Research progress of dual topoisomerase Ⅰ and Ⅱ inhibitors

JIANG Yan; SHENG Chunquan; DONG Guoqiang

doi:10.3969/j.issn.1006-0111.2015.04.004

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Article Navigation > Journal of Pharmaceutical Practice and Service > 2015 > 33(4): 303-308,379

SUN Nannan, LIU Jia, ZHENG Canhui, ZHOU Youjun. Synthesis,XRD analysis and anti-tumor activity of novel compounds containing tetrahydronaphthalen-2-ol[J]. Journal of Pharmaceutical Practice and Service, 2014, 32(3): 191-194. doi: 10.3969/j.issn.1006-0111.2014.03.007

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JIANG Yan, SHENG Chunquan, DONG Guoqiang. Research progress of dual topoisomerase Ⅰ and Ⅱ inhibitors[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(4): 303-308,379. doi: 10.3969/j.issn.1006-0111.2015.04.004

Research progress of dual topoisomerase Ⅰ and Ⅱ inhibitors

doi: 10.3969/j.issn.1006-0111.2015.04.004

Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2013-10-15
Rev Recd Date: 2014-02-19

Abstract

DNA topoisomerases (Tops) are essential enzymes that regulate the cellular processes such as replication, transcription, recombination and repair. DNA Tops can be classified into two types, topoisomerase Ⅰ (TopⅠ) and topoisomerase Ⅱ (TopⅡ). They catalyze the breakage and religation of DNA, maintaining the topological changes of DNA and various DNA metabolic processes. Due to their important role in DNA metabolism, the ability to interfere with the functions of Tops or generating Top-mediated DNA damage is an effective strategy for cancer chemotherapy. Tops have been considered as the most important targets for tumor chemotherapy. In this review, we used examples to describe the development of dual topoisomerase Ⅰ and Ⅱ inhibitors.
- topoisomerase Ⅰ,
- topoisomerase Ⅱ,
- dual inhibitors,
- anticancer drugs

References

[1]	Wall ME, Wani MC, Cook CE, et al. Plant antitumor agents Ⅰ. The isolation and structure of camptothecin, a noveⅠ alkaloidal leukemia and tumor inhibitor from camptotheca acuminata1,2[J]. J Am Chem Soc, 1966, 88(16): 3888-3890.
[2]	Hsiang YH, Hertzberg R, Hecht S, et al. Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase Ⅰ[J]. J Biol Chem, 1985, 260(27): 14873-14878.
[3]	Dallavalle S, Gattinoni S, Mazzini S, et al. Synthesis and cytotoxic activity of a new series of topoisomerase Ⅰ inhibitors[J]. Bioorg Med Chem Lett, 2008, 18(4): 1484-1489.
[4]	Kruczynski A, Barret JM, Van Hille B, et al. Decreased nucleotide excision repair activity and alterations of topoisomerase Ⅱ alpha are associated with the in vivo resistance of a P388 leukemia subline to F11782, a novel catalytic inhibitor of topoisomerases Ⅰ and Ⅱ[J]. Clin Cancer Res, 2004, 10(9): 3156(3168.
[5]	Kluza J, Mazinghien R, Irwin H, et al. Relationships between DNA strand breakage and apoptotic progression upon treatment of HL(60 leukemia cells with tafluposide or etoposide[J]. Anticancer Drugs, 2006, 17(2): 155(164.
[6]	Mucci(LoRusso P, Polin L, Bissery MC, et al. Activity of batracylin (NSC-320846) against solid tumors of mice[J]. Invest New Drugs, 1989, 7(4): 295-306.
[7]	Plowman J, Paull KD, Atassi G, et al. Preclinical antitumor activity of batracylin (NSC 320846)[J]. Invest New Drugs, 1988, 6(3): 147-153.
[8]	Rao VA, Agama K, Holbeck S, et al. Batracylin (NSC 320846), a dual inhibitor of DNA topoisomerases Ⅰ and Ⅱ induces histone gamma-H2AX as a biomarker of DNA damage[J]. Cancer Res, 2007, 67(20): 9971-9979.
[9]	Lewis LJ, Mistry P,Charlton PA,et al. Mode of action of the novel phenazine anticancer agents XR11576 and XR5944. Anticancer Drugs 2007, 18, 139-48.
[10]	de Jonge MJ, Kaye S, Verweij J, et al. Phase I and pharmacokinetic study of XR11576, an oral topoisomerase Ⅰ and Ⅱ inhibitor, administered on days 1-5 of a 3-weekly cycle in patients with advanced solid tumours[J]. Br J Cancer, 2004, 91(8): 1459-1465.
[11]	Verborg W, Thomas H, Bissett D, et al. First-into-man phase Ⅰ and pharmacokinetic study of XR5944.14, a novel agent with a unique mechanism of action[J]. Br J Cancer, 2007, 97(7): 844-850.
[12]	Montaner B, Castillo-Avila W, Martinell M, et al. DNA interaction and dual topoisomerase Ⅰ and Ⅱ inhibition properties of the anti-tumor drug prodigiosin[J]. Toxicol Sci, 2005, 85(2): 870-879.
[13]	Montaner B, Navarro S, Pique M, et al. Prodigiosin from the supernatant of Serratia marcescens induces apoptosis in haematopoietic cancer cell lines[J]. Br J Pharmacol, 2000, 131(3): 585-593.
[14]	Montaner B, Perez-Tomas R. Prodigiosin-induced apoptosis in human colon cancer cells[J]. Life Sci, 2001, 68(17): 2025-2036.
[15]	Lin JK. Molecular targets of curcumin[J]. Adv Exp Med Biol, 2007, 595: 227-243.
[16]	Lopez-Lazaro M, Willmore E, Jobson A, et al. Curcumin induces high levels of topoisomerase Ⅰ-and Ⅱ-DNA complexes in K562 leukemia cells[J]. J Nat Prod, 2007, 70(12): 1884-1888.
[17]	Dhandapani KM, Mahesh VB,Brann DW. Curcumin suppresses growth and chemoresistance of human glioblastoma cells via AP-Ⅰ and NF kappaB transcription factors[J]. J Neurochem, 2007, 102(2): 522-538.
[18]	Chih LL,Jen KL. Curcumin: a potential cancer chemopreventive agent through suppressing NF-κB signaling[J]. J Cancer Mol, 2008, 4(1): 11-16.
[19]	Choi JY, Seo CS, Zheng MS, et al. Topoisomerase Ⅰ and Ⅱ inhibitory constituents from the bark of Tilia amurensis[J]. Arch Pharm Res, 2008, 31(11): 1413-1418.
[20]	Ishiyama D, Kanai Y, Senda H, et al. Novel human topoisomerase Ⅰ inhibitors, topopyrones A, B, C and D. Ⅱ. Structure elucidation[J]. J Antibiot (Tokyo), 2000, 53(9): 873-878.
[21]	Kanai Y,Ishiyama D,Senda H,et al. Novel human topoisomerase Ⅰ inhibitors, topopyrones A, B, C and D. Ⅰ. Producing strain, fermentation, isolation, physico-chemical properties and biological activity. J Antibiot (Tokyo) 2000, 53, 863-72.
[22]	Khan QA, Elban MA; Hecht SM. The topopyrones poison human DNA topoisomerases Ⅰ and Ⅱ[J]. J Am Chem Soc, 2008, 130(39): 12888-12889.
[23]	Hecht SM, Khan QA, Maini R, et al. Topopyrones: Dual topoisomerase inhibitors. Patent PCT/US2009/050081, 2010.
[24]	López-Lázaro M, Willmore E,Austin CA. The dietary flavonoids myricetin and fisetin act as dual inhibitors of DNA topoisomerases Ⅰ and Ⅱ in cells[J]. Mutat Res, 2010, 696:41-47.
[25]	Demarquay D, Huchet M, Coulomb H, et al. BN80927: A novel homocamptothecin that inhibits proliferation of human tumor cells in vitro and in vivo[J]. Cancer Res, 2004, 64:4942-4949.
[26]	Lavergne O, Demarquay D, Bailly C, et al. Topoisomerase Ⅰ-mediated antiproliferative activity of enantiomerically pure fluorinated homocamptothecins[J]. J Med Chem, 2000, 43(11): 2285-2289.
[27]	Taniguchi K, Kohno K, Kawanami K, et al. Drug-induced down-regulation of topoisomerase Ⅰ in human epidermoid cancer cells resistant to saintopin and camptothecins[J]. Cancer Res, 1996, 56(10): 2348-2354.
[28]	Basnet A, Thapa P, Karki R, et al. 2,4,6-Trisubstituted pyridines: synthesis, topoisomerase Ⅰ and Ⅱ inhibitory activity, cytotoxicity, and structure-activity relationship[J]. Bioorg Med Chem, 2007, 15(13): 4351-4359.
[29]	Dalla Via L, Magno SM, Gia O, et al. Benzothiopyranoindole-based antiproliferative agents: synthesis, cytotoxicity, nucleic acids interaction, and topoisomerases inhibition properties[J]. J Med Chem, 2009, 52(17): 5429-5441.

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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

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Research progress of dual topoisomerase Ⅰ and Ⅱ inhibitors

Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2013-10-15

Rev Recd Date: 2014-02-19

Key words:

Abstract: DNA topoisomerases (Tops) are essential enzymes that regulate the cellular processes such as replication, transcription, recombination and repair. DNA Tops can be classified into two types, topoisomerase Ⅰ (TopⅠ) and topoisomerase Ⅱ (TopⅡ). They catalyze the breakage and religation of DNA, maintaining the topological changes of DNA and various DNA metabolic processes. Due to their important role in DNA metabolism, the ability to interfere with the functions of Tops or generating Top-mediated DNA damage is an effective strategy for cancer chemotherapy. Tops have been considered as the most important targets for tumor chemotherapy. In this review, we used examples to describe the development of dual topoisomerase Ⅰ and Ⅱ inhibitors.

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Reference (29)

[1]	Wall ME, Wani MC, Cook CE, et al. Plant antitumor agents Ⅰ. The isolation and structure of camptothecin, a noveⅠ alkaloidal leukemia and tumor inhibitor from camptotheca acuminata1,2[J]. J Am Chem Soc, 1966, 88(16): 3888-3890.
[2]	Hsiang YH, Hertzberg R, Hecht S, et al. Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase Ⅰ[J]. J Biol Chem, 1985, 260(27): 14873-14878.
[3]	Dallavalle S, Gattinoni S, Mazzini S, et al. Synthesis and cytotoxic activity of a new series of topoisomerase Ⅰ inhibitors[J]. Bioorg Med Chem Lett, 2008, 18(4): 1484-1489.
[4]	Kruczynski A, Barret JM, Van Hille B, et al. Decreased nucleotide excision repair activity and alterations of topoisomerase Ⅱ alpha are associated with the in vivo resistance of a P388 leukemia subline to F11782, a novel catalytic inhibitor of topoisomerases Ⅰ and Ⅱ[J]. Clin Cancer Res, 2004, 10(9): 3156(3168.
[5]	Kluza J, Mazinghien R, Irwin H, et al. Relationships between DNA strand breakage and apoptotic progression upon treatment of HL(60 leukemia cells with tafluposide or etoposide[J]. Anticancer Drugs, 2006, 17(2): 155(164.
[6]	Mucci(LoRusso P, Polin L, Bissery MC, et al. Activity of batracylin (NSC-320846) against solid tumors of mice[J]. Invest New Drugs, 1989, 7(4): 295-306.
[7]	Plowman J, Paull KD, Atassi G, et al. Preclinical antitumor activity of batracylin (NSC 320846)[J]. Invest New Drugs, 1988, 6(3): 147-153.
[8]	Rao VA, Agama K, Holbeck S, et al. Batracylin (NSC 320846), a dual inhibitor of DNA topoisomerases Ⅰ and Ⅱ induces histone gamma-H2AX as a biomarker of DNA damage[J]. Cancer Res, 2007, 67(20): 9971-9979.
[9]	Lewis LJ, Mistry P,Charlton PA,et al. Mode of action of the novel phenazine anticancer agents XR11576 and XR5944. Anticancer Drugs 2007, 18, 139-48.
[10]	de Jonge MJ, Kaye S, Verweij J, et al. Phase I and pharmacokinetic study of XR11576, an oral topoisomerase Ⅰ and Ⅱ inhibitor, administered on days 1-5 of a 3-weekly cycle in patients with advanced solid tumours[J]. Br J Cancer, 2004, 91(8): 1459-1465.
[11]	Verborg W, Thomas H, Bissett D, et al. First-into-man phase Ⅰ and pharmacokinetic study of XR5944.14, a novel agent with a unique mechanism of action[J]. Br J Cancer, 2007, 97(7): 844-850.
[12]	Montaner B, Castillo-Avila W, Martinell M, et al. DNA interaction and dual topoisomerase Ⅰ and Ⅱ inhibition properties of the anti-tumor drug prodigiosin[J]. Toxicol Sci, 2005, 85(2): 870-879.
[13]	Montaner B, Navarro S, Pique M, et al. Prodigiosin from the supernatant of Serratia marcescens induces apoptosis in haematopoietic cancer cell lines[J]. Br J Pharmacol, 2000, 131(3): 585-593.
[14]	Montaner B, Perez-Tomas R. Prodigiosin-induced apoptosis in human colon cancer cells[J]. Life Sci, 2001, 68(17): 2025-2036.
[15]	Lin JK. Molecular targets of curcumin[J]. Adv Exp Med Biol, 2007, 595: 227-243.
[16]	Lopez-Lazaro M, Willmore E, Jobson A, et al. Curcumin induces high levels of topoisomerase Ⅰ-and Ⅱ-DNA complexes in K562 leukemia cells[J]. J Nat Prod, 2007, 70(12): 1884-1888.
[17]	Dhandapani KM, Mahesh VB,Brann DW. Curcumin suppresses growth and chemoresistance of human glioblastoma cells via AP-Ⅰ and NF kappaB transcription factors[J]. J Neurochem, 2007, 102(2): 522-538.
[18]	Chih LL,Jen KL. Curcumin: a potential cancer chemopreventive agent through suppressing NF-κB signaling[J]. J Cancer Mol, 2008, 4(1): 11-16.
[19]	Choi JY, Seo CS, Zheng MS, et al. Topoisomerase Ⅰ and Ⅱ inhibitory constituents from the bark of Tilia amurensis[J]. Arch Pharm Res, 2008, 31(11): 1413-1418.
[20]	Ishiyama D, Kanai Y, Senda H, et al. Novel human topoisomerase Ⅰ inhibitors, topopyrones A, B, C and D. Ⅱ. Structure elucidation[J]. J Antibiot (Tokyo), 2000, 53(9): 873-878.
[21]	Kanai Y,Ishiyama D,Senda H,et al. Novel human topoisomerase Ⅰ inhibitors, topopyrones A, B, C and D. Ⅰ. Producing strain, fermentation, isolation, physico-chemical properties and biological activity. J Antibiot (Tokyo) 2000, 53, 863-72.
[22]	Khan QA, Elban MA; Hecht SM. The topopyrones poison human DNA topoisomerases Ⅰ and Ⅱ[J]. J Am Chem Soc, 2008, 130(39): 12888-12889.
[23]	Hecht SM, Khan QA, Maini R, et al. Topopyrones: Dual topoisomerase inhibitors. Patent PCT/US2009/050081, 2010.
[24]	López-Lázaro M, Willmore E,Austin CA. The dietary flavonoids myricetin and fisetin act as dual inhibitors of DNA topoisomerases Ⅰ and Ⅱ in cells[J]. Mutat Res, 2010, 696:41-47.
[25]	Demarquay D, Huchet M, Coulomb H, et al. BN80927: A novel homocamptothecin that inhibits proliferation of human tumor cells in vitro and in vivo[J]. Cancer Res, 2004, 64:4942-4949.
[26]	Lavergne O, Demarquay D, Bailly C, et al. Topoisomerase Ⅰ-mediated antiproliferative activity of enantiomerically pure fluorinated homocamptothecins[J]. J Med Chem, 2000, 43(11): 2285-2289.
[27]	Taniguchi K, Kohno K, Kawanami K, et al. Drug-induced down-regulation of topoisomerase Ⅰ in human epidermoid cancer cells resistant to saintopin and camptothecins[J]. Cancer Res, 1996, 56(10): 2348-2354.
[28]	Basnet A, Thapa P, Karki R, et al. 2,4,6-Trisubstituted pyridines: synthesis, topoisomerase Ⅰ and Ⅱ inhibitory activity, cytotoxicity, and structure-activity relationship[J]. Bioorg Med Chem, 2007, 15(13): 4351-4359.
[29]	Dalla Via L, Magno SM, Gia O, et al. Benzothiopyranoindole-based antiproliferative agents: synthesis, cytotoxicity, nucleic acids interaction, and topoisomerases inhibition properties[J]. J Med Chem, 2009, 52(17): 5429-5441.

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Research progress of dual topoisomerase Ⅰ and Ⅱ inhibitors

doi: 10.3969/j.issn.1006-0111.2015.04.004

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通讯作者: 陈斌, bchen63@163.com

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