Synthesis of Doxorubicin Conjugates Through 14-Hydroxy Group to Melanotransferrin P97

References

• Arcamone , F. 1981 . Doxorubicin Anticancer Antibiotics New York : Academic Press . chapter 2
   Google Scholar
• Wiernik , P.H. 1980 . Anthracyclines. Current Status and New Developments Edited by: Crooke , S.T. and Reich , S.D. 273 – 294 . New York : Academic Press .
   Google Scholar
• Dorr , R.T. and Von Hoff , D.D. 1994 . Cancer Chemotherapy Handbook, , 2nd Ed. New York : Appleton and Lange .
   Google Scholar
• Begley , D.J. , Bradbury , M.W. and Kreuter , J. 2000 . The Blood-Brain Barrier and Drug Delivery to the CNS New York : Marcel Dekker, Inc. .
   Google Scholar
• Fratz , F. , Beyer , U. , Roth , T. , Tarasova , N. , Collery , P. , Lechenault , F. , Cazabat , A. , Schumacher , P. , Unger , C. and Falken , U. 1998 . Transferrin conjugates of doxorubicin: synthesis, characterization, cellular uptake . J. Pharm. Sci. , 87 ( 3 ) : 338 – 346 .
   Google Scholar
• King , D.H. , Yurgaitis , D. , Willner , D. , Firestone , R.A. , Yang , M.B. , Lasch , S.J. , Hellstron , K.E. and Trail , P.A. 1999 . Monoclonal antibody conjugates of doxorubicin prepared with branched linkers: a novel method for increasing the potency of doxorubicin immunoconjugates . Bioconjugate Chem. , 10 ( 2 ) : 279 – 288 .
   Google Scholar
• Lau , A. , Berube , G. and Ford , C.H.J. 1995 . Conjugation of doxorubicin to monoclonal anticarcinoembryonic antigen antibody via novel thio-directed cross-linking reagents . Bioorg. Med. Chem. , 3 ( 10 ) : 1299 – 1304 .
   Google Scholar
• Froesch , B.A. , Stahel , R.A. and Zangemeister-Wittke , U. 1996 . Preparation and funtional evaluation of new doxorubicin immunoconjugates containing and acid-sensitive linker on small-cell lung cancer cells . Cancer Immunol. Immunother. , 42 ( 1 ) : 55 – 63 .
   PubMed Web of Science ®Google Scholar
• Godwin , A. , Hartenstein , M. , Muller , A.H.E. and Brocchini , S. 2001 . Narrow molecular weight distribution precursors for polymer-drug conjugates . Angew. Chem. Int. Ed. , 40 ( 3 ) : 594 – 597 .
   Google Scholar
• Yokoyama , M. , Fukushima , S. , Uehara , R. , Okamoto , K. , Kataoka , K. , Sakurai , Y. and Okano , T. 1998 . Characterization of physical entrapment and chemical conjugation of adriamycin in polymeric micelles and their design for in vivo delivery to a solid tumor . J. Control. Release , 50 ( 1 ) : 79 – 92 .
   PubMed Web of Science ®Google Scholar
• Nogusa , H. , Yano , T. , Kashima , N. , Yamamoto , K. , Okuno , S. and Hamana , H. 2000 . Structure-activity relationships of carboxymethylpullulan-peptide-doxorubicin conjugates—systematic modification of peptide spacer . Bioorg. Med. Chem. Lett. , 10 ( 3 ) : 227 – 230 .
   Google Scholar
• Dvorak , M. , Kopeckova , P. and Kopecek , J. 1999 . High-molecular weight HMPA copolymer-adriamycin conjugates . J. Control. Release , 60 ( 3 ) : 321 – 332 .
   Google Scholar
• Rodrigues , P.C.A. , Beyer , U. , Schumacher , P. , Roth , T. , Fiebig , H.H. , Unger , C. , Messori , L. , Orioli , P. , Paper , D.H. , Mulhaupt , R. and Kratz , F. 1999 . Acid-sensitive polyethylene glycol conjugates of doxorubicin: preparation, in vitro efficacy and intracellular distribution . Bioorg. Med. Chem. , 7 ( 11 ) : 2517 – 2524 .
   PubMed Web of Science ®Google Scholar
• Dubowchik , G.M. and Firestone , R.A. 1998 . Capthepsin B-sensitive dipeptide prodrugs. 1. A model study of structural requirements for efficient release of doxorubicin . Bioorg. Med. Chem. Lett. , 8 ( 23 ) : 3341 – 3346 .
   Google Scholar
• Dubowchik , G.M. , Mosure , K. , Knipe , J.O. and Firestone , R.A. 1998 . Capthepsin B-sensitive dipeptide prodrugs. 2. Models of anticancer drugs pacitaxel (Taxol), mitomycin C and doxorubicin . Bioorg. Med. Chem. Lett. , 8 ( 23 ) : 3347 – 3352 .
   Google Scholar
• Garnett , M.C. 2001 . Targeted drug conjugates: principles and progress . Adv. Drug Delivery Rev. , 53 ( 2 ) : 171 – 216 .
   PubMed Web of Science ®Google Scholar
• Rousselle , C. , Clair , P. , Lefauconnier , J.-M. , Kaczorek , M. , Scherrmann , J.-M. and Temsamani , J. 2000 . New advances in the transport of doxorubicin through the blood-brain barrier by a peptide vector-mediated strategy . Mol. Pharmacol. , 57 ( 4 ) : 679 – 686 .
   PubMed Web of Science ®Google Scholar
• Remsen , L.G. , Trail , P.A. , Hellstrom , I. , Hellstrom , K.E. and Neuwelt , E.A. 2000 . Enhanced delivery improves the efficacy of a tumor-specific doxorubicin immunoconjugate in a human brain tumor xenograft model . Neurosurgery , 46 ( 3 ) : 704 – 709 .
   Google Scholar
• Yamada , T. , Tsujioka , Y. , Taguchi , J. , Takahashi , M. , Tsuboi , Y. , Moroo , I. , Yang , J. and Jefferies , W.A. 1999 . Brain Research , 845 ( 1 ) : 1 – 5 .
   Google Scholar
• Rothenberger , S. , Food , M.R. , Gabthuler , R. , Kennard , M.L. , Yamada , T. , Yasuhara , O. , McGeer , P.L. and Jefferies , W.A. 1996 . Brain Research , 712 ( 1 ) : 117 – 121 .
   PubMed Web of Science ®Google Scholar
• Chen , Q. , Sowa , D. , Cai , L.J. and Gabathuler , R. 2003 . Efficient one-pot synthesis of doxorubicin conjugates through its amino group to melanotransferrin p97 . Synth. Commun. , 33 ( 14 ) : 2399 – 2419 .
   Google Scholar
• Chen , Q. , Sowa , D. and Gabathuler , R. 2003 . Synthesis of doxorubicin conjugates through hydrazone bonds to melanotransferrin p97 . Synth. Commun. , 33 ( 14 ) : 2375 – 2388 .
   Google Scholar
• Tanaka , H. , Komintao , K. , Yoshioka , T. , Iguchi , H. , Hirano , S.I. , Okajima , Y. , Yamamoto , R. , Shirai , M. , Nishida , H. , Tone , H. and Okamoto , R. Conjugate of Adriamycin and Cyclodextrin . US. Patent 5,183,883 . February 2, 1993 .
   Google Scholar
• Nagy , A. , Schally , A.V. , Halmos , G. , Armatis , P. , Cai , R.Z. , Csernus , V. , Kovacs , M. , Koppan , M. and Szepeshazi , K. 1998 . Synthesis and biological evaluation of cytoxic analogs of somatostatin containing doxorubicin or its intensely potent derivative, 2-pyrrolinodoxorubicin . Proc. Natl. Acad. Sci. USA , 95 ( 4 ) : 1794 – 1799 .
   Google Scholar
• Nagy , A. , Schally , A.V. , Armatis , P. , Szepeshazi , K. , Halmos , G. , Kovacs , M. , Zarandi , M. , Groot , K. , Miyazaki , M. , Jungwrith , A. and Horvath , J. 1996 . Cytotoxic analogs of luteinizing hormone-releasing hormone containing doxorubicin or 2-pyrrolinodoxorubicin, a deriv-ative 500–1000 times more potent . Proc. Natl. Acad. Sci. USA , 93 ( 14 ) : 7269 – 7273 .
   PubMed Web of Science ®Google Scholar
• Nagy , A. , Armatis , P. , Cai , R.Z. , Szepeshazi , K. , Halmos , G. and Schally , A.V. 1997 . Design, synthesis, and in vitro evaluation of cytotoxic analogs of bombesin-like, peptides containing doxorubicin or its intensely potent derivative, 2-pyrrolinodoxorubicin . Proc. Natl. Acad. Sci. USA , 94 ( 2 ) : 625 – 656 .
   Google Scholar
• Green , T.W. and Wuts , P.G.M. 1999 . Protective Groups in Organic Synthesis, , 3rd Ed. 506 – 507 . New York : John Wiley & Sons, Inc. .
   Google Scholar