Literature DB >> 23259865

Synthesis and biological evaluation of indenoisoquinolines that inhibit both tyrosyl-DNA phosphodiesterase I (Tdp1) and topoisomerase I (Top1).

Martin Conda-Sheridan1, P V Narasimha Reddy, Andrew Morrell, Brooklyn T Cobb, Christophe Marchand, Keli Agama, Adel Chergui, Amélie Renaud, Andrew G Stephen, Lakshman K Bindu, Yves Pommier, Mark Cushman.   

Abstract

Tyrosyl-DNA phosphodin class="Chemical">esterase I (Tdp1) plays a key role in the repair of damaged DNA resulting from the topoisomerase I (Top1) inhibitor camptothecin and a variety of other DNA-damaging anticancer agents. This report documents the design, synthesis, and evaluation of new indenoisoquinolines that are dual inhibitors of both Tdp1 and Top1. Enzyme inhibitory data and cytotoxicity data from human cancer cell cultures were used to establish structure-activity relationships. The potencies of the indenoisoquinolines against Tdp1 ranged from 5 μM to 111 μM, which places the more active compounds among the most potent known inhibitors of this target. The cytotoxicity mean graph midpoints ranged from 0.02 to 2.34 μM. Dual Tdp1-Top1 inhibitors are of interest because the Top1 and Tdp1 inhibitory activities could theoretically work synergistically to create more effective anticancer agents.

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Year:  2012        PMID: 23259865      PMCID: PMC3542538          DOI: 10.1021/jm3014458

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  34 in total

1.  Conversion of topoisomerase I cleavage complexes on the leading strand of ribosomal DNA into 5'-phosphorylated DNA double-strand breaks by replication runoff.

Authors:  D Strumberg; A A Pilon; M Smith; R Hickey; L Malkas; Y Pommier
Journal:  Mol Cell Biol       Date:  2000-06       Impact factor: 4.272

2.  Cellular topoisomerase I inhibition and antiproliferative activity by MJ-III-65 (NSC 706744), an indenoisoquinoline topoisomerase I poison.

Authors:  Smitha Antony; Glenda Kohlhagen; Keli Agama; Muthusamy Jayaraman; Shousong Cao; Farukh A Durrani; Youcef M Rustum; Mark Cushman; Yves Pommier
Journal:  Mol Pharmacol       Date:  2004-11-05       Impact factor: 4.436

3.  A systematic study of nitrated indenoisoquinolines reveals a potent topoisomerase I inhibitor.

Authors:  Andrew Morrell; Smitha Antony; Glenda Kohlhagen; Yves Pommier; Mark Cushman
Journal:  J Med Chem       Date:  2006-12-28       Impact factor: 7.446

4.  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

5.  Pathways for repair of topoisomerase I covalent complexes in Saccharomyces cerevisiae.

Authors:  J J Pouliot; C A Robertson; H A Nash
Journal:  Genes Cells       Date:  2001-08       Impact factor: 1.891

6.  Synthesis of benz[d]indeno[1,2-b]pyran-5,11-diones: versatile intermediates for the design and synthesis of topoisomerase I inhibitors.

Authors:  Andrew Morrell; Smitha Antony; Glenda Kohlhagen; Yves Pommier; Mark Cushman
Journal:  Bioorg Med Chem Lett       Date:  2006-01-25       Impact factor: 2.823

7.  New colorimetric cytotoxicity assay for anticancer-drug screening.

Authors:  P Skehan; R Storeng; D Scudiero; A Monks; J McMahon; D Vistica; J T Warren; H Bokesch; S Kenney; M R Boyd
Journal:  J Natl Cancer Inst       Date:  1990-07-04       Impact factor: 13.506

8.  Synthesis of nitrated indenoisoquinolines as topoisomerase I inhibitors.

Authors:  Andrew Morrell; Smitha Antony; Glenda Kohlhagen; Yves Pommier; Mark Cushman
Journal:  Bioorg Med Chem Lett       Date:  2004-07-16       Impact factor: 2.823

9.  Differential induction of topoisomerase I-DNA cleavage complexes by the indenoisoquinoline MJ-III-65 (NSC 706744) and camptothecin: base sequence analysis and activity against camptothecin-resistant topoisomerases I.

Authors:  Smitha Antony; Muthusamy Jayaraman; Gary Laco; Glenda Kohlhagen; Kurt W Kohn; Mark Cushman; Yves Pommier
Journal:  Cancer Res       Date:  2003-11-01       Impact factor: 12.701

10.  Novel high-throughput electrochemiluminescent assay for identification of human tyrosyl-DNA phosphodiesterase (Tdp1) inhibitors and characterization of furamidine (NSC 305831) as an inhibitor of Tdp1.

Authors:  Smitha Antony; Christophe Marchand; Andrew G Stephen; Laurent Thibaut; Keli K Agama; Robert J Fisher; Yves Pommier
Journal:  Nucleic Acids Res       Date:  2007-06-18       Impact factor: 16.971

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  18 in total

Review 1.  Tyrosyl-DNA-phosphodiesterases (TDP1 and TDP2).

Authors:  Yves Pommier; Shar-yin N Huang; Rui Gao; Benu Brata Das; Junko Murai; Christophe Marchand
Journal:  DNA Repair (Amst)       Date:  2014-05-22

2.  Discovery of potent indenoisoquinoline topoisomerase I poisons lacking the 3-nitro toxicophore.

Authors:  Daniel E Beck; Monica Abdelmalak; Wei Lv; P V Narasimha Reddy; Gabrielle S Tender; Elizaveta O'Neill; Keli Agama; Christophe Marchand; Yves Pommier; Mark Cushman
Journal:  J Med Chem       Date:  2015-04-24       Impact factor: 7.446

3.  Synthesis and biological evaluation of nitrated 7-, 8-, 9-, and 10-hydroxyindenoisoquinolines as potential dual topoisomerase I (Top1)-tyrosyl-DNA phosphodiesterase I (TDP1) inhibitors.

Authors:  Trung Xuan Nguyen; Monica Abdelmalak; Christophe Marchand; Keli Agama; Yves Pommier; Mark Cushman
Journal:  J Med Chem       Date:  2015-03-26       Impact factor: 7.446

4.  Identification of novel PARP inhibitors using a cell-based TDP1 inhibitory assay in a quantitative high-throughput screening platform.

Authors:  Junko Murai; Christophe Marchand; Sampada A Shahane; Hongmao Sun; Ruili Huang; Yiping Zhang; Adel Chergui; Jiuping Ji; James H Doroshow; Ajit Jadhav; Shunichi Takeda; Menghang Xia; Yves Pommier
Journal:  DNA Repair (Amst)       Date:  2014-04-29

5.  Synthesis, anti-cancer screening and tyrosyl-DNA phosphodiesterase 1 (Tdp1) inhibition activity of novel piperidinyl sulfamides.

Authors:  Jung Ho Jun; Vineet Kumar; Thomas S Dexheimer; Iwona Wedlich; Marc C Nicklaus; Yves Pommier; Sanjay V Malhotra
Journal:  Eur J Pharm Sci       Date:  2017-10-13       Impact factor: 4.384

6.  Design, synthesis, and biological evaluation of indenoisoquinoline rexinoids with chemopreventive potential.

Authors:  Martin Conda-Sheridan; Eun-Jung Park; Daniel E Beck; P V Narasimha Reddy; Trung X Nguyen; Bingjie Hu; Lian Chen; Jerry J White; Richard B van Breemen; John M Pezzuto; Mark Cushman
Journal:  J Med Chem       Date:  2013-03-08       Impact factor: 7.446

7.  Design, Synthesis, and Biological Evaluation of Potential Prodrugs Related to the Experimental Anticancer Agent Indotecan (LMP400).

Authors:  Peng-Cheng Lv; Mohamed S A Elsayed; Keli Agama; Christophe Marchand; Yves Pommier; Mark Cushman
Journal:  J Med Chem       Date:  2016-04-20       Impact factor: 7.446

8.  The influence of an enamine usnic acid derivative (a tyrosyl-DNA phosphodiesterase 1 inhibitor) on the therapeutic effect of topotecan against transplanted tumors in vivo.

Authors:  V P Nikolin; N A Popova; V I Kaledin; O A Luzina; A L Zakharenko; N F Salakhutdinov; O I Lavrik
Journal:  Clin Exp Metastasis       Date:  2021-08-09       Impact factor: 5.150

9.  Discovery, Synthesis, and Evaluation of Oxynitidine Derivatives as Dual Inhibitors of DNA Topoisomerase IB (TOP1) and Tyrosyl-DNA Phosphodiesterase 1 (TDP1), and Potential Antitumor Agents.

Authors:  Xiao-Ru Zhang; Hao-Wen Wang; Wen-Lin Tang; Yu Zhang; Hui Yang; De-Xuan Hu; Azhar Ravji; Christophe Marchand; Evgeny Kiselev; Kwabena Ofori-Atta; Keli Agama; Yves Pommier; Lin-Kun An
Journal:  J Med Chem       Date:  2018-10-31       Impact factor: 7.446

10.  Investigation of the Structure-Activity Relationships of Aza-A-Ring Indenoisoquinoline Topoisomerase I Poisons.

Authors:  Daniel E Beck; P V Narasimha Reddy; Wei Lv; Monica Abdelmalak; Gabrielle S Tender; Sophia Lopez; Keli Agama; Christophe Marchand; Yves Pommier; Mark Cushman
Journal:  J Med Chem       Date:  2016-04-12       Impact factor: 7.446

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