7 CARBORANYL)PROPYL]AMINO]BUTYL]THYMIDINE; 3 [[4 [4 (CLOSO 1,7 CARBORANYL)BUTYL]AMINO]BUTYL]THYMIDINE; 3',5' BIS O (TERT BUTYLDIMETHYLSILYL) 3 (METHOXYCARBONYLMETHYL)THYMIDINE; 3',5' BIS O (TERT BUTYLDIMETHYLSILYL) 3 [[2 [2 (CLOSO 1,7 CARBORANYL)ETHYL]AMINO]OXOETHYL]THYMIDINE; 3',5' BIS O (TERT BUTYLDIMETHYLSILYL) 3 [[3 (CLOSO 1,7 CARBORANYL)PROPYL]AMINO]THYMIDINE; 3',5' BIS O (TERT BUTYLDIMETHYLSILYL) N4 [2 (CLOSO 1,7 CARBORANYL)ETHYL] 5 METHYL 2' DEOXYCYTIDINE; 3',5' BIS O (TERT BUTYLDIMETHYLSILYL) N4 [3 (CLOSO 1,7 CARBORANYL)PROPYL] 5 METHYL 2' DEOXYCYTIDINE; 3,5' BIS O (TERT BUTYLDIMETHYLSILYL) N4 [4 (CLOSO 1,7 CARBORANYL)BUTYL] 5 METHYL 2' DEOXYCYTIDINE; ANTINEOPLASTIC AGENT; N4 [2 (CLOSO 1,7 CARBORANYL)ETHYL] 5 METHYL 2' DEOXYCYTIDINE; N4 [3 (CLOSO 1,7 CARBORANYL)PROPYL] 5 METHYL 2' DEOXYCYTIDINE; N4 [4 (CLOSO 1,7 CARBORANYL)BUTYL] 5 METHYL 2' DEOXYCYTIDINE; PYRIMIDINE NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; BORON DERIVATIVE; PROTEIN KINASE INHIBITOR; PYRIMIDINE NUCLEOSIDE; THYMIDINE KINASE; THYMIDINE KINASE 1;

EID: 84931262600     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2015.05.042     Document Type: Article
Times cited : (30)

References (49)
  • 1
    • 0029162556 scopus 로고
    • Mammalian deoxyribonuclease kinases
    • E.S. Arne, S. Eriksson, Mammalian deoxyribonuclease kinases, Pharmacol. Ther. 67 (1995) 155-186.
    • (1995) Pharmacol. Ther. , vol.67 , pp. 155-186
    • Arne, E.S.1    Eriksson, S.2
  • 4
    • 0021612278 scopus 로고
    • Thymidine kinase of bacteria: Activity of the enzyme in actinomycetes and related organisms
    • H. Saito, H. Tomioka, Thymidine kinase of bacteria: activity of the enzyme in actinomycetes and related organisms, J. Gen. Microbiol. 130 (1984) 1863-1870.
    • (1984) J. Gen. Microbiol. , vol.130 , pp. 1863-1870
    • Saito, H.1    Tomioka, H.2
  • 7
    • 0028318194 scopus 로고
    • Different regulation of thymidine kinase during the cell cycle of normal versus DNA tumor virus-transformed cells
    • M. Hengstschlaeger, M. Knoefler, E.W. Muellner, E. Ogris, E. Wintersberger, E. Wawra, Different regulation of thymidine kinase during the cell cycle of normal versus DNA tumor virus-transformed cells, J. Biol. Chem. 269 (1994) 13836-13842.
    • (1994) J. Biol. Chem. , vol.269 , pp. 13836-13842
    • Hengstschlaeger, M.1    Knoefler, M.2    Muellner, E.W.3    Ogris, E.4    Wintersberger, E.5    Wawra, E.6
  • 8
    • 0028008605 scopus 로고
    • Thymidine kinase is expressed differently in transformed versus normal cells: A novel test for malignancy
    • M. Hengstschlaeger, E.W. Muellner, E. Wawra, Thymidine kinase is expressed differently in transformed versus normal cells: a novel test for malignancy, Int. J. Oncol. 4 (1994) 207-210.
    • (1994) Int. J. Oncol. , vol.4 , pp. 207-210
    • Hengstschlaeger, M.1    Muellner, E.W.2    Wawra, E.3
  • 9
    • 0023951483 scopus 로고
    • Regulation of human thymidine kinase during the cell cycle
    • J.L. Sherley, T.J. Kelly, Regulation of human thymidine kinase during the cell cycle, J. Biol. Chem. 263 (1988) 8350-8358.
    • (1988) J. Biol. Chem. , vol.263 , pp. 8350-8358
    • Sherley, J.L.1    Kelly, T.J.2
  • 10
    • 2342531101 scopus 로고    scopus 로고
    • Antiviral drugs in current clinical use
    • E. De Clercq, Antiviral drugs in current clinical use, J. Clin. Virol. 30 (2004) 115-133.
    • (2004) J. Clin. Virol. , vol.30 , pp. 115-133
    • De Clercq, E.1
  • 11
    • 84876842084 scopus 로고    scopus 로고
    • N3-substituted thymidine bioconjugates for cancer therapy and imaging
    • A. Khalil, K. Ishita, T. Ali, W. Tjarks, N3-substituted thymidine bioconjugates for cancer therapy and imaging, Future Med. Chem. 5 (2013) 677-692.
    • (2013) Future Med. Chem. , vol.5 , pp. 677-692
    • Khalil, A.1    Ishita, K.2    Ali, T.3    Tjarks, W.4
  • 15
    • 79960668109 scopus 로고    scopus 로고
    • second ed., Elsevier, Amsterdam
    • R.N. Grimes, Carboranes, second ed., Elsevier, Amsterdam, 2011.
    • (2011) Carboranes
    • Grimes, R.N.1
  • 16
    • 85053022040 scopus 로고    scopus 로고
    • Polyhedral boron compounds for BNCT
    • N.S. Hosmane (Ed.), CRC Press, Boca Raton, FL
    • V.I. Bregadze, I.B. Sivaev, Polyhedral boron compounds for BNCT, in: N.S. Hosmane (Ed.), Boron Science. New Technologies and Applications, CRC Press, Boca Raton, FL, 2012, pp. 181-207.
    • (2012) Boron Science. New Technologies and Applications , pp. 181-207
    • Bregadze, V.I.1    Sivaev, I.B.2
  • 20
    • 0035927239 scopus 로고    scopus 로고
    • Structure-activity study of retinoid agonists bearing substituted dicarba-closo-dodecaborane. Relation between retinoidal activity and conformation of two aromatic nuclei
    • Y. Endo, T. Iijima, K. Yaguchi, E. Kawachi, N. Inoue, H. Kagechika, A. Kubo, A. Itai, Structure-activity study of retinoid agonists bearing substituted dicarba-closo-dodecaborane. Relation between retinoidal activity and conformation of two aromatic nuclei, Bioorg. Med. Chem. Lett. 11 (2001) 1307-1311.
    • (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 1307-1311
    • Endo, Y.1    Iijima, T.2    Yaguchi, K.3    Kawachi, E.4    Inoue, N.5    Kagechika, H.6    Kubo, A.7    Itai, A.8
  • 25
    • 36749053510 scopus 로고    scopus 로고
    • Quaternary structure change as a mechanism for the regulation of thymidine kinase 1-like enzymes
    • D. Segura-Pena, J. Lichter, M. Trani, M. Konrad, A. Lavie, S. Lutz, Quaternary structure change as a mechanism for the regulation of thymidine kinase 1-like enzymes, Structure 15 (2007) 1555-1566.
    • (2007) Structure , vol.15 , pp. 1555-1566
    • Segura-Pena, D.1    Lichter, J.2    Trani, M.3    Konrad, M.4    Lavie, A.5    Lutz, S.6
  • 26
    • 33846461153 scopus 로고    scopus 로고
    • Structural studies of thymidine kinases from Bacillus anthracis and Bacillus cereus provide insights into quaternary structure and conformational changes upon substrate binding
    • U. Kosinska, C. Carnrot, M.P. Sandrini, A.R. Clausen, L. Wang, J. Piskur, S. Eriksson, H. Eklund, Structural studies of thymidine kinases from Bacillus anthracis and Bacillus cereus provide insights into quaternary structure and conformational changes upon substrate binding, FEBS J. 274 (2007) 727-737.
    • (2007) FEBS J. , vol.274 , pp. 727-737
    • Kosinska, U.1    Carnrot, C.2    Sandrini, M.P.3    Clausen, A.R.4    Wang, L.5    Piskur, J.6    Eriksson, S.7    Eklund, H.8
  • 27
    • 33748563161 scopus 로고    scopus 로고
    • 10B-enriched 3-[5-{2-(2,3-dihydroxyprop-1-yl)-o-carboran-1-yl}pentan-1-yl]thymidine (N5-2OH), a new boron delivery agent for boron neutron capture therapy of brain tumors
    • 10B-enriched 3-[5-{2-(2,3-dihydroxyprop-1-yl)-o-carboran-1-yl}pentan-1-yl]thymidine (N5-2OH), a new boron delivery agent for boron neutron capture therapy of brain tumors, J. Med. Chem. 49 (2006) 5513-5523.
    • (2006) J. Med. Chem. , vol.49 , pp. 5513-5523
    • Byun, Y.1    Thirumamagal, B.T.S.2    Yang, W.3    Eriksson, S.4    Barth, R.F.5    Tjarks, W.6
  • 29
    • 84872158022 scopus 로고    scopus 로고
    • Synthesis of N3-substituted carboranyl thymidine bioconjugates and their evaluation as substrates of recombinant human thymidine kinase 1
    • H.K. Agarwal, C.A. McElroy, E. Sjuvarsson, S. Eriksson, M.V. Darby, W. Tjarks, Synthesis of N3-substituted carboranyl thymidine bioconjugates and their evaluation as substrates of recombinant human thymidine kinase 1, Eur. J. Med. Chem. 60 (2013) 456-468.
    • (2013) Eur. J. Med. Chem. , vol.60 , pp. 456-468
    • Agarwal, H.K.1    McElroy, C.A.2    Sjuvarsson, E.3    Eriksson, S.4    Darby, M.V.5    Tjarks, W.6
  • 31
    • 13944281680 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of neutral and zwitterionic 3-carboranyl thymidine analogues for boron neutron capture therapy
    • Y. Byun, J. Yan, A.S. Al-Madhoun, J. Johnsamuel, W. Yang, R.F. Barth, S. Eriksson, W. Tjarks, Synthesis and biological evaluation of neutral and zwitterionic 3-carboranyl thymidine analogues for boron neutron capture therapy, J. Med. Chem. 48 (2005) 1188-1198.
    • (2005) J. Med. Chem. , vol.48 , pp. 1188-1198
    • Byun, Y.1    Yan, J.2    Al-Madhoun, A.S.3    Johnsamuel, J.4    Yang, W.5    Barth, R.F.6    Eriksson, S.7    Tjarks, W.8
  • 32
    • 84865717944 scopus 로고    scopus 로고
    • Synthesis, chemical and enzymatic hydrolysis, and aqueous solubility of amino acid ester prodrugs of 3-carboranyl thymidine analogs for boron neutron capture therapy of brain tumors
    • S. Hasabelnaby, A. Goudah, H.K. Agarwal, M.S. Abdalla, W. Tjarks, Synthesis, chemical and enzymatic hydrolysis, and aqueous solubility of amino acid ester prodrugs of 3-carboranyl thymidine analogs for boron neutron capture therapy of brain tumors, Eur. J. Med. Chem. 55 (2012) 325-334.
    • (2012) Eur. J. Med. Chem. , vol.55 , pp. 325-334
    • Hasabelnaby, S.1    Goudah, A.2    Agarwal, H.K.3    Abdalla, M.S.4    Tjarks, W.5
  • 33
    • 0028932657 scopus 로고
    • A new route to 15N-labeled, N-alkyl, and N-amino nucleosides via N-nitration of uridines and inosines
    • X. Ariza, V. Bou, J. Vilarrasa, A new route to 15N-labeled, N-alkyl, and N-amino nucleosides via N-nitration of uridines and inosines, J. Am. Chem. Soc. 117 (1995) 3665-3673.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 3665-3673
    • Ariza, X.1    Bou, V.2    Vilarrasa, J.3
  • 37
    • 84872324496 scopus 로고    scopus 로고
    • Remarkable stabilization of antiparallel DNA triplexes by strong stacking effects of consecutively modified nucleobases containing thiocarbonyl groups
    • K. Yamada, Y. Hattori, T. Inde, T. Kanamori, A. Ohkubo, K. Seio, M. Sekine, Remarkable stabilization of antiparallel DNA triplexes by strong stacking effects of consecutively modified nucleobases containing thiocarbonyl groups, Bioorg. Med. Chem. Lett. 23 (2013) 776-778.
    • (2013) Bioorg. Med. Chem. Lett. , vol.23 , pp. 776-778
    • Yamada, K.1    Hattori, Y.2    Inde, T.3    Kanamori, T.4    Ohkubo, A.5    Seio, K.6    Sekine, M.7
  • 38
    • 64349104062 scopus 로고    scopus 로고
    • Acyl transfer catalysis with 1,2,4-triazole anion
    • X. Yang, V.B. Birman, Acyl transfer catalysis with 1,2,4-triazole anion, Org. Lett. 11 (2009) 1499-1502.
    • (2009) Org. Lett. , vol.11 , pp. 1499-1502
    • Yang, X.1    Birman, V.B.2
  • 40
    • 77956241327 scopus 로고    scopus 로고
    • Regulation and functional contribution of thymidine kinase 1 in repair of DNA damage
    • Y.-L. Chen, S. Eriksson, Z.-F. Chang, Regulation and functional contribution of thymidine kinase 1 in repair of DNA damage, J. Biol. Chem. 285 (2010) 27327-27335.
    • (2010) J. Biol. Chem. , vol.285 , pp. 27327-27335
    • Chen, Y.-L.1    Eriksson, S.2    Chang, Z.-F.3
  • 42
    • 42349114776 scopus 로고    scopus 로고
    • Synthetic lethality by lentiviral short hairpin RNA silencing of thymidylate kinase and doxorubicin in colon cancer cells regardless of the p53 status
    • C.-M. Hu, Z.-F. Chang, Synthetic lethality by lentiviral short hairpin RNA silencing of thymidylate kinase and doxorubicin in colon cancer cells regardless of the p53 status, Cancer Res. 68 (2008) 2831-2840.
    • (2008) Cancer Res. , vol.68 , pp. 2831-2840
    • Hu, C.-M.1    Chang, Z.-F.2
  • 44
    • 0028598335 scopus 로고
    • 3-Aminothymidine inhibits growth of cultured human T-cell acute lymphoblastoid leukemia cells
    • N. Ashida, S. Asano, K. Kohda, 3-Aminothymidine inhibits growth of cultured human T-cell acute lymphoblastoid leukemia cells, Anticancer Res. 14 (1994) 2061-2062.
    • (1994) Anticancer Res. , vol.14 , pp. 2061-2062
    • Ashida, N.1    Asano, S.2    Kohda, K.3
  • 45
    • 19044398476 scopus 로고    scopus 로고
    • Nitromethane as a scavenger of acrylonitrile in the deprotection of synthetic oligonucleotides
    • T. Umemoto, T. Wada, Nitromethane as a scavenger of acrylonitrile in the deprotection of synthetic oligonucleotides, Tetrahedron Lett. 46 (2005) 4251-4253.
    • (2005) Tetrahedron Lett. , vol.46 , pp. 4251-4253
    • Umemoto, T.1    Wada, T.2
  • 48
    • 69249226362 scopus 로고    scopus 로고
    • Rat brain tumor models in experimental neuro-oncology: The C6, 9L, T9, RG2, F98, BT4C, RT-2 and CNS-1 gliomas
    • R.F. Barth, B. Kaur, Rat brain tumor models in experimental neuro-oncology: the C6, 9L, T9, RG2, F98, BT4C, RT-2 and CNS-1 gliomas, J. Neurooncol. 94 (2009) 299-312.
    • (2009) J. Neurooncol. , vol.94 , pp. 299-312
    • Barth, R.F.1    Kaur, B.2
  • 49
    • 0026162095 scopus 로고
    • Determination of boron in tissues and cells using directcurrent plasma atomic emission spectroscopy
    • R.F. Barth, D.M. Adams, A.H. Soloway, E.B. Mechetner, F. Alam, A.K.M. Anisuzzaman, Determination of boron in tissues and cells using directcurrent plasma atomic emission spectroscopy, Anal. Chem. 63 (1991) 890-893.
    • (1991) Anal. Chem. , vol.63 , pp. 890-893
    • Barth, R.F.1    Adams, D.M.2    Soloway, A.H.3    Mechetner, E.B.4    Alam, F.5    Anisuzzaman, A.K.M.6


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