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Current Opinion on Therapeutic Patents Volume 2, 1992 - Issue 8
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Anticancers, Hormonals & Metabolic Disease Therapy

Overview: DNA Topoisomerase Targeted Anticancer Agents: New Trends and Developments

Tsann-Long Su Laboratories of Organic Chemistry and Biochemical Pharmacology, Memorial Sloan-Kettering Cancer Center, 1275 York Avenue, New York, NY, 10021, USA
,
Ting-Chao Chou Laboratories of Organic Chemistry and Biochemical Pharmacology, Memorial Sloan-Kettering Cancer Center, 1275 York Avenue, New York, NY, 10021, USA
&
Kyoichi A Watanabe Laboratories of Organic Chemistry and Biochemical Pharmacology, Memorial Sloan-Kettering Cancer Center, 1275 York Avenue, New York, NY, 10021, USA
Pages 1121-1139 | Published online: 02 Mar 2011

References to Primary Literature

  • Liu, LF D'Arpa, P Topoisomerase-targeting antitumor agents: Mechanism of cytotoxicity and resistance Important Advances in Oncology De Vita, VT, Hellman, S, Rosengerg, SA JB Lippincott Co Philadelphia 1992 79–89.
  • Schneider, E Hsiang, Y-H Liu, LF DNA topoisomerase as anticancer drug targets. Adv. in Pharmacol. 1990 21 149–181.
  • Wang, JC DNA topoisomerases. Ann. Rev. Biochem. 1985 54 665–697.
  • DNA-Topoisomerases in Cancer Potmesil, M, Kohn, KW Oxford University Press 1991.
  • Wall, ME Wani, MC Cook, CE Palmer, KH McPhail, AT Sim, GA Plant antitumor agents. I. Isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca accuminata. J. Am. Chem. Soc. 1966 88 3888–3890.
  • Schultz, AG Camptothecin. Chem. Rev. 1973 73 385–405.
  • Hutchinson, CR Camptothecin: Chemistry, biogenesis and medical chemistry. Tetrahedron 1981 37 1047–1065.
  • Cai, JC Hutchinson, CR Camptothecin Alkaloids: Chemistry and Pharmacology Brossi, A Academic Press New York 1983 Vol. 21 101–137.
  • Cai, JC Hutchinson, CR Camptothecin. Chem. Heterocycl. Compd. 1983 25 753–781.
  • Wall, ME Wani, MC Natschke, SM Nicholas, AW Plant antitumor agents. 22. Isolation of 11-hydroxycamptothecin from Camptotheca acuminata Decne: Total synthesis and biological activity. J. Med Chem. 1986 29 1553–1555.
  • Wani, MC Nicholas, AW Wall, ME Plant antitumor agents. 23. Synthesis and antileukemic activity of camptothecin analogues. J. Med. Chem. 1986 29 2358–2363.
  • Wani, MC Nicholas, AW Manikumar, G Wall, ME Plant antitumor agents. 25. Total synthesis and antileukemic activity of ring A substituted camptothecin analogues. Structure-activity correlations. J. Med. Chem. 1987 30 1774–1779.
  • Giovanella, BC Wall, ME Wani, MC Silber, R Stemlin, JS Hochster, M Potmesil, M Efficacy of camptothecin [NSC 94600], 9-aminocamtothecin [NSC 60371] and 10,11-methylenedioxy-camptothecin [NSC 606174] in the human cancer xenograft model. Proc. Am. Assoc. Cancer Res. 1992 33 432.
  • Wani, MC Ronman, PE Lindley, JT Wall, ME Plant antitumor agents. 18. Synthesis and biological activity of camptothecin analogues. J. Med. Chem. 1998 23 554–560.
  • Kinsbury, WD Boehm, JC Jakas, DR Holden, KG Hecht, SM Gallagher, G Caranfa, MJ McCabe, FL Faucette, LF Johnson, RK Hertzberg, RP Synthesis of water-soluble (aminoalkyl)-camptothecin analogues: Inhibition topoisomerase I and antitumor activity. J. Med. Chem. 1991 34 98–107.
  • Kuhn, J Wall, J Burris, S Rodriguez, M Marshall, M Smith, B Johnson, R Von Hoff, D Phase I clinical and pharmacokinetic trial of the topoisomerase I inhibitor, topotecan Abs. 49. Third Conference on DNA Topoisomerase in Therapy. 1990.
  • Haas, NB LaCreta, FP Walczak, J Hudes, GR Brennan, J Ozols, RF O'Dwyer, PJ Phase I/pharmacokinetic trial of topotecan on a weekly 24-hour infusion schedule. Proc. Am. Assoc. Cancer Res. 1992 35 523 More clinical trials on topotecan are reported in abstracts on the 7th NCI-EORTC Symposium on New Drugs in Cancer Chemotherapy. Amsterdam, March, 1992, p. 83–84, p. 118 (8 abstracts).
  • Clavel, M Mathieu-Boue, A Dumortier, A Chabot, GG Cote, C Bissery, MC Marty, M Phase I study of CPT-11 administered as a daily infusion for 3 consecutive days. Proc. Am. Assoc. Cancer Res. 1992 33 262 More clinical trials on CPT-11 are reported in abstracts of the 7th NCI-EORTC symposium on new drugs in cancer chemotherapy, Amsterdam, March 1992, pp 82–83, pp 117–119. (8 abstracts).
  • Wall, ME Alkaloids with antitumor activity Biochem. Physiol. Alkaloid, Int. Symp., 4th. 1969 Mothes, K 38–49 ( pub 1972).
  • Ohlendorf, HW Stranghöner, R Winterfeldt, E Die Synthese von 7-Acetoxycamptothecin. Synthesis 1976 741–742.
  • Miyasaka, T Sawada, S Nokata, K A selective one-step introduction of hydroxylic functions at the C-5 and C-7 positions of 20(S)-camptothecin, an alkaloid having antitumor activity. Heterocycles 1981 16 1713–1717.
  • Sugasawa, T Toyoda, T Uchida, N Yamaguchi, K Experiments on the synthesis of dl-camptothecin. 4. Synthesis and antileukemic activity of dl-camptothecin analogues. J. Med. Chem. 1976 19 675–679.
  • Danishefsky, S Volkmann, R Horwitz, SB Isocamptothecin. Tetrahedron Lett. 1973 2521–2524.
  • Wall, ME Wani, MC Camptothecin Anticancer Agents Based on Natural Product Models Cassady, JM, DOuros, JD Academic Press New York 1980 417–436.
  • Wani, MC Nicholas, AW Wall, ME Plant antitumor agents. 28. Resolution of a key tricyclic synthon. 5′-(RS)-1,5-dioxo-(5′-ethyl-5′-hydroxy-2′H,5′K,6′H-6-oxopyrano) [3′,4′-f]Δ6,8-tetrahydroindolizine: Total synthesis and antitumor activity of 20(S)- and 20(R)-camptothecin. J. Med. Chem. 1987 30 2317–2319.
  • Pommier, Y Jaxel, C Covey, JM Kerrigan, D Wani, MC Wall, ME Kohn, KW Structure-activity study of the relation between topoisomerase I inhibition and antitumor activity of camptothecin. Proc. Am. Assoc. Cancer Res. 1988 29 270.
  • Wall, ME Wani, MC Antineoplastic agents from plants. Annu. Rev. Pharmacol. Toxicol. 1977 17 117–132.
  • Hertzberg, RP Caranfa, MJ Holden, KG Jakas, DR Gallagher, G Mattern, MR Mong, SM Bartus, JO Johnson, RK Kinsbury, WD Modification of the hydroxy lactone ring of camptothecin: Inhibition mammalian topoisomerase I and biological activity. J. Med. Chem. 1989 32 715–720.
  • Gottlieb, JA Lucke, JK Treatment of malignant melanoma with camptothecin (NSC-100800). Cancer Chemother. Rep. 1972 56 103–105.
  • Moerrel, CG Schull, AJ Reitemeier, RJ Hahn, RG Phase II study of camptothecin (NSC-100800) in the treatment of advanced gastrointestinal cancer. Cancer Chemother. Rep. 1972 56 95–101.
  • DiMarco, A Arcamone, F Zunino, F Antibiotics. Coecoran, JW, Hahn, FE Springer Berlin 1974 Vol. 3 101–128.
  • Neidle, S The molecular basis for the action of some DNA-binding drugs. Prog. Med. Chem. 1979 16 151–220.
  • Tewey, KM Rowe, TC Yang, L Halligan, BC Liu, F Adriamycin-induced DNA damage mediated by mammalian DNA topoisomerase II. Science 1984 226 466–468.
  • Acamone, F Cassazza, A Cassinelli, G Di Marco, A Penco, S Doxorubicin and related compounds. II. Structure-activity considerations Anthracycline antibiotics in cancer therapy. Muggia, FM, Young, CW, Carter, SK Martinus Nijhoff Publischers Boston 1982 179–189.
  • Mathé, G Maral, R Second-generation anthracyclines Anthracycline antibiotics in cancer therapy. Muggia, FM, Young, CW, Carter, SK Martinus Nijhoff Publishers Boston 1982 190–124.
  • Oki, T Microbial transformation of anthracycline antibiotics and development of new anthracyclines Anthracycline antibiotics. El Khadem, HS Academic Press New York 1982 75–96.
  • Arcamone, F The development of new antitumor anthracyclines Anticancer agents based on natural product models. Cassady, JM, Douros, JD Academic Press New York 1984 1–41.
  • Acton, EM N-alkylation of anthracyclines Anthracyclines: Current status and new developments. Crooke, ST, Reich, SD Academic Press New York 1980 15–25.
  • Mosher, CS Wu, YH Fujiwara, AN Acton, EM Enhanced antitumor properties of 3′-(4-morpholinyl) and 3′-(4-methoxyl-1-piperidinyl) derivatives of 3′-deaminodaunorubicin. J. Med. Chem. 1982 25 18–24.
  • Acton, EM Tong, GL Mosher, CW Anderson, BS Intensely potent morpholinyl anthracyclines. J. Med. Chem. 1984 27 638–645.
  • Johnston, JB Habernicht, B Acton, EM Glaser, RI 3′-(3-Cyano-4-morpholinyl)-3′-deaminoadriamycin: A new anthracycline with intense potency. Biochem. Pharmacol. 1983 32 3255–3258.
  • Sikic, BI Ehsan, MN Harker, WG Friend, NF Brown, BW Newman, RA Hacker, MP Acton, EM Dissociation of antitumour potency from anthracycline cardiotoxicity in a doxorubicin analog. Science 1985 228 1544–1546.
  • Streeter, DG Taylor, DL Acton, EM Peters, JH Comparative cytotoxicity of various morpholinyl anthracyclines. Cancer Chemother. Pharmacol. 1985 14 160–164.
  • Guiliani, FC Barbieri, B Genoni, C Facchinetti, T Sasazza, AM Acton, EM Properties of cyanomorpholinyl-doxorubicin, a new anthracycline active agent against P388 resistant leukemia. Proc. Am. Assoc. Cancer. Res. 1984 25 305.
  • Sikic, BI Acton, EM Ehsan, MN Harker, WG Faran, MA Newman, RA Friend, NF Brown, BW Structure-activity of anthracyclines: 250 to 1500-fold increased potency in human tumors non-cross-resistance, and absence of cardiotoxicity in the cyano-morpholino derivative of doxorubicin. Proc. Am. Assoc. Cancer Res. 1984 25 306.
  • Jesson, MI Johnston, JB Anhalt, CD Begleiter, A Effects of 3′-(3-Cyano-4-morpholinyl)-3′-deaminoadriamycin and structural analogues on DNA in HT-29 human colon carcinoma cells. Cancer Res. 1987 47 5935–5938.
  • Smith, TH Fujiwara Henry, DW Adriamycin Analogues. Synthesis of 13-deoxyan-thracyclines. J. Med. Chem. 1978 21 280–283.
  • Zwelling, LA Michaels, S Erickson, LC Ungerleider, RS Nichols, M Kohn, DW Protein-associated deoxyribonucleic acid strand breaks in L1210 cell treated with the deoxyribonucleic acid intercalating agent 4′(9-acridinylamino)-methanesulfon-m-anisidide and adriamycin. Biochemistry 1981 20 6553–6563.
  • Nelson, EM Tewey, KM Liu, LF Mechanism of antitumor drugs. Poisoning of mammalian DNA topoisomerase II on DNA by an antitumor drug m-AMSA. Proc. Natl. Acad. Sci. USA 1984 81 1361–1365.
  • Shoemake, DD Cysyk, RL Padmanabhanan, S Bhat, HB Malspeis, L Identification of the principal biliary metabolite of 4′(9-acridinylamino)-methanesulfon-m-anisidide in rats. Drug Metab. Disp. 1982 10 35–39.
  • Schoemaker, DD Cysyk, RL Germeley, PE Desouza, JJV Malspeis, L Metabolism of 4′-(9-acridinylamino)methanesulfon-m-amsidide by rat liver microsomes. Cancer Res. 1984 44 1939–1945.
  • Chou, TC Kong, XB Ottor, GM Sirotnak, FM Ciszewska, G Su, TL Watanabe, KA Cytotoxicity, structure activity relationships and mechanism of action of new synthetic acridines that inhibit topoisomerase II. Proc. Am. Assoc. Cancer Res. 1984 32 435.
  • Tewey, KM Rowe, TC Yang, L Halligan, BC Liu, FL Adriamycin-induced DNA damage mediated by mammalian DNA topoisomerase II. Science 1984 226 466–468.
  • Archer, S Pica-Mattoccia, L Cioli, D Seyed-Mozaffari, A Zayed, A Preparation and antischitosomal and antitumor activity of hycanthone and some of its congeners. Evidence for the mode of action of hycanthone. J. Med. Chem. 1988 31 254–260.
  • Koyama, M Kelly, TR Watanabe, KA Novel type of potential, anticancer agents derived from chrysophanol and emodin. J. Med. Chem. 1988 31 283–284.
  • Koyama, M Takahashi, K Chou, TC Darzynkiewicz, Z Kapuscinski, T Kelly, R Watanabe, KA Intercalating agents with covalent bond forming capability. A novel type of potential anticancer agents. 2. Derivatives of chrysophanol and emodin. J. Med Chem. 1989 32 1594–1599.
  • Kong, XB Rubin, L Chen, LI Ciszewska, G Watanabe, KA Tong, WP Sirotnak, FM Chou, TC Topoisomerase II-mediated DNA cleavage activity and irreversibility of cleavable complex formation induced by DNA interclator with alkylating capability. Mol. Pharmacol. 1992 41 237–244.
  • Takahashi, K Ciszewska, G Watanabe, KA Potential anticancer agents derived from acridine. Intercalating agents with covalent bond forming capabilities. 3. Drugs of the Future 1990 15 605–610.
  • Tewey, KM Chen, GL Nelson, EM Liu, LF Intercalative antitumour drugs interfere with the breakage-reunion reaction of mammalian DNA topoisomerase II. J. Biol. Chem. 1984 259 9182–9187.
  • Hisang, YH Yiang, JB Liu, LF Topoisomerase II-mediated DNA cleavage by amonafide and its structural analogs. Mol. Pharmacol. 1989 36 371–376.
  • Kreis, W Budman, DR Allen, SL Vinciquerra, V Freeman, J Hock, K Akerman, S Fusco, D Mittelman, A Puccio, C Friedman, E McGuire, A Spiegelman Clinical pharmacokinetics of amonafide (NSC 30847) in 51 patients. Proc. Am. Assoc. Cancer Res. 1992 33 260.
  • Dorr, RT Remes, WA Sami, S Albert, DS Structure-activity relationships for anthracene derivatives of amonafide termed azonafides. Proc. Am. Assoc. Cancer Res. 1992 33 523.
  • Chen, GL Yang, L Rowe, T Halligan, BD Tewey, K Liu, L Nonintercalative antitumour drugs interfere with the breakage-reunion reaction of mammalian DNA topoisomerase II. J. Biol. Chem. 1984 259 13560–13566.
  • Ross, W Rowe, T Glisson, B Yalowich, J Liu, L Role of topoisomerase II in mediating epipodophillotoxin-induced DNA cleavage. Cancer Res. 1984 44 5857–5860.
  • Rowe, T Kuppfer, G Ross, W Inhibition of epipodophillotoxin cytotoxicity by interference with topoisomerase-mediated DNA cleavage. Biochem. Pharmacol. 1985 34 2483–2494.
  • Schreier, E Zur Struktur des Sikkimotoxins II. Partialsythese der 6,7-Dimetoxy Analogen von Podophylltoxin, Epi, Neo und Desoxy-podophyllotoxin. Helv. Chim. Acta 1964 47 1529–1555.
  • Ayres, DC Harris, JA Lignans and related phenols. Part XIV. Selective oxidation of aryl-tetrahydro-naphtalenes. J. Chem. Soc. Perkin Trans 1 1973 2059–2063.
  • Wang, ZQ Hu, H Chen, HX Cheng, YC Lee, KH Antitumor agents. 124. New 4β-substituted aniline derivatives of 6,7-O-O-demethylpodophyllotoxin and related compounds as potential inhibitors of human DNA topoisomerase II. J. Med. Chem. 1992 35 871–877.
  • Jardine, I Podophyllotoxins Anticancer agents based on Natural product models. Cassady, JM, Douros, J Academic Press New York 1980 319–351.
  • Doyle, TW The chemistry of etoposide Etoposide (VP-16) current status and new developments Issell, BF, Muggia, FM, Carter, SK Academic Press New York 1984 15–32.
  • Ayres, DC Lim, CK Modification of the pendant ring of podophyllotoxin. Cancer Chemother. Pharmacol. 1982 7 99–101.
  • Saulnier, MG Vyas, DM Langley, DR Doyle, TM Rose, WC Crosswell, AR Long, BH E-Ring desoxy analogues of etoposide. J. Med. Chem. 1989 32 1418–1420.
  • Long, BH LeBoulluec, K Saulnier, MG Fairchls, C Rose, WC Peterson, RW 4′-Deshydroxy-4′-methyl analogues of etoposide (VP-16) and teniposide (VM-26) possessing antitumour and DNA - topoisomerase II intermediate stabilization activities. Proc. Am. Assoc. Cancer Res. 1992 33 431.
  • Lee, KH Beers, SA Mori, M Wang, ZQ Kuol, YH Li, L Liu, SY Cheng, YC Antitumor agents. 111. New 4-hydroxylated and 4-halogenated anilino derivatives of 4-′-demethylepipodo-phyllotoxin as potent inhibitors of human DNA topoisomerase II. J. Med Chem. 1990 33 1364–1368.
  • Saito, H Yoshikawa, H Nishimura, Y Kondo, S Takeuchi, T Studies on lignan lactone antitumour agents. II. Synthesis of N-alkylamino- and 2,6-dideoxy-2-aminoglycosidic lignan variants related to podophyllotoxin. Chem. Pharm. Bull. 1986 34 3741–3746.
  • Wang, ZQ Kuo, YH Schnur, D Bowen, JP Liu, SY Han, FS Chang, JY Cheng, YC Lee, KH New 4β-aryamino derivatives of 4′-O-demethylepipodo-phyllotoxin and related compounds as potent inhibitors of human DNA topoisomerase II. J. Med. Chem. 1990 33 2660–2666.
  • Saito, H Nishimura, Y Kondo, S Komuro, K Takeuchi, T Studies of lignan lactone antitumour agents. V. 1-O-(Aminoethyl)ether of 4′-O-demethylepipodophyllotoxin. Bull. Chem. Soc. Japan 1988 61 2493–2497.
  • Zhou, XM Wang, ZQ Chang, JY Chen, HX Cheng, YC Lee, KH Antitumor agents. 120. New 4-substituted benzylamine and benzyl ether derivatives of 4′-O-demethylepipodop-hyllotoxin as potent inhibitors of human DNA topoisomerase II. J. Med. Chem. 1991 34 3346–3350.
  • Hu, H Wang, ZQ Liu, SY Cheng, YC Lee, KH Antitumor agents. 123. Synthesis and human DNA topoisomerase II inhibitory activity of 2′-chloro derivatives of etoposide and 4β-(aryamino)-4′-O-demethylpodophyllotoxins. J. Med. Chem. 1992 35 866–871.
  • Akiyama, T Ishida, J Nakagawa, S Ogawara, H Watanabe, S Itoh, N Shibuya, M Fukami, Y Genistein, a specific inhibitor of tyrosine-specific protein kinases. J. Biol. Chem. 1987 262 5592–5595.
  • Markovits, J Linassier, C Fossé, P Couprie, J Pierre, J Jacquemin-Sablon, A Saucier, JM Le Pecq, JB Larsen, AK Inhibitory effects of the tyrosine kinase inhibitor genistein on mammalian DNA topoisomerase II. Cancer Res. 1989 49 5111–5117.

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