메뉴 건너뛰기




Volumn 14, Issue 1, 2003, Pages 187-194

A stable bis-allyloxycarbonyl biotin aldehyde derivative for biotinylation via reductive alkylation: Application to the synthesis of a biotinylated doxorubicin derivative

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; ALKYLATION; SODIUM COMPOUNDS;

EID: 12244259679     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc0255992     Document Type: Article
Times cited : (13)

References (24)
  • 3
    • 0012918049 scopus 로고    scopus 로고
    • Synthesis and cytotoxicity of a biotinylated CC-1065 analogue
    • Wang, Y., Yuan, H., Wright, S. C., Wang, H., and Larrick, J. W. (2002) Synthesis and cytotoxicity of a biotinylated CC-1065 analogue. BMC. Chem. Biol. 2, 1. For optimization of the design of the biotin linkers see Wilbur, D. S., Chyan, M. K., Pathare, P. M., Hamlin, D. K., Frownfelter, M. B., Kegley, B. B. (2000) Biotin reagents for antibody pretargeting 4. Selection of biotin conjugates for in vivo application based on their dissociation rate from avidin and streptavidin. Bioconjugate Chem. 11, 569-583.
    • (2002) BMC. Chem. Biol. , vol.2 , pp. 1
    • Wang, Y.1    Yuan, H.2    Wright, S.C.3    Wang, H.4    Larrick, J.W.5
  • 4
    • 0033885715 scopus 로고    scopus 로고
    • Biotin reagents for antibody pretargeting 4. Selection of biotin conjugates for in vivo application based on their dissociation rate from avidin and streptavidin
    • Wang, Y., Yuan, H., Wright, S. C., Wang, H., and Larrick, J. W. (2002) Synthesis and cytotoxicity of a biotinylated CC-1065 analogue. BMC. Chem. Biol. 2, 1. For optimization of the design of the biotin linkers see Wilbur, D. S., Chyan, M. K., Pathare, P. M., Hamlin, D. K., Frownfelter, M. B., Kegley, B. B. (2000) Biotin reagents for antibody pretargeting 4. Selection of biotin conjugates for in vivo application based on their dissociation rate from avidin and streptavidin. Bioconjugate Chem. 11, 569-583.
    • (2000) Bioconjugate Chem. , vol.11 , pp. 569-583
    • Wilbur, D.S.1    Chyan, M.K.2    Pathare, P.M.3    Hamlin, D.K.4    Frownfelter, M.B.5    Kegley, B.B.6
  • 7
    • 0032510381 scopus 로고    scopus 로고
    • Intensely potent doxorubicin analogues: Structure-activity relationship
    • Farquhar, D., Cherif, A., Bakina, E., and Nelson, J. A. Intensely potent doxorubicin analogues: structure-activity relationship (1998) J. Med. Chem. 41, 965-972.
    • (1998) J. Med. Chem. , vol.41 , pp. 965-972
    • Farquhar, D.1    Cherif, A.2    Bakina, E.3    Nelson, J.A.4
  • 8
    • 0026737732 scopus 로고
    • N-(5,5-diacetoxypent-1-yl)doxorubicin: A new intensely potent doxorubicin analogue
    • Cherif, A., and Farquhar, D. (1992) N-(5,5-diacetoxypent-1-yl)doxorubicin: a new intensely potent doxorubicin analogue. J. Med. Chem. 35, 3208-3214.
    • (1992) J. Med. Chem. , vol.35 , pp. 3208-3214
    • Cherif, A.1    Farquhar, D.2
  • 9
    • 0018358087 scopus 로고
    • Avidin-biotin interaction. Synthesis, oxidation, and spectroscopic properties of linked models
    • Liu, F. T., and Leonard, N. J. (1979) Avidin-biotin interaction. Synthesis, oxidation, and spectroscopic properties of linked models. J. Am. Chem. Soc. 101, 996-1005.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 996-1005
    • Liu, F.T.1    Leonard, N.J.2
  • 10
    • 33947094829 scopus 로고
    • A total synthesis of biotin based on the stereoselective alkylation of sulfoxides
    • Lavielle, S., Bory, S., Moreau, B., Luche, M. J., and Marquet, A. (1978) A total synthesis of biotin based on the stereoselective alkylation of sulfoxides. J. Am. Chem. Soc. 100, 1558-1563.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 1558-1563
    • Lavielle, S.1    Bory, S.2    Moreau, B.3    Luche, M.J.4    Marquet, A.5
  • 13
    • 0021755634 scopus 로고
    • Ligands for insulin receptor isolation
    • Finn, F. M., Titus, G., and Hofmann, K. (1984) Ligands for insulin receptor isolation. Biochemistry. 23, 2554-2558.
    • (1984) Biochemistry , vol.23 , pp. 2554-2558
    • Finn, F.M.1    Titus, G.2    Hofmann, K.3
  • 14
    • 84986739524 scopus 로고
    • Application of twodimensional NMR spectroscopy to the complete analysis of the proton and carbon-13 NMR spectra of d-biotin in aqueous solution
    • Ikura, M., and Hikichi, K. (1982) Application of twodimensional NMR spectroscopy to the complete analysis of the proton and carbon-13 NMR spectra of d-biotin in aqueous solution. Organic Magnetic Resonance. 20(4), 266-273.
    • (1982) Organic Magnetic Resonance , vol.20 , Issue.4 , pp. 266-273
    • Ikura, M.1    Hikichi, K.2
  • 15
    • 0012917261 scopus 로고
    • A 500 MHz proton NMR study of the conformation of adriamycin
    • Barthwal, R., Srivastava, N., Sharma, U., and Govil, G. (1994) A 500 MHz proton NMR study of the conformation of adriamycin. J. Mol. Struct. 327, 201-220. See also: Mondelli, R., Ragg, E., Fronza, G., and Arnone, A. (1987) J. Chem. Soc., Perkin Trans. 2, 15-32.
    • (1994) J. Mol. Struct. , vol.327 , pp. 201-220
    • Barthwal, R.1    Srivastava, N.2    Sharma, U.3    Govil, G.4
  • 16
    • 37049084273 scopus 로고
    • Barthwal, R., Srivastava, N., Sharma, U., and Govil, G. (1994) A 500 MHz proton NMR study of the conformation of adriamycin. J. Mol. Struct. 327, 201-220. See also: Mondelli, R., Ragg, E., Fronza, G., and Arnone, A. (1987) J. Chem. Soc., Perkin Trans. 2, 15-32.
    • (1987) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 15-32
    • Mondelli, R.1    Ragg, E.2    Fronza, G.3    Arnone, A.4
  • 17
    • 0033885715 scopus 로고    scopus 로고
    • Biotin reagents for antibody pretargeting. 4. Selection of biotin conjugates for in vivo application based on their dissociation rate from avidin and streptavidin
    • Wilbur, D. S., Chyan, M.-K., Pathare, P. M., Hamlin, D. K., Frownfelter, M. B., and Kegley, B. B. (2000) Biotin reagents for antibody pretargeting. 4. Selection of biotin conjugates for in vivo application based on their dissociation rate from avidin and streptavidin. Bioconjate Chem. 11 (4), 569-583.
    • (2000) Bioconjate Chem. , vol.11 , Issue.4 , pp. 569-583
    • Wilbur, D.S.1    Chyan, M.-K.2    Pathare, P.M.3    Hamlin, D.K.4    Frownfelter, M.B.5    Kegley, B.B.6
  • 18
    • 0033884514 scopus 로고    scopus 로고
    • Evaluation of biotin-dye conjugates for use in an HPLC assay to assess relative binding of biotin derivatives with avidin and streptavidin
    • Wilbur, D. S., Pathare, P. M., Hamlin, D. K., Frownfelter, M. B., Kegley, B. B., Leung, W.-Y., Gee, K. R. (2000) Evaluation of biotin-dye conjugates for use in an HPLC assay to assess relative binding of biotin derivatives with avidin and streptavidin. Bioconjugate Chem. 11 (4), 584-598.
    • (2000) Bioconjugate Chem. , vol.11 , Issue.4 , pp. 584-598
    • Wilbur, D.S.1    Pathare, P.M.2    Hamlin, D.K.3    Frownfelter, M.B.4    Kegley, B.B.5    Leung, W.-Y.6    Gee, K.R.7
  • 19
    • 0024361716 scopus 로고
    • A chemical method of labeling oligodeoxyribonucleotides with biotin: A single step procedure using a solid-phase methodology
    • Alves, A. M., Holland, D., and Edge, M. D. (1989) A chemical method of labeling oligodeoxyribonucleotides with biotin: A single step procedure using a solid-phase methodology. Tetrahedron Lett. 30, 3089-3092.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 3089-3092
    • Alves, A.M.1    Holland, D.2    Edge, M.D.3
  • 20
    • 0033565009 scopus 로고    scopus 로고
    • Synthesis of a reaction intermediate analogue of biotindependent carboxylases via a selective derivatization of biotin
    • Amspacher, D. R., Blanchard, C. Z., Fronczek, F. R., Saraiva, M. C., Waldrop, G. L., and Strongin, R. M. (1999) Synthesis of a reaction intermediate analogue of biotindependent carboxylases via a selective derivatization of biotin. Organic Lett. 1, 99-102.
    • (1999) Organic Lett. , vol.1 , pp. 99-102
    • Amspacher, D.R.1    Blanchard, C.Z.2    Fronczek, F.R.3    Saraiva, M.C.4    Waldrop, G.L.5    Strongin, R.M.6
  • 22
    • 0027173285 scopus 로고
    • Palladium-catalyzed reactions in aqueous media. An efficient removal of allyloxycarbonyl protecting group from oxygen and nitrogen
    • Genet, J. P., Blart, E., Savignac, M., Lemeune, S., and Paris, J. M. (1993) Palladium-catalyzed reactions in aqueous media. An efficient removal of allyloxycarbonyl protecting group from oxygen and nitrogen. Tetrahedron Lett. 34, 4189-4192.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 4189-4192
    • Genet, J.P.1    Blart, E.2    Savignac, M.3    Lemeune, S.4    Paris, J.M.5
  • 23
    • 0030938480 scopus 로고    scopus 로고
    • Synthesis of peptides using palladium promoted selective removal of allyloxycarbonyl protecting groups in aqueous medium
    • Lemaire-Audoire, S., Savignac, M., Blart, E., Bernard, J. M., and Genet, J. P. (1997) Synthesis of Peptides Using Palladium Promoted Selective Removal of Allyloxycarbonyl Protecting Groups in Aqueous Medium. Tetrahedron Lett. 38, 2955-2958.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 2955-2958
    • Lemaire-Audoire, S.1    Savignac, M.2    Blart, E.3    Bernard, J.M.4    Genet, J.P.5
  • 24
    • 0032510011 scopus 로고    scopus 로고
    • Sonogashira cross-couplings using biocompatible conditions in water
    • Dibowski, H., Schmidtchen, F. P. (1998) Sonogashira CrossCouplings Using Biocompatible Conditions in Water. Tetrahedron Lett. 39, 525-528.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 525-528
    • Dibowski, H.1    Schmidtchen, F.P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.