The role of the iminium bond in the inhibition of reverse transcriptase by quaternary benzophenanthridines

Journal of Pharmacy and Pharmacology

Volumn 50, Issue 11, 1998, Pages 1307-1315

  Kerry, Mark A ^a   Duval, Olivier ^b   Waigh, Roger D ^c   Mackay, Simon P ^a  

^a UNIVERSITY OF SUNDERLAND   (United Kingdom)

^b UNIVERSITÉ D'ANGERS   (France)

^c UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOPHENANTHRIDINE DERIVATIVE; DNA; ETHOXIDINE; FAGARONINE; HYDROXIDINE; METHOXIDINE; RNA DIRECTED DNA POLYMERASE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CONTROLLED STUDY; DRUG DNA BINDING; DRUG MECHANISM; ENZYME INHIBITION; HUMAN; HUMAN CELL; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0031731436     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.2042-7158.1998.tb03350.x     Document Type: Article

References (39)

1. Arisawa, M., Pezzuto, J. M., Bevelle C., Cordell, G. A. (1984) Potential anticancer agents XXXI. N-Demethylation of fagaronine. J. Nat. Prod. 47: 453-458
2. Barret, Y., Sauvaire, Y. (1992) Fagaronine, a novel antileukaemic alkaloid. Phytother. Res. 6: 59-63
3. Caolo, M. A., Stermitz, F. R. (1979) Benzophenanthridine salt equilibria. Heterocycles. 12: 11-15
4. Casiano Torres, C. A., Baez, A. (1986) Effects of the antitumor drugs 3-nitrobenzothiazolo[3,2-a]quinolinium and fagaronine on nucleic acid and protein synthesis. Biochem. Pharmacol. 35: 679-685
5. Comoe, L., Jeannesson, P., Trentesaux, C., Desoize B., Jardillier, J.-C. (1987) The antileukemic alkaloid fagaronine and the human K562 leukemia cells: effects on growth and induction of erythroid differentiation. Leuk. Res. 11: 445-451
6. Comoe, L., Carpentier, Y., Desoize, B., Jardillier, J.-C. (1988) Effect of fagaronine on cell cycle progression of human erythroleukemia K562 cells. Leuk. Res. 12: 667-672
7. Dostal, J., Potacek, M. (1990) Quaternary benzo[c]phenanthridines. Collect. Czech. Chem. Commun. 55: 2841-2873
8. Fang, S.-D., Wang, L.-K., Hecht, S. M. (1993) Inhibitors of DNA topoisomerase I isolated from the roots of Zanthoxylum nitidum. J. Org. Chem. 58: 5025-5027
9. Grassy, G., Bonnafous, M., Loiseau, P., Adam, Y. (1985) Visualization of molecular electronic effects. Trends Pharmacol. Sci. 6: 57-59
10. Hejtmankova, N., Walterova, D., Preininger, V., Simanek, V. (1984) Antifungal activity of quaternary benzo[c]phenanthridine alkaloids from Chelidonium majus. Fitoterapia 55: 291-296
11. Kakiuchi, N., Hattori, M., Ishii, H., Namba, T. (1987) Effect of benzo[c]phenanthridine alkaloids on reverse transcriptase and their binding properties to nucleic acids. Planta Med. 53: 22-27
12. Larder, B. A., Purifoy, D. J. M., Powell, K. L., Darby, G. (1987) AIDS virus reverse transcriptase denned by high level expression in Escherichia coli. EMBO J. 6: 3133-3137
13. Larsen, A. K., Grondard, L., Couprie, J., Desoise, B., Comoe, L., Jardillier, J.-C., Riou, J.-F. (1993) The antileukaemic alkaloid fagaronine is an inhibitor of topoisomerase I and II. Biochem. Pharmacol. 46: 1403-1412
14. Lenfield, J., Kroutil, M., Marsalek, E., Slavik, J., Preininger, V., Simanek, V. (1981) Anti-inflammatory activity of quaternary benzophenanthridine alkaloids from Chelidonium majus. Planta Med. 43: 161-163
15. Mackay, S. P., Meth-Cohn, O., Waigh, R. D. (1996) Synthesis of quaternary benzo[c]phenanthridine alkaloids and their analogues. Adv. Heterocycl. Chem. 67: 345-387
16. Mackay, S. P., Comoe, L., Desoise, B., Duval, O., Jardillier, J.-C., Waigh, R. D. (1998) The effect of 12-alkoxy modification on the in vitro antileukaemic activity of N-methyl-2.3,8,9-tetramethoxybenzo[c]phenanthridinium salts. Anticancer Drug Design 13: 797-813
17. Maiti, M., Nandi, R., Chaudhuri, K. (1982) Sanguinarine: a monofunctional intercalating alkaloid. FEBS Lett. 142: 280-284
18. Maiti, M., Nandi, R., Chaudhuri, K. (1984) Interaction of sanguinarine with natural and synthetic deoxyribonucleic acids. Indian J. Biochem. Biophys. 21: 158-165
19. Messmer, W. M., Tin-Wa, M., Fong, H. H. S., Bevelle, C., Farnsworth, N. R., Abraham, D. J., Trojanek, J. (1972) Fagaronine, a new rumor inhibitor isolated from Fagara zanthoxyloides Lam. (Rutaceae). J. Pharm. Sci. 61: 1858-1861
20. Meunier, G., De Montauzon, D., Bernadou, J., Grassy, G., Bonnafous, M., Gros, S., Meunier, B. (1988) The bioxidation of cytotoxic ellipticine derivatives: a key to structure-activity relationship studies? Mol. Pharmacol. 33: 93-102
21. Nandi, R., Maiti, M. (1985) Binding of sanguinarine to deoxyribonucleic acids of differing base composition. Biochem. Pharmacol. 34: 321-324
22. Olugbade, T. A., Waigh, R. D., Mackay, S. P. (1990) A very short route to fully aromatic 2,3,8,9- and 2,3,8,9,12-oxygenated benzo[c]phenanthridines. J. Chem. Soc., Perkin Trans. 2657-2660
23. Parker, W. B., White, E. L., Shaddix, S. C., Ross, L. J., Buckheit, R. W., Germany, J. M., Secrist, J. A., Vince, R., Shannon. W. M. (1991) Mechanism of inhibition of human immunodeficiency virus type-1 reverse transcriptase and human DNA polymerase α, polymerase β and polymerase γ by the 5′-triphosphates of carbovir, 3′-azido-3′-deoxythymidine, 2′,3′-dideoxyguanosine and 3′-deoxythymidine - a novel RNA template for the evaluation of antiretroviral drugs. J. Biol. Chem. 266: 1754-1762
24. Pezzuto, J. M., Antosiak, S. K., Messmer, W. M., Slaytor, M. B., Honig, G. R. (1983) Interaction of the antileukemic alkaloid, 2-hydroxy-3,8,9-trimethoxy-5-methylbenzo[c] phenanthridine (fagaronine), with nucleic acids. Chem.-Biol. Interact. 43: 323-339
25. Poiesz, B. J., Ruscetti, F. W., Gazdar, A. F., Bunn, P., Minna, J., Gallo, R. C. (1980) Detection and isolation of type C retrovirus particles from fresh and cultured lymphocytes of a patient with cutaneous T-cell lymphoma. Proc. Natl Acad. Sci USA 77: 7415-7419
26. Sen, A., Maiti, M. (1994) Interaction of sanguinarine iminium and alkanolamine form with calf thymus DNA. Biochem. Pharmacol. 48: 2097-2102
27. Sethi, V. S. (1976) Inhibition of mammalian and oncorna-virus nucleic acid polymerase activities by alkoxybenzo-phenanthridine alkaloids. Cancer Res. 36: 2390-2395
28. Sethi, M. L. (1981) Screening of benzophenanthridine alkaloids for their inhibition of reverse transcriptase activity and preliminary reports on the structure-activity relationships. Can. J. Pharm. Sci. 16: 29-34
29. Sethi, M. L. (1984) Inhibition of reverse transcriptase activity by benzophenanthridine alkaloids. J. Med. Chem. 27: 544-547
30. Sethi, M. L. (1985a) Enzyme Inhibition VIII: mode of inhibition of reverse transcriptase activity by analogues, isomers and related alkaloids of coralyne. J. Pharm. Sci. 74: 889-891
31. Sethi, M. L. (1985b) Comparison of inhibition of reverse transcriptase and antileukemic activities exhibited by protoberberine and benzophenanthridine alkaloids and structure-activity relationships. Phytochemistry 24: 447-454
32. Simanek, V. (1985) Benzophenanthridine alkaloids. In: Brossi, A. (ed.) The Alkaloids, Vol. 26, Academic Press, New York, pp 185-240
33. Simanek, V., Preininger, V. (1977) Pseudobase formation from quaternary pyridinium, quinolinium and isoquinolinium cations. Heterocycles 6: 475-497
34. Simeon, S., Rios, J. L., Villar, A. (1989) Pharmacological activities of benzophenanthridine and phenanthrene alkaloids. Pharmazie 44: 593-597
35. Stermitz, F. R., Gillespie, J. P., Amoros, L. G., Romero, R., Stermitz, T. A., Larson, K. A., Earl, S., Oyz, J. E. (1975) Synthesis and biological activity of some antitumour benzophenanthridinium salts. J. Med. Chem. 18: 708-713
36. Tan, G. T., Miller, J. F., Kinghorn, A. D., Hughes, S. H., Pezzuto, J. M. (1992) HIV-1 and HIV-2 reverse transcriptases: a comparative study of sensitivity to inhibition by selected natural products. Biochem. Biophys. Res. Commun. 185: 370-378
37. Tisdale, M., Ertl, P., Larder, B. A., Purifoy, D. J. M., Darby, G., Powell, K. L. (1988). Characterization of human immunodeficiency virus type-1 reverse transcriptase by using monoclonal antibodies - role of the C-terminus in antibody reactivity and enzyme function. J. Virol. 62: 3662-3667
38. Wilson, W. G., Gough, A. N., Doyle, J. J. (1976) Coralyne. Intercalation with DNA as a possible mechanism of anti-leukaemic action. J. Med. Chem. 19: 1261-1263
39. Zee-Cheng, R. K.-Y., Cheng, C. C. (1975) Preparation and antileukaemic activity of some alkoxybenzo[c]phenanthridinium salts and corresponding dihydro derivatives. J. Med. Chem. 18: 66-71