Synthesis, in vitro antiproliferative activity, and DNA-binding properties of hybrid molecules containing pyrrolo[2,1-c][1,4] benzodiazepine and minor-groove-binding oligopyrrole carriers

Journal of Medicinal Chemistry

Volumn 42, Issue 25, 1999, Pages 5131-5141

  Baraldi, Pier Giovanni ^a   Balboni, Gianfranco ^a   Cacciari, Barbara ^a   Guiotto, Andrea ^a   Manfredini, Stefano ^a   Romagnoli, Romeo ^a   Spalluto, Giampiero ^a   Thurston, David E ^b   Howard, Philip W ^b   Bianchi, Nicoletta ^a   Rutigliano, Cristina ^a   Mischiati, Carlo ^a   Gambari, Roberto ^a  

^a UNIVERSITY OF FERRARA   (Italy)

^b UNIVERSITY OF PORTSMOUTH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,11A TETRAHYDRO 8 HYDROXY 7 METHOXY 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; ANTHRAMYCIN; BENZODIAZEPINE DERIVATIVE; DISTAMYCIN A; ESTROGEN RECEPTOR; PYRROLE DERIVATIVE;

ARTICLE; DNA BINDING; DNA FOOTPRINTING; DRUG DNA BINDING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LONG TERMINAL REPEAT; MITOSIS INHIBITION; NONHUMAN; ONCOGENE MYC; POLYMERASE CHAIN REACTION; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; BASE SEQUENCE; BENZODIAZEPINONES; CELL DIVISION; DNA; DNA FOOTPRINTING; DRUG SCREENING ASSAYS, ANTITUMOR; HIV LONG TERMINAL REPEAT; HUMANS; JURKAT CELLS; K562 CELLS; POLYMERASE CHAIN REACTION; PYRROLES; RECEPTORS, ESTROGEN; SPECTRUM ANALYSIS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0033576568     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm991033w     Document Type: Article

References (39)

1. (a) Arcamone, F.; Orezzi, P. G.; Barbieri, W., Nicolella, V.; Penco, S. Distamicina A. Isolamento e struttura dell'agente antivirale distamicina A. Gazz. Chim. Ital. 1967, 97, 1097-1115.
2. (b) Arcamone, F.; Penco, S.; Orezzi, P. G.; Nicolella, V.; Pirelli, A. Structure and synthesis of Distamycin A. Nature 1964, 203, 1064-1065.
3. (a) Arcamone, F.; Di Marco, A.; Gaetani, M.; Scotti, T. Isolation and antitumor activity of an antibiotic from Streptomyces. Giorn. Microbiol. 1961, 9, 83-90.
4. (b) Zimmer, C. Effect of the antibiotics netropsin and distamycin A on the structure and function of nucleic acids. Prog. Nucleic Acid Res. Mol. Biol. 1975, 15, 285-318.
5. 2 complex by 2D NMR and molecular mechanics. Biochemistry 1988, 27, 8088-8096.
6. (b) Coll, M.; Frederick, C. A.; Wang, A. H.; Rich, A. A bifurcated hydrogen-bonded conformation in the d(A,T) base pairs of the DNA dodecamer d(CGCAAATTTGCG) and its complex with distamycin. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 8385-8389.
7. Kopka, M. L.; Yoon, C.; Goodsell, D.; Pjura, P.; Dickerson, R. E. The molecular origin of DNA-drug specificity in netropsin and distamycin. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 1376-1380.
8. (a) Cozzi, P.; Mongelli, N. Cytotoxics derived from distamycin A and congeners. Curr. Pharm. Des. 1998, 4, 181-201.
9. (b) Baraldi, P. G.; Cacciari, B.; Guiotto, A.; Romagnoli, R.; Zaid, A. N.; Spalluto, G. Heterocyclic analogues of DNA minor groove alkylating agents. Curr. Pharm. Des. 1998, 4, 249-276.
10. Zunino, F.; Animati, F.; Capranico, G. DNA minor-groove binding drugs. Curr. Pharm. Des. 1995, 1, 83-94.
11. Lown, J. W.; Sondhi, S. M.; Praveen Reddy, B. S. Lexitropsin Conjugates: action on DNA targets. Curr. Med. Chem. 1997, 4, 313-358.
12. Thurston, D. E.; Bose, D. S.. Synthesis and DNA-interactive pyrrolo[2,1-c][1,4]benzodiazepines. Chem. Rev. 1994, 94, 433-465.
13. Leimgruber, W.; Batcho, A. D.; Czajkowski, R. C. Total synthesis of Anthramycin. J. Am. Chem. Soc. 1968, 90, 5641-5643.
14. 2 and a molecular explanation of specificity. Biochemistry 1994, 33, 13593-13610.
15. (a) Baraldi, P. G.; Cacciari, B.; Guiotto, A.; Romagnoli, R.; Spalluto, G.; Mongelli, N.; Thurston, D. E.; Howard, P. W.; Leoni, A.; Bianchi, N.; Gambari, R. Design, synthesis and biological activity of pyrrolo[2,1-c][1,4]benzodiazepine (PBD)-distamycin hybrid. Bioorg. Med. Chem. Lett. 1998, 8, 3019-3024.
16. (b) Damayanthi, Y.; Praveen Reddy, B. S.; Lown, J. W. Design and synthesis of novel pyrrolo[2,1-c][1,4]benzodiazepine-lexitropsin conjugates. J. Org. Chem. 1999, 64, 290-292.
17. Thurston, D. E.; Bose, D. S.; Thompson, A. S.; Howard, P. W.; Leoni, A.; Croker, S. J.; Jenkins, T. C.; Neidle, S.; Hartley, J. A.; Hurley, L. H. Synthesis of sequence-selective CS-linked pyrrolo[2,1-c][1,4]benzodiazepine DNA interstrand cross-linking agents. J. Org. Chem. 1996, 61, 8141-8147.
18. Windholz, T. B.; Johnston, D. B. R. Trichloroethoxycarbonyl. A generally applicable protecting group. Tetrahedron Lett 1967, 27, 2555-2557.
19. Dong, Q.; Anderson, C. E.; Ciufolini, M. A. Reductive cleavage of Troc group under neutral conditions with cadmium-lead couple. Tetrahedron Lett. 1995, 36, 5681-5682.
20. Lee, M.; Lown, J. W. Synthesis of (4S)- and (4R)-methyl 2-amino-1-pyrrolidine-5-carboxylates and their application to the preparation of (4S)-(+)- and (4fi)-(-)-dihydrokikumycin B. J. Org. Chem. 1987, 52, 5717-5721.
21. Lown, J. W.; Krowicki, K. Efficient total syntheses of the oligopeptide antibiotics netropsin and distamycin. J. Org. Chem. 1985, 50, 3774-3779.
22. D'Alessio, R.; Geroni, C.; Biasioli, G.; Pesenti, E.; Grandi, M.; Mongelli, N. Structure-activity relationship of novel distamycin A derivatives: synthesis and antitumor activity. Bioorg. Med. Chem. Lett. 1994, 4, 1467-1472.
23. (a) Saiki, R. K.; Gelfand D. H.; Stoffel, S.; Scharf, S. J.; Higuchi, R.; Horn, G. T.; Mullis, K. B.; Erlich, H. A. Primer-directed enzymatic amplification of DNA with a thermostable DNA polymerase. Science 1988, 239, 487-491.
24. (b) Passadore, M.; Feriotto, G.; Bianchi, N.; Aguiari, G. L.; Mischiati, C.; Piva, R.; Gambari, R. Polymerase-chain reaction as a tool for investigations on sequence-selectivity of DNA-drugs interactions. J. Biochem. Biophys. Methods 1994, 29, 307-319.
25. Passadore, M.; Bianchi, N.; Feriotto, G.; Mischiati, C.; Rutigliano, C.; Gambari, R. In vitro and in vivo binding of a CC-1065 analogue to human gene sequences: a polymerase-chain reaction study. Eur. J. Pharmacol. 1997, 379, 317-325.
26. Passadore, M.; Bianchi, N.; Feriotto, G.; Mischiati, C.; Giacomini, P.; Piva, R.; Gambari, R. Differential effects of distamycin analogues on amplification of human gene sequences by polymerase-chain reaction. Biochem. J. 1994,308, 513-524.
27. (e) Ponti, M.; Forrow, S. M.; Souami, R. L.; D'Incalci, M.; Hartley, J. A. Measurement of the sequence specificity of covalent DNA modification by antineoplastic agents using Taq DNA polymerase. Nucleic Acids Res. 1991, 19, 2929-2033.
28. Piva, R.; Gambari, R.; Zorzato, F.; Kumar, L.; Del Senno, L. Analysis of upstream sequences of the human estrogen receptor gene. Biochem. Biophys. Res. Commun. 1992, 183, 996-1002.
29. Bentley, D. L.; Groudine, M. Novel promoter upstream of the human c-myc gene and regulation of c-myc expression in B-cell lymphomas. Mol. Cell. Biol. 1986, 6, 3481-3489.
30. (a) Blanchi, N.; Passadore, M.; Rutigliano, C.; Feriotto, G.; Mischiati, C.; Gambari, R. Targeting of the Sp1 binding sites of HIV-1 long terminal repeat with chromomycin. Biochem. Pharmacol. 1996, 52, 1489-1498.
31. (b) Feriotto, G.; Mischiati, C.; Bianchi, N.; Passadore, M.; Gambari, R. Binding of distamycin and chromomycin to human immunodeficiency type 1 virus DNA: a nonradioactive automated footprinting study. Eur. J. Pharmacol. 1996, 290, 85-93.
32. Piva, R.; Del Senno, L. Analysis of a DNA sequence upstream of the human estrogen receptor gene. Ann. N.Y. Acad. Sci. 1993, 68, 235-238.
33. Snyder, R. C.; Ray, R.; Blume, S.; Miller D. M. Mithramycin blocks transcriptional initiation of the c-myc P1 and P2 promoters. Biochemistry 1991, 30, 4290-4297.
34. Bianchi, N.; Passadore, M.; Feriotto, G.; Mischiati, C.; Gambari, R.; Piva, R. Alteration of the expression of human estrogen receptor gene by distamycin. J. Steroid Biochem. Mol. Biol. 1995, 54, 211-215.
35. (a) Hurley, L. H. Pyrrolo[1,4]benzodiazepine antitumor antibiot-ics. Comparative aspects of anthramycin, tomamycin and sibiromycin. J. Antibiot. 1977, 20, 349-370.
36. (b) Thurston, D. E. Advances in the study of pyrrolo[2,1-c][1,4]benzodiazepine (PBD) antitumor antibiotics. In Molecular aspects of anticancer drug-DNA interactions; Neidle, S., Waring, M. J., Eds.; MacMillan Press Ltd. U.K., 1993; Vol. 1, pp 54-88.
37. Gambari et al. Manuscript in preparation.
38. (a) Krowicki, K.; Lown, J. W. Synthesis of novel imidazole-containing DNA minor groove binding oligopeptides related to the antiviral antibiotic netropsin. J. Org. Chem. 1987, 52, 3493-3501.
39. (b) Lee, M.; Rhodes, A. L.; Wyatt, M. D.; D'Incalci, M.; Forrow, S.; Hartley, J. A. In vitro cytotoxicity of GC sequence directed alkylating agents related to distamycin. J. Med. Chem. 1993, 36, 863-870.