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Volumn 5, Issue , 2014, Pages

Extracellular palladium-catalysed dealkylation of 5-fluoro-1-propargyl-uracil as a bioorthogonally activated prodrug approach

Author keywords

[No Author keywords available]

Indexed keywords

5 FLUORO 1 PROPARGYL URACIL; CYTOTOXIC AGENT; FLUOROURACIL; MACROGOL; PALLADIUM; POLYSTYRENE; PRODRUG; RESIN; UNCLASSIFIED DRUG; 5-FLUORO-1-PROPARGYLURACIL; ANTINEOPLASTIC ANTIMETABOLITE;

EID: 84913533758     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms4277     Document Type: Article
Times cited : (270)

References (37)
  • 1
    • 0034677879 scopus 로고    scopus 로고
    • Cell surface engineering by a modified staudinger reaction
    • Saxon, E. & Bertozzi, C. R. Cell Surface Engineering by a Modified Staudinger Reaction. Science 287, 2007-2010 (2000).
    • (2000) Science , vol.287 , pp. 2007-2010
    • Saxon, E.1    Bertozzi, C.R.2
  • 2
    • 9344227358 scopus 로고    scopus 로고
    • A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems
    • Agard, N. J., Prescher, J. & Bertozzi, C. R. A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. J. Am. Chem. Soc. 126, 15046-15047 (2004).
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 15046-15047
    • Agard, N.J.1    Prescher, J.2    Bertozzi, C.R.3
  • 3
    • 80052989876 scopus 로고    scopus 로고
    • From mechanism to mouse: A tale of two bioorthogonal reactions
    • Sletten, E. M. & Bertozzi, C. R. From mechanism to mouse: a tale of two bioorthogonal reactions. Acc. Chem. Res. 44, 666-676 (2011).
    • (2011) Acc. Chem. Res. , vol.44 , pp. 666-676
    • Sletten, E.M.1    Bertozzi, C.R.2
  • 4
    • 80053010069 scopus 로고    scopus 로고
    • A decade of bioorthogonal chemistry
    • Bertozzi, C. R. A decade of bioorthogonal chemistry. Acc. Chem. Res. 44, 651-653 (2011).
    • (2011) Acc. Chem. Res. , vol.44 , pp. 651-653
    • Bertozzi, C.R.1
  • 5
    • 80053028238 scopus 로고    scopus 로고
    • Photoinducible bioorthogonal chemistry: A spatiotemporally controllable tool to visualize and perturb proteins in live cells
    • Lim, R. K. & Lin, Q. Photoinducible bioorthogonal chemistry: a spatiotemporally controllable tool to visualize and perturb proteins in live cells. Acc. Chem. Res. 44, 828-839 (2011).
    • (2011) Acc. Chem. Res. , vol.44 , pp. 828-839
    • Lim, R.K.1    Lin, Q.2
  • 6
    • 84872237121 scopus 로고    scopus 로고
    • Photoremovable protecting groups in chemistry and biology: Reaction mechanisms and efficacy
    • Klán, P. et al. Photoremovable protecting groups in chemistry and biology: reaction mechanisms and efficacy. Chem. Rev. 113, 119-191 (2013).
    • (2013) Chem. Rev. , vol.113 , pp. 119-191
    • Klán, P.1
  • 7
    • 84864141034 scopus 로고    scopus 로고
    • In vivo light-driven DNA binding and cellular uptake of nucleic acid stains
    • Sánchez, M. I. et al. In vivo light-driven DNA binding and cellular uptake of nucleic acid stains. ACS Chem. Biol. 7, 1276-1280 (2012).
    • (2012) ACS Chem. Biol. , vol.7 , pp. 1276-1280
    • Sánchez, M.I.1
  • 8
    • 84865500785 scopus 로고    scopus 로고
    • Synthesis of polystyrene microspheres and functionalization with Pd(0) nanoparticles to perform bioorthogonal organometallic chemistry in living cells
    • Unciti-Broceta, A., Johansson, E. M. V., Yusop, R. M., Sánchez-Martín, R. M. & Bradley, M. Synthesis of polystyrene microspheres and functionalization with Pd(0) nanoparticles to perform bioorthogonal organometallic chemistry in living cells. Nat. Protoc. 7, 1207-1218 (2012).
    • (2012) Nat. Protoc. , vol.7 , pp. 1207-1218
    • Unciti-Broceta, A.1    Johansson, E.M.V.2    Yusop, R.M.3    Sánchez-Martín, R.M.4    Bradley, M.5
  • 9
    • 84873279753 scopus 로고    scopus 로고
    • Metal complex catalysis in living biological systems
    • Sasmal, P. K., Streu, C. N. & Meggers, E. Metal complex catalysis in living biological systems. Chem. Commun. 49, 1581-1587 (2013).
    • (2013) Chem. Commun. , vol.49 , pp. 1581-1587
    • Sasmal, P.K.1    Streu, C.N.2    Meggers, E.3
  • 10
    • 33748620928 scopus 로고    scopus 로고
    • Ruthenium-induced allylcarbamate cleavage in living cells
    • Streu, C. & Meggers, E. Ruthenium-induced allylcarbamate cleavage in living cells. Angew. Chem. Int. Ed. 45, 5645-5648 (2006).
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 5645-5648
    • Streu, C.1    Meggers, E.2
  • 12
    • 80053319803 scopus 로고    scopus 로고
    • Copper-free Sonogashira crosscoupling for functionalization of alkyne-encoded proteins in aqueous medium and in bacterial cells
    • Li, N., Lim, R. K., Edwardraja, S. & Lin, Q. Copper-free Sonogashira crosscoupling for functionalization of alkyne-encoded proteins in aqueous medium and in bacterial cells. J. Am. Chem. Soc 133, 15316-15319 (2011).
    • (2011) J. Am. Chem. Soc , vol.133 , pp. 15316-15319
    • Li, N.1    Lim, R.K.2    Edwardraja, S.3    Lin, Q.4
  • 13
    • 84855981546 scopus 로고    scopus 로고
    • Palladium-mediated cell surface labeling
    • Spicer, C. D., Triemer, T. & Davis, B. G. Palladium-mediated cell surface labeling. J. Am. Chem. Soc. 134, 800-803 (2012).
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 800-803
    • Spicer, C.D.1    Triemer, T.2    Davis, B.G.3
  • 14
    • 84866666959 scopus 로고    scopus 로고
    • A reaction-based fluorescent probe for selective imaging of carbon monoxide in living cells using a palladium-mediated carbonylation
    • Michel, B. W., Lippert, A. R. & Chang, C. J. A reaction-based fluorescent probe for selective imaging of carbon monoxide in living cells using a palladium-mediated carbonylation. J. Am. Chem. Soc. 134, 15668-15671 (2012).
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 15668-15671
    • Michel, B.W.1    Lippert, A.R.2    Chang, C.J.3
  • 15
    • 0003521824 scopus 로고    scopus 로고
    • World Health Organization, Geneva
    • Environmental Health Criteria 226: Palladium. World Health Organization, Geneva, http://whqlibdoc.who.int/ehc/WHO-EHC-226.pdf (2002).
    • (2002) Environmental Health Criteria 226: Palladium.
  • 16
    • 1442308888 scopus 로고    scopus 로고
    • Palladium in restorative dentistry: Superior physical properties make palladium an ideal dental metal
    • Rushforth, R. Palladium in restorative dentistry: superior physical properties make palladium an ideal dental metal. Platinum Metals Rev. 48, 30-31 (2004).
    • (2004) Platinum Metals Rev. , vol.48 , pp. 30-31
    • Rushforth, R.1
  • 17
    • 40149088986 scopus 로고    scopus 로고
    • Prodrugs: Design and clinical applications
    • Rautio, J. et al. Prodrugs: design and clinical applications. Nat. Rev. Drug Discov 7, 255-270 (2008).
    • (2008) Nat. Rev. Drug Discov , vol.7 , pp. 255-270
    • Rautio, J.1
  • 18
    • 72949086481 scopus 로고    scopus 로고
    • Pharmacokinetically guided dose adjustment of 5-fluorouracil: A rational approach to improving therapeutic outcomes
    • Saif, M. W., Choma, A., Salamone, S. J. & Chu, E. Pharmacokinetically guided dose adjustment of 5-fluorouracil: a rational approach to improving therapeutic outcomes. J. Natl Cancer Inst. 101, 1543-1552 (2009).
    • (2009) J. Natl Cancer Inst. , vol.101 , pp. 1543-1552
    • Saif, M.W.1    Choma, A.2    Salamone, S.J.3    Chu, E.4
  • 19
    • 0038387494 scopus 로고    scopus 로고
    • 5-Fluorouracil: Mechanisms of action and clinical strategies
    • Longley, D. B., Harkin, D. P. & Johnston, P. G. 5-Fluorouracil: mechanisms of action and clinical strategies. Nat. Rev. Cancer 3, 330-338 (2003).
    • (2003) Nat. Rev. Cancer , vol.3 , pp. 330-338
    • Longley, D.B.1    Harkin, D.P.2    Johnston, P.G.3
  • 20
    • 22144474787 scopus 로고    scopus 로고
    • Recent advances in ether dealkylation
    • Weissman, S. A. & Zewge, D. Recent advances in ether dealkylation. Tetrahedron 61, 7833-7863 (2005).
    • (2005) Tetrahedron , vol.61 , pp. 7833-7863
    • Weissman, S.A.1    Zewge, D.2
  • 21
    • 35348947454 scopus 로고    scopus 로고
    • A highly sensitive fluorescent sensor for palladium based on the allylic oxidative insertion mechanism
    • Song, F., Garner, A. L. & Koide, K. A highly sensitive fluorescent sensor for palladium based on the allylic oxidative insertion mechanism. J. Am. Chem. Soc. 129, 12354-12355 (2007).
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 12354-12355
    • Song, F.1    Garner, A.L.2    Koide, K.3
  • 22
    • 77952753941 scopus 로고    scopus 로고
    • Fluorescent detection of palladium species with an O-propargylated fluorescein
    • Santra, M., Ko, S.-K., Shin, I. & Ahnz, K. H. Fluorescent detection of palladium species with an O-propargylated fluorescein. Chem. Commun. 46, 3964-3966 (2010).
    • (2010) Chem. Commun. , vol.46 , pp. 3964-3966
    • Santra, M.1    Ko, S.-K.2    Shin, I.3    Ahnz, K.H.4
  • 23
    • 84863115215 scopus 로고    scopus 로고
    • A new ratiometric ESIPT sensor for detection of palladium species in aqueous solution
    • Liu, B. et al. A new ratiometric ESIPT sensor for detection of palladium species in aqueous solution. Chem. Commun. 48, 2867-2869 (2012).
    • (2012) Chem. Commun. , vol.48 , pp. 2867-2869
    • Liu, B.1
  • 24
    • 0141741339 scopus 로고    scopus 로고
    • Palladium-catalyzed cleavage of O/N-propargyl protecting groups in aqueous media under a copper-free condition
    • Pal, M., Parasuraman, K. & Yeleswarapu, K. R. Palladium-catalyzed cleavage of O/N-propargyl protecting groups in aqueous media under a copper-free condition. Org. Lett. 5, 348-352 (2003).
    • (2003) Org. Lett. , vol.5 , pp. 348-352
    • Pal, M.1    Parasuraman, K.2    Yeleswarapu, K.R.3
  • 25
    • 24944579952 scopus 로고    scopus 로고
    • Methods for the cleavage of allylic and propargylic C-N bonds in amines and amides - Selected alternative applications of the 1, 3-hydrogen shift
    • Escoubet, S., Gastaldi, S. & Bertrand, M. Methods for the cleavage of allylic and propargylic C-N bonds in amines and amides - selected alternative applications of the 1, 3-hydrogen shift. Eur. J. Org. Chem. 2005, 3855-3873 (2005).
    • (2005) Eur. J. Org. Chem. , vol.2005 , pp. 3855-3873
    • Escoubet, S.1    Gastaldi, S.2    Bertrand, M.3
  • 26
    • 84872832676 scopus 로고    scopus 로고
    • Pd/C mediated depropargylation of propargyl ethers/amines in water
    • Rambabua, D., Bhavani, S., Swamy, N. K. & Rao, M. V. B. Pd/C mediated depropargylation of propargyl ethers/amines in water. Tetrahedron Lett. 54, 1169-1173 (2013).
    • (2013) Tetrahedron Lett. , vol.54 , pp. 1169-1173
    • Rambabua, D.1    Bhavani, S.2    Swamy, N.K.3    Rao, M.V.B.4
  • 27
    • 0035127984 scopus 로고    scopus 로고
    • First principles calculation pka values for 5-substituted uracils
    • Jang, Y. H., Sowers, L. C., Cagin, T. & Goddard III, W. A. First principles calculation pka values for 5-substituted uracils. J. Phys. Chem. A 105, 274-280 (2001).
    • (2001) J. Phys. Chem. A , vol.105 , pp. 274-280
    • Jang, Y.H.1    Sowers, L.C.2    Cagin, T.3    Goddard, W.A.4
  • 28
    • 33646568827 scopus 로고    scopus 로고
    • Captured and cross-linked palladium nanoparticles
    • Cho, J. K. et al. Captured and cross-linked palladium nanoparticles. J. Am. Chem. Soc. 128, 6276-6277 (2006).
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 6276-6277
    • Cho, J.K.1
  • 29
    • 79960955664 scopus 로고    scopus 로고
    • In silico evidence for gluconeogenesis from fatty acids in humans
    • Kaleta, C. et al. In silico evidence for gluconeogenesis from fatty acids in humans. PLoS Comput. Biol. 7, e1002116 (2011).
    • (2011) PLoS Comput. Biol. , vol.7 , pp. e1002116
    • Kaleta, C.1
  • 30
    • 59249091498 scopus 로고    scopus 로고
    • Selection of cytotoxicity markers for the screening of new chemical entities in a pharmaceutical context: A preliminary study using a multiplexing approach. Toxicol
    • Gerets, H. H. et al. Selection of cytotoxicity markers for the screening of new chemical entities in a pharmaceutical context: a preliminary study using a multiplexing approach. Toxicol. In Vitro 2, 319-332 (2009).
    • (2009) Vitro , vol.2 , pp. 319-332
    • Gerets, H.H.1
  • 31
    • 65549088630 scopus 로고    scopus 로고
    • Tracing pathway activities with kinase inhibitors and reverse phase protein arrays
    • van Oostrum, J. et al. Tracing pathway activities with kinase inhibitors and reverse phase protein arrays. Proteomics Clin. Appl. 3, 412-422 (2009).
    • (2009) Proteomics Clin. Appl. , vol.3 , pp. 412-422
    • Van Oostrum, J.1
  • 32
    • 33746620404 scopus 로고    scopus 로고
    • Cellular response to 5-fluorouracil (5-FU) in 5-FU-resistant colon cancer cell lines during treatment and recovery
    • De Angelis, P. M., Svendsrud, D. H., Kravik, K. L. & Stokk, T. Cellular response to 5-fluorouracil (5-FU) in 5-FU-resistant colon cancer cell lines during treatment and recovery. Mol. Cancer 5, 20 (2006).
    • (2006) Mol. Cancer , vol.5 , pp. 20
    • De Angelis, P.M.1    Svendsrud, D.H.2    Kravik, K.L.3    Stokk, T.4
  • 33
    • 0037334407 scopus 로고    scopus 로고
    • Unique and conserved aspects of gut development in zebrafish
    • Wallace, K. N. & Pack, M. Unique and conserved aspects of gut development in zebrafish. Dev. Biol. 255, 12-29 (2003).
    • (2003) Dev. Biol. , vol.255 , pp. 12-29
    • Wallace, K.N.1    Pack, M.2
  • 34
    • 25844505439 scopus 로고    scopus 로고
    • Formation of the digestive system in zebrafish: III. Intestinal epithelium morphogenesis
    • Ng, A. N. et al. Formation of the digestive system in zebrafish: III. Intestinal epithelium morphogenesis. Dev. Biol. 286, 114-135 (2005).
    • (2005) Dev. Biol. , vol.286 , pp. 114-135
    • Ng, A.N.1
  • 35
    • 84887044199 scopus 로고    scopus 로고
    • Bioorthogonal chemistry: Strategies and recent developments
    • Lin, Q. & Ramil, C. P. Bioorthogonal chemistry: strategies and recent developments. Chem. Comm. 49, 11007-11022 (2013).
    • (2013) Chem. Comm. , vol.49 , pp. 11007-11022
    • Lin, Q.1    Ramil, C.P.2
  • 36
    • 84861912742 scopus 로고    scopus 로고
    • Fast, cell-compatible click chemistry with copperchelating azides for biomolecular labeling
    • Uttamapinant, C. et al. Fast, cell-compatible click chemistry with copperchelating azides for biomolecular labeling. Angew. Chemie Int. Ed. 51, 5852-5856 (2012).
    • (2012) Angew. Chemie Int. Ed. , vol.51 , pp. 5852-5856
    • Uttamapinant, C.1
  • 37
    • 33745537921 scopus 로고    scopus 로고
    • Photodynamic therapy and antitumour immunity
    • Castano, A. P., Mroz, P. & Hamblin, M. R. Photodynamic therapy and antitumour immunity. Nat. Rev. Cancer 6, 535-545 (2006).
    • (2006) Nat. Rev. Cancer , vol.6 , pp. 535-545
    • Castano, A.P.1    Mroz, P.2    Hamblin, M.R.3


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