Literature DB >> 23290252

Structure-based drug design and potent anti-cancer activity of tricyclic 5:7:5-fused diimidazo[4,5-d:4',5'-f][1,3]diazepines.

Atul Kondaskar1, Shilpi Kondaskar, James C Fishbein, Brandon A Carter-Cooper, Rena G Lapidus, Mariola Sadowska, Martin J Edelman, Ramachandra S Hosmane.   

Abstract

Judicial structural modifications of 5:7-fused ring-expanded class="Chemical">nucleosides (class="Chemical">n class="Chemical">RENs), based on molecular modeling studies with one of its known targets, human RNA helicase (hDDX3), led to the lead, novel, 5:7-5-fused tricyclic heterocycle (1). The latter exhibited promising broad-spectrum in vitro anti-cancer activity against a number of cancer cell lines screened. This paper describes our systematic, albeit limited, structure-activity relationship (SAR) studies on this lead compound, which produced a number of analogs with broad-spectrum in vitro anti-cancer activities against lung, breast, prostate, and ovarian cancer cell lines, in particular compounds 15i, 15j, 15m and 15n which showed IC(50) values in submicromolar to micromolar range, and are worthy of further explorations. The SAR data also enabled us to propose a tentative SAR model for future SAR efforts for ultimate realization of optimally active and minimally toxic anti-cancer compounds based on the diimidazo[4,5-d:4',5'-f][1,3]diazepine structural skeleton of the lead compound 1.
Copyright © 2012 Elsevier Ltd. All rights reserved.

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Year:  2012        PMID: 23290252      PMCID: PMC3546142          DOI: 10.1016/j.bmc.2012.11.050

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  22 in total

1.  The DEAD-box RNA helicase DDX3 interacts with DDX5, co-localizes with it in the cytoplasm during the G2/M phase of the cycle, and affects its shuttling during mRNP export.

Authors:  Yeo-Jin Choi; Seong-Gene Lee
Journal:  J Cell Biochem       Date:  2012-03       Impact factor: 4.429

2.  Novel ring-expanded nucleoside analogs exhibit potent and selective inhibition of hepatitis B virus replication in cultured human hepatoblastoma cells.

Authors:  Ramesh K Sood; Vishweshwar S Bhadti; Ali I Fattom; Robert B Naso; Brent E Korba; Earl R Kern; Huan-Ming Chen; Ramachandra S Hosmane
Journal:  Antiviral Res       Date:  2002-02       Impact factor: 5.970

3.  Novel, Broad Spectrum Anti-Cancer Agents Containing the Tricyclic 5:7:5-Fused Diimidazodiazepine Ring System.

Authors:  Atul Kondaskar; Shilpi Kondaskar; Raj Kumar; James C Fishbein; Nidal Muvarak; Rena G Lapidus; Mariola Sadowska; Martin J Edelman; Guus M Bol; Farhad Vesuna; Venu Raman; Ramachandra S Hosmane
Journal:  ACS Med Chem Lett       Date:  2010-12-31       Impact factor: 4.345

4.  Synthesis and in vitro anti-hepatitis B and C virus activities of ring-expanded ('fat') nucleobase analogues containing the imidazo[4,5-e][1,3]diazepine-4,8-dione ring system.

Authors:  Peng Zhang; Ning Zhang; Brent E Korba; Ramachandra S Hosmane
Journal:  Bioorg Med Chem Lett       Date:  2005-10-05       Impact factor: 2.823

Review 5.  RNA helicases at work: binding and rearranging.

Authors:  Eckhard Jankowsky
Journal:  Trends Biochem Sci       Date:  2011-01       Impact factor: 13.807

Review 6.  Ring-expanded ("Fat") nucleosides as broad-spectrum anticancer and antiviral agents.

Authors:  Ramachandra S Hosmane
Journal:  Curr Top Med Chem       Date:  2002-10       Impact factor: 3.295

Review 7.  The current understanding of Ded1p/DDX3 homologs from yeast to human.

Authors:  Woan-Yuh Tarn; Tien-Hsien Chang
Journal:  RNA Biol       Date:  2009-01-18       Impact factor: 4.652

8.  Ring-expanded ("fat") nucleoside and nucleotide analogues exhibit potent in vitro activity against flaviviridae NTPases/helicases, including those of the West Nile virus, hepatitis C virus, and Japanese encephalitis virus.

Authors:  Ning Zhang; Huan-Ming Chen; Verena Koch; Herbert Schmitz; Ching-Len Liao; Maria Bretner; Vishweshwar S Bhadti; Ali I Fattom; Robert B Naso; Ramachandra S Hosmane; Peter Borowski
Journal:  J Med Chem       Date:  2003-09-11       Impact factor: 7.446

9.  A motif unique to the human DEAD-box protein DDX3 is important for nucleic acid binding, ATP hydrolysis, RNA/DNA unwinding and HIV-1 replication.

Authors:  Anna Garbelli; Sandra Beermann; Giulia Di Cicco; Ursula Dietrich; Giovanni Maga
Journal:  PLoS One       Date:  2011-05-12       Impact factor: 3.240

Review 10.  DExD/H box RNA helicases: multifunctional proteins with important roles in transcriptional regulation.

Authors:  Frances V Fuller-Pace
Journal:  Nucleic Acids Res       Date:  2006-08-25       Impact factor: 16.971

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  4 in total

1.  RK-33 Radiosensitizes Prostate Cancer Cells by Blocking the RNA Helicase DDX3.

Authors:  Min Xie; Farhad Vesuna; Saritha Tantravedi; Guus M Bol; Marise R Heerma van Voss; Katriana Nugent; Reem Malek; Kathleen Gabrielson; Paul J van Diest; Phuoc T Tran; Venu Raman
Journal:  Cancer Res       Date:  2016-09-12       Impact factor: 12.701

2.  Structure-Based Optimization of Inhibitors of the Aspartic Protease Endothiapepsin.

Authors:  Alwin M Hartman; Milon Mondal; Nedyalka Radeva; Gerhard Klebe; Anna K H Hirsch
Journal:  Int J Mol Sci       Date:  2015-08-14       Impact factor: 5.923

3.  NZ51, a ring-expanded nucleoside analog, inhibits motility and viability of breast cancer cells by targeting the RNA helicase DDX3.

Authors:  Min Xie; Farhad Vesuna; Mahendran Botlagunta; Guus Martinus Bol; Ashley Irving; Yehudit Bergman; Ramachandra S Hosmane; Yoshinori Kato; Paul T Winnard; Venu Raman
Journal:  Oncotarget       Date:  2015-10-06

Review 4.  DDX3, a potential target for cancer treatment.

Authors:  Guus Martinus Bol; Min Xie; Venu Raman
Journal:  Mol Cancer       Date:  2015-11-05       Impact factor: 27.401

  4 in total

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