Design, modeling, synthesis and biological activity evaluation of camptothecin-linked platinum anticancer agents

European Journal of Medicinal Chemistry

Volumn 63, Issue , 2013, Pages 387-400

  Cincinelli, Raffaella ^a   Musso, Loana ^a   Dallavalle, Sabrina ^a   Artali, Roberto ^b   Tinelli, Stella ^c   Colangelo, Donato ^d   Zunino, Franco ^c   De Cesare, Michelandrea ^c   Beretta, Giovanni Luca ^c   Zaffaroni, Nadia ^c  

^a UNIVERSITY OF MILAN   (Italy)

^b Scientia Advice   (Italy)

^c NATIONAL CANCER INSTITUTE   (Italy)

^d UNIVERSITY OF EASTERN PIEDMONT   (Italy)

Author keywords

Antitumor compounds; Camptothecin; Diaminedichloro platinum (II); Docking

Indexed keywords

2,3 D,L DIAMONIUMTRIFLUOROACETATE N [2' (CAMPTOTHECIN 7 METHYLENEAMINOOXY)ETHYL]PROPIONAMIDE; 7 (6 AMINOHEXYLOXYIMINOMETHYL)CAMPTOTHECIN; [2 TERT BUTOXYCARBONYLAMINO 1 [2' (CAMPTOTHECIN 7 YLMETHYLENEAMINOOXY)ETHYLCARBAMOYL]ETHYL]CARBAMIC ACID TERT BUTYL ESTER; [6 (1,3 DIOXO 1,3 DIHYDRO ISOINDOL 2 YLOXY)HEXYL]CARBAMIC ACID TERT BUTYL ESTER; CAMPTOTHECIN DERIVATIVE; CISPLATIN; DICHLORO[2,3 D,L DIAMINO N [2' (CAMPTOTHECIN 7 YLMETHYLENEAMINOOXY)ETHYL]PROPIONAMIDE]PLATINUM; DICHLORO[2,3 D,L DIAMINO N [2' (CAMPTOTHECIN 7 YLMETHYLENEAMINOOXY)HEXYL]PROPIONAMIDE]PLATINUM; DNA; DNA TOPOISOMERASE; FIRTECAN; IRINOTECAN; O (6 AMINOHEXYL)HYDROXYLAMINE DIHYDROCHLORIDE; PLATINUM DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANCER RESISTANCE; CONTROLLED STUDY; CYTOTOXICITY; DNA ADDUCT; DNA DAMAGE; DRUG ACTIVITY; DRUG DESIGN; DRUG SYNTHESIS; DRUG TOLERABILITY; DRUG UPTAKE; HUMAN; HUMAN CELL; MOLECULAR MODEL; MOUSE; NONHUMAN; OSTEOSARCOMA; SACCHAROMYCES CEREVISIAE; TUMOR XENOGRAFT;

ANIMALS; ANTINEOPLASTIC AGENTS; CAMPTOTHECIN; CELL LINE, TUMOR; CELL SURVIVAL; DNA TOPOISOMERASES, TYPE I; DRUG DESIGN; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HUMANS; INHIBITORY CONCENTRATION 50; MICE; MICE, NUDE; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; ORGANOPLATINUM COMPOUNDS; PLATINUM; PROTEIN BINDING; PROTEIN STRUCTURE, TERTIARY; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84875007757     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.02.022     Document Type: Article

References (61)

1. B. Rosenberg, L. Van Camp, J.E. Trosko, and V. Mansour Platinum compounds: a new class of potent antitumour agents Nature 222 1969 385 386
2. L.R. Kendall, and N.P. Farrell Platinum-based Drugs in Cancer Therapy 2000 Humana Press Totowa, NJ
3. U. Olszewski, and G. Hamilton A better platinum-based anticancer drug yet to come? Anti-Cancer Agents Med. Chem. 10 2010 293 301
4. J. Zhang, L. Wang, Z. Xing, D. Liu, J. Sun, X. Li, and Y. Zhang Status of bi- and multi-nuclear platinum anticancer drug development Anti-Cancer Agents Med. Chem. 10 2010 272 282
5. R.T. Skeel Antineoplastic drugs and biologic response modifiers: classification, use and toxicity of clinically useful agents R.T. Skeel, Handbook of Cancer Chemotherapy seventh ed. 1999 Lippincott Williams and Wilkins 63 143
6. P.A. Andrews, and S.B. Howell Cellular pharmacology of cisplatin: perspectives on mechanisms of acquired resistance Cancer Cells 2 1990 35 43
7. M.M.K. Shahzad, G. Lopez-Berestein, and A.K. Sood Novel strategies for reversing platinum resistance Drug Resist. Updates 12 2009 148 152
8. J.J. Ju Unlocking the molecular mechanisms of DNA repair and platinum drug resistance in cancer chemotherapy Curr. Drug Ther. 4 2009 19 28
9. K.R. Harrap Initiatives with platinum- and quinazoline-based antitumor molecules-Fourteenth Bruce F. Cain memorial award lecture Cancer Res. 55 1995 2761 2768
10. A.V. Klein, and T.W. Hambley Platinum drug distribution in cancer cells and tumors Chem. Rev. 109 2009 4911 4920
11. H. Niedner, R. Christen, X. Lin, A. Kondo, and S.B. Howell Identification of genes that mediate sensitivity to cisplatin Mol. Pharmacol. 60 2001 1153 1160
12. Y. Nieto DNA-binding agents Cancer Chemother. Biol. Response Modif. 22 2005 163 203
13. R. Guddneppanavar, and U. Bierbach Adenine-N3 in the DNA minor groove-an emerging target for platinum containing anticancer pharmacophores Anti-Cancer Agents Med. Chem. 7 2007 125 138
14. R.P. Feazell, N. Nakayama-Ratchfor, H. Dai, and S.J. Lippard Soluble single-walled carbon nanotubes as longboat delivery systems for platinum(IV) anticancer drug design J. Am. Chem. Soc. 129 2007 8438 8439
15. F. Zunino, G. Pratesi, F. Formelli, and A. Pasini Evaluation of a platinum-doxorubicin complex in experimental tumor systems Invest. New Drugs 8 1990 341 345
16. M.D. Temple, W.D. McFadyen, R.J. Holmes, W.A. Denny, and V. Murray Interaction of cisplatin and DNA-targeted 9-aminoacridine platinum complexes with DNA Biochemistry 39 2000 5593 5599
17. M.D. Temple, P. Recabarren, W.D. McFadyen, R.J. Holmes, W.A. Denny, and V. Murray The interaction of DNA-targeted 9-aminoacridine-4-carboxamide platinum complexes with DNA in intact human cells Biochim. Biophys. Acta 1574 2002 223 230
18. 2(levrazoxane), of the topoisomerase II inhibitors dexrazoxane (ICRF-187) and levrazoxane (ICRF-186) J. Inorg. Biochem. 98 2004 616 624
19. M.S. Robillard, A. Valentijn, P.M. Rob, N.J. Meeuwenoord, G.A. Van der Marel, J.H. Van Boom, and J. Reedijk The first solid-phase synthesis of a peptide-tethered platinum(II) complex Angew. Chem. Int. Ed. 39 2000 3096 3099
20. R.A. Alderden, H.R. Mellor, S. Modok, T.W. Hambley, and R. Callaghan Cytotoxic efficacy of an anthraquinone linked platinum anticancer drug Biochem. Pharmacol. 71 2006 1136 1145
21. D. Gibson, I. Binyamin, M. Haj, I. Ringel, A. Ramu, and J. Katzhendler Anthraquinone intercalators as carrier molecules for second-generation platinum anticancer drugs Eur. J. Med. Chem. 32 1997 823 831
22. S. D'Errico, G. Oliviero, V. Piccialli, J. Amato, N. Borbone, V. D'Atri, F. D'Alessio, R. Di Noto, F. Ruffo, F. Salvatore, and G. Piccialli Solid-phase synthesis and pharmacological evaluation of novel nucleoside-tethered dinuclear platinum(II) complexes Bioorg. Med. Chem. Lett. 21 2011 5835 5838
23. W. Du Towards new anticancer drugs: a decade of advances in synthesis of camptothecins and related alkaloids Tetrahedron 59 2003 8649 8687
24. V.J. Venditto, and E.E. Simanek Cancer therapies utilizing the camptothecins: a review of the in vivo literature Mol. Pharma. 7 2010 307 349
25. Y.H. Hsiang, R. Hertzberg, S.M. Hecht, and L.F. Liu Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I J. Biol. Chem. 260 1985 14873 14878
26. L.F. Liu, S.D. Desai, T.K. Li, Y. Mao, M. Sun, and S.P. Sim Mechanism of action of camptothecin Ann. N. Y. Acad. Sci. 922 2000 1 10
27. Y. Pommier Topoisomerase I inhibitors: camptothecins and beyond Nat. Rev. Cancer 6 2006 789 802
28. E. Andreopoulou, T. Chen, L. Liebes, J. Curtin, S. Blank, R. Wallach, H. Hochster, and F. Muggia Phase 1/pharmacology study of intraperitoneal topotecan alone and with cisplatin: potential for consolidation in ovarian cancer Cancer Chemother. Pharmacol. 68 2011 457 463
29. J.P. van Meerbeeck, D.A. Fennell, and D.K. De Ruysscher Small-cell lung cancer Lancet 378 2011 1741 1755
30. A. Stein, and D. Arnold Oxaliplatin: a review of approved uses Exp. Opin. Pharmacother. 13 2012 125 137
31. S. Dallavalle, L. Merlini, G. Morini, L. Musso, S. Penco, G.L. Beretta, S. Tinelli, and F. Zunino Synthesis and cytotoxic activity of substituted 7-aryliminomethyl derivatives of camptothecin Eur. J. Med. Chem. 2004 507 513
32. S. Dallavalle, A. Ferrari, L. Merlini, S. Penco, N. Carenini, P. Perego, M. De Cesare, G. Pratesi, and F. Zunino Novel cytotoxic 7-iminomethyl and 7-aminomethyl derivatives of camptothecin Bioorg. Med. Chem. Lett. 11 2001 291 294
33. S. Dallavalle, A. Ferrari, B. Biasotti, L. Merlini, S. Penco, G. Gallo, M. Marzi, M.O. Tinti, R. Martinelli, C. Pisano, P. Carminati, N. Carenini, G. Beretta, P. Perego, M. De Cesare, G. Pratesi, and F. Zunino Novel 7-oxyiminomethyl derivatives of camptothecin with potent in vitro and in vivo antitumor activity J. Med. Chem. 44 2001 3264 3274
34. S. Dallavalle, G. Giannini, D. Alloatti, A. Casati, E. Marastoni, L. Musso, L. Merlini, G. Morini, S. Penco, C. Pisano, S. Tinelli, M. De Cesare, G.L. Beretta, and F. Zunino Synthesis and cytotoxic activity of polyamine analogues of camptothecin J. Med. Chem. 49 2006 5177 5186
35. C. Pisano, M. De Cesare, G.L. Beretta, V. Zuco, G. Pratesi, S. Penco, L. Vesci, R. Foderà, F.F. Ferrara, P. Carminati, S. Dallavalle, G. Morini, L. Merlini, A. Orlandi, and F. Zunino Preclinical profile of antitumor activity of a novel hydrophilic camptothecin, ST1968 Mol. Cancer Ther. 7 2008 2051 2059
36. M. De Cesare, G.L. Beretta, S. Tinelli, V. Benedetti, G. Pratesi, S. Penco, S. Dallavalle, L. Merlini, C. Pisano, P. Carminati, and F. Zunino Preclinical efficacy of ST1976, a novel camptothecin analog of the 7-oxyiminomethyl series Biochem. Pharmacol. 73 2007 656 664
37. G.L. Beretta, V. Zuco, M. De Cesare, P. Perego, and N. Zaffaroni Namitecan: a hydrophilic camptothecin with a promising preclinical profile Curr. Med. Chem. 19 2012 3488 3501
38. A.X. Zhu, N. Ready, J.W. Clark, H. Safran, A. Amato, N. Salem, S. Pace, X. He, N. Zvereva, T.J. Lynch, D.P. Ryan, and J.G. Supko Phase I and pharmacokinetic study of gimatecan given orally once a week for 3 of 4 weeks in patients with advanced solid tumors Clin. Cancer Res. 15 2009 374 381
39. S. Pecorelli, I. Ray-Coquard, O. Tredan, N. Colombo, G. Parma, G. Tisi, D. Katsaròs, C. Lhommé, A.A. Lissoni, J.B. Vermorken, A. du Bois, A. Poveda, L. Frigerio, P. Barbieri, P. Carminati, S. Brienza, and J.P. Guastalla Phase II of oral gimatecan in patients with recurrent epithelial ovarian, fallopian tube or peritoneal cancer, previously treated with platinum and taxanes Ann. Oncol. 21 2010 759 765
40. S. Dallavalle, D. Granza Rocchetta, L. Musso, L. Merlini, G. Morini, S. Penco, S. Tinelli, G.L. Beretta, and F. Zunino Synthesis and cytotoxic activity of new 9-substituted camptothecins Bioorg. Med. Chem. Lett. 18 2008 2781 2787
41. B.L. Stayer, M.D. Feese, M. Cushman, Y. Pommier, D. Zembower, L. Stewart, and A.B. Burgin Structures of three classes of anticancer agents bound to the human topoisomerase I-DNA covalent complex J. Med. Chem. 48 2005 2336 2345
42. S. Moradell, J. Lorenzo, and A. Rovira Water-soluble platinum(II) complexes of diamine chelating ligands bearing amino-acid type substituents: the effect of the linked amino acid and the diamine chelate ring size on antitumor activity, and interactions with 50-GMP and DNA J. Inorg. Biochem. 98 2004 1933 1946
43. J. Altman, and M. Wilchek Platinum (II) complexes with diaminopropionic acid as oxygen-bound unidentate, nitrogen-oxygen and nitrogen-nitrogen chelate complexes Inorg. Chim. Acta 101 1985 171 173
44. J. Ma, M. Maliepaard, K. Nooter, A.W. Boersma, J. Verweij, G. Stoter, and J.H. Schellens Synergistic cytotoxicity of cisplatin and topotecan or SN-38 in a panel of eight solid-tumor cell lines in vitro Cancer Chemother. Pharmacol. 41 1998 307 316
45. F. Goldwasser, L. Bozec, N. Zeghari-Squalli, and J.L. Misset Cellular pharmacology of the combination of oxaliplatin with topotecan in the IGROV-1 human ovarian cancer cell line Anticancer Drugs 10 1999 195 201
46. F. Goldwasser, M. Valenti, R. Torres, K.W. Kohn, and Y. Pommier Potentiation of cisplatin cytotoxicity by 9-aminocamptothecin Clin. Cancer Res. 2 1996 687 693
47. J.P. Lima, L.V. dos Santos, E.C. Sasse, C.S. Lima, and A.D. Sasse Camptothecins compared with etoposide in combination with platinum analog in extensive stage small cell lung cancer: systematic review with meta-analysis J. Thorac. Oncol. 12 2010 1986 1993
48. K. Aoe, K. Kiura, H. Ueoka, M. Tabata, M. Chikamori, H. Kohara, M. Harada, and M. Tanimoto Cisplatin down-regulates topoisomerase I activity in lung cancer cell lines Anticancer Res. 24 2004 3893 3897
49. J. Malina, O. Vrana, and V. Brabec Mechanistic studies of the modulation of cleavage activity of topoisomerase I by DNA adducts of mono- and bi-functional Pt-II complexes Nucleic Acids Res. 37 2009 5432 5442
50. D.E. Bergbreiter, P.L. Osburn, and C. Li Soluble polymer-supported catalysts containing azo dyes Org. Lett. 4 2002 737 740
51. J.J.P. Stewart Optimization of parameters for semiempirical methods V: modification of NDDO approximations and application to 70 elements J. Mol. Model. 13 2007 1173 1213
52. http://spdbv.vital-it.ch/content.html.
53. M. Sanner, and F. Python A programming language for software integration and development J. Mol. Graphics Model. 17 1999 57 61
54. J. Gasteiger, and M. Marsili Iterative partial equation of orbital electronegativity-a rapid access to atomic charges Tetrahedron 36 1980 3219 3228
55. G.M. Morris, D.S. Goodsell, R.S. Halliday, R. Huey, W.E. Hart, R.K. Belew, and A.J. Olson Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function J. Comput. Chem. 19 1998 1639 1662
56. R. Huey, G.M. Morris, A.J. Olson, and D.S. Goodsell A semiempirical free energy force field with charge-based desolvation J. Comput. Chem. 28 2007 1145 1152
57. G.W.T.M.J. Frisch, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J.;Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian 03, Revision C.02 2004 Gaussian, Inc. Wallingford CT
58. G.L. Beretta, M. Binaschi, E. Zagni, L. Capuani, and G. Capranico Tethering a type IB topoisomerase to a DNA site by enzyme fusion to a heterologous site-selective DNA-binding protein domain Cancer Res. 59 1999 3689 3697
59. G.L. Beretta, L. Gatti, S. Tinelli, E. Corna, D. Colangelo, F. Zunino, and P. Perego Cellular pharmacology of cisplatin in relation to the expression of human copper transporter CTR1 in different pairs of cisplatin-sensitive and -resistant cells Biochem. Pharmacol. 68 2004 283 291
60. E. Gabano, D. Colangelo, A.R. Ghezzi, and D. Osella The influence of temperature on antiproliferative effects, cellular uptake and DNA platination of the clinically employed Pt(II)-drugs J. Inorg. Biochem. 102 2008 629 635
61. G. Pratesi, C. Manzotti, M. Tortoreto, E. Prosperi, and F. Zunino Effects of 5-FU and cis-DDP combination on human colorectal tumor xenografts Tumori 75 1989 60 65