Skip to main content
SpringerLink
Log in

Doxorubicin Conjugates for Selective Delivery to Tumors

  • Chapter
  • First Online:
Anthracycline Chemistry and Biology II

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 283))

Abstract

With the aim of improving the therapeutic utility of doxorubicin, numerous conjugates or prodrugshave been prepared to be selectively activated at the tumor site while releasing the cytotoxic drug.

Among immuno-conjugates representing a widely studied class of doxorubicin derivatives,the clinical development of cBR96-Dox, undoubtedly the most quintessential derivative, was discontinueddue to severe secondary effects. More potent cBR-96 analogues and IMMU-110, another doxorubicin immunoconjugate,are still under study.

Antibody-directed prodrug therapy has been designed to overcome some of the problems associatedwith the treatment of solid tumors. Concerning the anthracycline-based prodrugs, two glucuronideconjugates have reached the preclinical level, HMR 1826 and DOX-GA3. Both conjugates were subsequentlyevaluated against several human cancer xenografts without preliminary administration of fusion protein.Among the novelty in ADEPT approaches, one of the most relevant was based on the design of multiplespacer systems.

Closely related to ADEPT, new approaches to selectively deliver prodrug-releasing enzymes intumor cells have been still studied or proposed by means of gene (GDEPT), polymer (PDEPT), bacteria(BDEPT), or exploiting endogenous carbohydrate-lectin binding (LEAPT).

Activation of conjugates by tumor-associated endogenous enzymes such as prostate specific antigen,plasmin, matrix metalloproteinase, and various extra and intracellular peptidases has also been reported,some of these conjugates like L377,202, a PSA substrate, having reached the clinical level. Doxorubicinpeptide conjugates were also designed to be activated by endopeptidase legumain, and extracellularthimet oligopeptidase to deliver Leu-Dox, known to be cleaved intracellularly by peptidase.

A third class of conjugates has been designed for receptor-mediated targeted delivery,including folate, somatostatin, bombesin, LHRH receptors or integrin and lectin.

Transportation of doxorubicin with peptide vectors has been simultaneously investigated to overcomethe problem of penetration in the brain or the problem of multidrug resistance.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Trail PA, King HD, Dubowchik GM (2003) Cancer Immunol Immunother 52:328

    CAS  Google Scholar 

  2. Wu AM, Senter PD (2005) Nat Biotechnol 23:1137

    Article  CAS  Google Scholar 

  3. Hamann PR (2005) Expert Opin Ther Patents 15:1087

    Article  CAS  Google Scholar 

  4. Trail PA, Willner D, Lasch JS, Henderson AJ, Hofstead SJ, Casazza AM, Firestone RA, Hellström I, Helström KE (1993) Science 261:212

    Article  CAS  Google Scholar 

  5. Saleh MN, Sugarman S, Murray J, Ostroff JB, Healey D, Jones D, Daniel CR, LeBherz D, Brewer H, Onetto N, LoBuglio AF (2000) J Clin Oncol 18:2282

    CAS  Google Scholar 

  6. Tolcher AW, Sugarman S, Gelmon KA, Cohen R, Saleh H, Isaacs C, Young L, Healey D, Onetto N, Slichenmyer W (1999) J Clin Oncol 17:478

    CAS  Google Scholar 

  7. Trail PA, Willner D, Bianchi AB, Henderson AJ, Mark D, TrailSmith MD, Girit E, Lasch S, Hellström I, Hellström KE (1999) Clin Cancer Res 5:3632

    CAS  Google Scholar 

  8. Smith S (2001) Curr Opin Mol Ther 3:295

    CAS  Google Scholar 

  9. Wall AF, Donaldson KL, Mixan BJ, Trail PA, Siegall CB (2001) Int J Cancer 93:590

    Article  Google Scholar 

  10. Ross HJ, Hart LL, Swanson PM, Rarick MU, Figlin RA, Jacobs AD, McCune DE, Rosenberg AH, Baron AD, Grove LE, Thorn MD, Miller DM, Drachman JG, Rudin CM (2006) Lung Cancer 54:69

    Article  Google Scholar 

  11. Seattle Genetics Provides Update on SGN-15 Phase II. Clinical Program at the 11th World Conference on Lung Cancer, July 3–6, 2005, Barcelona, Spain

    Google Scholar 

  12. Muldoon LL, Neuwelt EA (2003) J Neurooncol 65:49

    Article  Google Scholar 

  13. King HD, Staab AJ, Pham-Kaplita K, Yurgaitis D, Firestone RA, Lasch SJ, Trail PA (2003) Bioorg Med Chem Lett 13:2119

    Article  CAS  Google Scholar 

  14. King HD, Yurgaitis D, Willner D, Firestone RA, Yang MB, Lasch SJ, Hellström KE, Trail PA (1999) Bioconjugate Chem 10:279

    Article  CAS  Google Scholar 

  15. King HD, Dubowchik GM, Mastalerz H, Willner D, Hofstead SJ, Firestone RA, Lasch SJ, Trail PA (2002) J Med Chem 45:4336

    Article  CAS  Google Scholar 

  16. Dubowchik GM, Radia S, Mastalerz H, Walker MA, Firestone RA, King HD, Hofstead SJ, Willner D, Lasch SJ, Trail PA (2002) Bioorg Med Chem Lett 12:1529

    Article  CAS  Google Scholar 

  17. Acton EM, Tong GL, Mosher CW, Wolgemuth RL (1984) J Med Chem 27:638

    Article  CAS  Google Scholar 

  18. Cherif A, Farquhar DJ (1992) J Med Chem 35:3208

    Article  CAS  Google Scholar 

  19. Griffiths GL, Mattes MJ, Stein R, Govindan SV, Horak ID, Hansen HJ, Goldenberg DM (2003) Clin Cancer Res 9:6567

    CAS  Google Scholar 

  20. Sapra P, Stein R, Pickett J, Qu Z, Govindan SV, Cardillo TM, Hansen HJ, Horak ID, Griffiths GL, Goldenberg DM (2005) Clin Cancer Res 11:5257

    Article  CAS  Google Scholar 

  21. Hebert C, Norris K, Sauk JJ (2003) J Drug Target 11:101

    Article  CAS  Google Scholar 

  22. Inoh K, Muramatsu H, Torii S, Ikematsu S, Oda M, Kumai H, Sakuma S, Inui T, Kimura T, Muramatsu T (2006) Jpn J Clin Oncol 36:207

    Article  Google Scholar 

  23. Vega J, Ke S, Fan Z, Wallace S, Charsangavej C, Li C (2003) Pharm Res 20:826

    Article  CAS  Google Scholar 

  24. Shiah JG, Sun Y, Kopeckova P, Peterson CM, Straight RC, Kopecek J (2001) J Control Release 74:249

    Article  CAS  Google Scholar 

  25. Bagshawe KD (1989) Brit J Cancer 60:275

    Article  CAS  Google Scholar 

  26. Senter P, Springer C (2001) Adv Drug Deliv Rev 53:247

    Article  CAS  Google Scholar 

  27. Bagshawe KD, Sharma SK, Begent RH (2004) Expert Opin Biol Ther 4:1777

    Article  CAS  Google Scholar 

  28. Rooseboom M, Commandeur JNM, Vermeulen NPE (2004) Pharmacol Rev 56:53

    Article  CAS  Google Scholar 

  29. Florent JC, Dong X, Gaudel G, Mitaku S, Monneret C, Gesson JP, Jacquesy JC, Mondon M, Renoux B, Andrianomenjanahary S, Michel S, Koch M, Tillequin F, Gerken M, Czech J, Straub R, Bosslet K (1998) J Med Chem 41:3572

    Article  CAS  Google Scholar 

  30. Bosslet K, Czech J, Lorenz P, Sedlacek HH, Schuermann M, Seeman G (1992) Brit J Cancer 65:234

    Article  CAS  Google Scholar 

  31. Gerken M, Krause M, Czech J, Bosslet K, Seemann G, Hoffmann D, Sedlacek HH (1991) Eur Patent 91101096.5

    Google Scholar 

  32. Bosslet K, Czech J, Hoffmann D (1994) Cancer Res 54:2151

    CAS  Google Scholar 

  33. Platel D, Bonoron-Adèle S, Dix RK, Robert J (1999) Brit J Cancer 81:24

    Article  CAS  Google Scholar 

  34. Fishman WH, Anlyan MJ (1947) J Biol Chem 169:449

    CAS  Google Scholar 

  35. Connors TA, Whisson ME (1966) Nature 210:866

    Article  CAS  Google Scholar 

  36. Double JA, Workman P (1977) Cancer Treat Rep 61:909

    CAS  Google Scholar 

  37. Bosslet K, Czech J, Hoffmann D (1996) Tumor Target 1:45

    Google Scholar 

  38. Bosslet K, Straub R, Blumrich M, Czech J, Gerken M, Sperker B, Kroemer HK, Gesson JP, Koch M, Monneret C (1998) Cancer Res 58:1195

    CAS  Google Scholar 

  39. Murdter TE, Sperker B, Kivistö KT, McClellan M, Fritz P, Friedel G, Linder A, Bosslet K, Toomes H, Dierkesmann R, Kroemer HK (1997) Cancer Res 57:2440

    CAS  Google Scholar 

  40. Murdter TE, Friedel G, Backman JT, McClellan M, Schick M, Gerken M, Bosslet K, Fritz P, Toomes H, Kroemer HK, Sperker B (2002) J Pharmacol Exp Ther 301:223

    Article  CAS  Google Scholar 

  41. Woessner R, An Z, Li X, Hoffman RM, Dix R, Bitonti A (2000) Anticancer Res 20:2289

    CAS  Google Scholar 

  42. Sperker B, Werner U, Murdter TE, Tekkaya C, Fritz P, Rainer W, Adam U, Gerken M, Drewelow B, Kroemer HK (2000) Naunyn-Schmiedeberg’s Arch Pharmacol 362:110

    Article  CAS  Google Scholar 

  43. Sperker B, Werner U, Murdter TE, Tekkaya C, Fritz P, Rainer W, Adam U, Gerken M, Drewelow B, Kroemer HK (2000) Chem Abstr 133:271539v

    Google Scholar 

  44. Leenders RTGG, Gerritz KAA, Ruijtenbeek R, Scheeren HW, Haisma HJ, Boven E (1995) Tetrahedron Lett 26:1701

    Article  Google Scholar 

  45. Leenders RTGG, Damen EWP, Bijsterweld EJA, Scheeren HW, Houba PHJ, van der Meulen-Muileman IH, Boven E, Haisma HJ (1999) Bioorg Med Chem 7:1597

    Article  CAS  Google Scholar 

  46. de Groot FMH, Damen EWP, Scheeren HW (2001) Curr Med Chem 8:1093

    Article  Google Scholar 

  47. Houba PHJ, Boven E, Haisma HJ (1996) Bioconj Chem 7:606

    Article  CAS  Google Scholar 

  48. Houba PHJ, Leenders RGG, Boven E, Scheeren JW, Pinedo HM, Haisma HJ (1996) Biochem Pharmacol 52:455

    Article  CAS  Google Scholar 

  49. Houba PHJ, Boven E, Van Der Meulen-Muileman IH, Leenders RGG, Scheeren JW, Pinedo HM, Haisma HJ (2001) Int J Cancer 91:550

    Article  CAS  Google Scholar 

  50. De Graaf M, Boven E, Oosterhoff D, van der Meulen-Muileman IH, Huls GA, Gerritsen WR, Haisma HJ, Pinedo HM (2002) Brit J Cancer 86:811

    Article  Google Scholar 

  51. de Graaf M, Nevalainen TJ, Scheeren HW, Pinedo HM, Haisma HJ, Boven E (2004) Biochem Pharmacol 68:2273

    Article  CAS  Google Scholar 

  52. Houba PHJ, Boven E, Erkelen CAM, Leenders RGG, Scheeren JW, Pinedo HM, Haisma HJ (1998) Brit J Cancer 78:1600

    Article  CAS  Google Scholar 

  53. Vrudhula VM, Svensson HP, Senter PD (1995) J Med Chem 38:1380

    Article  CAS  Google Scholar 

  54. Harding FA, Liu AD, Stickler M, Razo OJ, Chin R, Faravashi N, Viola W, Graycar T, Yeung VP, Aehle W, Meijer D, Wong S, Rashid MH, Valdes AM, Schellenberger V (2005) Mol Cancer Ther 4:1791

    Article  CAS  Google Scholar 

  55. Alderson RF, Toki BE, Roberge M, Geng W, Basler J, Chin R, Liu A, Ueda R, Hodges D, Escandon E, Chen T, Kanavarioti T, Babé L, Senter PD, Fox JA, Schellenberger V (2006) Bioconjugate Chem 17:410

    Article  CAS  Google Scholar 

  56. Andrianomenjanahary S, Dong X, Florent JC, Gaudel G, Gesson JP, Jacquesy JC, Koch M, Michel S, Mondon M, Monneret C, Petit P, Renoux B, Tillequin F (1992) Bioorg Med Chem Lett 2:1093

    Article  CAS  Google Scholar 

  57. Gesson JP, Jacquesy JC, Mondon M, Petit P, Renoux B, Andrianomenjanahary S, Dufat-Trinh Van H, Koch M, Michel S, Tillequin F, Florent JC, Monneret C, Bosslet K, Czech J, Hoffmann D (1994) Anti-Cancer Drug Design 9:409

    CAS  Google Scholar 

  58. Gosh AK, Kan SR, Farquha RD (1999) Chem Commun 24:2527

    Article  Google Scholar 

  59. Bakina E, Farquhar D (1999) Anti-Cancer Drug Design 14:505

    Google Scholar 

  60. Farqhar D, Cherif A, Bakina E, Nelson J (1998) J Med Chem 41:965

    Article  Google Scholar 

  61. Torgov MY, Alley SC, Cerveny CG, Farquhar D, Senter PD (2005) Bioconjugate Chem 16:717

    Article  CAS  Google Scholar 

  62. Heinis C, Alessi P, Neri D (2004) Biochem 43:6293

    Article  CAS  Google Scholar 

  63. Gopin A, Pessah N, Shamis M, Rader C, Shabat D (2003) Angew Chem Int Ed 42:327

    Article  CAS  Google Scholar 

  64. Amir RJ, Pessah N, Shamis M, Shabat D (2003) Angew Chem Int Ed 42:4494

    Article  CAS  Google Scholar 

  65. Shabat D, Amir RJ, Gopin A, Pessah N, Shamis M (2004) Chem Eur 10:2626

    Article  CAS  Google Scholar 

  66. Shamis M, Lode HN, Shabat D (2004) J Am Chem Soc 126:1726

    Article  CAS  Google Scholar 

  67. Shabat D, Popkov M, Shamis M, Lerner RA, Barbas III CF, Shabat D (2005) Angew Chem Int Ed 44:718

    Google Scholar 

  68. de Groot FM, Albretch C, Koekkoek R, Beusker PH, Scheeren HW (2003) Angew Chem Int Ed 42:4490

    Article  CAS  Google Scholar 

  69. Szalai ML, Kevwitch RM, McvGrath DV (2003) J Am Chem Soc 125:15688

    Article  CAS  Google Scholar 

  70. de Groot FMH, Loos WJ, Koekkoek R, van Berkom LW, Busscher GF, Seelen AE, Albretch C, de Bruijn P, Scheeren HW (2001) J Org Chem 66:8815

    Article  CAS  Google Scholar 

  71. Bridgewater G, Springer CJ, Knox R, Minton N, Michael P, Collins M (1995) Eur J Cancer 31A:2362

    Article  CAS  Google Scholar 

  72. Niculescu-Duvaz D, Niculescu-Duvaz I, Friedlos F, Spooner R, Martin J, Marais R, Springer CJ (1999) J Med Chem 42:2485

    Article  CAS  Google Scholar 

  73. Weyel D, Sedlacek HH, Müller R, Brüsselbach S (2000) Gene Therapy 7:224

    Article  CAS  Google Scholar 

  74. de Graaf M, Pinedo HM, Oosterhoff D, van der Meulen-Muileman IH, Gerritsen WR, Haisma HJ, Boven E (2004) Human Gene Ther 15:229

    Article  CAS  Google Scholar 

  75. Hay MP, Wilson WR, Denny WA (2005) Bioorg Med Chem 13:4043

    Article  CAS  Google Scholar 

  76. Mauger AB, Burke PJ, Somani HH, Friedlos F, Kox RJ (1994) J Med Chem 37:3452

    Article  CAS  Google Scholar 

  77. Niculescu-Duvaz I, Niculescu-Duvaz D, Friedlos F, Spooner R, Martin J, Marais R, Springer C (1999) J Med Chem 42:2485

    Article  CAS  Google Scholar 

  78. Vrudhula VM, Senter PD, Fischer KJ, Wallace PM (1993) J Med Chem 36:919

    Article  CAS  Google Scholar 

  79. Maeda H, Wu J, Sawa T, Matsumura Y, Hori K (2000) J Contr Release 65:271

    Article  CAS  Google Scholar 

  80. Duncan R, Kopeckova-Rejmanova P, Strohalm J, Hume I, Cable HC, Pohl J, Llyod JB, Kopecek J (1987) Br J Cancer 55:165

    Article  CAS  Google Scholar 

  81. Duncan R (1992) Anti-Cancer Drugs 3:175

    Article  CAS  Google Scholar 

  82. Vasey PA, Kaye SB, Morrison R, Twelves C, Wilson P, Duncan R, Thomson AH, Murray LS, Hilditch TE, Murray Y, Burtles S, Fraier D, Frigerio E, Cassidy J (1999) Clin Cancer Res 5:83

    CAS  Google Scholar 

  83. Satchi-Fainaro R, Connors TA, Duncan R (2001) Brit J Cancer 85:1070

    Article  CAS  Google Scholar 

  84. Seymour LW, Ferry DR, Anderson D, Hesslewood S, Julyan PJ, Poyner R, Doran J, Young AM, Burtles S, Kerr DJ (2002) J Clin Oncol 20:1668

    Article  CAS  Google Scholar 

  85. Duncan R, Vicent MJ, Greco F, Nicholson RI (2005) Endocrine-Related Cancer 12:S189

    Article  CAS  Google Scholar 

  86. Satchi-Fainaro R, Hailu A, Davies JW, Summerford C, Duncan R (2003) Bioconjugate Chem 14:797

    Article  CAS  Google Scholar 

  87. Senter PD, Svensson HP, Schreiber GJ, Rodriguez JL, Vrudhula VM (1995) Bioconjugate Chem 6:389

    Article  CAS  Google Scholar 

  88. Minton NP, Mauchline ML, Lemmon MJ, Brehm JK, Fox M, Michael NP, Giaccia A, Brown JM (1995) FEMS Microbiol Rev 17:357

    Article  CAS  Google Scholar 

  89. Theys J, Pennington O, Dubois L, Anlezark G, Vaughan T, Mengesha A, Landuyt W, Anné J, Burke PJ, Dûrre P, Wouters BG, Minton NP, Lambin P (2006) Brit J Cancer 95:1212

    Article  CAS  Google Scholar 

  90. Dang LH, Bettegowda C, Huso DL, Kinzler KW, Vogelstein B (2001) Proc Natl Acad Sci USA 98:15155

    Article  CAS  Google Scholar 

  91. Agrawal N, Bettegowda C, Cheong I, Geschwind JF, Drake CG, Hipkiss EL, Tatsumi M, Dang LH, Diaz LA Jr, Pomper M, Abusedera M, Wahl RL, Kinzler KW, Zhou S, Huso DL, Vogelstein B (2004) Proc Natl Acad Sci USA 101:15172

    Article  CAS  Google Scholar 

  92. Cheong I, Huang X, Bettegowda C, Diaz LA Jr, Kinzler KW, Zhou S, Vogelstein B (2006) Science 314:1308

    Article  CAS  Google Scholar 

  93. Robinson MA, Charlton ST, Garnier P, Wang XT, Davis SS, Perkins AC, Frier M, Duncan R, Savage TJ, Wyatt DA, Watson SA, Davis BG (2004) Proc Natl Acad Sci USA 101:14527

    Article  CAS  Google Scholar 

  94. Denny WA (2004) Cancer Investigat 22:604

    Article  CAS  Google Scholar 

  95. DeFeo-Jones D, Garsky VM, Wong BK, Feng DM, Bolyar T, Haskell K, Kiefer DM, Leander K, McAvoy E, Lumma P, Wai J, Senderak ET, Motzel SL, Keenan K, Van Zwieten M, Lin JH, Freidinger R, Huff J, Oliff A, Jones RE (2000) Nat Med 6:1248

    Article  CAS  Google Scholar 

  96. Denmeade SR, Nagy A, Gao J, Lilja H, Schally AV, Isaacs JT (1998) Cancer Res 58:2537

    CAS  Google Scholar 

  97. Levesque M, Yu H, D’Costa M, Tadross L, Diamandis EP (1995) J Clin Lab Anal 9:375

    Article  CAS  Google Scholar 

  98. Catalona WJ, Smith DS, Ratliff TL, Dodds KM, Coplen DE, Yuan JJ, Petros JA, Andriole GL (1991) New Engl J Med 324:1156

    Article  CAS  Google Scholar 

  99. Catalona WJ, Smith DS, Ratliff TL, Dodds KM, Coplen DE, Yuan JJ, Petros JA, Andriole GL (1991) Erratum. N Engl J Med 325:1324

    Google Scholar 

  100. Garsky VM, Lumma PK, Feng DM, Wai J, Ramjit HG, Sardana MK, Oliff A, Jones RE, DeFeo-Jones D, Freidinger RM (2001) J Med Chem 44:4216

    Article  CAS  Google Scholar 

  101. DiPaola RS, Rinehart J, Nemunaitis J, Ebbinghaus S, Rubin R, Capanna T, Ciardella M, Doyle-Lindrud S, Goodwin S, Fontaine M, Adams N, Williams A, Schwartz M, Winchell G, Wickersham K, Deutsch P, Yao SL (2002) J Clin Oncol 20:1874

    Article  CAS  Google Scholar 

  102. Wong BK, DeFeo-Jones D, Jones RE, Garsky VM, Feng DM, Oliff A, Chiba M, Ellis JD, Lin JH (2001) Drug Metab Dispos 29:313

    CAS  Google Scholar 

  103. Foekens JA, Peters HA, Look MP, Portengen H, Schmitt M, Kramer MD, Brünner N, Jäniccke F, Meijer-van Gelder ME, Henzen-Logmans SC, van Putten WL, Klijn JG (2000) Cancer Res 60:636

    CAS  Google Scholar 

  104. Noel A, Albert V, Bajou K, Bisson C, Devy L, Frankenne F, Maquoi E, Masson V, Sounni NE, Foidart JM (2001) Surg Oncol Clin N Am 10:417

    CAS  Google Scholar 

  105. Ganesh S, Sier CFM, Heerding MM, Vankrieken JHJM, Griffioen G, Welvaart K, van de Velde CJ, Verheijen JH, Lamers CB, Verspaget HW (1996) Cancer 77:1035

    Article  CAS  Google Scholar 

  106. Ganesh S, Sier CFM, Griffioen G, Vloedgraven HJM, de Boer A, Welvaart K, van de Velde CJ, van Krieken JH, Verheijen JH, Lamers CB, Verspaget HW (1994) Cancer Res 54:4065

    CAS  Google Scholar 

  107. Chakravarty PK, Carl PL, Weber MJ, Katzenellenbogen JA (1983) J Med Chem 26:638

    Article  CAS  Google Scholar 

  108. Eisenbrand G, Lauck-Birkel S, Tang WC (1996) Synthesis 1246

    Google Scholar 

  109. de Groot FMH, de Bart ACW, Verheijen JH, Scheeren HW (1999) J Med Chem 42:5277

    Article  CAS  Google Scholar 

  110. Devy L, de Groot FMH, Blacher S, Hajitou A, Beusker PH, Scheeren HW, Foidart JM, Noel A (2004) FASEB 18:565

    CAS  Google Scholar 

  111. Egeblad M, Werb Z (2002) Nat Rev Cancer 2:161

    Article  CAS  Google Scholar 

  112. Strongin A, Collier I, Bannikov G, Marmer BL, Grant GA, Goldberg GI (1995) J Biol Chem 270:5331

    Article  CAS  Google Scholar 

  113. McCawley L, Matrisian L (2001) Curr Opin Cell Biol 13:534

    Article  CAS  Google Scholar 

  114. Kline T, Torgov MY, Mendelsohn BA, Cerveny CG, Senter PD (2004) Mol Pharm 1:9

    Article  CAS  Google Scholar 

  115. Albright CF, Graciani N, Han W, Yue E, Stein R, Lai Z, Diamond M, Dowling R, Grimminger L, Zhang SY, Behrens D et al. (2005) Mol Cancer Ther 4:751

    Article  CAS  Google Scholar 

  116. Chen JM, Dando PM, Rawlings NB, Brown MA, Yong ME, Stevens RA, Hewitt E, Watts C, Barrett AJ (1997) J Biol Chem 272:8090

    Article  CAS  Google Scholar 

  117. Murthy RV, Arbman G, Gao J, Roodman GD, Sun XF (2005) Clin Cancer Res 11:2293

    Article  CAS  Google Scholar 

  118. Liu C, Sun C, Huang H, Janda K, Edgington T (2003) Cancer Res 63:2957

    CAS  Google Scholar 

  119. de Jong J, Klein I, Bast A, van der Vijgh WJ (1992) Cancer Chemother Pharmacol 31:156

    Article  Google Scholar 

  120. Fernandez AM, Van Derpoorten K, Dasnois L, Lebtahi K, Dubois V, Lobl TJ, Gangwar S, Oliyai C, Lewis ER, Shochat D, Trouet A (2001) J Med Chem 44:3750

    Article  CAS  Google Scholar 

  121. Trouet A, Passioukov A, Van derpoorten K, Fernandez AM, Abarca-Quinones J, Baurain R, Lobl TJ, Oliyai C, Shochat D, Dubois V (2001) Cancer Res 61:2843

    CAS  Google Scholar 

  122. Dubois V, Dasnois L, Lebtahi K, Collot F, Heylen N, Havaux N, Fernandez AM, Lobl TJ, Oliyai C, Nieder M, Shochat D, Yarranton GT, Trouet A (2002) Cancer Res 62:2327

    CAS  Google Scholar 

  123. Dubois V, Nieder M, Collot F, Negrouk A, Nguyen TT, Gangwar S, Reitz B, Wattiez R, Dasnois L, Trouet A (2006) Eur J Cancer 42:3049

    Article  CAS  Google Scholar 

  124. Low PS (2004) Adv Drug Deliver Rev 56:1055

    Article  CAS  Google Scholar 

  125. Reddy JA, Allagada VM, Leamon CP (2005) Curr Pharm Biotechnol 6:131

    Article  CAS  Google Scholar 

  126. Hilgenbrink AR, Low PS (2005) J Pharm Sci 94:2135

    Article  CAS  Google Scholar 

  127. Yoo HS, Park TG (2004) J Control Rel 96:273

    Article  CAS  Google Scholar 

  128. Yoo HS, Park TG (2004) J Control Rel 100:247

    Article  CAS  Google Scholar 

  129. Goren D, Horowitz AT, Tzemach D, Tarshish M, Zalipsky S, Gabizon A (2000) Clin Cancer Res 6:1949

    CAS  Google Scholar 

  130. Shmeeda H, Mak L, Tzemach D, Astrahan P, Tarshish M, Gabizon A (2006) Mol Cancer Ther 5:818

    Article  CAS  Google Scholar 

  131. Gabizon AA, Shmeeda H, Zalipsky S (2006) Liposome Res 16:175

    Article  CAS  Google Scholar 

  132. Pan XQ, Lee RJ (2004) Expert Opin Drug Deliv 1:7

    Article  CAS  Google Scholar 

  133. Pan XQ, Lee RJ (2005) Anticancer Res 25(1A):343

    CAS  Google Scholar 

  134. Saul JM, Annapragada AV, Bellamkonda RV (2006) J Control Rel 114:277

    Article  CAS  Google Scholar 

  135. Mishra PR, Jain NK (2003) Drug Deliv 10:277

    Article  CAS  Google Scholar 

  136. Ren Y, Wong SM, Lim LY (2007) Bioconjugate Chem 18:836

    Article  CAS  Google Scholar 

  137. Vrudhula VM, Senter PD, Fisher KJ, Wallace PM (1993) J Med Chem 36:919

    Article  CAS  Google Scholar 

  138. Zhang Q, Xiang G, Zhang Y, Yang K, Fan W, Lin J, Zeng F, Wu J (2006) J Pharm Sci 95:2266

    Article  CAS  Google Scholar 

  139. Nagy A, Schally AV, Halmos G, Armatis P, Cai RZ, Csernus V, Kovács M, Koppán M, Szepesházi K, Kahán Z (1998) Proc Natl Acad Sci USA 95:1794

    Article  CAS  Google Scholar 

  140. Koppán M, Nagy A, Schally AV, Arencibia JM, Plonowski A, Halmos G (1998) Cancer Res 58:4132

    Google Scholar 

  141. Engel JB, Schally AV, Halmos G, Baker B, Nagy A, Keller G (2005) Cancer 104:1312

    Article  CAS  Google Scholar 

  142. Keller G, Engel JB, Schally AV, Nagy A, Hammann B, Halmos G (2005) Int J Cancer 114:831

    Article  CAS  Google Scholar 

  143. Cuttitta F, Carney DN, Mulshine J, Moody TW, Fedorko J, Fischler A, Minna JD (1985) Nature 316:823

    Article  CAS  Google Scholar 

  144. Nagy A, Armatis P, Cai RZ, Szepeshazi K, Halmos G, Schally AV (1997) Proc Natl Acad Sci USA 94:652

    Article  CAS  Google Scholar 

  145. Keller G, Schally AV, Nagy A, Halmos G, Baker B, Engel JB (2005) Cancer 104:2266

    Article  CAS  Google Scholar 

  146. Engel JB, Schally AV, Halmos G, Baker B, Nagy AA, Keller G (2005) Endocr Relat Cancer 12:999

    Article  CAS  Google Scholar 

  147. Engel JB, Schally AV, Halmos G, Baker B, Nagy AA, Keller G (2005) Endocr Relat Cancer 73:851

    Google Scholar 

  148. Engel JB, Schally AV, Halmos G, Baker B, Nagy AA, Keller G (2005) Eur J Cancer 41:1824

    Article  CAS  Google Scholar 

  149. Stangelberger A, Schally AV, Letsch M, Szepeshazi K, Nagy A, Halmos G, Kanashiro CA, Corey E, Vessella R (2006) Int J Cancer 118:222

    Article  CAS  Google Scholar 

  150. Wang X, Kebs LJ, Al-Nuri M, Pudavar H, Ghosal S, Liebow C, Nagy A, Schally AV, Prasad PN (1996) Proc Natl Acad Sci USA 96:11081

    Article  Google Scholar 

  151. Bajo AM, Schally AV, Halmos G, Nagy A (2003) Clinical Cancer Research 9:3742

    CAS  Google Scholar 

  152. Keller G, Schally AV, Gaiser T, Nagy A, Baker B, Halmos G, Engel JB (2005) Clin Cancer Res 11:5549

    Article  CAS  Google Scholar 

  153. Keller G, Schally AV, Gaiser T, Nagy A, Baker B, Halmos G, Engel JB (2005) Eur J Cancer 41:2196

    Article  CAS  Google Scholar 

  154. Keller G, Schally AV, Gaiser T, Nagy A, Baker B, Westphal G, Halmos G, Engel JB (2005) Cancer Res 65:5857

    Article  CAS  Google Scholar 

  155. Nagy A, Schally AV (2005) Biol Reprod 73:851

    Article  CAS  Google Scholar 

  156. de Groot FMH, Broxterman HJ, Adams HP, van Vliet A, Tesser GI, Elderkamp YW, Schraa AJ, Kok RJ, Molema G, Pinedo HM, Scheeren HW (2002) Mol Cancer Ther 1:901

    Google Scholar 

  157. Ceh B, Winterhalter M, Frederik PM, Vallner JJ, Lasic DD (1997) Adv Drug Deliv Rev 24:165

    Article  CAS  Google Scholar 

  158. Maeda H, Wu J, Sawa T, Matsumura Y, Hori K (2000) J Control Release 65:271

    Article  CAS  Google Scholar 

  159. Dvorak HF (1990) Prog Clin Biol Res 354A:317

    CAS  Google Scholar 

  160. Yuan F, Leunig M, Huang SK, Berk DA, Papahadjopoulos D, Jain RK (1994) Cancer Res 54:3352

    CAS  Google Scholar 

  161. Harvie P, Wong FM, Bally MB (2000) J Pharm Sci 89:652

    Article  CAS  Google Scholar 

  162. Ruoslahti E (1996) Annu Rev Cell Dev Biol 12:697

    Article  CAS  Google Scholar 

  163. Schiffelers RM, Koning GA, ten Hagen TL, Fens MH, Schraa AJ, Janssen AP, Kok RJ, Molema G, Storm G (2003) J Control Release 91:115

    Article  CAS  Google Scholar 

  164. Xiong XB, Huang Y, Lu WL, Zhang X, Zhang H, Nagai T, Zhang Q (2005) J Control Release 107:262

    Article  CAS  Google Scholar 

  165. Bibbya DC, Talmadgeb JE, Dalala MK, Kurzb SG, Chytilb KM, Barrya SE, Shanda DG, Steier M (2005) Int J Pharm 293:281–290

    Article  CAS  Google Scholar 

  166. Rousselle C, Clair P, Lefauconnier JM, Kaczorek M, Scherrmann JM, Temsamani J (2000) Mol Pharmacol 57:679

    CAS  Google Scholar 

  167. Rousselle C, Smirnova M, Clair P, Lefauconnier JM, Chavanieu A, Calas B, Scherrmann JM, Temsamani J (2001) J Pharmacol Exp Ther 296:124

    CAS  Google Scholar 

  168. Mazel M, Clair P, Rousselle C, Vidal P, Scherrmann JM, Mathieu D, Temsamani J (2001) Anti-Cancer Drugs 12:107

    Article  CAS  Google Scholar 

  169. Meyer-Losic F, Quinonero J, Dubois V, Alluis B, Dechambre M, Michel M, Cailler F, Fernandez AM, Trouet A, Kearsey J (2006) J Med Chem 49:6908

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Laboratoire de Pharmacochimie, Institut Curie, 26 rue d’Ulm, 75248, Paris cedex 05, France

    Jean-Claude Florent & Claude Monneret

Authors
  1. Jean-Claude Florent
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Claude Monneret
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Claude Monneret .

Editor information

Karsten Krohn

Rights and permissions

Reprints and permissions

Copyright information

© 2007 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Florent, JC., Monneret, C. (2007). Doxorubicin Conjugates for Selective Delivery to Tumors. In: Krohn, K. (eds) Anthracycline Chemistry and Biology II. Topics in Current Chemistry, vol 283. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2007_12

Download citation

Publish with us

Policies and ethics

Search

Navigation