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Volumn 38, Issue 20, 1995, Pages 3891-3894

A New Paclitaxel Photoaffinity Analog with a 3-(4-Benzoylphenyl)propanoyl Probe for Characterization of Drug-Binding Sites on Tubulin and P-Glycoprotein

Author keywords

[No Author keywords available]

Indexed keywords

3' N [3 (4 BENZOYLPHENYL)PROPIONYL] 3' N DEBENZOYLPACLITAXEL; BACCATIN III; GLYCOPROTEIN P; PACLITAXEL DERIVATIVE; TRIETHYLAMINE; TUBULIN; UNCLASSIFIED DRUG;

EID: 0028825869     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00020a001     Document Type: Article
Times cited : (54)

References (31)
  • 3
    • 0018387446 scopus 로고
    • Promotion of Microtubule Assembly in vitro by Taxol
    • Schiff, F. B.; Fant, J.; Horwitz, S. B. Promotion of Microtubule Assembly in vitro by Taxol. Nature 1979, 277, 665-667.
    • (1979) Nature , vol.277 , pp. 665-667
    • Schiff, F.B.1    Fant, J.2    Horwitz, S.B.3
  • 4
    • 0000297058 scopus 로고
    • Taxol Stabilizes Microtubules in Mouse Fibroblast Cells
    • Schiff, P. B.; Horwitz, S. B. Taxol Stabilizes Microtubules in Mouse Fibroblast Cells. Proc. Natl, Acad. Sci. U. S. A. 1980, 77, 1561-1565.
    • (1980) Proc. Natl, Acad. Sci. U. S. A. , vol.77 , pp. 1561-1565
    • Schiff, P.B.1    Horwitz, S.B.2
  • 5
    • 0019859353 scopus 로고
    • Taxol Binds to Polymerized Tubulin in vitro
    • Parness, J.; Horwitz, S. B. Taxol Binds to Polymerized Tubulin in vitro. J. Cell Biol. 1981, 91, 479-487.
    • (1981) J. Cell Biol. , vol.91 , pp. 479-487
    • Parness, J.1    Horwitz, S.B.2
  • 6
    • 0026747827 scopus 로고
    • Direct Photoaffinity Labeling of Tubulin with Taxol
    • Rao, S.; Horwitz, S. B.; Ringel, I. Direct Photoaffinity Labeling of Tubulin with Taxol. J. Natl. Cancer lust. 1992, 84, 785-788.
    • (1992) J. Natl. Cancer lust. , vol.84 , pp. 785-788
    • Rao, S.1    Horwitz, S.B.2    Ringel, I.3
  • 8
    • 0028123221 scopus 로고
    • Synthesis of a Photoaffinity Taxol Analogue and Its Use in Labeling Tubulin
    • Dasgupta, D.; Park, H.; Harriman, G. C. B.; Georg, G. I.; Himes, R. H. Synthesis of a Photoaffinity Taxol Analogue and Its Use in Labeling Tubulin. J. Med. Chem. 1994, 37, 2976-2980.
    • (1994) J. Med. Chem. , vol.37 , pp. 2976-2980
    • Dasgupta, D.1    Park, H.2    Harriman, G.C.B.3    Georg, G.I.4    Himes, R.H.5
  • 10
    • 0027218689 scopus 로고
    • Biochemistry of Multidrug Resis-tance Mediated by the Multidrug Transporter
    • Gottesman, M. M.; Pastan, T. Biochemistry of Multidrug Resis-tance Mediated by the Multidrug Transporter. Annu. Rev. Biochem. 1993, 62, 385-427.
    • (1993) Annu. Rev. Biochem. , vol.62 , pp. 385-427
    • Gottesman, M.M.1    Pastan, T.2
  • 11
    • 0024441318 scopus 로고
    • Cytoplasmic Orientation and Two-Domain Structure of the Multidrug Transporter, P-Glycoprotein, Demonstrated with Sequence-Specific Antibodies
    • Yoshimura, A.; Kuwazuru, Y.; Sumizawa, T.; Ichikawa, M.; Ikeda, S.-L.; Uda, T.; Akiyama, S.-I. Cytoplasmic Orientation and Two-Domain Structure of the Multidrug Transporter, P-Glycoprotein, Demonstrated with Sequence-Specific Antibodies. J. Biol. Chem. 1989, 264, 16282-16291.
    • (1989) J. Biol. Chem. , vol.264 , pp. 16282-16291
    • Yoshimura, A.1    Kuwazuru, Y.2    Sumizawa, T.3    Ichikawa, M.4    Ikeda, S.-L.5    Uda, T.6    Akiyama, S.-I.7
  • 12
    • 0025872032 scopus 로고
    • Domain Mapping of the Photoaffinity Drug-Binding Sites in P-Glycoprotein Encoded by Mouse mdrlb. J. Biol
    • Greenberger, L. M.; Lisanti, Ç, J.; Silva, J. T.; Horwitz, S. B. Domain Mapping of the Photoaffinity Drug-Binding Sites in P-Glycoprotein Encoded by Mouse mdrlb. J. Biol. Chem, 1991, 266, 20744-20751.
    • (1991) Chem , vol.266 , pp. 20744-20751
    • Greenberger, L.M.1    Lisanti, Ç.J.2    Silva, J.T.3    Horwitz, S.B.4
  • 13
    • 0024971222 scopus 로고
    • Two Different Regions of Phosphoglycoprotein are Photoaf-finity-Labeled by Azidopine
    • Bruggemann, E. P.; Germano, U. A.; Gottesman, M. M.; Pastan, I. Two Different Regions of Phosphoglycoprotein are Photoaf-finity-Labeled by Azidopine. J. Biol. Chem. 1989, 264, 15483-15488.
    • (1989) J. Biol. Chem. , vol.264 , pp. 15483-15488
    • Bruggemann, E.P.1    Germano, U.A.2    Gottesman, M.M.3    Pastan, I.4
  • 15
    • 0028235205 scopus 로고
    • Benzophenone Photophores in Biochemistry
    • and references cited therein
    • Dormân, G.; Prestwich, G. D. Benzophenone Photophores in Biochemistry. Biochemistry 1994, 33, 5661-5673 and references cited therein.
    • (1994) Biochemistry , vol.33 , pp. 5661-5673
    • Dormân, G.1    Prestwich, G.D.2
  • 16
    • 0027450067 scopus 로고
    • Inositol 1, 4, 5-Triphosphate Receptors: Labeling the Inositol 1, 4, 5-Triphosphate Binding Site with Photoaffinity Ligands
    • Mourey, R. J.; Estevez, V. A.; Marecek, J. F.; Barrow, R. K.; Prestwich, G. D.; Snyder, S. H. Inositol 1, 4, 5-Triphosphate Receptors: Labeling the Inositol 1, 4, 5-Triphosphate Binding Site with Photoaffinity Ligands. Biochemistry 1993, 32, 1719-1726.
    • (1993) Biochemistry , vol.32 , pp. 1719-1726
    • Mourey, R.J.1    Estevez, V.A.2    Marecek, J.F.3    Barrow, R.K.4    Prestwich, G.D.5    Snyder, S.H.6
  • 17
    • 0028348005 scopus 로고
    • Schotten-Baumann Acylation of Baccatin III 13-[(2′R, 3′S)- 3-phenylisoserinate]: An Efficient Route to N-Acyl Taxol Analogues and Their Microtubule Assembly Activity
    • Georg, G. I.; Boge, T. C.; Cheruvallath, Z. S.; Harriman, G. C. B.; Hepperle, M.; Park, H.; Himes, R. H. Schotten-Baumann Acylation of Baccatin III 13-[(2′R, 3′S)- 3-phenylisoserinate]: An Efficient Route to N-Acyl Taxol Analogues and Their Microtubule Assembly Activity. Bioorg. Med. Chem. Lett. 1994, 4, 335-338.
    • (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 335-338
    • Georg, G.I.1    Boge, T.C.2    Cheruvallath, Z.S.3    Harriman, G.C.B.4    Hepperle, M.5    Park, H.6    Himes, R.H.7
  • 19
    • 0027935479 scopus 로고
    • Synthesis and Structure-Activity Relationship of New Antitumor Taxoids. Effects of Cyclohexyl Substitution at the C-3′ and/or C-2 of Taxotere (Docetaxel)
    • Ojima, I.; Duclos, O.; Zucco, M.; Bissery, M.-C.; Combeau, C.; Vrignaud, P.; Riou, J.-F.; Lavelle, F. Synthesis and Structure-Activity Relationship of New Antitumor Taxoids. Effects of Cyclohexyl Substitution at the C-3′ and/or C-2 of Taxotere (Docetaxel). J. Med Chem. 1994, 37, 2602-2608.
    • (1994) J. Med Chem. , vol.37 , pp. 2602-2608
    • Ojima, I.1    Duclos, O.2    Zucco, M.3    Bissery, M.-C.4    Combeau, C.5    Vrignaud, P.6    Riou, J.-F.7    Lavelle, F.8
  • 22
  • 23
    • 0026686518 scopus 로고
    • New and Efficient Approaches to the Semisynthesis of Taxol and Its C-13 Side Chain Analogs by Means of β-Lactam Synthon Method
    • Ojima, I.; Habus, I.; Zhao, M.; Zucco, M.; Park, Y. H.; Sun, C. M.; Brigaud, T. New and Efficient Approaches to the Semisynthesis of Taxol and Its C-13 Side Chain Analogs by Means of β-Lactam Synthon Method. Tetrahedron 1992, 48, 6985-7012.
    • (1992) Tetrahedron , vol.48 , pp. 6985-7012
    • Ojima, I.1    Habus, I.2    Zhao, M.3    Zucco, M.4    Park, Y.H.5    Sun, C.M.6    Brigaud, T.7
  • 24
    • 85127651620 scopus 로고
    • Semisynthesis of Taxol and Taxotere
    • Suffness, M., Ed.; CRC Press: New York, Chapter 5, and references cited therein
    • Holton, R. A.; Biediger, R. J.; Boatman, P. D. Semisynthesis of Taxol and Taxotere. In Taxol: Science and Applications; Suffness, M., Ed.; CRC Press: New York, 1995; Chapter 5, pp 97-121 and references cited therein.
    • (1995) In Taxol: Science and Applications , pp. 97-121
    • Holton, R.A.1    Biediger, R.J.2    Boatman, P.D.3
  • 26
    • 0026498769 scopus 로고
    • Synthesis of Biologically Active Taxol Analogues with Modified Phenylisoserine Side Chains
    • Georg, G. I.; Cheruvallath, Z. S. Synthesis of Biologically Active Taxol Analogues with Modified Phenylisoserine Side Chains. J. Med. Chem. 1992, 35, 4230-4237.
    • (1992) J. Med. Chem. , vol.35 , pp. 4230-4237
    • Georg, G.I.1    Cheruvallath, Z.S.2
  • 28
    • 0028200190 scopus 로고
    • Characterization of Two Taxol Photoaffinity Analogs Bearing Azide and Benzophenone-Related Photoreactive Substituents in the A-ring Side Chain
    • Swindell, C. S.; Heerding, J. M.; Krauss, N. E.; Horwitz, S. B.; Rao, S.; Ringel, I. Characterization of Two Taxol Photoaffinity Analogs Bearing Azide and Benzophenone-Related Photoreactive Substituents in the A-ring Side Chain. J. Med. Chem. 1994, 37, 1446-1449.
    • (1994) J. Med. Chem. , vol.37 , pp. 1446-1449
    • Swindell, C.S.1    Heerding, J.M.2    Krauss, N.E.3    Horwitz, S.B.4    Rao, S.5    Ringel, I.6
  • 29
    • 0028178514 scopus 로고
    • Predominant Labeling of ß-over a-Tubulin from Porcine Brain by a Photoactivatable Taxoid Derivative
    • Combeau, C.; Commerçon, A.; Mioskowski, C.; Rousseau, B.; Aubert, F.; Goeldner, M. Predominant Labeling of ß-over a-Tubulin from Porcine Brain by a Photoactivatable Taxoid Derivative. Biochemistry 1994, 33, 6676-6683.
    • (1994) Biochemistry , vol.33 , pp. 6676-6683
    • Combeau, C.1    Commerçon, A.2    Mioskowski, C.3    Rousseau, B.4    Aubert, F.5    Goeldner, M.6
  • 30
    • 0013682470 scopus 로고
    • Distinct P-Glycoprotein Precursors are Overproduced in Independently Isolated Drug-Resistant Cell Lines
    • Greenberger, L. M.; Lothstein, L.; Williams, S. S.; Horwitz, S. B. Distinct P-Glycoprotein Precursors are Overproduced in Independently Isolated Drug-Resistant Cell Lines. Proc. Natl. Acad. Sci. U. SA. 1988, 85, 3762-3766.
    • (1988) Proc. Natl. Acad. Sci. U. SA. , vol.85 , pp. 3762-3766
    • Greenberger, L.M.1    Lothstein, L.2    Williams, S.S.3    Horwitz, S.B.4
  • 31
    • 0023241702 scopus 로고
    • Biosynthesis of Heterogeneous Forms of Multidrug Resistance-Associated Glycoproteins
    • Greenberger, L. M.; Williams, S. S.; Horwitz, S. B. Biosynthesis of Heterogeneous Forms of Multidrug Resistance-Associated Glycoproteins. J. Biol. Chem. 1987, 262, 13685-13689.
    • (1987) J. Biol. Chem. , vol.262 , pp. 13685-13689
    • Greenberger, L.M.1    Williams, S.S.2    Horwitz, S.B.3


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