Literature DB >> 18824603

Activity of indenoisoquinolines against African trypanosomes.

Rahul P Bakshi1, Dongpei Sang, Andrew Morrell, Mark Cushman, Theresa A Shapiro.   

Abstract

African trypanosomiasis (sleeping sickness), caused by protozoan Trypanosoma brucei species, is a debilitating disease that is lethal if untreated. Available drugs are antiquated, toxic, and compromised by emerging resistance. The indenoisoquinolines are a class of noncamptothecin topoisomerase IB poisons that are under development as anticancer agents. We tested a variety of indenoisoquinolines for their ability to kill T. brucei. Indenoisoquinolines proved trypanocidal at submicromolar concentrations in vitro. Structure-activity analysis yielded motifs that enhanced potency, including alkylamino substitutions on N-6, methoxy groups on C-2 and C-3, and a methylenedioxy bridge between C-8 and C-9. Detailed analysis of eight water-soluble indenoisoquinolines demonstrated that in trypanosomes the compounds inhibited DNA synthesis and acted as topoisomerase poisons. Testing these compounds on L1210 mouse leukemia cells revealed that all eight were more effective against trypanosomes than against mammalian cells. In preliminary in vivo experiments one compound delayed parasitemia and extended survival in mice subjected to a lethal trypanosome challenge. The indenoisoquinolines provide a promising lead for the development of drugs against sleeping sickness.

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Year:  2008        PMID: 18824603      PMCID: PMC2612167          DOI: 10.1128/AAC.00650-07

Source DB:  PubMed          Journal:  Antimicrob Agents Chemother        ISSN: 0066-4804            Impact factor:   5.191


  41 in total

1.  Evaluation of indenoisoquinoline topoisomerase I inhibitors using a hollow fiber assay.

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Journal:  Bioorg Med Chem Lett       Date:  2006-06-05       Impact factor: 2.823

2.  Effects of minor groove binding drugs on camptothecin-induced DNA lesions in L1210 nuclei.

Authors:  M M McHugh; R D Sigmund; T A Beerman
Journal:  Biochem Pharmacol       Date:  1990-02-15       Impact factor: 5.858

Review 3.  Understanding the dose-effect relationship: clinical application of pharmacokinetic-pharmacodynamic models.

Authors:  N H Holford; L B Sheiner
Journal:  Clin Pharmacokinet       Date:  1981 Nov-Dec       Impact factor: 6.447

4.  Synthesis and evaluation of indenoisoquinoline topoisomerase I inhibitors substituted with nitrogen heterocycles.

Authors:  Muthukaman Nagarajan; Andrew Morrell; Alexandra Ioanoviciu; Smitha Antony; Glenda Kohlhagen; Keli Agama; Melinda Hollingshead; Yves Pommier; Mark Cushman
Journal:  J Med Chem       Date:  2006-10-19       Impact factor: 7.446

5.  Polyamine derivatives as inhibitors of trypanothione reductase and assessment of their trypanocidal activities.

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Journal:  Bioorg Med Chem       Date:  1997-12       Impact factor: 3.641

6.  Synthesis and anticancer activity of simplified indenoisoquinoline topoisomerase I inhibitors lacking substituents on the aromatic rings.

Authors:  Muthukaman Nagarajan; Andrew Morrell; Brian C Fort; Marintha Rae Meckley; Smitha Antony; Glenda Kohlhagen; Yves Pommier; Mark Cushman
Journal:  J Med Chem       Date:  2004-11-04       Impact factor: 7.446

7.  Synthesis of nitrated indenoisoquinolines as topoisomerase I inhibitors.

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Journal:  Bioorg Med Chem Lett       Date:  2004-07-16       Impact factor: 2.823

8.  Antitrypanosomal activity of camptothecin analogs. Structure-activity correlations.

Authors:  A L Bodley; M C Wani; M E Wall; T A Shapiro
Journal:  Biochem Pharmacol       Date:  1995-09-28       Impact factor: 5.858

9.  Protein-linked DNA strand breaks induced by NSC 314622, a novel noncamptothecin topoisomerase I poison.

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Journal:  Mol Pharmacol       Date:  1998-07       Impact factor: 4.436

10.  Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I.

Authors:  Y H Hsiang; R Hertzberg; S Hecht; L F Liu
Journal:  J Biol Chem       Date:  1985-11-25       Impact factor: 5.157

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Journal:  Antimicrob Agents Chemother       Date:  2012-07-30       Impact factor: 5.191

4.  Activity of Aromathecins against African Trypanosomes.

Authors:  Nathaniel P Nenortas; Maris A Cinelli; Andrew E Morrell; Mark Cushman; Theresa A Shapiro
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5.  Neglected disease - african sleeping sickness: recent synthetic and modeling advances.

Authors:  Sarvesh K Paliwal; Ankita Narayan Verma; Shailendra Paliwal
Journal:  Sci Pharm       Date:  2011-05-10

6.  Indole trimers with antibacterial activity against Gram-positive organisms produced using combinatorial biocatalysis.

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Journal:  AMB Express       Date:  2015-06-26       Impact factor: 3.298

Review 7.  Trypanosomatids topoisomerase re-visited. New structural findings and role in drug discovery.

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8.  Topoisomerase IB poisons induce histone H2A phosphorylation as a response to DNA damage in Leishmania infantum.

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9.  Antiparasitic effect of synthetic aromathecins on Leishmania infantum.

Authors:  Rosa M Reguera; Raquel Álvarez-Velilla; Bárbara Domínguez-Asenjo; Camino Gutiérrez-Corbo; Rafael Balaña-Fouce; Mark Cushman; Yolanda Pérez-Pertejo
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