메뉴 건너뛰기




Volumn 53, Issue 7, 2010, Pages 2902-2912

3′-[4-Aryl-(1,2,3-triazol-1-yl)]-3′-deoxythymidine analogues as potent and selective inhibitors of human mitochondrial thymidine kinase

Author keywords

[No Author keywords available]

Indexed keywords

1,4 TRIAZOLE DERIVATIVE; 1,5 TRIAZOLE DERIVATIVE; 2,3' ANHYDRO 5' O TRIPHENYLMETHYL BETA 5 (2 BROMOVINYL) 2' DEOXYURIDINE; 3 ' AZIDO 3' DEOXY BETA 5 (2 BROMOVINYL) 2' DEOXYURIDINE; 3' (4 BENZYL 1,2,3 TRIAZOL 1 YL) 3' DEOXY BETA DEXTRO THYMIDINE; 3' (4 BUTYL 1,2,3 TRIAZOL 1 YL) 3' DEOXY BETA DEXTRO THYMIDINE; 3' (4 CHLOROPHENYL 1,2,3 TRIAZOL 1 YL) 3' DEOXY BETA 5 (2 BROMOVINYL) 2' DEOXYURIDINE; 3' (4 CHLOROPHENYL 1,2,3 TRIAZOL 1 YL) 3' DEOXY BETA DEXTRO THYMIDINE; 3' (4 CYLOPENTYLMETHYL 1,2,3 TRIAZOL 1 YL) 3' DEOXY BETA DEXTRO THYMIDINE; 3' [4 5 (2 BROMOVINYL)(1,2,3 TRIAZOL 1 YL)] 3' DEOXYTHYMIDINE; 3' [5 (4 CHLOROPHENYL 1,2,3 TRIAZOL 1 YL] 3' DEOXY BETA DEXTRO THYMIDINE; 3' AZIDO 3' DEOXY 5' O TRIPHENYLMETHYL BETA 5 (2 BROMOVINYL)2' DEOXYURIDINE; 3' DEOXY 3' (4 PHENYL 1,2,3 TRIAZOL 1 YL) 3' DEOXY BETA DEXTRO THYMIDINE; 3' DEOXY 3' (4 PHENYL 1,2,3 TRIAZOL 1 YL) BETA 5 (2 BROMOVINYL) 2' DEOXYURIDINE; 3' DEOXY 3' [4 (3,4 DICHLOROPHENYL) 1,2,3 TRIAZOL 1 YL]BETA DEXTRO THYMIDINE; 3' DEOXY 3' [4 PYRIDIN 2 YL 1,2,3 TRIAZOL 1 YL]BETA DEXTRO THYMIDINE; 3' DEOXY 3' [5 PHENYL 1,2,3 TRIAZOL 1 YL]BETA DEXTRO THYMIDINE; 5' O TRIPHENYLMETHYL BETA 5 (2 BROMOVINYL) 2' DEOXYURIDINE; ADENOSINE TRIPHOSPHATE; ALKYNE DERIVATIVE; COPPER; MITOCHONDRIAL ENZYME; RUTHENIUM; THYMIDINE DERIVATIVE; THYMIDINE KINASE; THYMIDINE KINASE 1; THYMIDINE KINASE 2; THYMIDINE KINASE INHIBITOR; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; ZIDOVUDINE; DRUG DERIVATIVE; ENZYME INHIBITOR; THYMIDINE;

EID: 77950558113     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm901532h     Document Type: Article
Times cited : (37)

References (44)
  • 2
    • 3042520589 scopus 로고    scopus 로고
    • The role of thymidine kinases in the activation of pyrimidine nucleoside analogs
    • Al-Madhoun, A. S.; Tjarks, W.; Eriksson, S. The role of thymidine kinases in the activation of pyrimidine nucleoside analogs Mini Rev. Med. Chem. 2004, 4, 341 - 350
    • (2004) Mini Rev. Med. Chem. , vol.4 , pp. 341-350
    • Al-Madhoun, A.S.1    Tjarks, W.2    Eriksson, S.3
  • 3
    • 0035179561 scopus 로고    scopus 로고
    • Mutant mitochondrial thymidine kinase in mitochondrial DNA depletion myopathy
    • Saada, A.; Shaag, A.; Mandel, H.; Nevo, Y.; Eriksson, S.; Elpeleg, O. Mutant mitochondrial thymidine kinase in mitochondrial DNA depletion myopathy Nat. Genet. 2001, 29, 342 - 344
    • (2001) Nat. Genet. , vol.29 , pp. 342-344
    • Saada, A.1    Shaag, A.2    Mandel, H.3    Nevo, Y.4    Eriksson, S.5    Elpeleg, O.6
  • 4
    • 0028990381 scopus 로고
    • Mitochondrial toxicity of antiviral drugs
    • Lewis, W.; Dalakas, M. C. Mitochondrial toxicity of antiviral drugs Nat. Med. 1995, 1, 417 - 422
    • (1995) Nat. Med. , vol.1 , pp. 417-422
    • Lewis, W.1    Dalakas, M.C.2
  • 5
    • 0242363266 scopus 로고    scopus 로고
    • Mitochondrial toxicity of NRTI antiviral drugs: An integrated cellular perspective
    • Lewis, W.; Day, B. J.; Copeland, W. C. Mitochondrial toxicity of NRTI antiviral drugs: An integrated cellular perspective Nature Rev. Drug Discovery 2003, 2, 812 - 822
    • (2003) Nature Rev. Drug Discovery , vol.2 , pp. 812-822
    • Lewis, W.1    Day, B.J.2    Copeland, W.C.3
  • 6
    • 0034306265 scopus 로고    scopus 로고
    • Novel ribofuranosylnucleoside lead compounds for potent and selective inhibitors of mitochondrial thymidine kinase-2
    • Balzarini, J.; Zhu, C. Y.; De Clercq, E.; Pérez-Pérez, M. J.; Chamorro, C.; Camarasa, M. J.; Karlsson, A. Novel ribofuranosylnucleoside lead compounds for potent and selective inhibitors of mitochondrial thymidine kinase-2 Biochem. J. 2000, 351, 167 - 171
    • (2000) Biochem. J. , vol.351 , pp. 167-171
    • Balzarini, J.1    Zhu, C.Y.2    De Clercq, E.3    Pérez-Pérez, M.J.4    Chamorro, C.5    Camarasa, M.J.6    Karlsson, A.7
  • 7
    • 0032839923 scopus 로고    scopus 로고
    • Substrate/inhibitor properties of human deoxycytidine kinase (dCK) and thymidine kinase (TK1 and TK2) towards the sugar moiety of nucleosides, including O ′-alkyl analogues
    • Kierdaszuk, B.; Krawiec, K.; Kazimierczuk, Z.; Jacobsson, U.; Johansson, N. G.; Munch-Petersen, B.; Eriksson, S.; Shugar, D. Substrate/inhibitor properties of human deoxycytidine kinase (dCK) and thymidine kinase (TK1 and TK2) towards the sugar moiety of nucleosides, including O ′-alkyl analogues Nucleosides, Nucleotides Nucleic Acids 1999, 18, 1883 - 1903
    • (1999) Nucleosides, Nucleotides Nucleic Acids , vol.18 , pp. 1883-1903
    • Kierdaszuk, B.1    Krawiec, K.2    Kazimierczuk, Z.3    Jacobsson, U.4    Johansson, N.G.5    Munch-Petersen, B.6    Eriksson, S.7    Shugar, D.8
  • 8
    • 0035866551 scopus 로고    scopus 로고
    • 2′-O-acyl/alkyl-substituted arabinosyl nucleosides as inhibitors of human mitochondrial thymidine kinase
    • DOI 10.1016/S0006-2952(01)00529-9, PII S0006295201005299
    • Balzarini, J.; Degrève, B.; Zhu, C. Y.; Durini, E.; Porcu, L.; De Clercq, E.; Karlsson, A.; Manfredini, S. 2′- O -Acyl/alkyl-substituted arabinosyl nucleosides as inhibitor of human mitochondrial thymidine kinase Biochem. Pharmacol. 2001, 61, 727 - 732 (Pubitemid 32239426)
    • (2001) Biochemical Pharmacology , vol.61 , Issue.6 , pp. 727-732
    • Balzarinia, J.1    Degreve, B.2    Zhu, C.3    Durini, E.4    Porcu, L.5    De Clercq, E.6    Karlsson, A.7    Manfredini, S.8
  • 11
    • 66049117566 scopus 로고    scopus 로고
    • Human mitochondrial thymidine kinase is selectively inhibited by 3′-thiourea derivatives of beta-thymidine: Identification of residues crucial for both inhibition and catalytic activity
    • Balzarini, J.; Van Daele, I.; Negri, A.; Solaroli, N.; Karlsson, A.; Liekens, S.; Gago, F.; Van Calenbergh, S. Human mitochondrial thymidine kinase is selectively inhibited by 3′-thiourea derivatives of beta-thymidine: identification of residues crucial for both inhibition and catalytic activity Mol. Pharmacol. 2009, 75, 1127 - 1136
    • (2009) Mol. Pharmacol. , vol.75 , pp. 1127-1136
    • Balzarini, J.1    Van Daele, I.2    Negri, A.3    Solaroli, N.4    Karlsson, A.5    Liekens, S.6    Gago, F.7    Van Calenbergh, S.8
  • 12
    • 1442274747 scopus 로고    scopus 로고
    • Comparative cytotoxicity of N -substituted N ′-(4-imidazole-ethyl)- thiourea in precision-cut rat liver slices
    • Onderwater, R. C. A.; Commandeur, J. N. M.; Vermeulen, N. P. E. Comparative cytotoxicity of N -substituted N ′-(4-imidazole-ethyl)- thiourea in precision-cut rat liver slices Toxicology 2004, 197, 80 - 90
    • (2004) Toxicology , vol.197 , pp. 80-90
    • Onderwater, R.C.A.1    Commandeur, J.N.M.2    Vermeulen, N.P.E.3
  • 13
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes
    • Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes Angew. Chem., Int. Ed. 2002, 41, 2596 - 2599
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, K.B.4
  • 14
    • 0037012920 scopus 로고    scopus 로고
    • Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes to azides
    • Tornøe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes to azides J. Org. Chem. 2002, 67, 3057 - 3064
    • (2002) J. Org. Chem. , vol.67 , pp. 3057-3064
    • Tornoøe, C.W.1
  • 15
    • 39549111477 scopus 로고    scopus 로고
    • Click chemistry reactions in medicinal chemistry: Applications of the 1,3-dipolar cycloaddition between azides and alkynes
    • Tron, G. C.; Pirali, T.; Billington, R. A.; Canonico, P. L.; Sorba, G.; Genazzani, A. A. Click chemistry reactions in medicinal chemistry: applications of the 1,3-dipolar cycloaddition between azides and alkynes Med. Res. Rev. 2008, 28, 278 - 308
    • (2008) Med. Res. Rev. , vol.28 , pp. 278-308
    • Tron, G.C.1    Pirali, T.2    Billington, R.A.3    Canonico, P.L.4    Sorba, G.5    Genazzani, A.A.6
  • 16
    • 0037462409 scopus 로고    scopus 로고
    • Click chemistry to construct fluorescent oligonucleotides for DNA sequencing
    • Seo, T. S.; Li, Z.; Ruparel, H.; Ju, J. Click chemistry to construct fluorescent oligonucleotides for DNA sequencing J. Org. Chem. 2003, 68, 609 - 612
    • (2003) J. Org. Chem. , vol.68 , pp. 609-612
    • Seo, T.S.1    Li, Z.2    Ruparel, H.3    Ju, J.4
  • 17
    • 0042125393 scopus 로고    scopus 로고
    • A potent and highly selective inhibitor of human α-1,3- fucosyltransferase via click chemistry
    • Lee, L. V.; Mitchell, M. L.; Huang, S. J.; Fokin, V. V.; Sharpless, K. B.; Wong, C. H. A potent and highly selective inhibitor of human α-1,3-fucosyltransferase via click chemistry J. Am. Chem. Soc. 2003, 125, 9588 - 9589
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 9588-9589
    • Lee, L.V.1    Mitchell, M.L.2    Huang, S.J.3    Fokin, V.V.4    Sharpless, K.B.5    Wong, C.H.6
  • 18
    • 33748609388 scopus 로고    scopus 로고
    • Click chemistry as a reliable method for the high-density postsynthetic functionalization of alkyne-modified
    • Gierlich, J.; Burley, G. A.; Gramlich, P. M. E.; Hammond, D. M.; Carell, T. Click chemistry as a reliable method for the high-density postsynthetic functionalization of alkyne-modified DNA Org. Lett. 2006, 8, 3639 - 3642
    • (2006) DNA Org. Lett. , vol.8 , pp. 3639-3642
    • Gierlich, J.1    Burley, G.A.2    Gramlich, P.M.E.3    Hammond, D.M.4    Carell, T.5
  • 19
    • 33751550874 scopus 로고    scopus 로고
    • Synthesis of coumarin-nucleoside conjugates via Huisgen 1,3-dipolar cycloaddition
    • Kosiova, I.; Kovackova, S.; Kois, P. Synthesis of coumarin-nucleoside conjugates via Huisgen 1,3-dipolar cycloaddition Tetrahedron 2007, 63, 312 - 320
    • (2007) Tetrahedron , vol.63 , pp. 312-320
    • Kosiova, I.1    Kovackova, S.2    Kois, P.3
  • 20
    • 34250023096 scopus 로고    scopus 로고
    • Nucleosides and oligonucleotides with diynyl side chains: Base pairing and functionalization of 2′-deoxyuridine derivatives by the copper(I)-catalyzed alkyne-azide "click" cycloaddition
    • Seela, F.; Sirivolu, V. R. Nucleosides and oligonucleotides with diynyl side chains: Base pairing and functionalization of 2′-deoxyuridine derivatives by the copper(I)-catalyzed alkyne-azide "click" cycloaddition Helv. Chim. Acta 2007, 90, 535 - 552
    • (2007) Helv. Chim. Acta , vol.90 , pp. 535-552
    • Seela, F.1    Sirivolu, V.R.2
  • 21
    • 54849405215 scopus 로고    scopus 로고
    • Self-organizing oligothiophene-nucleoside conjugates: Versatile synthesis via "click"-chemistry
    • Jatsch, A.; Kopyshev, A.; Mena-Osteritz, E.; Baeuerle, P. Self-organizing oligothiophene-nucleoside conjugates: versatile synthesis via "click"-chemistry Org. Lett. 2008, 10, 961 - 964
    • (2008) Org. Lett. , vol.10 , pp. 961-964
    • Jatsch, A.1    Kopyshev, A.2    Mena-Osteritz, E.3    Baeuerle, P.4
  • 22
    • 33845481152 scopus 로고    scopus 로고
    • 2-Triazole-substituted adenosines: A new class of selective A(3) adenosine receptor agonists, partial agonists, and antagonists
    • Cosyn, L.; Palaniappan, K. K.; Kim, S.-K.; Duong, H. T.; Gao, Z. G.; Jacobson, K. A.; Van Calenbergh, S. 2-Triazole-substituted adenosines: a new class of selective A(3) adenosine receptor agonists, partial agonists, and antagonists J. Med. Chem. 2006, 49, 7373 - 7383
    • (2006) J. Med. Chem. , vol.49 , pp. 7373-7383
    • Cosyn, L.1    Palaniappan, K.K.2    Kim, S.-K.3    Duong, H.T.4    Gao, Z.G.5    Jacobson, K.A.6    Van Calenbergh, S.7
  • 23
    • 34248994947 scopus 로고    scopus 로고
    • Synthesis of bitriazolyl nucleosides and unexpectedly different reactivity of azidotriazole nucleoside isomers in the Huisgen reaction
    • Xia, Y.; Li, W.; Qu, F.; Fan, Z.; Liu, X.; Berro, C.; Rauzy, E.; Peng, L. Synthesis of bitriazolyl nucleosides and unexpectedly different reactivity of azidotriazole nucleoside isomers in the Huisgen reaction Org. Biomol. Chem. 2007, 5, 1695 - 1701
    • (2007) Org. Biomol. Chem. , vol.5 , pp. 1695-1701
    • Xia, Y.1    Li, W.2    Qu, F.3    Fan, Z.4    Liu, X.5    Berro, C.6    Rauzy, E.7    Peng, L.8
  • 24
    • 44749089222 scopus 로고    scopus 로고
    • A concise route for the preparation of nucleobase-simplified cADPR mimics by click chemistry
    • Li, L.; Lin, B.; Yang, Z.; Zhang, L.; Zhang, L. A concise route for the preparation of nucleobase-simplified cADPR mimics by click chemistry Tetrahedron Lett. 2008, 49, 4491 - 4493
    • (2008) Tetrahedron Lett. , vol.49 , pp. 4491-4493
    • Li, L.1    Lin, B.2    Yang, Z.3    Zhang, L.4    Zhang, L.5
  • 27
    • 38349164488 scopus 로고    scopus 로고
    • Study of copper(I) catalysts for the synthesis of carbanucleosides via azide-alkyne 1,3-dipolar cycloaddition
    • Broggi, J.; Diez-Gonzalez, S.; Petersen, J. L.; Berteina-Raboin, S.; Nolan, S. P.; Agrofoglio, L. A. Study of copper(I) catalysts for the synthesis of carbanucleosides via azide-alkyne 1,3-dipolar cycloaddition Synthesis 2008, 141 - 148
    • (2008) Synthesis , pp. 141-148
    • Broggi, J.1    Diez-Gonzalez, S.2    Petersen, J.L.3    Berteina-Raboin, S.4    Nolan, S.P.5    Agrofoglio, L.A.6
  • 28
    • 34249794857 scopus 로고    scopus 로고
    • Template-directed oligonucleotide strand ligation, covalent intramolecular DNA circularization and catenation using click chemistry
    • Kumar, R.; El-Sagheer, A.; Tumpane, J.; Lincoln, P.; Wilhelmsson, L. M.; Brown, T. Template-directed oligonucleotide strand ligation, covalent intramolecular DNA circularization and catenation using click chemistry J. Am. Chem. Soc. 2007, 129, 6859 - 6864
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 6859-6864
    • Kumar, R.1    El-Sagheer, A.2    Tumpane, J.3    Lincoln, P.4    Wilhelmsson, L.M.5    Brown, T.6
  • 29
  • 30
    • 70349144073 scopus 로고    scopus 로고
    • Cu(I)-catalyzed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in nucleoside, nucleotide, and oligonucleotide chemistry
    • Amblard, F.; Cho, J. H.; Schinazi, R. F. Cu(I)-catalyzed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in nucleoside, nucleotide, and oligonucleotide chemistry Chem. Rev. 2009, 109, 4207 - 4220
    • (2009) Chem. Rev. , vol.109 , pp. 4207-4220
    • Amblard, F.1    Cho, J.H.2    Schinazi, R.F.3
  • 33
    • 0024956123 scopus 로고
    • 3′-(1,2,3-Triazol-1-yl)-2′,3′-dideoxythymidine and 3′-(1,2,3-triazol-1-yl)-2′,3′-dideoxyuridine
    • Wigerinck, P.; Van Aerschot, A.; Claes, P.; Balzarini, J.; De Clercq, E.; Herdewijn, P. 3′-(1,2,3-Triazol-1-yl)-2′,3′-dideoxythymidine and 3′-(1,2,3-triazol-1-yl)-2′,3′-dideoxyuridine J. Heterocycl. Chem. 1989, 26, 1635 - 1642
    • (1989) J. Heterocycl. Chem. , vol.26 , pp. 1635-1642
    • Wigerinck, P.1    Van Aerschot, A.2    Claes, P.3    Balzarini, J.4    De Clercq, E.5    Herdewijn, P.6
  • 36
    • 42449151667 scopus 로고    scopus 로고
    • Structural studies of nucleoside analog and feedback inhibitor binding to Drosophila melanogaster multisubstrate deoxyribonucleoside kinase
    • Mikkelsen, N. E.; Munh-Petersen, B.; Eklund, H. Structural studies of nucleoside analog and feedback inhibitor binding to Drosophila melanogaster multisubstrate deoxyribonucleoside kinase FEBS J. 2008, 275, 2151 - 2160
    • (2008) FEBS J. , vol.275 , pp. 2151-2160
    • Mikkelsen, N.E.1    Munh-Petersen, B.2    Eklund, H.3
  • 37
    • 33847369015 scopus 로고    scopus 로고
    • Functional studies of active-site mutants from Drosophila melanogaster deoxyribonucleoside kinase. Investigations of the putative catalytic glutamate-arginine pair and of residues responsible for substrate specificity
    • Egeblad-Welin, L.; Sonntag, Y.; Eklund, H.; Munch-Petersen, B. Functional studies of active-site mutants from Drosophila melanogaster deoxyribonucleoside kinase. Investigations of the putative catalytic glutamate-arginine pair and of residues responsible for substrate specificity FEBS J. 2007, 274, 1542 - 51
    • (2007) FEBS J. , vol.274 , pp. 1542-51
    • Egeblad-Welin, L.1    Sonntag, Y.2    Eklund, H.3    Munch-Petersen, B.4
  • 39
    • 3042524904 scopus 로고
    • A well-behaved electrostatic potential based method using charge-restraints for deriving charges: The RESP model
    • Bayly, C. I.; Cieplak, P.; Cornell, W. D.; Kollman, P. A. A well-behaved electrostatic potential based method using charge-restraints for deriving charges: The RESP model J. Phys. Chem. 1993, 97, 10269 - 10280
    • (1993) J. Phys. Chem. , vol.97 , pp. 10269-10280
    • Bayly, C.I.1    Cieplak, P.2    Cornell, W.D.3    Kollman, P.A.4
  • 43
    • 0344796204 scopus 로고
    • Ion-water interaction potentials derived from free energy perturbation simulations
    • Aqvist, J. Ion-water interaction potentials derived from free energy perturbation simulations J. Phys. Chem. 1990, 94, 8021 - 8024
    • (1990) J. Phys. Chem. , vol.94 , pp. 8021-8024
    • Aqvist, J.1
  • 44
    • 77950593041 scopus 로고    scopus 로고
    • DeLano scientific LLC
    • version 0.99;: Palo Alto, CA.
    • De Lano, W. PyMOL version 0.99; DeLano Scientific LLC: Palo Alto, CA, 2006; http://www.pymol.org/.
    • (2006) PyMOL
    • De Lano, W.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.