메뉴 건너뛰기




Volumn 41, Issue 6, 1998, Pages 981-987

Design, synthesis, and evaluation of the multidrug resistance-reversing activity of D-glucose mimetics of hapalosin

Author keywords

[No Author keywords available]

Indexed keywords

GLUCOSE; GLYCOPROTEIN P; HAPALOSIN; MULTIDRUG RESISTANCE PROTEIN; UNCLASSIFIED DRUG;

EID: 0032510391     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970709p     Document Type: Article
Times cited : (49)

References (40)
  • 1
    • 0024329881 scopus 로고
    • The Biochemistry of P-GlycoproteinMediated Multidrug Resistance
    • (a) Endicott, J. A.; Ling, V. The Biochemistry of P-GlycoproteinMediated Multidrug Resistance. Annu. Rev. Biochem. 1989,58, 137-171.
    • (1989) Annu. Rev. Biochem. , vol.58 , pp. 137-171
    • Endicott, J.A.1    Ling, V.2
  • 5
    • 0028054888 scopus 로고
    • Overexpression of Multidrug Resistance-Associated Protein (MRP) Increases Resistance to Natural Product Drugs
    • (b) Grant, C. E.; Valdimarsson, G.; Hipfner, D. R.; Almquist, K. C.; Cole, S. P. C.; Deeley, R. G. Overexpression of Multidrug Resistance-Associated Protein (MRP) Increases Resistance to Natural Product Drugs. Cancer Res. 1994, 54, 357-361.
    • (1994) Cancer Res. , vol.54 , pp. 357-361
    • Grant, C.E.1    Valdimarsson, G.2    Hipfner, D.R.3    Almquist, K.C.4    Cole, S.P.C.5    Deeley, R.G.6
  • 6
    • 0027960078 scopus 로고
    • Pharmacological Characterization of Multidrug Resistant MRP-Transfected Human Tumor Cells
    • Cole, S. P. C.; Sparks, K. E.; Fraser, K; Loe, D. W.; Grant, C. E.; Wilson, G. M.; Deeley, R. G. Pharmacological Characterization of Multidrug Resistant MRP-Transfected Human Tumor Cells. Cancer Res. 1994, 54, 5902-5910.
    • (1994) Cancer Res. , vol.54 , pp. 5902-5910
    • Cole, S.P.C.1    Sparks, K.E.2    Fraser, K.3    Loe, D.W.4    Grant, C.E.5    Wilson, G.M.6    Deeley, R.G.7
  • 7
    • 0027136660 scopus 로고
    • Clinical Trials of Agents that Reverse Multidrug Resistance
    • (a) Raderer, M.; Scheithauer, W. Clinical Trials of Agents That Reverse Multidrug Resistance. Cancer 1993, 72, 3553-3563.
    • (1993) Cancer , vol.72 , pp. 3553-3563
    • Raderer, M.1    Scheithauer, W.2
  • 8
    • 0025007511 scopus 로고
    • Pharmacology of Drugs that Alter Multidrug Resistance in Cancer
    • (b) Ford, J.M.; Hait, W. N. Pharmacology of Drugs That Alter Multidrug Resistance in Cancer. Pharmacol. Rev. 1990, 42, 155-199.
    • (1990) Pharmacol. Rev. , vol.42 , pp. 155-199
    • Ford, J.M.1    Hait, W.N.2
  • 9
    • 0028598490 scopus 로고
    • Hapalosin, a Cyanobacterial Cyclic Depsipeptide with Multidrug Resistance-Reversing Activity
    • Stratmann, K.; Burgoyne, D. L.; Moore, R. E.; Patterson, G. M. L.; Smith, C. D. Hapalosin, a Cyanobacterial Cyclic Depsipeptide with Multidrug Resistance-Reversing Activity. J. Org. Chem. 1994, 59, 7219-7226.
    • (1994) J. Org. Chem. , vol.59 , pp. 7219-7226
    • Stratmann, K.1    Burgoyne, D.L.2    Moore, R.E.3    Patterson, G.M.L.4    Smith, C.D.5
  • 10
    • 0029556694 scopus 로고
    • A Convergent Total Synthesis of the Multidrug ResistanceReversing Agent Hapalosin
    • For syntheses of hapalosin, see: (a) Dinh, T. Q.; Armstrong, R. W. A Convergent Total Synthesis of the Multidrug ResistanceReversing Agent Hapalosin. J. Org. Chem. 1995, 60, 8118-8119.
    • (1995) J. Org. Chem. , vol.60 , pp. 8118-8119
    • Dinh, T.Q.1    Armstrong, R.W.2
  • 11
    • 33744702044 scopus 로고    scopus 로고
    • A Convergent, Enantioselective Total Synthesis of Hapalosin: A Drug with Multidrug Resistance-Reversing Activity
    • (b) Gosh, A. K.; Liu, W.; Xu, Y.; Chen, Z. A Convergent, Enantioselective Total Synthesis of Hapalosin: A Drug with Multidrug Resistance-Reversing Activity. Angew. Chem., Int. Ed. Engl. 1996, 35, 74-76.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 74-76
    • Gosh, A.K.1    Liu, W.2    Xu, Y.3    Chen, Z.4
  • 12
    • 0030009931 scopus 로고    scopus 로고
    • Synthetic Study on Hapalosin, a Cyclic Depsipeptide Possessing Multidrug Resistance Reversing Activities
    • Ohmori, K.; Okuno, T.; Nishiyama, S.; Yamamura, S. Synthetic Study on Hapalosin, a Cyclic Depsipeptide Possessing Multidrug Resistance Reversing Activities. Tetrahedron Lett. 1996, 37, 3467-3470.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 3467-3470
    • Ohmori, K.1    Okuno, T.2    Nishiyama, S.3    Yamamura, S.4
  • 13
    • 0029795238 scopus 로고    scopus 로고
    • Synthesis and Conformational Analysis of the Multidrug Resistance-Reversing Agent Hapalosin and Its Non-N-Methyl Analog
    • Dinh, T. Q.; Du, X.; Armstrong, R. W. Synthesis and Conformational Analysis of the Multidrug Resistance-Reversing Agent Hapalosin and Its Non-N-Methyl Analog. J. Org. Chem. 1996, 61, 6606-6616.
    • (1996) J. Org. Chem. , vol.61 , pp. 6606-6616
    • Dinh, T.Q.1    Du, X.2    Armstrong, R.W.3
  • 14
    • 0030565527 scopus 로고    scopus 로고
    • Synthesis of Hapalosin and 8-Deoxy-Hapalosin
    • (e) Wagner, B.; Beugelmans, R.; Zhu, J. Synthesis of Hapalosin and 8-Deoxy-Hapalosin. Tetrahedron Lett. 1996,37,6557-6560.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 6557-6560
    • Wagner, B.1    Beugelmans, R.2    Zhu, J.3
  • 15
    • 0030592790 scopus 로고    scopus 로고
    • Chemical Study on Hapalosin, a Cyclic Depsipeptide Possessing Multidrug Resistance Reversing Activities: Synthesis, Structure and Biological Activity
    • (f) Okuno, T.; Ohmori, K.; Nishiyama, S.; Yamamura, S.; Nakar, mura, K; Houk, K N.; Okamoto, K. Chemical Study on Hapalosin, a Cyclic Depsipeptide Possessing Multidrug Resistance Reversing Activities: Synthesis, Structure and Biological Activity. Tetrahedron 1996, 52, 14723-14734.
    • (1996) Tetrahedron , vol.52 , pp. 14723-14734
    • Okuno, T.1    Ohmori, K.2    Nishiyama, S.3    Yamamura, S.4    Nakar Mura, K.5    Houk, K.N.6    Okamoto, K.7
  • 16
    • 0030951560 scopus 로고    scopus 로고
    • Analogs Incorporating trans-4-Hydroxy-L-Proline that Reverse Multidrug Resistance Better than Hapalosin
    • Dinh, T. Q.; Smith, C. D.; Armstrong, R. W. Analogs Incorporating trans-4-Hydroxy-L-Proline That Reverse Multidrug Resistance Better Than Hapalosin. J. Org. Chem. 1997, 62, 790-791.
    • (1997) J. Org. Chem. , vol.62 , pp. 790-791
    • Dinh, T.Q.1    Smith, C.D.2    Armstrong, R.W.3
  • 17
    • 0030761540 scopus 로고    scopus 로고
    • Synthesis, Conformational Analysis, and Evaluation of the Multidrug Resistance-Reversing Activity of the Triamide and Proline Analogs of Hapalosin
    • Dinh, T. Q.; Du, X.; Smith, C. D.; Armstrong, R. W. Synthesis, Conformational Analysis, and Evaluation of the Multidrug Resistance-Reversing Activity of the Triamide and Proline Analogs of Hapalosin. J. Org. Chem. 1997, 62, 6773-6783.
    • (1997) J. Org. Chem. , vol.62 , pp. 6773-6783
    • Dinh, T.Q.1    Du, X.2    Smith, C.D.3    Armstrong, R.W.4
  • 20
    • 0344778061 scopus 로고
    • Semianalytical Treatment of Solvation for Molecular Mechanics and Dynamics
    • Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. Semianalytical Treatment of Solvation for Molecular Mechanics and Dynamics. J. Am. Chem. Soc. 1990, 112, 6127-6129.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 6127-6129
    • Still, W.C.1    Tempczyk, A.2    Hawley, R.C.3    Hendrickson, T.4
  • 21
    • 0000460451 scopus 로고
    • Highly Stereoselective C-Allylation of Glycopyranosides with Allylsilanes Catalyzed by Silyl Triflate or lodosilane
    • Hosomi, A.; Sakata, Y.; Sakurai, H. Highly Stereoselective C-Allylation of Glycopyranosides with Allylsilanes Catalyzed by Silyl Triflate or lodosilane. Tetrahedron Lett. 1984,25, 2383-2386.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 2383-2386
    • Hosomi, A.1    Sakata, Y.2    Sakurai, H.3
  • 22
  • 24
    • 0001205939 scopus 로고
    • Diacetone D-glucose can be purchased from the Aldrich Chemical Co. or prepared according to: Schmidt, O. T. Methods Carbohydr. Chem. 1963,2, 318.
    • (1963) Methods Carbohydr. Chem. , vol.2 , pp. 318
    • Schmidt, O.T.1
  • 25
    • 0002487780 scopus 로고
    • A Facile Cleavage of Benzylidene Acetals with Diisobutylaluminum Hydride
    • (a) Takano, S.; Akiyama, M.; Sato, S.; Ogasawara, K. A Facile Cleavage of Benzylidene Acetals with Diisobutylaluminum Hydride. Chem. Lett. 1983, 1593-1596.
    • (1983) Chem. Lett. , pp. 1593-1596
    • Takano, S.1    Akiyama, M.2    Sato, S.3    Ogasawara, K.4
  • 26
    • 0001285828 scopus 로고
    • Enantioselective Synthesis of (6S,7S,9R,10R)-6,9-Epoxynonadec-18-ene-7,10-diol, a Marine Natural Product
    • (b) Hatakeyama, S.; Sakurai, K.; Saijo, K.; Takano, S. Enantioselective Synthesis of (6S,7S,9R,10R)-6,9-Epoxynonadec-18-ene-7,10-diol, a Marine Natural Product. Tetrahedron Lett. 1985, 26, 1333-1336.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 1333-1336
    • Hatakeyama, S.1    Sakurai, K.2    Saijo, K.3    Takano, S.4
  • 27
    • 0017849572 scopus 로고
    • A New Stereoselective Synthesis of Racemic Disparlure, the Sex Pheromone of Gypsy Moth
    • Tolstikov, G. A.; Odinokov, V. N.; Galeeva, R. L; Bakeeva, R. S. A New Stereoselective Synthesis of Racemic Disparlure, the Sex Pheromone of Gypsy Moth. Tetrahedron Lett. 1978, 1857-1858.
    • (1978) Tetrahedron Lett. , pp. 1857-1858
    • Tolstikov, G.A.1    Odinokov, V.N.2    Galeeva, R.L.3    Bakeeva, R.S.4
  • 28
    • 0030999573 scopus 로고    scopus 로고
    • Oxiranyl Anions in Organic Synthesis: Application to the Synthesis of Hemibrevetoxin B
    • Mori, Y.; Yaegashi, K.; Furukawa, H. Oxiranyl Anions in Organic Synthesis: Application to the Synthesis of Hemibrevetoxin B. J. Am. Chem. Soc. 1997, 119, 4557-4558.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 4557-4558
    • Mori, Y.1    Yaegashi, K.2    Furukawa, H.3
  • 29
    • 37049077199 scopus 로고
    • Syntheses of Novel 25-Hydroxyvitamin Da Haptens Having Chemical Bridges at the C-11α Position
    • Kobayashi, N.; Hisada, A.; Shimada, K. Syntheses of Novel 25-Hydroxyvitamin Da Haptens Having Chemical Bridges at the C-11α Position. J. Chem. Soc., Perkin Trans, l 1993, 31-37.
    • (1993) J. Chem. Soc., Perkin Trans, L , pp. 31-37
    • Kobayashi, N.1    Hisada, A.2    Shimada, K.3
  • 30
    • 37049142468 scopus 로고
    • Sodium Metaperiodate: A Mild Oxidizing Agent for the Generation of Di-imide from Hydrazine
    • Huffman, J. M.; Schlessinger, R. H. Sodium Metaperiodate: A Mild Oxidizing Agent for the Generation of Di-imide from Hydrazine. J. Chem. Soc., Chem. Commun. 1971, 1245-1246.
    • (1971) J. Chem. Soc., Chem. Commun. , pp. 1245-1246
    • Huffman, J.M.1    Schlessinger, R.H.2
  • 32
    • 0000414605 scopus 로고
    • Alkene Reductions Employing Ethyl Acetate-Hydroxylamine, a Useful New Source of Diimide
    • Wade, P. A.; Amin, N. V. Alkene Reductions Employing Ethyl Acetate-Hydroxylamine, a Useful New Source of Diimide. Synth. Commun. 1982,12, 287-291.
    • (1982) Synth. Commun. , vol.12 , pp. 287-291
    • Wade, P.A.1    Amin, N.V.2
  • 34
    • 0009578223 scopus 로고
    • Hydrogenation with Diimide
    • (b) Miller, C. E. Hydrogenation with Diimide. J. Chem. Educ. 1965, 42, 254-259.
    • (1965) J. Chem. Educ. , vol.42 , pp. 254-259
    • Miller, C.E.1
  • 35
    • 46149140781 scopus 로고
    • On the Selectivity of Deprotection of Benzyl, MPM (4-Methoxybenzyl) and DMPM (3,4-Dimethoxybenzyl) Protecting Groups for Hydroxy Functions
    • Horita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y.; Yonemitsu, O. On the Selectivity of Deprotection of Benzyl, MPM (4-Methoxybenzyl) and DMPM (3,4-Dimethoxybenzyl) Protecting Groups for Hydroxy Functions. Tetrahedron 1986, 42, 3021-3028.
    • (1986) Tetrahedron , vol.42 , pp. 3021-3028
    • Horita, K.1    Yoshioka, T.2    Tanaka, T.3    Oikawa, Y.4    Yonemitsu, O.5
  • 37
    • 0022458951 scopus 로고
    • Isolation and Characterization of Adriamycin-Resistant HL-60 Cells which Are not Defective in the Initial Intracellular Accumulation of Drug
    • Marsh, W.; Sicheri, R.; Center, M. S. Isolation and Characterization of Adriamycin-Resistant HL-60 Cells Which Are Not Defective in the Initial Intracellular Accumulation of Drug. Cancer Res. 1986, 47, 4053-4057.
    • (1986) Cancer Res. , vol.47 , pp. 4053-4057
    • Marsh, W.1    Sicheri, R.2    Center, M.S.3
  • 38
    • 0028076805 scopus 로고
    • Reversal of Multiple Drug Resistance by Tolyporphin, a Novel Cyanobacterial Natural Product
    • (a) Smith, C. D.; Prinsep, M. R.; Caplan, F. R.; Moore, R. E.; Patterson, G. M. L. Reversal of Multiple Drug Resistance by Tolyporphin, a Novel Cyanobacterial Natural Product. Oncol. Res. 1994,6, 211-218.
    • (1994) Oncol. Res. , vol.6 , pp. 211-218
    • Smith, C.D.1    Prinsep, M.R.2    Caplan, F.R.3    Moore, R.E.4    Patterson, G.M.L.5
  • 39
    • 0028944619 scopus 로고
    • Welwitindolinone Analogues that Reverse P-Glycoprotein-Mediated Multiple Drug Resistance
    • (b) Smith, C. D.; Zilfou, J. T.; Stratmann, K.; Patterson, G. M. L.; Moore, R. E. Welwitindolinone Analogues That Reverse P-Glycoprotein-Mediated Multiple Drug Resistance. Mol. Pharmacol. 1995, 47, 241-247.
    • (1995) Mol. Pharmacol. , vol.47 , pp. 241-247
    • Smith, C.D.1    Zilfou, J.T.2    Stratmann, K.3    Patterson, G.M.L.4    Moore, R.E.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.