Development of derivatives of 3, 3′-diindolylmethane as potent Leishmania donovani Bi-subunit topoisomerase IB poisons

PLoS ONE

Volumn 6, Issue 12, 2011, Pages

  Roy, Amit ^a   Chowdhury, Sayan ^a   Sengupta, Souvik ^a   Mandal, Madhumita ^a   Jaisankar, Parasuraman ^a   D'Annessa, Ilda ^b   Desideri, Alessandro ^b   Majumder, Hemanta K ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

^b UNIVERSITY OF ROME TOR VERGATA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2,2' DIMETHYL 3,3' DIINDOLYLMETHANE; 2,2' DIPHENYL 3,3' DIINDOLYLMETHANE; 3,3' DIINDOLYLMETHANE; 5,5' DIMETHOXY 3,3' DIINDOLYLMETHANE; ADENINE; ANTILEISHMANIAL AGENT; DNA; DNA TOPOISOMERASE; GENOMIC DNA; GUANOSINE; HETERODIMER; POISON; PROTEIN SUBUNIT; THYMINE; UNCLASSIFIED DRUG; 3,3'-DIINDOLYLMETHANE; DNA BINDING PROTEIN; DNA TOPOISOMERASE INHIBITOR; INDOLE DERIVATIVE;

ANIMAL CELL; APOPTOSIS; ARTICLE; BINDING ASSAY; CATALYSIS; CELL VIABILITY; CONTROLLED STUDY; DNA CLEAVAGE; DNA FRAGMENTATION; DRUG STRUCTURE; DRUG SYNTHESIS; GROWTH INHIBITION; LEISHMANIA DONOVANI; LEISHMANIASIS; MOLECULAR DOCKING; MOUSE; NONHUMAN; PROMASTIGOTE; SPECTROFLUOROMETRY; WILD TYPE; ANIMAL; BAGG ALBINO MOUSE; CELL CULTURE; CELL DEATH; CHEMICAL STRUCTURE; CHEMISTRY; CYTOLOGY; DRUG ANTAGONISM; DRUG EFFECT; DRUG RESISTANCE; ENDOCYTOSIS; ENZYMOLOGY; FLUORESCENCE; GENETICS; GENOME; GROWTH, DEVELOPMENT AND AGING; LIFE CYCLE STAGE; MACROPHAGE; METABOLISM; PARASITE; PARASITOLOGY; PROTEIN SUBUNIT;

ANIMALS; CELL DEATH; CELLS, CULTURED; DNA; DNA CLEAVAGE; DNA FRAGMENTATION; DNA TOPOISOMERASES, TYPE I; DNA-BINDING PROTEINS; DRUG RESISTANCE; ENDOCYTOSIS; FLUORESCENCE; GENOME; INDOLES; LEISHMANIA DONOVANI; LIFE CYCLE STAGES; MACROPHAGES; MICE; MICE, INBRED BALB C; MODELS, MOLECULAR; PARASITES; PROTEIN SUBUNITS; TOPOISOMERASE I INHIBITORS;

EID: 83155164547     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0028493     Document Type: Article

References (23)

1. Champoux JJ, (2001) DNA topoisomerases: structure, function, and mechanism. Annu Rev Biochem 70: 369-413.
2. Liu LF, (1989) DNA topoisomerase poisons as antitumor drugs. Annu Rev Biochem 58: 351-375.
3. Wang JC, (1996) DNA topoisomerases. Annu Rev Biochem 65: 635-692.
4. Das BB, Sen N, Ganguly A, Majumder HK, (2004) Reconstitution and functional characterization of the unusual bisubunit type I DNA Topoisomerase from Leishmania donovani. FEBS Letts 565: 81-88.
5. Das BB, Sen N, Roy A, Dasgupta SB, Ganguly A, et al. (2006) 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 Res 34: 1121-1132.
6. Hsiang YH, Hertzberg R, Hecht S, Liu LF, (1985) Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I. J Biol Chem 260: 14873-14878.
7. Das A, Sengupta T, Dasgupta A, Majumder HK, (2004) Toppisomerases of kinetoplastid parasites as potential chemotherapeutic targets. Trends in Parasitol 20: 381-387.
8. Roy A, Das BB, Ganguly A, Dasgupta SB, Khalkho NV, et al. (2008) An insight into the mechanism of inhibition of unusual bi-subunit topoisomerase I from Leishmania donovani by 3,3′-di-indolylmethane, a novel DNA topoisomerase I poison with a strong binding affinity to the enzyme. Biochem J 409: 611-622.
9. Hong C, Kim HA, Firestone GL, Bjeldanes LF, (2002) 3,3′-Diindolylmethane (DIM) induces a G (1) cell cycle arrest in human breast cancer cells that is accompanied by Sp1-mediated activation of p21 (WAF1/CIP1) expression. Carcinogenesis 23: 1297-1305.
10. Hong C, Firestone GL, Bjeldanes LF, (2002) Bcl-2 family-mediated apoptotic effects of 3,3′-diindolylmethane (DIM) in human breast cancer cells. Biochem Pharmacol 63: 1085-97.
11. Gong Y, Firestone GL, Bjeldanes LF, (2006) 3,3′-diindolylmethane is a novel topoisomerase II alpha catalytic inhibitor that induces S-phase retardation and mitotic delay in human hepatoma HepG2 cells. Mol Pharmacol 69: 1320-1327.
12. Roy A, Ganguly A, BoseDasgupta S, Das BB, Pal C, et al. (2008) Mitochondria dependent ROS-mediated programmed cell death (PCD) induced by 3, 3′-Diindolylmethane (DIM) through Inhibition of F0F1-ATP synthase in unicellular protozoan parasite Leishmania donovani. Mol Pharmacol 74: 1292-1307.
13. Roy A, BoseDasgupta S, Ganguly A, Jaisankar P, Majumder HK, (2009) Topoisomerase I gene mutations at F270 in the large subunit and N184 in the small subunit contribute to the resistance mechanism of the unicellular parasite Leishmania donovani towards 3,3′-diindolylmethane. Antimicrob Agents Chemother 53 (6): 2589-98.
14. Pal C, Dey S, Mahato SK, Vinayagam J, Pradhan PK, et al. (2007) Eco-friendly synthesis and study of new plant growth promoters: 3,3′-Diindolylmethane and its derivatives. Bioorg Med Chem Lett 17: 4924-4928.
15. Davies DR, Mushtaq A, Interthal H, Champoux JJ, Hol WG, (2006) The structure of the transition state of the heterodimeric topoisomerase I of Leishmania donovani as a vanadate complex with nicked DNA. J Mol Biol 357: 1202-1210.
16. Guex N, Diemand A, Peitsch MC, (1999) Protein modelling for all. TiBS 24: 364-367.
17. Staker BL, Hjerrild K, Feese MD, Behnke CA, Burgin AB Jr, et al. (2002) The mechanism of topoisomerase I poisoning by a camptothecin analog. Proc Natl Acad Sci U S A 99: 15387-15392.
18. Morris GM, Huey R, Lindstrom W, Sanner MF, Belew RK, et al. (2009) AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. J Comput Chem 30: 2785-2791.
19. Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, et al. (1998) Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J Comput Chem 19: 1639-1662.
20. Humphrey W, Dalke A, Schulten K, (1996) VMD: visual molecular dynamics. J Mol Graph 33: 27-28.
21. Compton MM, (1992) A biochemical hallmark of apoptosis: internucleosomal degradation of the genome. Cancer Metastasis Rev 11: 105-119.
22. Guharay J, Sengupta B, Sengupta PK, (2001) Protein-flavonol interaction: fluorescence spectroscopic study. Proteins 43 (2): 75-81.
23. Tesauro C, Fiorani P, D'Annessa I, Chillemi G, Turchi G, et al. (2010) Erybraedin C, a natural compound from the plant Bituminaria bituminosa, inhibits both the cleavage and religation activities of human topoisomerase I. Biochem J 425: 531-539.