메뉴 건너뛰기




Volumn 24, Issue 7, 2013, Pages 1210-1217

Highly reactive trans-cyclooctene tags with improved stability for diels-alder chemistry in living systems

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODIES; CHEMICAL STABILITY; CYCLOADDITION; ISOMERIZATION; ISOMERS; MAMMALS; PROBES;

EID: 84880356534     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc400153y     Document Type: Article
Times cited : (221)

References (48)
  • 2
    • 80053031240 scopus 로고    scopus 로고
    • Biomedical applications of tetrazine cycloadditions
    • Devaraj, N. K. and Weissleder, R. (2011) Biomedical applications of tetrazine cycloadditions Acc. Chem. Res. 44, 816-827
    • (2011) Acc. Chem. Res. , vol.44 , pp. 816-827
    • Devaraj, N.K.1    Weissleder, R.2
  • 3
    • 80052989876 scopus 로고    scopus 로고
    • From mechanism to mouse: A tale of two bioorthogonal reactions
    • Sletten, E. M. and Bertozzi, C. R. (2011) From mechanism to mouse: a tale of two bioorthogonal reactions Acc. Chem. Res. 44, 666-676
    • (2011) Acc. Chem. Res. , vol.44 , pp. 666-676
    • Sletten, E.M.1    Bertozzi, C.R.2
  • 5
    • 77951248023 scopus 로고    scopus 로고
    • Different ways to improve the clinical effectiveness of radioimmunotherapy in solid tumors
    • Chatal, J. F., Davodeau, F., Cherel, M., and Barbet, J. (2009) Different ways to improve the clinical effectiveness of radioimmunotherapy in solid tumors J. Cancer Res. Ther. 5, 36-40
    • (2009) J. Cancer Res. Ther. , vol.5 , pp. 36-40
    • Chatal, J.F.1    Davodeau, F.2    Cherel, M.3    Barbet, J.4
  • 6
    • 33644869654 scopus 로고    scopus 로고
    • Antibody pretargeting advances cancer radioimmunodetection and radioimmunotherapy
    • Goldenberg, D. M., Sharkey, R. M., Paganelli, G., Barbet, J., and Chatal, J.-F. (2006) Antibody pretargeting advances cancer radioimmunodetection and radioimmunotherapy J. Clin. Oncol. 24, 823-834
    • (2006) J. Clin. Oncol. , vol.24 , pp. 823-834
    • Goldenberg, D.M.1    Sharkey, R.M.2    Paganelli, G.3    Barbet, J.4    Chatal, J.-F.5
  • 7
    • 77951261728 scopus 로고    scopus 로고
    • Rates and equilibria for probe capture by an antibody with infinite affinity
    • Aweda, T. A., Beck, H. E., Wu, A. M., Wei, L. H., Weber, W. A., and Meares, C. F. (2010) Rates and equilibria for probe capture by an antibody with infinite affinity Bioconjugate Chem. 21, 784-791
    • (2010) Bioconjugate Chem. , vol.21 , pp. 784-791
    • Aweda, T.A.1    Beck, H.E.2    Wu, A.M.3    Wei, L.H.4    Weber, W.A.5    Meares, C.F.6
  • 9
    • 53849105464 scopus 로고    scopus 로고
    • Tetrazine ligation: Fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity
    • Blackman, M. L., Royzen, M., and Fox, J. M. (2008) Tetrazine ligation: fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity J. Am. Chem. Soc. 130, 13518-13519
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 13518-13519
    • Blackman, M.L.1    Royzen, M.2    Fox, J.M.3
  • 10
    • 84863443015 scopus 로고    scopus 로고
    • Genetic encoding of bicyclononynes and trans -cyclooctenes for site-specific protein labeling in vitro and in live mammalian cells via rapid fluorogenic Diels-Alder reactions
    • Lang, K., Davis, L., Wallace, S., Mahesh, M., Cox, D. J., Blackman, M. L., Fox, J. M., and Chin, J. W. (2012) Genetic encoding of bicyclononynes and trans -cyclooctenes for site-specific protein labeling in vitro and in live mammalian cells via rapid fluorogenic Diels-Alder reactions J. Am. Chem. Soc. 134, 10317-10320
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 10317-10320
    • Lang, K.1    Davis, L.2    Wallace, S.3    Mahesh, M.4    Cox, D.J.5    Blackman, M.L.6    Fox, J.M.7    Chin, J.W.8
  • 11
    • 80054797650 scopus 로고    scopus 로고
    • Modular strategy for the construction of radiometalated antibodies for positron emission tomography based on inverse electron demand Diels-Alder click chemistry
    • Zeglis, B. M., Mohindra, P., Weissmann, G. I., Divilov, V., Hilderbrand, S. A., Weissleder, R., and Lewis, J. S. (2011) Modular strategy for the construction of radiometalated antibodies for positron emission tomography based on inverse electron demand Diels-Alder click chemistry Bioconjugate Chem. 22, 2048-2059
    • (2011) Bioconjugate Chem. , vol.22 , pp. 2048-2059
    • Zeglis, B.M.1    Mohindra, P.2    Weissmann, G.I.3    Divilov, V.4    Hilderbrand, S.A.5    Weissleder, R.6    Lewis, J.S.7
  • 12
    • 70349925246 scopus 로고    scopus 로고
    • Fast and sensitive pretargeted labeling of cancer cells through a tetrazine/trans-cyclooctene cycloaddition
    • Devaraj, N. K., Upadhyay, R., Haun, J. B., Hilderbrand, S. A., and Weissleder, R. (2009) Fast and sensitive pretargeted labeling of cancer cells through a tetrazine/trans-cyclooctene cycloaddition Angew. Chem., Int. Ed. 48, 7013-7016
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 7013-7016
    • Devaraj, N.K.1    Upadhyay, R.2    Haun, J.B.3    Hilderbrand, S.A.4    Weissleder, R.5
  • 17
    • 78349292832 scopus 로고
    • 14C]biotin for kinetic studies and for assay
    • 14C]biotin for kinetic studies and for assay Biochem. J. 89, 585-591
    • (1963) Biochem. J. , vol.89 , pp. 585-591
    • Green, N.M.1
  • 18
    • 0025876152 scopus 로고
    • Kinetic analysis of monoclonal antibody-antigen interactions with a new biosensor based analytical system
    • Karlsson, R., Michaelsson, A., and Mattsson, L. (1991) Kinetic analysis of monoclonal antibody-antigen interactions with a new biosensor based analytical system J. Immunol. Methods 145, 229-240
    • (1991) J. Immunol. Methods , vol.145 , pp. 229-240
    • Karlsson, R.1    Michaelsson, A.2    Mattsson, L.3
  • 19
    • 79551688075 scopus 로고    scopus 로고
    • Engineering an antibody with picomolar affinity to DOTA chelates of multiple radionuclides for pretargeted radioimmunotherapy and imaging
    • Orcutt, K. D., Slusarczyk, A. L., Cieslewicz, M., Ruiz-Yi, B., Bhushan, K. R., Frangioni, J. V., and Wittrup, K. D. (2010) Engineering an antibody with picomolar affinity to DOTA chelates of multiple radionuclides for pretargeted radioimmunotherapy and imaging Nucl. Med. Biol. 38, 223-233
    • (2010) Nucl. Med. Biol. , vol.38 , pp. 223-233
    • Orcutt, K.D.1    Slusarczyk, A.L.2    Cieslewicz, M.3    Ruiz-Yi, B.4    Bhushan, K.R.5    Frangioni, J.V.6    Wittrup, K.D.7
  • 20
    • 79959506826 scopus 로고    scopus 로고
    • Design and synthesis of highly reactive dienophiles for the tetrazine- trans -cyclooctene ligation
    • Taylor, M. T., Blackman, M. L., Dmitrenko, O., and Fox, J. M. (2011) Design and synthesis of highly reactive dienophiles for the tetrazine- trans -cyclooctene ligation J. Am. Chem. Soc. 133, 9646-9649
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 9646-9649
    • Taylor, M.T.1    Blackman, M.L.2    Dmitrenko, O.3    Fox, J.M.4
  • 23
    • 0036933125 scopus 로고    scopus 로고
    • Thermodynamic and spectroscopic study of Cu(II) and Ni(II) binding to bovine serum albumin
    • Zhang, Y. and Wilcox, D. E. (2002) Thermodynamic and spectroscopic study of Cu(II) and Ni(II) binding to bovine serum albumin J. Biol. Inorg. Chem. 7, 327-337
    • (2002) J. Biol. Inorg. Chem. , vol.7 , pp. 327-337
    • Zhang, Y.1    Wilcox, D.E.2
  • 28
    • 84858741572 scopus 로고    scopus 로고
    • Preventing thiol-yne addition improves the specificity of strain-promoted azide-alkyne cycloaddition
    • van Geel, R., Pruijn, G. J. M., van Delft, F. L., and Boelens, W. C. (2012) Preventing thiol-yne addition improves the specificity of strain-promoted azide-alkyne cycloaddition Bioconjugate Chem. 23, 392-398
    • (2012) Bioconjugate Chem. , vol.23 , pp. 392-398
    • Van Geel, R.1    Pruijn, G.J.M.2    Van Delft, F.L.3    Boelens, W.C.4
  • 30
    • 0025151316 scopus 로고
    • Reaktivität einfacher offenkettiger und cyclischer dienophile bei Diels-Alder-reaktionen mit inversem elektronenbedarf
    • Thalhammer, F., Wallfahrer, U., and Sauer, J. R. (1990) Reaktivität einfacher offenkettiger und cyclischer dienophile bei Diels-Alder-reaktionen mit inversem elektronenbedarf Tetrahedron Lett. 31, 6851-6854
    • (1990) Tetrahedron Lett. , vol.31 , pp. 6851-6854
    • Thalhammer, F.1    Wallfahrer, U.2    Sauer, J.R.3
  • 31
    • 33947490675 scopus 로고
    • Molecular asymmetry of olefins. IV. Kinetics of racemization of (+ or -)- trans -cyclooctene
    • Cope, A. C. and Pawson, B. A. (1965) Molecular asymmetry of olefins. IV. Kinetics of racemization of (+ or -)- trans -cyclooctene J. Am. Chem. Soc. 87, 3649-3651
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 3649-3651
    • Cope, A.C.1    Pawson, B.A.2
  • 32
    • 27844449741 scopus 로고
    • On the thermal isomerization of trans-cyclooctene to cis-cyclooctene
    • Holle Andrews, U., Baldwin, J. E., and Grayston, M. W. (1982) On the thermal isomerization of trans-cyclooctene to cis-cyclooctene J. Org. Chem. 47, 287-292
    • (1982) J. Org. Chem. , vol.47 , pp. 287-292
    • Holle Andrews, U.1    Baldwin, J.E.2    Grayston, M.W.3
  • 33
    • 0347809005 scopus 로고
    • Reinvestigation of triplet-sensitized cis-trans photoisomerization of cyclooctene. Alkene-concentration and sensitizer-ET dependence of photostationary trans / cis ratio
    • Inoue, Y., Kobata, T., and Hakushi, T. (1985) Reinvestigation of triplet-sensitized cis-trans photoisomerization of cyclooctene. Alkene-concentration and sensitizer-ET dependence of photostationary trans / cis ratio J. Phys. Chem. 89, 1973-1976
    • (1985) J. Phys. Chem. , vol.89 , pp. 1973-1976
    • Inoue, Y.1    Kobata, T.2    Hakushi, T.3
  • 35
    • 0000954343 scopus 로고    scopus 로고
    • Transferrins
    • in (Messerschmidt, A. Huber, R. Wieghardt, K. and Poulos, T. Eds.) pp, John Wiley & Sons, Ltd, Chichester.
    • Lindley, P. F. (2001) Transferrins, in Handbook of metalloproteins (Messerschmidt, A., Huber, R., Wieghardt, K., and Poulos, T., Eds.) pp 793-810, John Wiley & Sons, Ltd, Chichester.
    • (2001) Handbook of Metalloproteins , pp. 793-810
    • Lindley, P.F.1
  • 36
    • 0343397481 scopus 로고
    • Investigations into Euglena method for the assay of the vitamin B12 in serum
    • Anderson, B. B. (1964) Investigations into Euglena method for the assay of the vitamin B12 in serum J. Clin. Pathol. 17, 14-26
    • (1964) J. Clin. Pathol. , vol.17 , pp. 14-26
    • Anderson, B.B.1
  • 39
    • 0021236274 scopus 로고
    • Albumin bound and alpha-2-macroglobulin bound zinc concentrations in the sera of healthy adults
    • Foote, J. W. and Delves, H. T. (1984) Albumin bound and alpha-2-macroglobulin bound zinc concentrations in the sera of healthy adults J. Clin. Pathol. 37, 1050-1054
    • (1984) J. Clin. Pathol. , vol.37 , pp. 1050-1054
    • Foote, J.W.1    Delves, H.T.2
  • 41
    • 0002103594 scopus 로고    scopus 로고
    • Ceruloplasmin
    • in (Messerschmidt, A. Huber, R. Wieghardt, K. and Poulos, T. Eds.) pp, John Wiley & Sons, Ltd, Chichester.
    • Lindley, P. F. (2001) Ceruloplasmin, in Handbook of metalloproteins (Messerschmidt, A., Huber, R., Wieghardt, K., and Poulos, T., Eds.) pp 1369-1380, John Wiley & Sons, Ltd, Chichester.
    • (2001) Handbook of Metalloproteins , pp. 1369-1380
    • Lindley, P.F.1
  • 42
    • 0242521579 scopus 로고    scopus 로고
    • Activation of protein-bound copper ions during early glycation: Study on two proteins
    • Argirova, M. D. and Ortwerth, B. J. (2003) Activation of protein-bound copper ions during early glycation: study on two proteins Arch. Biochem. Biophys. 420, 176-184
    • (2003) Arch. Biochem. Biophys. , vol.420 , pp. 176-184
    • Argirova, M.D.1    Ortwerth, B.J.2
  • 44
    • 67849087099 scopus 로고    scopus 로고
    • Ring strain energy in the cyclooctyl system. The effect of strain energy on [3 + 2] cycloaddition reactions with azides
    • Bach, R. D. (2009) Ring strain energy in the cyclooctyl system. The effect of strain energy on [3 + 2] cycloaddition reactions with azides J. Am. Chem. Soc. 131, 5233-5243
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 5233-5243
    • Bach, R.D.1
  • 45
    • 33748032239 scopus 로고
    • Determination of the active site and mechanism for alkene isomerization in CuII exchanged Y-type zeolite
    • John, C. S. and Leach, H. F. (1977) Determination of the active site and mechanism for alkene isomerization in CuII exchanged Y-type zeolite J. Chem. Soc., Faraday Trans. 1 (73) 1595-1604
    • (1977) J. Chem. Soc., Faraday Trans. , vol.1 , Issue.73 , pp. 1595-1604
    • John, C.S.1    Leach, H.F.2
  • 46
    • 41149117469 scopus 로고    scopus 로고
    • A photochemical synthesis of functionalized trans -cyclooctenes driven by metal complexation
    • Royzen, M., Yap, G. P. A., and Fox, J. M. (2008) A photochemical synthesis of functionalized trans -cyclooctenes driven by metal complexation J. Am. Chem. Soc. 130, 3760-3761
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 3760-3761
    • Royzen, M.1    Yap, G.P.A.2    Fox, J.M.3
  • 47
    • 84863972619 scopus 로고    scopus 로고
    • Site-specific one-pot dual labeling of DNA by orthogonal cycloaddition chemistry
    • Schoch, J., Staudt, M., Samanta, A., Wiessler, M., and Jäschke, A. (2012) Site-specific one-pot dual labeling of DNA by orthogonal cycloaddition chemistry Bioconjugate Chem. 23, 1382-1386
    • (2012) Bioconjugate Chem. , vol.23 , pp. 1382-1386
    • Schoch, J.1    Staudt, M.2    Samanta, A.3    Wiessler, M.4    Jäschke, A.5
  • 48
    • 0025145460 scopus 로고
    • Characterization of the shed form of the human tumor-associated glycoprotein (TAG-72) from serous effusions of patients with different types of carcinomas
    • Katari, R. S., Fernsten, P. D., and Schlom, J. (1990) Characterization of the shed form of the human tumor-associated glycoprotein (TAG-72) from serous effusions of patients with different types of carcinomas Cancer Res. 50, 4885-4890
    • (1990) Cancer Res. , vol.50 , pp. 4885
    • Katari, R.S.1    Fernsten, P.D.2    Schlom, J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.