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Ametantrone

Description of Ametantrone: Ametantrone (AM) is a synthetic 9,10-anthracenedione bearing two (hydroxyethylamino)ethylamino residues at positions 1 and 4; along with other anthraquinones and anthracyclines, it shares a polycyclic intercalating moiety and charged side chains that stabilize DNA binding. Ametantrone is the second anthracene derivative to enter clinical trials. 

Ametantrone is anticancer drug candidate targeting DNA. Ametantrone induces interstrand DNA cross-links in HeLa S3 cells. These cross-links were observed only in cellular system suggesting that metabolism of the drugs is a necessary step leading to DNA cross-linking. Biologically inactive analogue of mitoxantrone, compound NSC 321458, did not induce cross-links in DNA of tumour cells which suggests that DNA cross-linking is associated with the cytotoxic and anti-tumour activity of these compounds. Source: Br J Cancer. 2000 Apr;82(7):1300-4. or  http://www.ncbi.nlm.nih.gov/pubmed/10755405.

Current developer:   

1: Gianoncelli A, Basili S, Scalabrin M, Sosic A, Moro S, Zagotto G, Palumbo M, Gresh N, Gatto B. Rational design, synthesis, and DNA binding properties of novel sequence-selective peptidyl congeners of ametantrone. ChemMedChem. 2010 Jul 5;5(7):1080-91. PubMed PMID: 20458714.

2: Shchekotikhin AE, Glazunova VA, Dezhenkova LG, Luzikov YN, Sinkevich YB, Kovalenko LV, Buyanov VN, Balzarini J, Huang FC, Lin JJ, Huang HS, Shtil AA, Preobrazhenskaya MN. Synthesis and cytotoxic properties of 4,11-bis[(aminoethyl)amino]anthra[2,3-b]thiophene-5,10-diones, novel analogues of antitumor anthracene-9,10-diones. Bioorg Med Chem. 2009 Mar 1;17(5):1861-9. Epub 2009 Jan 27. PubMed PMID: 19208482.

3: Hsin LW, Wang HP, Kao PH, Lee O, Chen WR, Chen HW, Guh JH, Chan YL, His CP, Yang MS, Li TK, Lee CH. Synthesis, DNA binding, and cytotoxicity of 1,4-bis(2-amino-ethylamino)anthraquinone-amino acid conjugates. Bioorg Med Chem. 2008 Jan 15;16(2):1006-14. Epub 2007 Oct 10. PubMed PMID: 17962028.

4: Morley JO, Furlong PJ. Synthesis and calculated properties of some 1,4-bis(amino)anthracene-9,10-diones. Org Biomol Chem. 2006 Nov 7;4(21):4005-14. Epub 2006 Oct 2. PubMed PMID: 17047882.

5: Shchekotikhin AE, Glazunova VA, Luzikov YN, Buyanov VN, Susova OY, Shtil AA, Preobrazhenskaya MN. Synthesis and structure-activity relationship studies of 4,11-diaminonaphtho[2,3-f]indole-5,10-diones. Bioorg Med Chem. 2006 Aug 1;14(15):5241-51. Epub 2006 May 2. PubMed PMID: 16631372.

6: Reszka KJ, Wagner BA, Burns CP, Britigan BE. Effects of peroxidase substrates on the Amplex red/peroxidase assay: antioxidant properties of anthracyclines. Anal Biochem. 2005 Jul 15;342(2):327-37. PubMed PMID: 15913534.

7: Tarasiuk J, Mazerski J, Tkaczyk-Gobis K, Borowski E. Molecular basis of the low activity of antitumor anthracenediones, mitoxantrone and ametantrone, in oxygen radical generation catalyzed by NADH dehydrogenase. Enzymatic and molecular modelling studies. Eur J Med Chem. 2005 Apr;40(4):321-8. Epub 2004 Dec 15. PubMed PMID: 15804531.

8: Huang HS, Chou CL, Guo CL, Yuan CL, Lu YC, Shieh FY, Lin JJ. Human telomerase inhibition and cytotoxicity of regioisomeric disubstituted amidoanthraquinones and aminoanthraquinones. Bioorg Med Chem. 2005 Mar 1;13(5):1435-44. PubMed PMID: 15698759.

9: Sadeghi-Aliabadi H, Tabarzadi M, Zarghi A. Synthesis and cytotoxic evaluation of two novel anthraquinone derivatives. Farmaco. 2004 Aug;59(8):645-9. PubMed PMID: 15262534.

10: O'Malley YQ, Reszka KJ, Britigan BE. Direct oxidation of 2',7'-dichlorodihydrofluorescein by pyocyanin and other redox-active compounds independent of reactive oxygen species production. Free Radic Biol Med. 2004 Jan 1;36(1):90-100. PubMed PMID: 14732293.

11: Johnson JL, Ahmad A, Khan S, Wang YF, Abu-Qare AW, Ayoub JE, Zhang A, Ahmad I. Improved liquid chromatographic method for mitoxantrone quantification in mouse plasma and tissues to study the pharmacokinetics of a liposome entrapped mitoxantrone formulation. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Jan 5;799(1):149-55. PubMed PMID: 14659447.

12: Skladanowski A, Konopa J. Mitoxantrone and ametantrone induce interstrand cross-links in DNA of tumour cells. Br J Cancer. 2000 Apr;82(7):1300-4. PubMed PMID: 10755405; PubMed Central PMCID: PMC2374491.

13: Yang XL, Robinson H, Gao YG, Wang AH. Binding of a macrocyclic bisacridine and ametantrone to CGTACG involves similar unusual intercalation platforms. Biochemistry. 2000 Sep 12;39(36):10950-7. PubMed PMID: 10998231.

14: Jamison JM, Gilloteaux J, Thiry M, Authelet M, Goessens G, Summers JL. Ultrastructural nucleolar alterations induced by an ametantrone--poly r(A-U) complex. Tissue Cell. 1998 Aug;30(4):475-84. PubMed PMID: 9787478.

15: Babaian IuS, Sngrian AE, Kazarian RS, Avetisian MG, Sogomonian LR, Garibian DV. [The study of the interaction of antineoplastic drugs mitoxantrone and ametantrone with DNA using the analysis of changes in circular dichroism spectra]. Biofizika. 1998 May-Jun;43(3):422-6. Russian. PubMed PMID: 9702332.

16: Routier S, Bernier JL, Catteau JP, Riou JF, Bailly C. Synthesis, DNA binding, topoisomerase II inhibition and cytotoxicity of two guanidine-containing anthracene-9,10-diones. Anticancer Drug Des. 1998 Jul;13(5):407-15. PubMed PMID: 9702207.

17: Mazerski J, Martelli S, Borowski E. The geometry of intercalation complex of antitumor mitoxantrone and ametantrone with DNA: molecular dynamics simulations. Acta Biochim Pol. 1998;45(1):1-11. PubMed PMID: 9701490.

18: Thiry M, Jamison JM, Gilloteaux J, Summers JL, Goessens G. Ultrastructural nucleolar alterations induced by an ametantrone/polyr(A-U) complex. Exp Cell Res. 1997 Oct 10;236(1):275-84. PubMed PMID: 9344608.

19: Kellner U, Hutchinson L, Seidel A, Lage H, Danks MK, Dietel M, Kaufmann SH. Decreased drug accumulation in a mitoxantrone-resistant gastric carcinoma cell line in the absence of P-glycoprotein. Int J Cancer. 1997 May 29;71(5):817-24. PubMed PMID: 9180151.

20: de Isabella P, Palumbo M, Sissi C, Carenini N, Capranico G, Menta E, Oliva A, Spinelli S, Krapcho AP, Giuliani FC, Zunino F. Physicochemical properties, cytotoxic activity and topoisomerase II inhibition of 2,3-diaza-anthracenediones. Biochem Pharmacol. 1997 Jan 24;53(2):161-9. PubMed PMID: 9037248.

21: Gatto B, Zagotto G, Sissi C, Cera C, Uriarte E, Palù G, Capranico G, Palumbo M. Peptidyl anthraquinones as potential antineoplastic drugs: synthesis, DNA binding, redox cycling, and biological activity. J Med Chem. 1996 Aug 2;39(16):3114-22. PubMed PMID: 8759632.

22: Rentsch KM, Schwendener RA, Hänseler E. Determination of mitoxantrone in mouse whole blood and different tissues by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1996 Apr 26;679(1-2):185-92. PubMed PMID: 8998559.

23: Bailly C, Routier S, Bernier JL, Waring MJ. DNA recognition by two mitoxantrone analogues: influence of the hydroxyl groups. FEBS Lett. 1996 Feb 5;379(3):269-72. PubMed PMID: 8603704.

24: Augustin E, Wheatley DN, Lamb J, Konopa J. Imidazoacridinones arrest cell-cycle progression in the G2 phase of L1210 cells. Cancer Chemother Pharmacol. 1996;38(1):39-44. PubMed PMID: 8603450.

25: Dackiewicz P, Skladanowski A, Konopa J. 32P-postlabelling analysis of adducts formed by mitoxantrone and ametantrone with DNA and homopolydeoxyribonucleotides after enzymatic activation. Chem Biol Interact. 1995 Nov 17;98(2):153-66. PubMed PMID: 8548855.

26: Antonini I, Cola D, Polucci P, Bontemps-Gracz M, Borowski E, Martelli S. Synthesis of (dialkylamino)alkyl-disubstituted pyrimido[5,6,1- de]acridines, a novel group of anticancer agents active on a multidrug resistant cell line. J Med Chem. 1995 Aug 18;38(17):3282-6. PubMed PMID: 7650682.

27: De Isabella P, Palumbo M, Sissi C, Capranico G, Carenini N, Menta E, Oliva A, Spinelli S, Krapcho AP, Giuliani FC, et al. Topoisomerase II DNA cleavage stimulation, DNA binding activity, cytotoxicity, and physico-chemical properties of 2-aza- and 2-aza-oxide-anthracenedione derivatives. Mol Pharmacol. 1995 Jul;48(1):30-8. PubMed PMID: 7623772.

28: Gandolfi CA, Beggiolin G, Menta E, Palumbo M, Sissi C, Spinelli S, Johnson F. Chromophore-modified antitumor anthracenediones: synthesis, DNA binding, and cytotoxic activity of 1,4-bis[(aminoalkyl)amino]benzo[g]-phthalazine-5,10-diones. J Med Chem. 1995 Feb 3;38(3):526-36. PubMed PMID: 7853345.

29: Priston MJ, Sewell GJ. Improved LC assay for the determination of mitozantrone in plasma: analytical considerations. J Pharm Biomed Anal. 1994 Sep;12(9):1153-62. PubMed PMID: 7803567.

30: Krapcho AP, Petry ME, Getahun Z, Landi JJ Jr, Stallman J, Polsenberg JF, Gallagher CE, Maresch MJ, Hacker MP, Giuliani FC, et al. 6,9-Bis[(aminoalkyl)amino]benzo[g]isoquinoline-5,10-diones. A novel class of chromophore-modified antitumor anthracene-9,10-diones: synthesis and antitumor evaluations. J Med Chem. 1994 Mar 18;37(6):828-37. PubMed PMID: 8145234.

31: De Isabella P, Capranico G, Palumbo M, Sissi C, Krapcho AP, Zunino F. Sequence selectivity of topoisomerase II DNA cleavage stimulated by mitoxantrone derivatives: relationships to drug DNA binding and cellular effects. Mol Pharmacol. 1993 May;43(5):715-21. PubMed PMID: 8388987.

32: Shipp NG, Dorr RT, Alberts DS, Dawson BV, Hendrix M. Characterization of experimental mitoxantrone cardiotoxicity and its partial inhibition by ICRF-187 in cultured neonatal rat heart cells. Cancer Res. 1993 Feb 1;53(3):550-6. PubMed PMID: 8425187.

33: Stefańska B, Dzieduszycka M, Martelli S, Tarasiuk J, Bontemps-Gracz M, Borowski E. 6-[(aminoalkyl)amino]-substituted 7H-benzo[e]perimidin-7-ones as novel antineoplastic agents. Synthesis and biological evaluation. J Med Chem. 1993 Jan 8;36(1):38-41. PubMed PMID: 8421288.

34: Tarasiuk J, Garnier-Suillerot A, Stefańska B, Borowski E. The essential role of anthraquinones as substrates for NADH dehydrogenase in their redox cycling activity. Anticancer Drug Des. 1992 Aug;7(4):329-40. PubMed PMID: 1324690.

35: Fisher GR, Gutierrez PL, Oldcorne MA, Patterson LH. NAD(P)H (quinone acceptor) oxidoreductase (DT-diaphorase)-mediated two-electron reduction of anthraquinone-based antitumour agents and generation of hydroxyl radicals. Biochem Pharmacol. 1992 Feb 4;43(3):575-85. PubMed PMID: 1311584.

36: Morier-Teissier E, Bernier JL, Coulaud D, Hénichart JP, Delain E. Electron microscopic observations of the effects of anthraquinone derivatives on plasmid DNA. J Biomol Struct Dyn. 1992 Feb;9(4):653-66. PubMed PMID: 1616624.

37: Fisher GR, Patterson LH. Lack of involvement of reactive oxygen in the cytotoxicity of mitoxantrone, CI941 and ametantrone in MCF-7 cells: comparison with doxorubicin. Cancer Chemother Pharmacol. 1992;30(6):451-8. PubMed PMID: 1394801.

38: Ossowska G, Juszkiewicz M, Kleinrok Z. Pharmacological properties of ametantrone. Ann Univ Mariae Curie Sklodowska Med. 1992;47:183-93. PubMed PMID: 1365795.

39: Winkle SA, Aloyo MC, Morales N, Zambrano TY, Sheardy RD. Enhanced reactivity of a B-Z junction for cleavage by the restriction enzyme MboI. Biochemistry. 1991 Nov 5;30(44):10601-6. PubMed PMID: 1931982.

40: Lassota P, Melamed MR, Darzynkiewicz Z. Release of specific proteins from nuclei of HL-60 and MOLT-4 cells by antitumor drugs having affinity to nucleic acids. Biochem Pharmacol. 1991 Mar 15-Apr 1;41(6-7):1055-65. PubMed PMID: 2009074.

41: Babaian IuS, Manzinii D, Ksodo LE. [Binding of mitoxantrone and ametantrone with poly(d(G-C)) on the B---Z transition, stimulated by NaCl]. Biofizika. 1991 Mar-Apr;36(2):266-70. Russian. PubMed PMID: 1892903.

42: de Vries AJ, Nooter K. Quantification of mitoxantrone in bone marrow by high-performance liquid chromatography with electrochemical detection. J Chromatogr. 1991 Feb 15;563(2):435-42. PubMed PMID: 2056008.

43: Morier-Teissier E, Bernier JL, Lohez M, Catteau JP, Hénichart JP. Free radical production and DNA cleavage by copper chelating peptide-anthraquinones. Anticancer Drug Des. 1990 Aug;5(3):291-305. PubMed PMID: 2400540.

44: Denny WA, Wakelin LP. Kinetics of the binding of mitoxantrone, ametantrone and analogues to DNA: relationship with binding mode and anti-tumour activity. Anticancer Drug Des. 1990 May;5(2):189-200. PubMed PMID: 2357264.

45: Tarasiuk J, Kolodziejczyk P, Borowski E. Enzymatic studies of the effect of Cu (II) on oxygen radical production stimulated by daunorubicin and ametantrone. Biochem Pharmacol. 1990 May 1;39(9):1405-10. PubMed PMID: 2159304.

46: Hartley JA, Forrow SM, Souhami RL, Reszka K, Lown JW. Photosensitization of human leukemic cells by anthracenedione antitumor agents. Cancer Res. 1990 Mar 15;50(6):1936-40. PubMed PMID: 2306743.

47: Wu C, Guo P, Song H. [Ion-paired high performance liquid chromatographic determination of mitoxantrone hydrochloride injection]. Hua Xi Yi Ke Da Xue Xue Bao. 1990 Mar;21(1):39-41. Chinese. PubMed PMID: 2365339.

48: Jamison JM, Krabill K, Flowers DG, Tsai CC. Polyribonucleotide-anthraquinone interactions: in vitro antiviral activity studies. Cell Biol Int Rep. 1990 Mar;14(3):219-28. PubMed PMID: 1693102.

49: Jamison JM, Krabill K, Flowers DG, Tsai C. Enhancement of the antiviral activity of poly r(A-U) by ametantrone and mitoxantrone. Life Sci. 1990;46(9):653-61. PubMed PMID: 2155366.

50: al-Gailany KA. Spectrofluorometric studies on the binding of the antitumor drugs ametantrone and mitoxantrone to bovine serum albumin. Biomed Biochim Acta. 1990;49(10):1091-6. PubMed PMID: 2127883.

51: Antonello C, Uriarte E, Palumbo M. Diethylaminopropionamido-hydroxy-anthraquinones as potential anticancer agents: synthesis and characterization. Arch Pharm (Weinheim). 1989 Sep;322(9):541-4. PubMed PMID: 2610587.

52: Bartkowiak J, Kapuscinski J, Melamed MR, Darzynkiewicz Z. Selective displacement of nuclear proteins by antitumor drugs having affinity for nucleic acids. Proc Natl Acad Sci U S A. 1989 Jul;86(13):5151-4. PubMed PMID: 2525781; PubMed Central PMCID: PMC297575.

53: Giaccone G. The European Organization for Research and Treatment of Cancer (EORTC) trials of new agents for advanced non-small cell lung cancer. Semin Oncol. 1988 Dec;15(6 Suppl 7):46-8. PubMed PMID: 2851178.

54: al-Gailany KA, Alwan AH. Interactions of the anti-tumor ametantrone and mitoxantrone with rat hepatic microsomes. Biochem Pharmacol. 1988 Oct 15;37(20):3803-6. PubMed PMID: 3142480.

55: Mirabelli CK, Sung CM, McCabe FL, Faucette LF, Crooke ST, Johnson RK. A murine model to evaluate the ability of in vitro clonogenic assays to predict the response to tumors in vivo. Cancer Res. 1988 Oct 1;48(19):5447-54. PubMed PMID: 3046738.

56: Reszka K, Kolodziejczyk P, Tsoungas PG, Lown JW. Photosensitization by antitumor agents--6. Production of superoxide radical and hydrogen peroxide during illumination of diaminoanthracenediones in the presence of NADH in aqueous solutions: an EPR study. Photochem Photobiol. 1988 May;47(5):625-33. PubMed PMID: 2841701.

57: Kolodziejczyk P, Garnier-Suillerot A. Circular dichroism study of the interaction of mitoxantrone, ametantrone and their Pd(II) complexes with deoxyribonucleic acid. Biochim Biophys Acta. 1987 Dec 7;926(3):249-57. PubMed PMID: 3689823.

58: Kharasch ED, Wendel NK, Novak RF. Anthracenedione antineoplastic agent effects on drug metabolism in vitro and in vivo: relationship between structure and mechanism of inhibition. Fundam Appl Toxicol. 1987 Jul;9(1):18-25. PubMed PMID: 3114031.

59: Kuhn JG, Balmer CE, Ludden TM, Loesch DM, Von Hoff DD, Bender JF, Grillo-Lopez AJ. Pharmacokinetics of ametantrone acetate (NSC-287513). Cancer Chemother Pharmacol. 1987;19(2):133-7. PubMed PMID: 3568271.

60: Petrere JA, Kim SN, Anderson JA, Fitzgerald JE, de la Iglesia FA, Schardein JL. Teratology studies of ametantrone acetate in rats and rabbits. Teratology. 1986 Dec;34(3):271-8. PubMed PMID: 3798363.

61: Krishnamoorthy CR, Yen SF, Smith JC, Lown JW, Wilson WD. Stopped-flow kinetic analysis of the interaction of anthraquinone anticancer drugs with calf thymus DNA, poly[d(G-C)].poly[d(G-C)], and poly[d(A-T)].poly[d(A-T)]. Biochemistry. 1986 Oct 7;25(20):5933-40. PubMed PMID: 3790495.

62: Kapuscinski J, Darzynkiewicz Z. Relationship between the pharmacological activity of antitumor drugs Ametantrone and mitoxantrone (Novatrone) and their ability to condense nucleic acids. Proc Natl Acad Sci U S A. 1986 Sep;83(17):6302-6. PubMed PMID: 3462696; PubMed Central PMCID: PMC386491.

63: Watkins JR, Kim SN, Jayasekara U, Anderson JA, Fitzgerald JE, de la Iglesia FA. Preclinical toxicity of the new antineoplastic agent, ametantrone acetate, in mice and dogs. J Appl Toxicol. 1986 Feb;6(1):31-6. PubMed PMID: 3958426.

64: Bron D, Dodion P, Rozencweig M, Delforge A, Mattelaer MA, Kenis Y, Stryckmans P. Quantitation of differential sensitivity of normal marrow myeloid progenitor cells to anthracene derivatives. Invest New Drugs. 1986;4(1):11-6. PubMed PMID: 3700036.

65: Harris GJ, Turner JN, Von Hoff DD. Growth of carcinoma of the esophagus and gastroesophageal junction in a human tumor cloning assay. Cancer Drug Deliv. 1986 Fall;3(4):273-8. PubMed PMID: 3567847.

66: Fountzilas G, Ohnuma T, Rammos K, Mindich B, Holland JF. Comparison of mitoxantrone and ametantrone in human acute myelocytic leukemia cells in culture and in bone marrow granulocyte-macrophage progenitor cells. Cancer Drug Deliv. 1986 Spring;3(2):93-100. PubMed PMID: 3458518.

67: Kapuscinski J, Darzynkiewicz Z. Interactions of antitumor agents Ametantrone and Mitoxantrone (Novatrone) with double-stranded DNA. Biochem Pharmacol. 1985 Dec 15;34(24):4203-13. PubMed PMID: 4074383.

68: Leopold WR, Nelson JM, Plowman J, Jackson RC. Anthrapyrazoles, a new class of intercalating agents with high-level, broad spectrum activity against murine tumors. Cancer Res. 1985 Nov;45(11 Pt 1):5532-9. PubMed PMID: 4053027.

69: Kharasch ED, Novak RF. Mitoxantrone and ametantrone inhibit hydroperoxide-dependent initiation and propagation reactions in fatty acid peroxidation. J Biol Chem. 1985 Sep 5;260(19):10645-52. PubMed PMID: 2993283.

70: Lown JW, Morgan AR, Yen SF, Wang YH, Wilson WD. Characteristics of the binding of the anticancer agents mitoxantrone and ametantrone and related structures to deoxyribonucleic acids. Biochemistry. 1985 Jul 16;24(15):4028-35. PubMed PMID: 4052381.

71: Rozencweig M, Sanders C, Rombaut W, Crespeigne N, Kenis Y, Klastersky J. Phase II study of ametantrone in a human tumor cloning assay. Eur J Cancer Clin Oncol. 1985 Feb;21(2):195-8. PubMed PMID: 3987756.

72: van Belle SJ, Schoemaker TJ, Verwey SL, Paalman AC, McVie JG. Ion-paired high-performance liquid chromatographic determination of mitoxantrone in physiological fluids. J Chromatogr. 1985 Jan 11;337(1):73-80. PubMed PMID: 3980659.

73: Gams RA, Ostroy F, Bender JF, Grillo-López AJ. A phase I trial of ametantrone acetate (NSC-287513). Invest New Drugs. 1985;3(4):383-8. PubMed PMID: 4086246.

74: Novak RF, Kharasch ED. Mitoxantrone: propensity for free radical formation and lipid peroxidation--implications for cardiotoxicity. Invest New Drugs. 1985;3(2):95-9. PubMed PMID: 2991163.

75: Kharasch ED, Novak RF. Spectroscopic evidence for anthracenedione antineoplastic agent self-association and complex formation with flavin nucleotides. Arch Biochem Biophys. 1984 Nov 1;234(2):497-512. PubMed PMID: 6497384.

76: Warner MR, Rappaport MS, Krieger NS, Novak RF, Stern PH. Ametantrone inhibits prostaglandin--mediated resorption in bone organ culture. Prostaglandins. 1984 Oct;28(4):469-76. PubMed PMID: 6335259.

77: Lathan B, Von Hoff DD, Elslager E. Use of a human tumor cloning system to evaluate analogs of methotrexate and mitoxantrone. Cancer Treat Rep. 1984 May;68(5):733-8. PubMed PMID: 6233003.

78: Showalter HD, Johnson JL, Werbel LM, Leopold WR, Jackson RC, Elslager EF. 5-[(Aminoalkyl)amino]-substituted anthra[1,9-cd]pyrazol-6(2H)-ones as novel anticancer agents. Synthesis and biological evaluation. J Med Chem. 1984 Mar;27(3):253-5. PubMed PMID: 6699870.

79: Schabel FM Jr, Corbett TH, Griswold DP Jr, Laster WR Jr, Trader MW. Therapeutic activity of mitoxantrone and ametantrone against murine tumors. Cancer Treat Rev. 1983 Dec;10 Suppl B:13-21. Review. PubMed PMID: 6362874.

80: Baguley BC, Kernohan AR, Wilson WR. Divergent activity of derivatives of amsacrine (m-AMSA) towards Lewis lung carcinoma and P388 leukaemia in mice. Eur J Cancer Clin Oncol. 1983 Nov;19(11):1607-13. PubMed PMID: 6688994.

81: Loesch DM, Von Hoff DD, Kuhn J, Coltman CA, Tio F, Chaudhuri TK, Bender JF, Grillo-Lopez AJ. Phase I investigation of ametantrone. Cancer Treat Rep. 1983 Nov;67(11):987-91. PubMed PMID: 6640557.

82: Locher SE, Meyn RE. Relationship between cytotoxicity and DNA damage in mammalian cells treated with anthracenedione derivatives. Chem Biol Interact. 1983 Sep 15;46(3):369-79. PubMed PMID: 6357512.

83: Kharasch ED, Novak RF. Inhibitory effects of anthracenedione antineoplastic agents on hepatic and cardiac lipid peroxidation. J Pharmacol Exp Ther. 1983 Aug;226(2):500-6. PubMed PMID: 6875860.

84: Ogawa M. [Current clinical status of new anticancer drugs]. Gan No Rinsho. 1983 Aug;29(10):1049-52. Japanese. PubMed PMID: 6415310.

85: Kharasch ED, Novak RF. Bis(alkylamino)anthracenedione antineoplastic agent metabolic activation by NADPH-cytochrome P-450 reductase and NADH dehydrogenase: diminished activity relative to anthracyclines. Arch Biochem Biophys. 1983 Jul 15;224(2):682-94. PubMed PMID: 6408991.

86: Drewinko B, Yang LY, Barlogie B, Trujillo JM. Comparative cytotoxicity of bisantrene, mitoxantrone, ametantrone, dihydroxyanthracenedione, dihydroxyanthracenedione diacetate, and doxorubicin on human cells in vitro. Cancer Res. 1983 Jun;43(6):2648-53. PubMed PMID: 6850582.

87: Patterson LH, Gandecha BM, Brown JR. 1,4-Bis(2-[(2-hydroxyethyl)amino]ethylamino)-9,10-anthracenedione, an anthraquinone antitumour agent that does not cause lipid peroxidation in vivo; comparison with daunorubicin. Biochem Biophys Res Commun. 1983 Jan 27;110(2):399-405. PubMed PMID: 6838527.

88: Cheng CC, Zee-Cheng RK. The design, synthesis and development of a new class of potent antineoplastic anthraquinones. Prog Med Chem. 1983;20:83-118. Review. PubMed PMID: 6356227.

89: Kharasch ED, Novak RF. Inhibition of adriamycin-stimulated microsomal lipid peroxidation by mitoxantrone and ametantrone, two new anthracenedione antineoplastic agents. Biochem Biophys Res Commun. 1982 Oct 15;108(3):1346-52. PubMed PMID: 6295377.

90: Kharasch ED, Novak RF. Inhibition of microsomal oxidative drug metabolism by 1,4-bis (2-[(2-hydroxyethyl)amino]-ethylamino)-9,10-anthracenedione diacetate, a new antineoplastic agent. Mol Pharmacol. 1982 Sep;22(2):471-8. PubMed PMID: 6815478.

91: Roboz J, Richardson CL, Holland JF. Comparison of the interaction of antineoplastic aminoanthraquinone analogs with DNA using competitive fluorescence polarization. Life Sci. 1982 Jul 5;31(1):25-30. PubMed PMID: 7109851.

92: Zbinden G, Beilstein AK. Comparison of cardiotoxicity of two anthracenediones and doxorubicin in rats. Toxicol Lett. 1982 May;11(3-4):289-97. PubMed PMID: 7101322.

93: Kharasch ED, Novak RF. Anthracenedione activation by NADPH-cytochrome P-450 reductase; comparison with anthracyclines. Biochem Pharmacol. 1981 Oct;30(20):2881-4. PubMed PMID: 6274352.

94: Piccart M, Rozencweig M, Abele R, Cumps E, Dodion P, Dupont D, Kisner D, Kenis Y. Phase I clinical trial with ametantrone (NSC-287513). Eur J Cancer Clin Oncol. 1981 Jul;17(7):775-9. PubMed PMID: 7199472.

95: Au WW, Butler MA, Matney TS, Loo TL. Comparative structure-genotoxicity study of three aminoanthraquinone drugs and doxorubicin. Cancer Res. 1981 Feb;41(2):376-9. PubMed PMID: 7448780.

96: Lu K, Loo TL. Pharmacological disposition of 1,4-bis (2-[(2-hydroxyethyl)amino]-ethylamino)-9,10-anthracenedione diacetate in the dog. Cancer Res. 1980 May;40(5):1427-30. PubMed PMID: 7370981.

97: Evenson DP, Traganos F, Darzynkiewicz Z, Staiano-Coico L, Melamed MR. Effects of 9,10-anthracenedione, 1,4-bis[[2-[(2-hydroxyethyl)amino]-ethyl]amino]-, diacetate on cell morphology and nucleic acids of friend leukemia cells. J Natl Cancer Inst. 1980 Apr;64(4):857-66. PubMed PMID: 6928997.

98: Taylor RF, Gaudio LA. High-performance liquid chromatography of cancer chemotherapeutic agents: bis(substituted aminoalkylamino)anthraquinones. J Chromatogr. 1980 Jan 4;187(1):212-7. PubMed PMID: 7358816.