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Sabarubicin

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Anthracycline Chemistry and Biology II

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

Abstract

Disaccharide derivatives in the daunorubicin and in the 4-demethoxy (idarubicin) series in whichthe first sugar moiety linked to the aglycone is a non-aminated sugar, namely 2-deoxy-l-rhamnose or 2-deoxy-l-fucose andthe second moiety is daunosamine, have been obtained upon synthesis of the appropriate activated sugarintermediate and glycosylation of the corresponding aglycones. The compounds containing 2-deoxy-l-fucose exhibit superior pharmacological properties with respect to thestereoisomers containing 2-deoxy-l-rhamnose. The doxorubicinanalog 7-O-(α-l-daunosaminyl-α(1–4)-2-deoxy-l-fucosyl)-4-demethoxy-adriamycinone (sabarubicin) was prepared startingfrom 14-acetoxyidarubicinone. Solution properties and molecular interactions are compared with thoseof doxorubicin. Sabarubicin exhibits a superior antitumor efficacy, presumably related to theactivation of p53-independent apoptosis. A number of sabarubicin analogues have also been synthesized.

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References

  1. Brockmann H (1963) Forschr Chem Organ Naturst 21:121

    CAS  Google Scholar 

  2. O'Hagan D (1991) The polyketide metabolites. Ellis Horwood, Chichester UK

    Google Scholar 

  3. Arcamone F, Cassinelli G (1998) Curr Med Chem 5:391

    CAS  Google Scholar 

  4. Fujii I, Ebizuka Y (1997) Chem Rev 97:2511

    Article  CAS  Google Scholar 

  5. Hutchinson CR (1997) Chem Rev 97:2525

    Article  CAS  Google Scholar 

  6. Hopwood DA (1997) Chem Rev 97:2465

    Article  CAS  Google Scholar 

  7. Arcamone F, Di Marco A, Gaetani M, Scotti T (1961) Giorn Microbiol 9:83

    CAS  Google Scholar 

  8. Arcamone F, Franceschi G, Penco S, Selva A (1969) Tetrahedron Lett 1007

    Google Scholar 

  9. Arcamone F (1980) The development of new antitumor anthracyclines. In: Cassady J, Douros J (eds) Anticancer Agents Based on Natural Products Models. Academic, New York, chap 1

    Google Scholar 

  10. Arcamone F (1981) Doxorubicin Anticancer Antibiotics. Academic, New York

    Google Scholar 

  11. Takeuchi T (1995) J Cancer Res Clin Oncol 121:505

    Article  CAS  Google Scholar 

  12. Nielsen D, Maare C, Skovsgaard T (1996) Gen Pharmacol 27:255

    Google Scholar 

  13. Weiss RB (1992) Semin Oncol 19:670

    CAS  Google Scholar 

  14. Arcamone F, Animati F, Capranico G, Lombardi P, Pratesi G, Manzini S, Supino R, Zunino F (1997) Pharmacol Ther 76:117

    Article  CAS  Google Scholar 

  15. Wang AH-J (1992) Curr Opin Struct Biol 2:361

    Article  CAS  Google Scholar 

  16. Stutter E, Schuetz H, Berg H (1981) Quantitative determination of cooperative anthracycline-DNA binding. In: Cassady J, Douros J (eds) Anticancer Agents Based on Natural Products Models. Academic, New York, p 245

    Google Scholar 

  17. Ughetto G (1981) X-Ray diffraction analysis of anthracycline-oligonucleotide complexes. In: Cassady J, Douros J (eds) Anticancer Agents Based on Natural Products Models. Academic, New York, p 296

    Google Scholar 

  18. Pullman B (1981) Binding affinities and sequence selectivity in the interaction of antitumor anthracyclines and anthracenediones with double stranded polynucleotides and DNA. In: Cassady J, Douros J (eds) Anticancer Agents Based on Natural Products Models. Academic, New York, p 371

    Google Scholar 

  19. Chaires JB, Herrera JE, Waring JM (1990) Biochemistry 29:6145

    Article  CAS  Google Scholar 

  20. Frederick CA, Williams LD, Ughetto G, van der Marel GA, van Boom JH, Rich A, Wang AH-J (1990) Biochemistry 29:2538

    Article  CAS  Google Scholar 

  21. Tewey KM, Rowe TC, Yang L, Halligan BD, Liu LF (1984) Science 226:466

    Article  CAS  Google Scholar 

  22. Capranico G, Zunino F, Kohn KW, Pommier Y (1990) Biochemistry 29:562

    Article  CAS  Google Scholar 

  23. Capranico G, Kohn KW, Pommier Y (1990) Nucleic Acids Res 22:6611

    Article  Google Scholar 

  24. Zunino F, Capranico G (1990) Anticancer Drug Des 4:307

    Google Scholar 

  25. Binaschi M, Capranico G, Dal Bo L, Zunino F (1997) Mol Pharmacol 6:1053

    Google Scholar 

  26. Gerwitz DA (1992) Biochem Pharmacol 57:727

    Article  Google Scholar 

  27. Ishikawa T, Sies H (1984) J Biol Chem 239:3838

    Google Scholar 

  28. Formelli F, Zedeck MS, Sternberget SS, Philips FS (1978) Cancer Res 38:3286

    CAS  Google Scholar 

  29. Ellis CN, Ellis MB, Blakemore WS (1987) Biochem J 245:309

    CAS  Google Scholar 

  30. Ito H, Miller SC, Billingham ME, Akimoto H, Torti SV, Wade R, Gahlmann R, Lyons G, Kedes L, Torti FM (1990) Proc Natl Acad Sci USA 87:4275

    Article  CAS  Google Scholar 

  31. Arcamone F, Penco S (1989) Gann Monographs Cancer Res 36:81

    CAS  Google Scholar 

  32. Capranico G, De Isabella P, Penco S, Tinelli S, Zunino F (1989) Cancer Res 49:2022

    CAS  Google Scholar 

  33. Capranico G, Supino R, Binaschi M, Capolongo L, Grandi M, Suarato A, Zunino F (1994) Mol Pharmacol 45:908

    CAS  Google Scholar 

  34. Gresh N, Pullman B, Arcamone F, Menozzi M, Tonani R (1988) Mol Pharmacol 35:251

    Google Scholar 

  35. Boivin J, Monneret C, Pais M (1981) Tetrahedron 37:4219

    Article  CAS  Google Scholar 

  36. El Khadem HS, Matsura D (1982) Carboydr Res 101:C1

    Article  Google Scholar 

  37. Horton D, Priebe W, Sznaidman ML, Varela O (1993) J Antibiot 46:1720

    Article  CAS  Google Scholar 

  38. Borchmann P, Hubel K, Schnell R, Engert A (1997) Int J Clin Pharmacol Ther 35:80

    CAS  Google Scholar 

  39. Animati F, Berettoni M, Cipollone A, Franciotti M, Lombardi P, Monteagudo P, Arcamone F (1996) J Chem Soc Perkin Trans I:1327

    Article  Google Scholar 

  40. Arcamone F, Animati F, Bigioni M, Capranico G, Caserini C, Cipollone A, De Cesare M, Ettorre A, Guano F, Manzini S, Monteagudo E, Pratesi G, Salvatore C, Supino R, Zunino F (1999) Biochem Pharmacol 57:1133

    Article  CAS  Google Scholar 

  41. Arcamone F, Animati F, Berettoni M, Bigioni M, Capranico G, Casazza AM, Caserini C, Cipollone A, De Cesare M, Franciotti M, Lombardi P, Madami A, Manzini S, Monteagudo E, Polizzi D, Pratesi G, Righetti SC, Salvatore C, Supino R, Zunino F (1997) J Nat Cancer Inst 89:1217

    Article  CAS  Google Scholar 

  42. Monteagudo E, Madami A, Animati F, Lombardi P, Arcamone F (1997) Carbohydr Res 300:11

    Article  CAS  Google Scholar 

  43. Ragg E, Mondelli R, Penco S (1988) J Chem Soc Perkin Trans II:1673

    Google Scholar 

  44. Cicero DO, Barbato G, Bazzo R (1995) J Am Chem Soc 117:1027

    Article  CAS  Google Scholar 

  45. Messori L, Temperini C, Piccioli F (2001) Bioorg Med Chem 9:938

    Article  Google Scholar 

  46. Temperini C, Messori L, Orioli P, Di Bugno C, Animati F, Ughetto G (2003) Nucleic Acids Res 31:1464

    Article  CAS  Google Scholar 

  47. Bos AME, De Vries EGE, Dombernovsky P, Aamdal S, Uges DRA, Shuijvers D, Wanders J, Roelwink MWJ, Hanauske AR, Bortini S, Capriati A, Crea AEG, Vermorken JB (2001) Cancer Chemother Pharmacol 48:361

    Article  CAS  Google Scholar 

  48. Messori L, Piccioli F, Gabrielli S, Orioli P, Angeloni L, Di Bugno C (2002) Bioorg Med Chem 10:3425

    Article  CAS  Google Scholar 

  49. Pratesi G, De Cesare M, Caserini C, Perego P, Supino R, Bigioni M, Manzini S, Iafrate E, Salvatore C, Casazza AM, Arcamone F, Zunino F (1998) Clin Cancer Res 4:2833

    CAS  Google Scholar 

  50. Pratesi G, Polizzi D, Perego P, Dal Bo L, Zunino F (2000) Biochem Pharmacol 60:77

    Article  CAS  Google Scholar 

  51. Bigioni M, Salvatore C, Bullo A, Bellarosa D, Iafrate E, Animati F, Capranico G, Goso C, Maggi CA, Pratesi G, Zunino F, Manzini S (2001) Biochem Pharmacol 62:63

    Article  CAS  Google Scholar 

  52. Gonzales-Paz O, Polizzi D, De Cesare M, Zunino F, Bigioni M, Maggi CA, Manzini S, Pratesi G (2001) Eur J Cancer 37:431

    Article  Google Scholar 

  53. Cirillo R, Sacco G, Venturella S, Brightwell J, Giachetti A, Manzini S (2000) Cardiovasc Pharmacol 35:100

    Article  CAS  Google Scholar 

  54. Zucchi R, Yu G, Ghelardoni S, Ronca F, Ronca-Testoni S (2000) Brit J Pharmaco1 131:342

    Article  CAS  Google Scholar 

  55. Roelvink M, Aamdal S, Dombernowsky P, Wanders J, Peters S, Bortini S, Crea A, Animati F, Hanauske AR (1999) Eur J Cancer 35(Suppl 4):1161

    Google Scholar 

  56. Schrivers D, Bos AME, Dyck J, de Vries EGE, Wanders J, Roelvik M, Fumoleau P, Bortii S, Vermorke JB (2002) Ann Oncol 13:385

    Article  Google Scholar 

  57. Tjan-Heijnen VCG, Gerritsen A, ten Valde GPM, Giaccone G, Gamucci T, Comandini A, Capriati A, Mordiva A, Nurmohamed S, Ruland-Adank S (2002) Ann Oncol 13(Suppl 5):148

    Google Scholar 

  58. Dickgreber NJ, Welte T, Gillissen A, Dunlop D, Eberhardt W, Wagner T, Swinson D, Capriati A, O'Byrne K (2003) Proc Am Soc Clin Oncol 22:703

    Google Scholar 

  59. Caponigro F, Willems P, Sorio R, Floquet A, van Belle S, Demol J, Tambaro R, Comandini A, Capriati A, Adank S, Wanders J (2005) Invest New Drugs 23:85

    Article  CAS  Google Scholar 

  60. Fiedler W, Tchen N, Bloch J, Fargeot P, Sorio R, Vermorken JB, Collette L, Lacombe D, Twelves C (2006) Eur J Cancer 42:200

    Article  CAS  Google Scholar 

  61. Cipollone A, Berettoni M, Bigioni M, Binaschi M, Cermele C, Monteagudo E, Olivieri L, Palomba D, Animati F, Goso C, Maggi CA (2002) Bioorg Med Chem 10:1459

    Article  CAS  Google Scholar 

  62. Bigioni M, Salvatore C, Cipollone A, Berettoni M, Maggi CA, Binaschi M (2005) Lett Drug Design Discovery 2:68

    Article  CAS  Google Scholar 

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  1. Menarini Ricerche, Via Livornese 893, 56010, Pisa, Italy

    Federico-Maria Arcamone

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  1. Federico-Maria Arcamone
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Correspondence to Federico-Maria Arcamone .

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Karsten Krohn

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© 2007 Springer-Verlag Berlin Heidelberg

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Arcamone, FM. (2007). Sabarubicin. 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_1

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