Topoisomerase I and II inhibitors: Chemical structure, mechanisms of action and role in cancer chemotherapy

Russian Chemical Reviews

Volumn 83, Issue 1, 2014, Pages 82-94

  Dezhenkova, L G ^a   Tsvetkov, V B ^b,c   Shtil, A A ^d  

^a GAUSE INSTITUTE OF NEW ANTIBIOTICS   (Russian Federation)

^b TOPCHIEV INSTITUTE OF PETROCHEMICAL SYNTHESIS   (Russian Federation)

^c INSTITUTE OF BIOMEDICAL CHEMISTRY   (Russian Federation)

^d N N BLOKHIN RUSSIAN CANCER RESEARCH CENTER   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84893244792     PISSN: 0036021X     EISSN: 14684837     Source Type: Journal    
DOI: 10.1070/RC2014v083n01ABEH004363     Document Type: Review

References (127)

1. T-K Li, L F Liu Annu. Rev. Pharmacol. Toxicol. 40 53 (2001)
2. E A Yakubovskaya, A G Gabibov Mol. Biol. (Moscow) 33 318 (1999) [Mol. Biol. 33 368 (1999)]
3. D V Bugreev, G A Nevinsky Biochemistry (Moscow) 74 1467 (2009) [Usp. Biol. Khim. 49 129 (2009)]
4. Y Pommier, P Pourquier, Y Fan, D Strumberg Biochim. Biophys. Acta: Gene Struct. Express. 1400 83 (1998)
5. D V Bugreev, V N Buneva, G A Nevinsky Mol. Biol. (Moscow) 37 281 (2003) [Mol. Biol. 37 325 (2003)]
6. J Robert, A K Larsen Biochimie 80 247 (1998)
7. C Conti, J A Seiler, Y Pommier Cell Cycle 6 2760 (2007)
8. A K Larsen, A E Escargeuil, A Skladanowski Prog. Cell Cycle Res. 5 295 (2003)
9. A K Larsen, A E Escargueil, A Skladanowski Pharmacol. Ther. 99 167 (2003)
10. R Garcia-Carbonero, J G Supko Clin. Cancer Res. 8 641 (2002)
11. L-h Meng, Z-y Liao, Y Pommier Curr. Top. Med. Chem. 3 305 (2003)
12. W A Denny Expert Opin. Emerg. Drugs 9 105 (2004)
13. K Cheng,N J Rahier, B M Eisenhauer,R Gao, S J Thomas, S M Hecht J. Am. Chem. Soc. 127 838 (2005)
14. C J Thomas, N J Rahier, S M Hecht Bioorg. Med. Chem. 12 1585 (2004)
15. C Bailly Methods Enzymol. 340 610 (2001)
16. Y Pommier, J Cherfils Trends Pharmacol. Sci. 26 138 (2005)
17. Y Pommier Chem. Rev. 109 2894 (2009)
18. Y Pommier ACS Chem. Biol. 18 82 (2013)
19. S L Grokhovsky, S A Strel'tsov, A L Zhuze Mol. Biol. (Moscow) 37 888 (2003) [Mol. Biol. 37 1045 (2003)]
20. Q-Y Li, Y-G Zu, R-Z Shi, L-P Yao Curr. Med. Chem. 13 2021 (2006)
21. B L Staker,KHjerrild,MDFreese, CABehnke, A B Burgin, L Steward Jr Proc. Natl. Acad. Sci. USA 99 15387 (2002)
22. SAStrel'tsov, S L Grokhovskii, IAKudelina,V A Oleinikov, A L Zhuze Mol. Biol. (Moscow) 35 365 (2001) [Mol. Biol. 35 432 (2001)]
23. S A Strel'tsov, A L Mikheikin, Yu D Nechipurenko Mol. Biol. (Moscow) 35 374 (2001) [Mol. Biol. 35 442 (2001)]
24. S Streltsov, A Sukhanova, A Mikheikin, S Grokhovsky, A Zhuze, I Kudelina, K Mochalov, V Oleinikov, J-C Jardillier, I Nabiev J. Phys. Chem. B 105 9643 (2001)
25. S A Strel'tsov, A L Mikheikin, S L Grokhovsky, V A Oleinikov, A L Zhuze Mol. Biol. (Moscow) 36 400 (2002) [Mol. Biol. 36 511 (2002)]
26. D S Thakur Int. J. Pharm. Sci. Nanotechnol. 3 1173 (2011)
27. S L Pitts,MJ Jablonksy,MDuca,D Dauzonne, C Monneret, P B Arimondo, C Anklin, D E Graves, N Osheroff Biochemistry 50 5058 (2011)
28. C J Li, L Averboukh, A B Pardee J. Biol. Chem. 268 22463 (1993)
29. M Chen,W T Beck Cancer Res. 53 5946 (1993)
30. N A Gormley, G Orphanides, A Meyer, P M Cullis, A Maxwell Biochemistry 35 5083 (1996)
31. G Rappa, A Lorico, A C Sartorelli Cancer Res. 53 5487 (1993)
32. N Hajji, S Mateos, N Pastor, I Dominguez, F Cortes Mutation Res. 583 26 (2005)
33. V A Rao, K Agama, S Holbeck, Y Pommier Cancer Res. 67 9971 (2007)
34. B L Staker, M D Freese,M Cushman, Y Pommier, D Zembower, L Stewart, A B Burgin J. Med. Chem. 48 2336 (2005)
35. T S Dexheimer, Y Pommier Nat. Protocols 3 1736 (2008)
36. Y-C Tse-Dinh Infect. Disord. - Drug Targets 3 3 (2007)
37. MA Cinelli, A Morrell, T S Dexheimer, E S Scher, Y Pommier,M Cushman J. Med. Chem. 51 4609 (2008)
38. B H Long,W C Rose, D M Vyas, J A Matson, S Forenza Curr. Med. Chem.: Anticancer Agents 2 255 (2002)
39. G Zhang, J Shen, H Cheng, L Zhu, L Fang, S Luo, M T Muller, G E Lee, L Wei, Y Du, D Sun, P G Wang J. Med. Chem. 48 2600 (2005)
40. M Prudhomme Curr. Med. Chem. 7 1189 (2000)
41. P Moreau, N Gaillard, C Marminon, F Anizon, N Dias, B Baldeyrou, C Bailly, A Pierre, J Hickman, B Pfeiffer, P Renard,M Prudhomme Bioorg. Med. Chem. 11 4871 (2003)
42. Y Yamashita, N Fujii, C Murakata, T Ashizawa, M Okabe, H Nakano Biochemistry 31 12069 (1992)
43. E A Kohn, N D Ruth, M K Brown,M Livingstone, A Eastman J. Biol. Chem. 277 26553 (2002)
44. E A Sausville, S G Arbuck, R Messmann, D Headlee, K S Bauer, R M Lush, A Murgo,W D Figg, T Lahusen, S Jaken, X-x Jing,M Roberge, E Fuse, T Kuwabara, A M Senderowicz J. Clin. Oncol. 19 2319 (2001)
45. M Cushman, L Cheng J. Org. Chem. 43 3781 (1978)
46. G Kohlhagen, K D Paull, MCushman, P Nagafuji, Y Pommier Mol. Pharmacol. 54 50 (1998)
47. K E Peterson,M A Cinelli, A E Morrell, A Mehta, T S Dexheimer, K Agama, S Antony, Y Pommier, M Cushman J. Med. Chem. 54 4937 (2011).
48. E Kiselev, S DeGuire,A Morrell,K Agama, T S Dexheimer, Y Pommier,M Cushman J. Med. Chem. 54 6106 (2011)
49. DStrumberg,YPommier,KPaull,MJayaraman, P Nagafuji, M Cushman J. Med. Chem. 42 446 (1999)
50. NWu, X-W Wu,KAgama,YPommier, J Du,D Li, L-Q Gu, Z-S Huang, L-K An Biochemistry 49 10131 (2010)
51. P S Kingma, N Osherff Biochem. Biophys. Acta 1400 223 (1998)
52. P Pourquier, L M Vend, J Fertala, D Wang, H J Park, J M Essigmann,M A Bjornsti, Y Pommier J. Biol. Chem. 274 8516 (1999)
53. M Esselen, U Boettler, N Teller, S Bachler,M Hutter, E Rufer, S Skrbek, D Marco J. Agric. Food Chem. 59 6966 (2011)
54. S Neidle Curr. Opin. Struct. Biol. 19 239 (2009)
55. S M Haider, S Neidle Biochimie 93 1239 (2011)
56. D N Kaluzhny, V V Tatarskiy Jr, L G Dezhenkova, I L Plikhtyak, T D Miniker, A K Shchyolkina, S A Strel'tsov, G G Chilov, F N Novikov, I Yu Kubasova, Z S Smirnova, S Ya Mel'nik, M A Livshits, O F Borisova, A A Shtil ChemMedChem 4 1641 (2009)
57. D N Kaluzhny, A K Shchyolkina, N S Ilyinsky, O F Borisova, A A Shtil J. Nucleic Acids Article ID 184735 (2011)
58. N Fujii, Y Yamashita, T Mizukami, H Nakano Mol. Pharmacol. 51 269 (1997)
59. Y Yamashita, S Kawada, N Fujii, H Nakano Biochemistry 30 5838 (1991).
60. T Syrovets, B Buchele, E Gedig, J R Slupsky, T Simmet Mol. Pharmacol. 58 71 (2000)
61. W A Denny, B C Baquley Curr. Top. Med. Chem. 3 339 (2003)
62. X Pan, J M Hartley, J A Hartley, K N White, Z Wang, S W Bligh Phytomedicine 19 618 (2012)
63. S Kennedy, J C DiCesare, R J Sheaff Biochem. Biophys. Res. Commun. 408 94 (2011)
64. L G Dezhenkova, O Y Susova, A E Shchekotikhin, M N Preobrazhenskaya, A A Shtil Bull. Exp. Biol. Med. 145 334 (2008) [Byull. Eksperim. Biol. Med. 145 304 (2008)]
65. A E Shchekotikhin, L G Dezhenkova, O Y Susova, V AGlazunova,YNLuzikov,Y B Sinkevich,V N Buyanov, A A Shtil,M N Preobrazhenskaya Bioorg. Med. Chem. 15 2651 (2007)
66. A E Shchekotikhin, L G Dezhenkova, O Y Susova, V A Glazunova, A A Shtil,M N Preobrazhenskaya, H-S Huang Ann. Oncol. 19 iii28 (2008)
67. A E Shchekotikhin, V A Glazunova, L G Dezhenkova, E K Shevtsova, V F Traven, J Balzarini, H-S Huang, A A Shtil,M N Preobrazhenskaya Eur. J. Med. Chem. 46 423 (2011)
68. Ch Zimmer Prog. Nucleic Acid Res. Mol. Biol. 15 285 (1975)
69. Ch Zimmer, U Wahnert Prog. Biophys. Mol. Biol. 47 31 (1986)
70. P D Foglesong, C Reckord, S Swink Cancer Chemother. Pharmacol. 30 123 (1992)
71. D K Trask, M T Muller Proc. Natl. Acad. Sci. USA 85 1417 (1998)
72. J L Nitiss, P Pourquier, Y Pommier Cancer Res. 57 4564 (1997)
73. D J Bridewell, G J Finlay, B C Baguley Oncol. Res. 9 535 (1997)
74. KKik,KStudzian,MWasowska-Lukawska, I Oszczapowicz, L Szmigiero Acta Biochim. Pol. 56 135 (2009)
75. D Dal Ben, M Palumbo, G Zagotto, G Capranico, S Moro Curr. Pharm. Des. 13 2766 (2007)
76. K Wassermann, J Markovits, C Jaxel, G Capranico, K W Kohn, Y Pommier Mol. Pharmacol. 38 38 (1990)
77. L G Dezhenkova, A N Tevyashova, E N Olsuf'eva, I D Treshchalin, A A Shtil,M N Preobrazhenskaya Russ. J. Bioorg. Chem. 34 387 (2008) [Bioorg. Khim. 34 430 (2008)]
78. S Banerji,M Los Cancer Biol. Ther. 5 965 (2006)
79. A Y Chen, C Yu, B Gatto, L F Liu Proc. Natl. Acad. Sci. USA 90 8131 (1993)
80. U Pindur,M Jansen, T Lemster Curr. Med. Chem. 12 2805 (2005)
81. A Gabibov, E Yakubovskaya, M Lukin, P Favorov, A Reshetnyak,M Monastyrsky FEBS J. 272 6336 (2005)
82. D Kaluzhny, N Ilyinsky, A Shchekotikhin, Yu Sinkevich, P Tsvetkov, V Tsvetkov, A Veselovsky, MLivshits, O Borisova, A Shtil, A Shchyolkina PLoS One 6 e27151 (2011)
83. D V Kolesnikova, A L Zhuze, A S Zasedatelev DNK-Spetsifichnye Nizkomolekulyarnye Soedineniya (DNA-specific Low-molecular-weight Compounds) (Moscow: Moscow Institute of Physics and Technology, 1998)
84. A S Zasedatelev, A L Zhuze, K Tsimmer, S L Grokhovskii, V G Tumanyan, G V Gurskii, B P Gottikh Dokl. Akad. Nauk SSSR 231 1006 (1976
85. ASukhanova, S Grokhovsky, AZhuze,D Roper, I Bronstein Biochem. Mol. Biol. Int. 44 997 (1998)
86. A Sukhanova, S Grokhovsky,M Ermishov, K Mochalov, A Zhuze, V Oleinikov, I Nabiev Biochem. Pharmacol. 64 79 (2002)
87. A Sukhanova, S Grokhovsky, A Zhuze, J Devy,M Pluot, V Oleinikov, I Nabiev Anticancer Res. 23 2609 (2003)
88. T A Beerman, M M McHugh, R Sigmund, J W Lown, K E Rao, Y Bathini Biochim. Biophys. Acta: Gene Struct. Express. 1131 53 (1992)
89. Q Sun, B Gatto, Ch Yu, L F Liu, E J LaVoie J. Med. Chem. 38 3638 (1995)
90. M-H Hou, W-J Lu, H-Y Lin, J-M P Yuann Biochemistry 47 5493 (2008)
91. A N Tevyashova, E N Olsufyeva, J Balzarini, A A Shtil, L G Dezhenkova, V M Bukhman, V B Zbarsky, M N Preobrazhenskaya J. Antibiotics 62 37 (2009)
92. I B Cheglakov, A N Tevyashova, L K Kurbatov, V V Tatarsky Jr, A V Samusenko, M N Preobrazhenskaya, A A Shtil Dokl. Biochem. Biophys. 435 320 (2010) [Dokl. Akad. Nauk 435 554 (2010)]
93. VKh Brikenshtein, L R Pitina,GMBarenboim,G V Gurskii Mol. Biol. 18 1606 (1984
94. F Lombo , N Menendez, J A Salas, C Mendez Appl. Microbiol. Biotechnol. 73 1 (2006)
95. V S Simonova, A V Samusenko, N A Filippova, A N Tevyashova, L S Lyniv, G I Kulik, V F Chekhun, A A Shtil Bull. Exp. Biol. Med. 139 455 (2005) [Byull. Eksp. Biol. Med. 139 451 (2005)]
96. W Behr, K Honikel, G Hartmann Eur. J. Biochem. 9 82 (1969)
97. T Hayasaka, Y Inoue Biochemistry 8 2342 (1969)
98. L G Dezhenkova, Candidate Thesis in Chemical Sciences, G F Gause Institute of New Antibiotics, Russian Academy of Medical Sciences, Moscow, 2008
99. C Bailly, J-F Riou, P Colson, C Houssier, E Rodrigues-Pereira, M Prudhomme Biochemistry 36 3917 (1997)
100. K Bandyopadhyay, R A Gjerset Biochemistry 50 704 (2011)
101. A A Terentiev, N T Moldogazieva, K V Shaitan Biochemistry (Moscow) 74 1586 (2009) [Usp. Biol. Khim. 49 429 (2009)]
102. Y Fan, J N Weinstein, K W Kohn, L M Shi, Y Pommier J. Med. Chem. 41 2216 (1998)
103. F N Novikov, V S Stroylov, A A Zeifman, O V Stroganov, V Kulkov, G G Chilov J. Comput.-Aided Mol. Des. 26 725 (2012)
104. A A Zeifman, V S Stroylov, F N Novikov, O V Stroganov, A L Zakharenko, S N Khodyreva, O I Lavrik, G G Chilov J. Mol. Model. 18 2553 (2012)
105. O V Stroganov, F N Novikov, A A Zeifman, V S Stroylov, G G Chilov Proteins: Struct., Funct., Bioinform. 79 2693 (2011)
106. F N Novikov, A A Zeifman, O V Stroganov, V S Stroylov, V Kulkov, G G Chilov J. Chem. Inform. Model. 51 2090 (2011)
107. A Yu Sukhorukov, S A Andryushkevich, G G Chilov, A A Zeifman, I V Svitanko, S L Ioffe Mendeleev Commun. 21 183 (2011)
108. LVRomashov,AAZeifman,AL Zakharenko, FNNovikov, V S Stroilov, O V Stroganov, G G Chilov, S N Khodyreva, O I Lavrik, I Yu Titov, I V Svitan'ko Mendeleev Commun. 22 15 (2012)
109. OAKovaleva,VB Tsvetkov,AKShchyolkina,OF Borisova, V A Ol'shevskaya, A V Makarenkov, A S Semeikin, A A Shtil, D N Kaluzhny Eur. Biophys. J. 41 723 (2012)
110. G S Laco PLoS One 6 e24314 (2011)
111. J Koska, V Z Spassov, A J Maynard, L Yan, N Austin, P K Flook, C M Venkatachalam J. Chem. Inform. Model. 48 1965 (2008)
112. D S Goodsell, G M Morris, A J Olson J. Mol. Recognit. 9 1 (1996)
113. G M Morris, D S Goodsell, R S Halliday, R Huey, W E Hart, R K Belew, A J Olson J. Comput. Chem. 19 1639 (1998)
114. A Lauria,M Ippolito, A M Almerico J. Mol. Model. 13 393 (2007)
115. O Vassallo, S Castelli, A Biswas, S Sengupta, P K Das, I D'Annessa, F Oteri, ALeoni, P Tagliatesta,HKMajumder, A Desideri Open Antimicrob. Agents J. 3 23 (2011)
116. A Nematollahi, N Aminimoghadamfarouj, C Wiart Int. J. ChemTech Res. 3 1622 (2011)
117. GMMorris, RHuey,WLindstrom,MF Sanner,R K Belew, D S Goodsell, A J Olson J. Comput. Chem. 30 2785 (2009)
118. D S Goodsell, A J Olson Proteins: Struct., Funct., Bioinform. 8 195 (1990)
119. V Kettmann, D Kost'a lova, H D Holtje J. Comput.-Aided Mol. Des. 18 785 (2004)
120. M Totrov, R Abagyan Proteins: Struct., Funct., Bioinform. 29 (Suppl. 1) 215 (1997)
121. G M El Taliawi, E I Ali, G H Hegazy, N S M Ismail, W Ramadan J. Am. Sci. 6 (11) 148 (2010)
122. C Tesauro, P Fiorani, I D'Annessa, G Chillemi, G Turchi, A Desideri Biochem. J. 425 531 (2010)
123. D van der Spoel, E Lindahl, B Hess, G Groenhof, A E Mark, H J C Berendsen J. Comput. Chem. 26 1701 (2005)
124. G Mancini, I D'Annessa, A Coletta, N Sanna, G Chillemi, A Desideri PLoS One 5 e10934 (2010)
125. R Clark, F Deane, N Anthony, B Johnston, F McCarthy, S Mackay Bioorg. Med. Chem. 15 4741 (2007)
126. N G Anthony, G Huchet, B F Johnston, B F Parkinson, C J Suckling, R D Waigh, S P Mackay J. Chem. Inform. Model. 45 1896 (2005)
127. D Winkler Bioorg. Med. Chem. 19 1450 (2011)