Inhibition of NF-kB/DNA Interactions and HIV-1 LTR Directed Transcription by Hybrid Molecules Containing Pyrrolo [2,1-c] [1,4] Benzodiazepine (PBD) and Oligopyrrole Carriers

Drug Development Research

Volumn 60, Issue 3, 2003, Pages 173-185

  Borgatti, Monica ^a   Rutigliano, Cristina ^a   Bianchi, Nicoletta ^a   Mischiati, Carlo ^a   Baraldi, Pier Giovanni ^a   Romagnoli, Romeo ^a   Gambari, Roberto ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 METHYL 4 [8 (2' CARBOXAMIDOETHYLOXY) 11 HYDROXY 7 METHOXY 11,2,3,11A TETRAHYDRO 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE]PYRROLE 2 CARBOXAMIDOPROPIONAMIDINE; 8 (2' CARBOMETHOXYETHYLOXY) 7 METHOXY 1,2,3,11A TETRAHYDRO 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; BENZODIAZEPINE DERIVATIVE; DEOXYRIBONUCLEASE; DISTAMYCIN A; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; OLIGOPYRROLE CARRIER; PYRROLE DERIVATIVE; PYRROLO[2,1 C][1,4]BENZODIAZEPINE; UNCLASSIFIED DRUG; VIRUS DNA;

ANTIVIRAL ACTIVITY; ARTICLE; CELL PROLIFERATION; CONTROLLED STUDY; DNA BINDING; DRUG ACTIVITY; DRUG DNA BINDING; DRUG EFFECT; DRUG STRUCTURE; GENE SEQUENCE; HUMAN; HUMAN CELL; HUMAN T CELL LEUKEMIA VIRUS 1; HYBRID; LEUKEMIA CELL LINE; LONG TERMINAL REPEAT; POLYMERASE CHAIN REACTION; PROTEIN DNA INTERACTION; PROTEIN PROTEIN INTERACTION; STRUCTURE ACTIVITY RELATION; TRANSCRIPTION TERMINATION; VIRUS GENE; VIRUS TRANSCRIPTION;

EID: 0242331236     PISSN: 02724391     EISSN: None     Source Type: Journal    
DOI: 10.1002/ddr.10280     Document Type: Article

References (27)

1. Arcamone F, Penco S, Orezzi PG, Nicolella V, Pirelli A. 1964. Structure and synthesis of Distamycin A. Nature 203:1064-1065.
2. Baraldi PG, Cacciari B, Guiotto A, Romagnoli R, Zaid AN, Spalluto G. 1998a. Heterocyclic analogs of DNA minor groove alkylating agents. Curr Pharm Des 4:249-276.
3. Baraldi PG, Cacciari B, Guiotto A, Romagnoli R, Spalluto G, Mongelli N, Thurston DE, Howard PW, Leoni A, Bianchi N, Gambari R. 1998b. Design, synthesis and biological activity of pyrrolo [2,1-c][1,4] benzodiazepine (PBD)-distamycin hybrid. Bioorg Med Chem Lett 8:3019-3024.
4. Baraldi PG, Balboni G, Cacciari B, Guiotto A, Manfredini S, Romagnoli R, Spalluto G, Thurston DE, Howard PW, Bianchi N, Rutigliano C, Mischiati C, Gambari R. 1999. 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. J Med Chem 42:5131-5141.
5. Baraldi PG, Cacciari B, Guiotto A, Romagnoli R, Spalluto G, Leoni A, Bianchi N, Feriotto G, Rutigliano C, Mischiati C, Gambari R. 2000. [2,1-c][1,4]benzodiazepine (PBD)-distamycin hybrid inhibits DNA binding to transcription factor Sp1. Nucleosides Nucleic Acids 19:1219-1229.
6. Bianchi N, Passadore M, Feriotto G, Mischiati C, Gambari R, Piva R. 1995. Alteration of the expression of human oestrogen receptor gene by distamycin. J Steroid Biochem Mol Biol 54:211-215.
7. Bianchi N, Passadore M, Rutigliano C, Feriotto G, Mischiati C, Gambari R. 1996. Targeting of the Sp1 binding sites of HIV-1 long terminal repeat with chromomycin. Biochem Pharmacol 52:1489-1498.
8. Borgatti M, Breda L, Cortesi R, Nastruzzi C, Romanelli A, Saviano M, Bianchi N, Mischiati C, Pedone C, Gambari R. 2002. Cationic liposomes as delivery systems for double-stranded PNA-DNA chimeras exhibiting decoy activity against NF-kappaB transcription factors. Biochem Pharmacol 64:609-616.
9. Coll M, Frederick CA, Wang AH, Rich AA. 1987. 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 USA 84:8385-8389.
10. Cozzi P, Mongelli N. 1998. Cytotoxics derived from distamycin A and congeners. Curr Pharm Des 4:181-201.
11. Feriotto G, Mischiati C, Bianchi N, Passadore M, Gambari R. 1996. Binding of distamycin and chromomycin to human immuno-deficiency type 1 virus DNA: a non-radioactive automated footprinting study. Eur J Pharmacol 290:85-93.
12. Gambari R. 2001. Biospecific interaction analysis: a tool for drug discovery and development. Am J Pharmacogenom 1:119-135.
13. Gambari R, Feriotto G, Rutigliano C, Bianchi N, Mischiati C. 2000. Biospecific interaction analysis (BIA) of low-molecular weight DNA-binding drugs. J Pharmacol Exp Ther 294:370-377.
14. Hurley LH. 1977. Pyrrolo[1,4]benzodiazepine antitumor antibiotics. Comparative aspects of anthramycin, tomamycin and sibiromycin. J Antibiot 20:349-370.
15. Kopka ML, Yoon C, Goodsell D, Pjura P, Dickerson RE. 1985. The molecular origin of DNA-drug specificity in netropsin and distamycin. Proc Natl Acad Sci USA 82:1376-1380.
16. Lown JW, Sondhi SM, Praveen Reddy BS. 1997. Lexitropsin conjugates: action on DNA targets. Curr Med Chem 4:313-358.
17. Mischiati C, Feriotto G, Borgatti M, Giacomini P, Gambari R. 2000. Characterization of a major histocompatibility complex class II X-box-binding protein enhancing tat-induced transcription directed by the human immunodeficiency virus type 1 long terminal repeat. J Virol 74:8989-9001.
18. Mischiati C, Borgatti M, Feriotto G, Rutigliano C, Breda L, Bianchi N, Gambari R. 2002. Inhibition of HIV-1 LTR-driven in vitro transcription by molecular hybrids based on peptide nucleic acids mimicking the NF-kappaB binding site. Int J Mol Med 9:633-639.
19. Passadore M, Feriotto G, Bianchi N, Aguiari GL, Mischiati C, Piva R, Gambari R. 1994. Polymerase-chain reaction as a tool for investigations on sequence-selectivity of DNA-drugs interactions. J Biochem Biophys Methods 29:307-319.
20. Passadore M, Bianchi N, Feriotto G, Mischiati C, Rutigliano C, Gambari R. 1997. In vitro and in vivo binding of a CC-1065 analogue to human gene sequences: a polymerase-chain reaction study. Eur J Pharmacol 319:317-325.
21. 2 complex 2D NMR and molecular mechanics. Biochemistry 27:8088-8096.
22. Pompeia C, Boaventura MF, Curi R. 2001. Antiapoptotic effect of dipyrone on HL-60, Jurkat and Raji cell lines submitted to UV irradiation, arachidonic acid and cycloheximide treatments. Int Immunopharmacol 1:2173-2182.
23. Saiki RK, Gelfand DH, Stoffel S, Scharf SJ, Higuchi R, Horn GT, Mullis KB, Erlich H.A. 1988. Primer-directed enzymatic amplification of DNA with a thermostable DNA polymerase. Science 239:487-491.
24. Thurston DE. 1993. Advances in the studi of pyrrolo[2,1-c][1,4]benzodiazepine (PBD) antitumor antibiotics. In: Neidle S, Waring MJ, editors. Molecular aspects of anticancer drug-DNA interactions. London: MacMillan Press Ltd. p 54-88.
25. Thurston DE, Bose DS. 1994. Synthesis and DNA-interactive pyrrole pyrrolo [2,1-c][1,4]benzo-diazepines. Chem Rev 94:433-465.
26. Thurston DE, Bose DS, Thompson AS, Howard PW, Leoni A, Croker SJ, Jenkins TC, Neidle S, Hartley JA, Hurley LH. 1996. Synthesis of sequence-selective C8-linked pyrrolo [2,1-c][1,4]benzodiazepine DNA interstrand cross-linking agents. J Org Chem 61:8141-8147.
27. Zunino F, Animati F, Capranico G. 1995. DNA minor-groove binding drugs. Curr Pharm Des 1:83-94.