Literature DB >> 24900847

Digitoxin analogues with improved anticytomegalovirus activity.

Hongyi Cai1, Hua-Yu L Wang2, Rajkumar Venkatadri1, De-Xue Fu1, Michael Forman3, Sumit O Bajaj2, Hongyan Li2, George A O'Doherty2, Ravit Arav-Boger1.   

Abstract

Cardiac glycosides are potent inhibitors of cancer cell growth and possess antiviral activities at nanomolar concentrations. In this study we evaluated the anticytomegalovirus (CMV) activity of digitoxin and several of its analogues. We show that sugar type and sugar length attached to the steroid core structure affects its anticytomegalovirus activity. Structure-activity relationship (SAR) studies identified the l-sugar containing cardiac glycosides as having improved anti-CMV activity and may lead to better understanding of how these compounds inhibit CMV replication.

Entities:  

Keywords:  Cardiac glycosides; cytomegalovirus; digitoxin analogues; virus inhibition

Year:  2014        PMID： 24900847      PMCID： PMC4027591          DOI： 10.1021/ml400529q

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  25 in total

1.  Digitoxin inhibits the growth of cancer cell lines at concentrations commonly found in cardiac patients.

Authors:  Miguel López-Lázaro; Nuria Pastor; Sami S Azrak; María Jesús Ayuso; Caroline A Austin; Felipe Cortés
Journal:  J Nat Prod       Date:  2005-11       Impact factor: 4.050

2.  Selectivity of digitalis glycosides for isoforms of human Na,K-ATPase.

Authors:  Adriana Katz; Yael Lifshitz; Elizabeta Bab-Dinitz; Einat Kapri-Pardes; Rivka Goldshleger; Daniel M Tal; Steven J D Karlish
Journal:  J Biol Chem       Date:  2010-04-13       Impact factor: 5.157

3.  Synthesis and Evaluation of the α-D-/α-L-Rhamnosyl and Amicetosyl Digitoxigenin Oligomers as Anti-tumor Agents.

Authors:  Hua-Yu Leo Wang; Yon Rojanasakul; George A O'Doherty
Journal:  ACS Med Chem Lett       Date:  2011-04-14       Impact factor: 4.345

4.  A stereoselective synthesis of digitoxin and digitoxigen mono- and bisdigitoxoside from digitoxigenin via a palladium-catalyzed glycosylation.

Authors:  Maoquan Zhou; George A O'Doherty
Journal:  Org Lett       Date:  2006-09-14       Impact factor: 6.005

5.  A Direct Comparison of the Anticancer Activities of Digitoxin MeON-Neoglycosides and O-Glycosides: Oligosaccharide Chain Length-Dependent Induction of Caspase-9-Mediated Apoptosis.

Authors:  Anand Krishnan V Iyer; Maoquan Zhou; Neelam Azad; Hosam Elbaz; Leo Wang; Derek K Rogalsky; Yon Rojanasakul; George A O'Doherty; Joseph M Langenhan
Journal:  ACS Med Chem Lett       Date:  2010-07-12       Impact factor: 4.345

6.  De novo approach to 2-deoxy-beta-glycosides: asymmetric syntheses of digoxose and digitoxin.

Authors:  Maoquan Zhou; George A O'Doherty
Journal:  J Org Chem       Date:  2007-03-06       Impact factor: 4.354

Review 7.  Myocardial Na,K-ATPase: the molecular basis for the hemodynamic effect of digoxin therapy in congestive heart failure.

Authors:  K Kjeldsen; A Nørgaard; M Gheorghiade
Journal:  Cardiovasc Res       Date:  2002-09       Impact factor: 10.787

Review 8.  The de novo synthesis of oligosaccharides: application to the medicinal chemistry SAR-study of digitoxin.

Authors:  Maoquan Zhou; George O'Doherty
Journal:  Curr Top Med Chem       Date:  2008       Impact factor: 3.295

9.  C3'/C4'-Stereochemical Effects of Digitoxigenin α-L-/α-D-Glycoside in Cancer Cytotoxicity.

Authors:  John W Hinds; Sean B McKenna; Ehesan U Sharif; Hua-Yu L Wang; Novruz G Akhmedov; George A O'Doherty
Journal:  ChemMedChem       Date:  2012-11-08       Impact factor: 3.466

10.  Discrepancies between metabolic activity and DNA content as tool to assess cell proliferation in cancer research.

Authors:  Verena M C Quent; Daniela Loessner; Thor Friis; Johannes C Reichert; Dietmar W Hutmacher
Journal:  J Cell Mol Med       Date:  2010-01-15       Impact factor: 5.310
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  11 in total

1.  Modular Total Synthesis and Cell-Based Anticancer Activity Evaluation of Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of Oxygenation.

Authors:  Hem Raj Khatri; Bijay Bhattarai; Will Kaplan; Zhongzheng Li; Marcus John Curtis Long; Yimon Aye; Pavel Nagorny
Journal:  J Am Chem Soc       Date:  2019-03-14       Impact factor: 15.419

2.  Regioselective single pot C3-glycosylation of strophanthidol using methylboronic acid as a transient protecting group.

Authors:  Jia-Hui Tay; Valentin Dorokhov; Sibin Wang; Pavel Nagorny
Journal:  J Antibiot (Tokyo)       Date:  2019-04-04       Impact factor: 2.649

3.  Digitoxin Suppresses Human Cytomegalovirus Replication via Na+, K+/ATPase α1 Subunit-Dependent AMP-Activated Protein Kinase and Autophagy Activation.

Authors:  Rupkatha Mukhopadhyay; Rajkumar Venkatadri; Jenny Katsnelson; Ravit Arav-Boger
Journal:  J Virol       Date:  2018-02-26       Impact factor: 5.103

4.  Synthesis and direct comparison of the anticancer activities of phomopsolides D and E and two 7-oxa-/7-aza-analogues.

Authors:  Alhanouf Z Aljahdali; Seth A Freedman; Jana Scott; Miaosheng Li; George A O'Doherty
Journal:  Medchemcomm       Date:  2019-05-08       Impact factor: 3.597

5.  Reagent Controlled Direct Dehydrative Glycosylation with 2-Deoxy Sugars: Construction of the Saquayamycin Z Pentasaccharide.

Authors:  J Colin Mizia; Clay S Bennett
Journal:  Org Lett       Date:  2019-07-15       Impact factor: 6.005

6.  Stereochemical Structure Activity Relationship Studies (S-SAR) of Tetrahydrolipstatin.

Authors:  Xiaofan Liu; Yanping Wang; Richard I Duclos; George A O'Doherty
Journal:  ACS Med Chem Lett       Date:  2018-02-21       Impact factor: 4.345

7.  Convallatoxin-Induced Reduction of Methionine Import Effectively Inhibits Human Cytomegalovirus Infection and Replication.

Authors:  Tobias Cohen; John D Williams; Timothy J Opperman; Roberto Sanchez; Nell S Lurain; Domenico Tortorella
Journal:  J Virol       Date:  2016-11-14       Impact factor: 5.103

8.  A ring closing metathesis strategy for carbapyranosides of xylose and arabinose.

Authors:  Clayton E Mattis; David R Mootoo
Journal:  Carbohydr Res       Date:  2016-03-16       Impact factor: 2.104

Review 9.  GDP-Mannose 3,5-Epimerase: A View on Structure, Mechanism, and Industrial Potential.

Authors:  Koen Beerens; Ophelia Gevaert; Tom Desmet
Journal:  Front Mol Biosci       Date:  2022-01-11

Review 10.  Bright and Early: Inhibiting Human Cytomegalovirus by Targeting Major Immediate-Early Gene Expression or Protein Function.

Authors:  Catherine S Adamson; Michael M Nevels
Journal:  Viruses       Date:  2020-01-16       Impact factor: 5.048
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