Differential induction of Leishmania donovani bi-subunit topoisomerase I-DNA cleavage complex by selected flavones and camptothecin: Activity of flavones against camptothecin-resistant topoisomerase I

Nucleic Acids Research

Volumn 34, Issue 4, 2006, Pages 1121-1132

  Das, Benu Brata ^b   Sen, Nilkantha ^b   Roy, Amit ^b   Dasgupta, Somdeb Bose ^b   Ganguly, Agneyo ^b   Mohanta, Bikash Chandra ^a   Dinda, Biswanath ^a   Majumder, Hemanta K ^b  

^a TRIPURA UNIVERSITY   (India)

^b INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; BAICALEIN; CAMPTOTHECIN; DNA TOPOISOMERASE; DNA TOPOISOMERASE INHIBITOR; FLAVONE DERIVATIVE; LUTEOLIN; MUTANT PROTEIN; OLIGONUCLEOTIDE; PROTOZOAL DNA; QUERCETIN; TRITERPENOID; DNA; ENZYME INHIBITOR; FLAVANONE DERIVATIVE; FLAVONOID; PROTEIN SUBUNIT; PROTOZOAL PROTEIN;

ARTICLE; COMPLEX FORMATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DATA ANALYSIS; DNA CLEAVAGE; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG DNA BINDING; DRUG MECHANISM; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG RESISTANCE; ENZYME INDUCTION; ENZYME INHIBITION; ENZYME STABILITY; ENZYME SUBSTRATE; ENZYME SUBUNIT; IC 50; IN VITRO STUDY; IN VIVO STUDY; INTERCALATION COMPLEX; LEISHMANIA DONOVANI; LIGAND BINDING; MOLECULAR STABILITY; NONHUMAN; PRIORITY JOURNAL; ANIMAL; CHEMISTRY; DRUG EFFECT; ENZYMOLOGY; GENETICS; METABOLISM; MUTATION;

KINETOPLASTIDA; LEISHMANIA DONOVANI; TRYPANOSOMA;

ANIMALS; CAMPTOTHECIN; DNA; DNA TOPOISOMERASES, TYPE I, EUKARYOTIC; ENZYME INHIBITORS; FLAVANONES; FLAVONOIDS; LEISHMANIA DONOVANI; LUTEOLIN; MUTATION; PROTEIN SUBUNITS; PROTOZOAN PROTEINS; QUERCETIN;

EID: 33644862907     PISSN: 03051048     EISSN: 13624962     Source Type: Journal    
DOI: 10.1093/nar/gkj502     Document Type: Article

References (42)

1. Wang,J.C. (2002) Cellular roles of DNA topoisomerases: A molecular perspective. Nature Rev. Mol. Cell. Biol., 3, 430-440.
2. Champoux,J.J. (2001) DNA topoisomerases: Structure, function, and mechanism. Annu. Rev. Biochem., 70, 369-413.
3. Wang,J.C. (1996) DNA topoisomerases. Annu. Rev. Biochem., 65, 635-692.
4. Das,A., Dasgupta,A., Sengupta,T. and Majumder,H.K. (2004) Topoisomerases of kinetoplastid parasites as potential chemotherapeutic targets. Trends Parasitol., 20, 381-387.
5. Das,B.B., Sen,N., Ganguly,A. and Majumder,H.K. (2004) Reconstitution and functional characterization of the unusual bi-subunit type I DNA topoisomerase from Leishmania donovani. FEBS Lett., 565, 81-88.
6. Das,B.B., Sen,N., Dasgupta,S.B., Ganguly,A. and Majumder,H.K. (2005) N-terminal region of the large subunit of Leishmania donovani bisubunit topoisomerase I is involved in DNA relaxation and interaction with the smaller subunit. J. Biol. Chem., 280, 16335-16344.
7. Li,T.K. and Liu,L.F. (2001) Tumor cell death induced by topoisomerase-targeting drugs. Annu. Rev. Pharmacol. Toxicol., 41, 53-77.
8. Hertzberg,R.P., Caranfa,M.J. and Hecht,S.M. (1989) On the mechanism of topoisomerase I inhibition by camptothecin: Evidence for binding to an enzyme-DNA complex. Biochemistry, 28,4629-4638.
9. Li,C.J., Averboukh,L. and Pardee,A.B. (1993) beta-Lapachone, a novel DNA topoisomerase I inhibitor with a mode of action different from camptothecin. J. Biol. Chem., 268, 22463-22468.
10. Pommier,Y., Pourquier,P., Fan,Y. and Stumberg,D. (1998) Mechanism of action of eukaryotic DNA topoisomerase I and drugs targeted to the enzyme. Biochim. Biophys. Acta, 1400, 83-105.
11. Staker,B.L., Hjerrild,K., Feese,M.D., Behnke,C.A., Burgin,A.B., Jr and, Stewart,L. (2002) The mechanism of topoisomerase I poisoining by camptothecin analog. Proc. Natl Acad. Sci. USA, 99, 15387-15392.
12. Sen,N., Das,B.B., Ganguly,A., Mukherjee,T., Tripathi,G., Bandyopadhyay,S., Rakshit,S., Sen,T. and Majumder,H.K. (2004) Camptothecin induced mitochondrial dysfunction leading to programmed cell death in unicellular hemoflagellate Leishmania donovani. Cell Death Differ., 8, 924-936.
13. Sen,N., Das,B.B., Ganguly,A., Mukherjee,T., Bandyopadhyay,S. and Majumder,H.K. (2004) Camptothecin-induced imbalance in intracellular cation homeostasis regulates programmed cell death in unicellular hemoflagellate Leishmania donovani. J. Biol. Chem., 279, 52366-52375.
14. Bodley,A.L. and Shapiro,T.A. (1995) Molecular and cytotoxic effects of camptothecin a topoisomerase I inhibitor, on trypanosomes and Leishmania. Proc. Natl Acad. Sci. USA, 92, 3726-3730.
15. Marquis,J.F., Hardy,I. and Olivier,M. (2005) Topoisomerase I amino acid substitutions, Gly185Arg and Asp325Glu, confer camptothecin resistance in Leishmania donovani. Antimicrob. Agents Chemother., 49, 1441-1446.
16. Havsteen,B. (1983) Flavonoids, a class of natural products of high pharmacological potency. Biochem. Parmacol., 32, 1141-1148.
17. Vrijsen,R., Everaert,L. and Boeye,A. (1988) Antiviral activity of flavones and potentiation by ascorbate. J. Gen. Virol., 69, 1749-1751.
18. Yoshida,M., Sakai,T., Hosokawa,N., Marui,N., Matsumoto,K., Fujioka,A., Nishino,H. and Aoike,A. (1990) The effect of quercetin on cell cycle progression and growth of human gastric cancer cells. FEBS Lett., 260, 10-13.
19. Mittra,B., Saha,A., Chowdhury,A.R., Pal,C., Mandal,S., Mukhopadhyay,S., Bandopadhyay,S. and Majumder,H.K. (2000) Luteolin, an abundant dietary component is a potent anti-leishmanial agent that acts by inducing topoisomerase II-mediated kinetoplast DNA cleavage leading to apoptosis. Mol. Med., 6, 527-541.
20. Ciesielska,E., Gwardys,A. and Metodiewa,D. (2002) Anticancer, antiradical and antioxidative actions of novel Antoksyd S and its major components, baicalin and baicalein. Anticancer Res., 5, 2885-2891.
21. Ono,K., Nakane,H., Fukushima,M., Chermann,J.C. and Barre-Sinoussi,F. (1989) Inhibition of reverse transcriptase activity by a flavonoid compound, 5,6,7-trihydroxyflavone. Biochem. Biophys. Res. Commun., 160, 982-987.
22. Austin,C.A., Patel,S., Ono,K., Nakane,H. and Fisher,L.M. (1992) Site-specific DNA cleavage by mammalian DNA topoisomerase II induced by novel flavone and catechin derivatives. Biochem. J., 282, 883-889.
23. Zhu,M., Rajamani,S., Kaylor,J., Han,S., Zhou,F. and Fink,A.L. (2004) The flavonoid baicalein inhibits fibrillation of alpha-synuclein and disaggregates existing fibrils. J. Biol. Chem., 279, 26846-26857.
24. Chowdhury,A.R., Mandal,S., Goswami,A., Ghosh,M., Mandal,L., Chakraborty,D., Ganguly,A., Tripathi,G., Mukhopadhyay,S., Bandyopadhyay,S. and Majumder,H.K (2003) Mol. Med., 9, 26-36.
25. Guharay,J., Sengupta,B. and Sengupta,P.K. (2001) Protein-flavonol interaction: Fluorescence spectroscopic study. Proteins, 43, 75-81.
26. Chen,G.L., Yang,L., Rowe,T.C., Halligan,B.D., Tewey,K.M. and Liu,L.F. (1984) Nonintercalative antitumor drugs interfere with the breakage-reunion reaction of mammalian DNA topoisomerase II. J. Biol. Chem., 259, 13560-13566.
27. Chowdhury,A.R., Sharma,S., Mandal,S., Goswami,A., Mukhopadhyay,S. and Majumder,H.K. (2002) Luteolin, an emerging anti-cancer flavonoid, poisons eukaryotic DNA topoisomerase I. Biochem. J., 366, 653-661.
28. Fortune,J.M. and Osheroff,N. (1998) Merbarone inhibits the catalytic activity of human topoisomerase IIα by blocking DNA cleavage. J. Biol. Chem., 273, 17643-17650.
29. Li,C.J., Averboukh,L. and Pardee,A.B. (1993) β-Lapachone, a novel DNA topoisomerase I inhibitor with a mode of action different from camptothecin. J. Biol. Chem., 268, 22463-22468.
30. Ahn,H.C., Lee,S.Y., Kim,J.W., Son,W.S., Shin,C.G. and Lee,B.J. (2001) Binding aspects of baicalein to HIV-1 integrase. Mol. Cells, 12, 127-130.
31. Scatchard,G. (1949) Attraction of protein for small molecules and ions. Ann. N.Y. Acad. Sci., 51, 660-671.
32. Capranico,G., Binaschi,M., Borgnetto,M.E., Zunino,F. and Palumbo,M. (1997) A protein-mediated mechanism for the DNA sequence-specific action of topoisomerase II poisons. Trends Pharmacol. Sci., 18, 323-329.
33. Redinbo,M.R., Stewart,L., Kuhn,P., Champoux,J.J. and Hol,W.G. (1998) Crystal structures of human topoisomerase I in covalent and noncovalent complexes with DNA. Science, 279, 1504-1513.
34. Redinbo,M.R., Champoux,J.J. and Hol,W.G. (1999) Structural insights into the function of type IB topoisomerases. Curr. Opin. Struct. Biol., 9, 29-36.
35. Champoux,J.J. (2000) Structure-based analysis of the effects of camptothecin on the activities of Human topoisomerase I. Ann. N.Y. Acad. Sci., 922, 56-64.
36. Boege,F., Straub,T., Kehr,A., Bosenberg,C., Christiansen,K., Anderson,A., Jacob,F. and Kohrle,J. (1996) Selected novel flavones inhibit the DNA binding or the DNA relaxation step of eukaryotic topoisomerase I. J. Biol. Chem., 271, 2262-2270.
37. Webb,M.R. and Ebeller,S.E. (2004) Comparative analysis of topoisomerase IB inhibition and DNA intercalation by flavonoids and similar compounds: structural determinates of activity. Biochem. J., 384, 527-541.
38. Sengupta,T., Mukherjee,M., Das,A., Mandal,C., Das,R., Mukherjee,T. and Majumder,H.K. (2005) Characterization of the ATPase activity of topoisomerase II from Leishmania donovani and identification of residues conferring resistance to etoposide. Biochem J., 390, 419-426.
39. Xu,H., Ziegelin,G., Schroder,W., Frank,J., Ayora,S., Alonso,J.C., Lanka,E. and Saenger,W. (2001) Flavones inhibit the hexameric replicative helicase RepA. Nucleic Acids Res., 29, 5058-5066.
40. Wadkins,R.M. and Graves,D.E. (1989) Thermodynamics of the interactions of m-AMSA and o-AMSA with nucleic acids: Influence of ionic strength and DNA base composition. Nucleic Acids Res., 17, 9933-9946.
41. Chow,K.C., Macdonald,T.L. and Ross,W.E. (1988) DNA binding by epipodophyllotoxins and N-acetyl anthracyclines: Implication for mechanism of topoisomerase II inhibition. Mol. Pharmacol., 34, 467-473.
42. LePecq,J.B. and Paoletti,C. (1976) A fluorescence complex between ethidium bromide and nucleic acids. Physical-chemical characterization. J. Mol. Biol., 27, 87-106.