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Volumn 14, Issue 9, 2004, Pages 455-468

PEG prodrugs of 6-mercaptopurine for parenteral administration using benzyl elimination of thiols

Author keywords

6 Mercaptopurine; Benzyl elimination; Parenteral administration; Poly(ethylene glycol); Prodrug

Indexed keywords

6 MERCAPTOPURINE DERIVATIVE; DRUG VEHICLE; MACROGOL; MERCAPTOPURINE; PRODRUG; THIOL DERIVATIVE;

EID: 4644353135     PISSN: 09650407     EISSN: None     Source Type: Journal    
DOI: 10.3727/0965040041791446     Document Type: Article
Times cited : (11)

References (34)
  • 1
    • 0024375599 scopus 로고
    • The purine path to chemotherapy
    • Elion, G. B. The purine path to chemotherapy. Angew Chem. Int. Ed. Eng. 28:870-878; 1989.
    • (1989) Angew Chem. Int. Ed. Eng. , vol.28 , pp. 870-878
    • Elion, G.B.1
  • 2
    • 0020534019 scopus 로고
    • Variable bioavailability of oral mercaptopurine. Is maintenance chemotherapy in acute lymphoblastic leukemia being optimally delivered?
    • Zimm, S.; Collins, J. M.; Riccardi, R.; O'Neill, D.; Narang, P. K.; Chabner, B.; Poplack, D. G. Variable bioavailability of oral mercaptopurine. Is maintenance chemotherapy in acute lymphoblastic leukemia being optimally delivered? N. Engl. J. Med. 308:1005-1009; 1983.
    • (1983) N. Engl. J. Med. , vol.308 , pp. 1005-1009
    • Zimm, S.1    Collins, J.M.2    Riccardi, R.3    O'Neill, D.4    Narang, P.K.5    Chabner, B.6    Poplack, D.G.7
  • 4
    • 33947466108 scopus 로고
    • Synthesis of potential anticancer agents. XIII. Ribosides of 6-substituted purines
    • James, A.; Johnson, H., Jr.; Thomas, J.; Schaeffer, H. J. Synthesis of potential anticancer agents. XIII. Ribosides of 6-substituted purines. J. Am. Chem. Soc. 80:699-702; 1958.
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 699-702
    • James, A.1    Johnson Jr., H.2    Thomas, J.3    Schaeffer, H.J.4
  • 7
    • 0029931612 scopus 로고    scopus 로고
    • Rational design of novel immunosuppressive drugs: Analogues of azathioprine lacking the 6-mercaptopurine substituent retain or have enhanced immunosuppressive effects
    • Duncan, J. K.; Crawford, J. L.; Maddocks, D.; Jones, N.; Szawlowski, P. Rational design of novel immunosuppressive drugs: Analogues of azathioprine lacking the 6-mercaptopurine substituent retain or have enhanced immunosuppressive effects. J. Med. Chem. 39:2690-2695; 1996.
    • (1996) J. Med. Chem. , vol.39 , pp. 2690-2695
    • Duncan, J.K.1    Crawford, J.L.2    Maddocks, D.3    Jones, N.4    Szawlowski, P.5
  • 9
    • 0000231181 scopus 로고
    • 1,4- and 1,6-Eliminations from hydroxy and amino-substituted benzyl systems: Chemical and biochemical applications
    • Wakselman, M. 1,4- and 1,6-Eliminations from hydroxy and amino-substituted benzyl systems: Chemical and biochemical applications. Nouv. J. Chem. 7:439-447; 1983.
    • (1983) Nouv. J. Chem. , vol.7 , pp. 439-447
    • Wakselman, M.1
  • 10
    • 0001144611 scopus 로고
    • Use of o- and p-hydroxybenzyl functions as blocking groups which are removable with base
    • Taylor, L. D.; Grasshoff, J. M.; Pluhar, M. Use of o- and p-hydroxybenzyl functions as blocking groups which are removable with base. J. Org. Chem. 43:1197-1200; 1978.
    • (1978) J. Org. Chem. , vol.43 , pp. 1197-1200
    • Taylor, L.D.1    Grasshoff, J.M.2    Pluhar, M.3
  • 11
    • 0033539039 scopus 로고    scopus 로고
    • Drug delivery systems employing 1,4- or 1,6-elimination: Poly (ethylene glycol) prodrugs of amine containing compounds
    • Greenwald, R. B.; Pendri, A.; Conover, C. D.; Zhao, H.; Choe, Y. H.; Martinez, A.; Shum, K.; Guan, S. Drug delivery systems employing 1,4- or 1,6-elimination: Poly (ethylene glycol) prodrugs of amine containing compounds. J. Med. Chem. 42:3657-3667; 1999.
    • (1999) J. Med. Chem. , vol.42 , pp. 3657-3667
    • Greenwald, R.B.1    Pendri, A.2    Conover, C.D.3    Zhao, H.4    Choe, Y.H.5    Martinez, A.6    Shum, K.7    Guan, S.8
  • 12
    • 0034628515 scopus 로고    scopus 로고
    • Drug delivery systems based on trimethyl lock lactonization: Poly (ethylene glycol) prodrugs of amine containing compounds
    • Greenwald, R. B.; Choe, Y. H.; Conover, C. D.; Zhao, H.; Shum, K.; Wu, D.; Royzen, M. Drug delivery systems based on trimethyl lock lactonization: Poly (ethylene glycol) prodrugs of amine containing compounds. J. Med. Chem. 43:475-487; 2000.
    • (2000) J. Med. Chem. , vol.43 , pp. 475-487
    • Greenwald, R.B.1    Choe, Y.H.2    Conover, C.D.3    Zhao, H.4    Shum, K.5    Wu, D.6    Royzen, M.7
  • 13
    • 0030071043 scopus 로고    scopus 로고
    • Drug delivery systems: Water soluble taxol 2′-poly(ethylene glycol) ester prodrugs-design and in vivo effectiveness
    • Greenwald, R. B.; Gilbert, C. W.; Pendri, A.; Conover, C. D.; Xia, J.; Martinez, A. Drug delivery systems: Water soluble taxol 2′-poly(ethylene glycol) ester prodrugs-design and in vivo effectiveness. J. Med. Chem. 39:424-431; 1996.
    • (1996) J. Med. Chem. , vol.39 , pp. 424-431
    • Greenwald, R.B.1    Gilbert, C.W.2    Pendri, A.3    Conover, C.D.4    Xia, J.5    Martinez, A.6
  • 15
    • 0020264574 scopus 로고
    • Quantitation of 6-mercaptopurine in biologic fluids using high-performance liquid chromatography: A selective and novel procedure
    • Narang, P. K.; Yeager, R. L.; Chatterji, D. C. Quantitation of 6-mercaptopurine in biologic fluids using high-performance liquid chromatography: A selective and novel procedure. J. Chromatogr. 230:373-380; 1982.
    • (1982) J. Chromatogr. , vol.230 , pp. 373-380
    • Narang, P.K.1    Yeager, R.L.2    Chatterji, D.C.3
  • 19
    • 0030294010 scopus 로고    scopus 로고
    • PEG thiazolidine-2-thione, a novel reagent for facile protein modification: Conjugation of bovine hemoglobin
    • Greenwald, R. B.; Pendri, A.; Martinez, A.; Gilbert, C.; Bradley, R. PEG thiazolidine-2-thione, a novel reagent for facile protein modification: Conjugation of bovine hemoglobin. Bioconjugate Chem. 7:638-641; 1996.
    • (1996) Bioconjugate Chem. , vol.7 , pp. 638-641
    • Greenwald, R.B.1    Pendri, A.2    Martinez, A.3    Gilbert, C.4    Bradley, R.5
  • 20
    • 0001099083 scopus 로고
    • Potential purine antagonists. XXX. Purine betaines and related derivatives prepared by direct methylation of the simple purines
    • Jones, J. W.; Robins, R. K. Potential purine antagonists. XXX. Purine betaines and related derivatives prepared by direct methylation of the simple purines. J. Am. Chem. Soc. 84:1914-1919; 1962.
    • (1962) J. Am. Chem. Soc. , vol.84 , pp. 1914-1919
    • Jones, J.W.1    Robins, R.K.2
  • 22
    • 0031956262 scopus 로고    scopus 로고
    • The design of selectively-activated anti-cancer prodrugs for use in antibody-directed and gene-directed enzyme-prodrug therapies
    • Denny, W. A.; Wilson, W. R. The design of selectively-activated anti-cancer prodrugs for use in antibody-directed and gene-directed enzyme-prodrug therapies. J. Pharm. Pharmacol. 50:387-394; 1998.
    • (1998) J. Pharm. Pharmacol. , vol.50 , pp. 387-394
    • Denny, W.A.1    Wilson, W.R.2
  • 23
    • 0004444422 scopus 로고
    • Alkaline hydrolysis of some carbamic acid esters
    • Christenson, I. Alkaline hydrolysis of some carbamic acid esters. Acta Chem. Scand. 18:904-922; 1964.
    • (1964) Acta Chem. Scand. , vol.18 , pp. 904-922
    • Christenson, I.1
  • 24
    • 0000682257 scopus 로고
    • The mechanism of the alkaline hydrolysis of p-nitrophenyl N-methylcarbamate
    • Bender, M. L.; Homer, R. B. The mechanism of the alkaline hydrolysis of p-nitrophenyl N-methylcarbamate. J. Org. Chem. 30:3975-3978; 1965.
    • (1965) J. Org. Chem. , vol.30 , pp. 3975-3978
    • Bender, M.L.1    Homer, R.B.2
  • 25
    • 0023134539 scopus 로고
    • Site-specific drug delivery
    • Friend, D. R.; Pangbum, S. Site-specific drug delivery. Med. Res. Rev. 7:53-106; 1987.
    • (1987) Med. Res. Rev. , vol.7 , pp. 53-106
    • Friend, D.R.1    Pangbum, S.2
  • 28
    • 4644322213 scopus 로고
    • Effects of 6-mercaptopurine on experimental tumors
    • Skipper, H. E. Effects of 6-mercaptopurine on experimental tumors. Ann. NY Acad. Sci. 60:267-272; 1954.
    • (1954) Ann. NY Acad. Sci. , vol.60 , pp. 267-272
    • Skipper, H.E.1
  • 29
    • 0019410690 scopus 로고
    • Evaluation of Madison 109 lung carcinoma as a model for screening antitumor drugs
    • Rose, W. C. Evaluation of Madison 109 lung carcinoma as a model for screening antitumor drugs. Cancer Treat. Rep. 65:299-312; 1981.
    • (1981) Cancer Treat. Rep. , vol.65 , pp. 299-312
    • Rose, W.C.1
  • 31
    • 0025297987 scopus 로고
    • Determination of 6-mercaptopurine and its metabolites in plasma or serum by high performance liquid chromatography
    • Sahnoun, Z.; Serre-Debeauvais, F.; Lang J.; Faucon, G.; Gavend, M. Determination of 6-mercaptopurine and its metabolites in plasma or serum by high performance liquid chromatography. Biomed. Chromatogr. 4:144-147; 1990.
    • (1990) Biomed. Chromatogr. , vol.4 , pp. 144-147
    • Sahnoun, Z.1    Serre-Debeauvais, F.2    Lang, J.3    Faucon, G.4    Gavend, M.5
  • 32
    • 0020076892 scopus 로고
    • High-performance liquid chromatographic determination of plasma 6-mercaptopurine in clinically relevant concentrations
    • De Abreu, R. A.; Van Baal, J. M.; Schouten, T. J.; Schretlen, E. D. A. M.; De Bruyn, C. H. M. M. High-performance liquid chromatographic determination of plasma 6-mercaptopurine in clinically relevant concentrations. J. Chromatogr. 12:526-533; 1982.
    • (1982) J. Chromatogr. , vol.12 , pp. 526-533
    • De Abreu, R.A.1    Van Baal, J.M.2    Schouten, T.J.3    Schretlen, E.D.A.M.4    De Bruyn, C.H.M.M.5
  • 33
    • 0037155531 scopus 로고    scopus 로고
    • Protease-mediated fragmentation of p-amidobenzylethers: A new strategy for the activation of anticancer prodrugs
    • Toki, B. E.; Cerveny, C. G.; Wahl, A. F.; Senter, P. D. Protease-mediated fragmentation of p-amidobenzylethers: A new strategy for the activation of anticancer prodrugs. J. Org. Chem. 67:1866-1872; 2002.
    • (2002) J. Org. Chem. , vol.67 , pp. 1866-1872
    • Toki, B.E.1    Cerveny, C.G.2    Wahl, A.F.3    Senter, P.D.4
  • 34
    • 0026926609 scopus 로고
    • Conjugates of anticancer agents and polymers: Advantages of macromolecular therapeutics in vivo
    • Maeda, H.; Seymour, L. W.; Miyamoto, Y. Conjugates of anticancer agents and polymers: Advantages of macromolecular therapeutics in vivo. Bioconjugate Chem. 3:351-362; 1992.
    • (1992) Bioconjugate Chem. , vol.3 , pp. 351-362
    • Maeda, H.1    Seymour, L.W.2    Miyamoto, Y.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.