Antitumor AHMA linked to DNA minor groove binding agents: Synthesis and biological evaluation

Journal of Medicinal Chemistry

Volumn 45, Issue 20, 2002, Pages 4485-4493

  Rastogi, Kamesh ^a   Chang, Jang Yang ^b   Pan, Wen Yu ^b   Chen, Ching Huang ^a   Chou, Ting Chao ^c   Chen, Li Tzong ^b   Su, Tsann Long ^a  

^a INSTITUTE OF BIOMEDICAL SCIENCES   (Taiwan)

^b NATIONAL HEALTH RESEARCH INSTITUTES   (Taiwan)

^c MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2' [4 [3 (9 ACRIDINYLAMINO) 5 HYDROXYMETHYLANILINO]CARBONYLPROPOXYPHENYL] 5 (4 METHYL 1 PIPERAZINYL) 2,5' BI 1H BENZIMIDAZOLE; 3 (9 ACRIDINYLAMINO) 5 HYDROXYMETHYLANILINE DERIVATIVE; AMIDE; ANILINE DERIVATIVE; ANTINEOPLASTIC ANTIBIOTIC; BENZIMIDAZOLE; CONGOCIDINE DERIVATIVE; HO 33258; N [2 (DIMETHYLAMINO)ETHYL] 1 METHYL 4 [1 METHYL 4 [1 METHYL 4 [[[3 (9 ACRIDINYLAMINO) 5 HYDROXYMETHYLANILINO]CARBONYLPROPANOYL]AMINO]PYRROLE 2 CARBOXAMIDO]PYRROLE 2 CARBOXAMIDE; N [2 (DIMETHYLAMINO)ETHYL] 1 METHYL 4 [1 METHYL 4 [[[3 (9 ACRIDINYLAMINO) 5 (ETHOXYCARBONYLAMINO)BENZYLOXY]CARBONYLBUTANOYL]AMINO]PYRROLE 2 CARBOXAMIDO]PYRROLE 2 CARBOXAMIDE; N [2 (DIMETHYLAMINO)ETHYL] 1 METHYL 4 [1 METHYL 4 [[[3 (9 ACRIDINYLAMINO)BENZYLOXY]CARBONYLPROPANOYL]AMINO]PYRROLE 2 CARBOXAMIDO]PYRROLE 2 CARBOXAMIDE; N [2 (DIMETHYLAMINO)ETHYL] 1 METHYL 4 [1 METHYL [[[3 (9 ACRIDINYLAMINO) 5 HYDROXYMETHYLANILINO]CARBONYLBUTANOYL]AMINO]PYRROLE 2 CARBOXAMIDO]PYRROLE 2 CARBOXAMIDE; N [2 (DIMETHYLAMINO)ETHYL] 1 METHYL 4 [[[3 (9 ACRIDINYLAMINO) 5 (ETHOXYCARBONYLAMINO)BENZYLOXY]CARBONYLBUTANOYL]AMINOPYRROLE 2 CARBOXAMIDE; N [2 (DIMETHYLAMINO)ETHYL] 1 METHYL 4 [[[3 (9 ACRIDINYLAMINO) 5 (ETHOXYCARBONYLAMINO)BENZYLOXY]CARBONYLPROPANOYL]AMINO]PYRROLE 2 CARBOXAMIDE; N [2 (DIMETHYLAMINO)ETHYL] 1 METHYL 4 [[[3 (9 ACRIDINYLAMINO) 5 HYDROXYMETHYLANILINO]CARBONYLBUTANOYL]AMINO]PYRROLE 2 CARBOXAMIDE; N [2 (DIMETHYLAMINO)ETHYL] 1 METHYL 4 [[[3 (9 ACRIDINYLAMINO) 5 HYDROXYMETHYLANILINO]CARBONYLPROPANOYL]AMINO]PYRROLE 2 CARBOXAMIDE; N METHYLPYRROLECARBOXAMIDE; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DNA BINDING; DRUG POTENCY; DRUG SOLUBILITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOLECULAR INTERACTION;

ACRIDINES; ANILINE COMPOUNDS; ANTINEOPLASTIC AGENTS; CARBAMATES; CELL DIVISION; DNA; DNA TOPOISOMERASES, TYPE II; DNA, SUPERHELICAL; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; HUMANS; NETROPSIN; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 0037179615     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0200714     Document Type: Article

References (51)

1. Takusagawa, F.; Dabrow, M.; Neidle, S.; Berman, H. M. The Structure of a Pseudo Intercalated Complex Between Actinomycin and the DNA Binding Sequence d(GpC). Nature 1982, 296, 466-469.
2. Frederick, C. A.; Williams, L. D.; Ughetto, G.; Van der Marel, G.; Van Boom, J. H.; Rich, A.; Wang, A. H. J. Structural Comparison of Anticancer Drug-DNA Complexes: Adriamycin and Daunomycin. Biochemistry 1990, 29, 2538-2549.
3. Quigley, G. J.; Wang, A. H.; Ughetto, G.; Van der Marel, G. A.; Van Boom, J. H.; Rich, A. Molecular Structure of an Anticancer Drug-DNA Complex: Daunomycin Plus d(CpGpTpApCpG). Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 7204-7208.
4. Ughetto, G.; Wang, A. H.; Quigley, G. J.; Van der Marel, G. A.; Van Boom, J. H.; Rich, A. A Comparison of the Structure of Echinomycin and Triostin A Complexed to a DNA Fragment. Nucleic Acids Res. 1985, 13, 2305-2323.
5. Sugiura, Y.; Shiraki, T.; Konishi, M.; Oki, T. DNA Intercalation and Cleavage of an Antitumor Antibiotic Dynemicin that Contains Anthracycline and Enediyne Cores. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 3831-3835.
6. Lee, S. H.; Goldberg, I. H. Sequence-Specific, Strand-Selective, and Directional Binding of Neocarzinostatin Chromophore to Oligodeoxyribonucleotides. Biochemistry 1989, 28, 1019-1026.
7. Pjura, P. E.; Grzeskowiak, K.; Dickerson, R. E. Binding of Hoechst 33258 to the Minor Groove of B-DNA. J. Mol. Biol. 1987, 197, 257-271.
8. Durand, R. E.; Oliver, P. L. Cytotoxicity, Mutagenicity, and DNA Damage by Hoechst 33342. J. Histochem. Cytochem. 1982, 30, 111-116.
9. Kopka, M. L.; Yoon, C.; Goodsell, D.; Pjura, P.; Dickerson, R. E. The Molecular Origin of DNA-Drug Specificity in Netropsin and Diastamycin. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 1376-1380.
10. Dattagupta, N.; Hogan, M.; Crothers, D. M. Interaction of Netropsin and Distamycin with Deoxyribonucleic Acid: Electric Dichroism Study. Biochemistry 1980, 19, 5998-6005.
11. Coll, M.; Frederick, C. A.; Wang, A.-H.; Rich, A. A Bifurcated Hydrogen-Bonded Conformation in the d(AT) Base Pairs of the DNA Dodecamer d(CGCAAATTTGCG) and its Complex with Distamycin. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 8385-8389.
12. Gilbert, D. E.; Feigon, J. Structure Analysis of Drug-DNA Interaction. Curr. Opin. Struct. Biol. 1991, 1, 439-445.
13. Neidle, S.; Pearl, L. H.; Skelly, J. V. DNA Structure and Perturbation by Drug Binding. Biochem. J. 1987, 243, 1-13.
14. Smith, P. J.; Bell, S. M.; Dee, A.; Sykes, H. Involvement of DNA Topoisomerase II in the Selective Resistance of a Mammalian Cell Mutant to DNA Minor Groove Ligands, Ligand-Induced DNA-Protein Cross-linking and Responses to Topoisomerase Poisons. Carcinogenesis 1990, 11, 659-665.
15. Hirschberg, J.; Lavi, U.; Goitein, R.; Marcus, M. The Pleiotropic effects of 33258 Hoechst on the Cell Cycle in Chinese Hamster Cells in vitro. Exp. Cell Res. 1980, 130, 63-72.
16. Kusyk, C. J.; Hsu, T. C. Induction of High Frequencies of Endoreduplication in Mammalian Cell Cultures with 33258 Hoechst and Rubidazone. Cytogenet. Cell Genet. 1979, 23, 39-43.
17. McHugh, M. M.; Woynarowski, J. M.; Sigmund, R. D.; Beerman, T. A. Effects of Minor Groove Binding Drugs on Mammalian Topoisomerase I Activity. Biochem. Pharmacol. 1989, 38, 2323-2328.
18. Chen, A. Y.; Yu, C.; Gatto, B.; Liu, L. F. DNA Minor Groove-Binding Ligands: A Different Class of Mammalian DNA Topoisomerase I Inhibitors. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 8131-8135.
19. Woynarowski, J. M.; McHugh, M.; Sigmund, R. D.; Beerman, T. A. Modulation of Topoisomerase II Catalytic Activity by DNA Minor Groove Binding Agents Distamycin, Hoechst 33258, and 4′,6-Diamidine-2-phenylindole. Mol. Pharmacol. 1989, 35, 177-182.
20. Fesen, M.; Pommier, Y. Mammalian Toposiomerase II Activity Is Modulated by the DNA Minor Groove Binder Distamycin in Simian Virus 40 DNA. J. Biol. Chem. 1989, 264, 11354-11359.
21. Henichart, J. P.; Waring, M. J.; Riou, J. F.; Denny, W. A.; Bailly, C. Copper-Dependent Oxidative and Topoisomerase II-Mediated DNA Cleavage by a Netropsin/4′-(9-Acridinylamino)methane-sulfon-m-anisidide Combilexin. Mol. Pharmacol. 1997, 51, 448-461.
22. Gupta, R.; Huang, L.; Wang, H.; Lown, J. W. Design, Synthesis, DNA Sequence Preferential Alkylation and Biological Evaluation of N-Mustard Derivatives of Hoechst 33258 Analogues. AntiCancer Drug Des. 1995, 10, 25-41.
23. Arcamone, F. M.; Animati, F.; Barbieri, B.; Configliacchi, E.; D'Alessio, R.; Geroni, C.; Giuliani, F. C.; Lazzari, E.; Menozzi, M.; Mongelli, N. Synthesis, DNA-Binding Properties, and Antitumor Activity of Novel Distamycin Derivatives. J. Med. Chem. 1989, 32, 774-778.
24. Broggini, M.; Erba, E.; Ponti, M.; Ballinari, D.; Geroni, C.; Spreafico, F.; D'Incalci, M. Selective DNA Interaction of the Novel Distamycin Derivative FCE 24517. Cancer Res. 1991, 51, 199-204.
25. Baraldi, P. G.; Balboni, G.; Romagnoli, R.; Spalluto, G.; Cozzi, P.; Geroni, C.; Mongelli, N.; Rutigliano, C.; Bianchi, N.; Gambari, R. PNU 157977: a New Potent Antitumor Agent Exhibiting Low In Vivo Toxicity in Mice Injected with L1210 Leukaemia Cells. Anti-Cancer Drug Des. 1999, 14, 71-76.
26. Turner, P. R.; Ferguson, L. R.; Denny, W. A. Polybenzamide Mustards: Structure-Activity Relationships for DNA Sequence-Specific Alkylation. Anti-Cancer Drug Des. 1999, 14, 61-70.
27. Cozzi, P.; Beria, I.; Caldarelli, M.; Capolongo, L.; Geroni, C.; Mazzini, S.; Ragg, E. Phenyl Sulfur Mustard Derivatives of Distamycin A. Bioorg. Med. Chem. Lett. 2000, 10, 1653-1656.
28. Walker, W. L.; Kopka, M. L.; Filipowsky, M. E.; Dickerson, R. E.; Goodsell, D. S. Design of B-DNA Cross-Linking and Sequence-Reading Molecules. Biopolymers 1995, 35, 543-553.
29. Herfeld, P.; Helissey, P.; Giorgi-Renault, S.; Goulaouic, H.; Pager, J.; Auclair, C. Poly(pyrrolecarboxamides) Linked to Photoactivable Chromophore Isoalloxazine. Synthesis, Selective Binding, and DNA Cleaving Properties. Bioconjugate Chem. 1994, 5, 67-76.
30. Paz, M. M.; Das, T. A.; Tomasz, M. Mitomycin C Linked to DNA Minor Groove Binding Agents: Synthesis, Reductive Activation, DNA Binding and Cross-Linking Properties and In Vitro Antitumor Activity. Bioorg. Med. Chem. 1999, 7, 2713-2726.
31. Bailly, C.; Leclere, V.; Pommery, N.; Colson, P.; Houssier, C.; Rivalle, C.; Bisagni, E.; Hénichart, J.-P. Binding to DNA, Cellular Uptake and Biological Activity of a Distamycin-Ellipticine Hybrid Molecule. Anti-Cancer Drug Des. 1993, 8, 145-164.
32. Bailly, C.; O'Hugin, C.; Houssin, R.; Colson, P.; Houssier, C.; Rivalle, C.; Bisagni, E.; Hénichart, J.-P.; Waring, M. J. DNA-Binding Properties of Distamycin-Ellipticine Hybrid Molecule. Mol. Pharmcol. 1995, 41, 845-855.
33. Arcamone, F. Design and Synthesis of Anthracycline and Distamycin Derivaitves as New Sequence-Specific, DNA-Binding Pharmacological Agents. Gene 1994, 149, 57-61.
34. Eliadis, A.; Phillips, D. R.; Reiss, J. A.; Skorobogaty, A. The Synthesis and DNA Footprinting of Acridine-Linked Netropsin and Distamycin Bifunctional Mixed Ligands. J. Chem. Soc., Chem. Commun. 1988, 1049-1052.
35. Bailly, C.; Collyn-D'Hooghe, M.; Lantoine, D.; Fournier, C.; Hecquet, B.; Fosse, P.; Saucier, J.-M.; Colson, P.; Houssier, C.; Hénichart, J.-P. Biological Activity and Molecular Interaction of a Netropsin-Acridine Hydrid Ligand with Chromatin and Topoisomerase II. Biochem. Pharmacol. 1992, 43, 457-466.
36. Bourdouxhe-Housiaux, C.; Colson, P.; Houssier, C.; Waring, M. J.; Bailly, C. Interaction of a DNA-Threading Netropsin-Amsacrine Combilexin with DNA and Chromatin. Biochemistry 1996, 35, 4251-4264.
37. Rene, B.; Fosse, P.; Khelifa, T.; Jacquemin-Sablon, A.; Bailly, C. The 1′-Substituent on the Anilino Ring of the Antitumor Drug Amsacrine is a Critical Element for Topoisomerase II Inhibition and Cytotoxicity. Mol. Pharmacol. 1996, 49, 343-350.
38. Su, T.-L.; Chou, T.-C.; Kim, J. Y.; Huang, J.-T.; Ciszewska, G.; Ren, W.-Y.; Otter, G. M.; Sirotnak, F. M. Watanabe, K. A. 9-Substituted Acridine Derivatives with Long Half-Life and Potent Antitumor Activity: Synthesis and Structure Activity Relationships. J. Med. Chem. 1995, 38, 3226-3235.
39. Su, T.-L.; Chen, C.-H.; Huang, L.-F.; Chen, C.-H.; Basu, M. K.; Zhang, X.-G.; and Chou, T.-C. Synthesis and Structure-Activity Relationships of Potential Anticancer Agents: Alkylcarbamates of 3-(9-Acridinylamino)-5-hydroxymethylaniline J. Med. Chem. 1999, 42, 4741-4748.
40. Su, T.-L.; Chou, T.-C. Development of 3-(9-Acridinylamino)-5-hydroxymethylaniline as Potential Topoisomerase II-Mediated Anticancer Agents. Cancer Detect. Prev. 2000/Suppl. 2000, 24, 211.
41. Scarborough, A.; Su, T.-L.; Leteutre, F. F.; Pommier, Y.; Chou, T.-C. DNA Interaction and Topoisomerase II Inhibition by the Antitumor Agent 3-(9-Acridinylamino)-5′-hydroxymethylaniline and Derivatives. Bioorg. Med. Chem. 1996, 24, 229-241.
42. Corey, E. J.; Nicolaou, K. C. Effect and Mild Lactonization Method for the Synthesis of Macrolides. J. Am. Chem. Soc. 1974, 96, 5614-5616.
43. Rastogi, K.; Chou, T.-C.; Ting, C.-Y.; Chen, K.-T.; Hwang, J.; Su, T.-L. Synthesis and Biological Activity of AHMA-EDTA Conjugates. Submitted for publication.
44. Scudiero, D. A.; Shoemaker, R. H.; Paull, K. D.; Monks, A.; Tierney, S.; Nofziger, T. H.; Currens, M. J.; Seniff, D.; Boyd, M. R. Evaluation of Soluble Tetrazolium/Formazan Assay for Cell Growth and Drug Sensitivity in Culture Using Human and Other Tumor Cell Lines. Cancer Res. 1988, 48, 4827-4833.
45. Chou, T.-C.; Talalay, P. Quantitative Analysis of Dose-Effect Relationships: The Combined Effects of Multiple Drugs or Enzyme Inhibitors. Adv. Enzyme Regul. 1984, 22, 27-55.
46. Chou, T.-C. The Median-Effect Principle and the Combination Index for Quantitation of Synergism and Antagonism. In Synergism and Antagonism in Chemotherapy; Chou, T.-C., Rideout D., Eds.; Academic Press: New York, 1991; pp 61-102.
47. 50, Synergism, Antagonism, Low-Dose Risk, Receptor-Ligands Binding and Enzyme Kinetics; Biosoft: Cambridge, U.K., 1987.
48. Yamashita, Y.; Kawada, S.; Fujii, N.; Nakano, H. Induction of Mammalian DNA Topoisomerase I and II Mediated DNA Cleavage by Saintopin, a New Antitumor Agent from Fungus. Biochemistry 1991, 30, 5838-5845.
49. Rowe, T. C.; Chen, G. L.; Hsiang, Y. H.; Liu, L. F. DNA Damage by Antitumor Acridines Mediated by Mammalian DNA Topoisomerase II. Cancer Res. 1986, 46, 2021-2026.
50. Camilloni, G.; Seta, F. D.; Negri, R.; Ficca, A. G.; Di Mauro, E. Structure of RNA Polymerase II Promoters: Conformational Alterations and Template Properties of Circularized Saccharomyces cerevisiae GAL1-GAL10 Divergent Promoters. EMBO J. 1986, 5, 763-771.
51. Montecucco, A.; Pedrali-Noy, G.; Spadari, S.; Zanolin, E.; Ciarrocchi, G. DNA Unwinding and Inhibition of T4 DNA Ligase by Anthracyclines. Nucleic Acids Res. 1988, 16, 3907-3918.