Synthesis, in vitro antiproliferative activity and DNA-interaction of benzimidazoquinazoline derivatives as potential anti-tumor agents

Farmaco

Volumn 56, Issue 3, 2001, Pages 159-167

  Dalla Via, Lisa ^a   Gia, Ornella ^a   Marciani Magno, Sebastiano ^a   Da Settimo, Antonio ^b   Marini, Anna Maria ^b   Primofiore, Giampaolo ^b   Da Settimo, Federico ^b   Salerno, Silvia ^b  

^a UNIVERSITY OF PADOVA   (Italy)

^b UNIVERSITY OF PISA   (Italy)

Author keywords

Antiproliferative activity; Benzimidazoquinazoline; DNA binding

Indexed keywords

6 (BETA ETHANOLAMINOETHYL)BENZIMIDAZO[2,1 B]QUINAZOLIN 12(6H) ONE; ANTINEOPLASTIC AGENT; BENZIMIDAZO[2,1 B]QUINAZOLIN 12(6H) ONE DERIVATIVE; BENZIMIDAZOQUINAZOLINE DERIVATIVE; DNA; ELLIPTICINE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CANCER INHIBITION; CONTROLLED STUDY; CYTOTOXICITY; DRUG DNA INTERACTION; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; FLUOROMETRY; HUMAN; HUMAN CELL; PROMYELOCYTIC LEUKEMIA; REACTION ANALYSIS; SQUAMOUS CELL CARCINOMA; STRUCTURE ACTIVITY RELATION; TITRIMETRY; TUMOR CELL LINE; UTERINE CERVIX CARCINOMA;

ANTINEOPLASTIC AGENTS; BENZIMIDAZOLES; CIRCULAR DICHROISM; DNA; DNA, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; HL-60 CELLS; HUMANS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; QUINAZOLINES; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET; TUMOR CELLS, CULTURED;

EID: 0035305645     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-827X(01)01079-5     Document Type: Article

References (18)

1. Baguley B.C. DNA intercalating anti-tumor agents. Anti-Cancer Drug Des. 6:1991;1-35.
2. Denny W.A., Rewcastle G.W., Baguley B.C. Potential antitumor agents. 59. Structure-activity relationships for 2-phenylbenzimidazole-4-carboxamides, a new class of minimal DNA-intercalating agents which may not act via topoisomerase II. J. Med. Chem. 33:1990;814-819.
3. Braña W.F., Castellano J.M., Keilhauer G., Machuca A., Martín Y., Redondo C., Schlick E., Walker N. Benzimidazo[1,2-c]quinazolines: a new class of antitumor compounds. Anti-Cancer Drug Des. 9:1994;527-538.
4. Garuti L., Roberti M., Rossi T., Cermelli C., Portolani M., Malagoli M., Castelli M. Synthesis, antiviral and antiproliferative activity of some N-benzenesulphonyl-2-(2- or 3-pyridylethyl)-benzimidazoles. Anti-Cancer Drug Des. 13:1998;397-406.
5. Werbel L.M., Angelo M., Fry D.W., Worth D.F. Basically substituted ellipticine analogues as potential antitumor agents. J. Med. Chem. 29:1986;1321-1322.
6. White R.J., Durr F.E. Development of mitoxantrone. Investig. New Drugs. 3:1985;85-93.
7. Koeller J., Eble M. Mitoxantrone: a novel anthracycline derivative. Clin. Pharmacol. 7:1988;574-581.
8. Da Settimo A., Da Settimo F., Marini A.M., Primofiore G., Salerno S., Viola G., Dalla Via L., Marciani Magno S. Synthesis, DNA binding and in vitro antiproliferative activity of purinoquinazoline, pyridopyrimidopurine and pyridopyrimidobenzimidazole derivatives as potential antitumor agents. Eur. J. Med. Chem. 33:1998;685-696.
9. Lunn W.H.W., Harper R.W. Methods for preparing benzimidazo[2,1-b]quinazolin-12-ones and related compounds. J. Heterocycl. Chem. 8:1971;141-147.
10. Wada A., Kozawa S. Instrument for the studies of differential flow dichroism of polymer solutions. J. Polym. Sci., Part A. 2:1964;853-864.
11. Nordén B. Applications of linear dichroism spectroscopy. Appl. Spectrosc. Rev. 14:1978;157-248.
12. Nordén B., Kubista M., Kurucsev T. Linear dichroism spectroscopy of nucleic acid. Q. Rev. Biophys. 25:1992;51-170.
13. Scatchard G. The attractions of proteins for small molecules and ions. Ann. N. Y. Acad. Sci. 51:1949;660-672.
14. McGhee J.D., von Hippel P.H. Theoretical aspects of DNA-protein interaction: co-operative and non co-operative binding of large ligands to one dimensional homogeneous lattice. J. Mol. Biol. 86:1974;469-489.
15. Waring M.J. DNA modification and cancer. Annu. Rev. Biochem. 50:1981;159-192.
16. Sehlstedt U., Kim S.K., Carter P., Goodisman J., Vollano J.F., Nordén B., Dabrowiak J.C. Interaction of cationic porphyrins with DNA. Biochemistry. 33:1994;417-426.
17. Nordén B., Kurucsev T. Analysing DNA complexes by circular and linear dichroism. J. Mol. Recognit. 7:1994;141-156.
18. 1H-NMR spectroscopy: effect of size of the heterocyclic ring system. Biopolymers. 34:1994;599-609.