Literature DB >> 20667821

Structure-function correlation of G6, a novel small molecule inhibitor of Jak2: indispensability of the stilbenoid core.

Anurima Majumder1, Lakshmanan Govindasamy, Andrew Magis, Róbert Kiss, Tímea Polgár, Rebekah Baskin, Robert W Allan, Mavis Agbandje-McKenna, Gary W Reuther, György M Keseru, Kirpal S Bisht, Peter P Sayeski.   

Abstract

Somatic mutations in the Jak2 protein, such as V617F, cause aberrant Jak/STAT signaling and can lead to the development of myeloproliferative neoplasms. This discovery has led to the search for small molecule inhibitors that target Jak2. Using structure-based virtual screening, our group recently identified a novel small molecule inhibitor of Jak2 named G6. Here, we identified a structure-function correlation of this compound. Specifically, five derivative compounds of G6 having structural similarity to the original lead compound were obtained and analyzed for their ability to (i) inhibit Jak2-V617F-mediated cell growth, (ii) inhibit the levels of phospho-Jak2, phospho-STAT3, and phospho-STAT5; (iii) induce apoptosis in human erythroleukemia cells; and (iv) suppress pathologic cell growth of Jak2-V617F-expressing human bone marrow cells ex vivo. Additionally, we computationally examined the interactions of these compounds with the ATP-binding pocket of the Jak2 kinase domain. We found that the stilbenoid core-containing derivatives of G6 significantly inhibited Jak2-V617F-mediated cell proliferation in a time- and dose-dependent manner. They also inhibited phosphorylation of Jak2, STAT3, and STAT5 proteins within cells, resulting in higher levels of apoptosis via the intrinsic apoptotic pathway. Finally, the stilbenoid derivatives inhibited the pathologic growth of Jak2-V617F-expressing human bone marrow cells ex vivo. Collectively, our data demonstrate that G6 has a stilbenoid core that is indispensable for maintaining its Jak2 inhibitory potential.

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Year:  2010        PMID: 20667821      PMCID: PMC2951214          DOI: 10.1074/jbc.M110.168211

Source DB:  PubMed          Journal:  J Biol Chem        ISSN: 0021-9258            Impact factor:   5.157


  43 in total

1.  Activated Jak2 with the V617F point mutation promotes G1/S phase transition.

Authors:  Christoph Walz; Brian J Crowley; Heidi E Hudon; Jessica L Gramlich; Donna S Neuberg; Klaus Podar; James D Griffin; Martin Sattler
Journal:  J Biol Chem       Date:  2006-04-21       Impact factor: 5.157

Review 2.  A BCR-JAK2 fusion gene as the result of a t(9;22)(p24;q11.2) translocation in a patient with a clinically typical chronic myeloid leukemia.

Authors:  Frank Griesinger; Heike Hennig; Frauke Hillmer; Martina Podleschny; Rainer Steffens; Andreas Pies; Bernhard Wörmann; Detlef Haase; Stefan K Bohlander
Journal:  Genes Chromosomes Cancer       Date:  2005-11       Impact factor: 5.006

3.  A unique clonal JAK2 mutation leading to constitutive signalling causes polycythaemia vera.

Authors:  Chloé James; Valérie Ugo; Jean-Pierre Le Couédic; Judith Staerk; François Delhommeau; Catherine Lacout; Loïc Garçon; Hana Raslova; Roland Berger; Annelise Bennaceur-Griscelli; Jean Luc Villeval; Stefan N Constantinescu; Nicole Casadevall; William Vainchenker
Journal:  Nature       Date:  2005-04-28       Impact factor: 49.962

4.  The structural basis of Janus kinase 2 inhibition by a potent and specific pan-Janus kinase inhibitor.

Authors:  Isabelle S Lucet; Emmanuelle Fantino; Michelle Styles; Rebecca Bamert; Onisha Patel; Sophie E Broughton; Mark Walter; Christopher J Burns; Herbert Treutlein; Andrew F Wilks; Jamie Rossjohn
Journal:  Blood       Date:  2005-09-20       Impact factor: 22.113

5.  Identification of an acquired JAK2 mutation in polycythemia vera.

Authors:  Runxiang Zhao; Shu Xing; Zhe Li; Xueqi Fu; Qingshan Li; Sanford B Krantz; Zhizhuang Joe Zhao
Journal:  J Biol Chem       Date:  2005-04-29       Impact factor: 5.157

6.  The t(8;9)(p22;p24) is a recurrent abnormality in chronic and acute leukemia that fuses PCM1 to JAK2.

Authors:  Andreas Reiter; Christoph Walz; Ann Watmore; Claudia Schoch; Ilona Blau; Brigitte Schlegelberger; Ute Berger; Nick Telford; Shilani Aruliah; John A Yin; Danny Vanstraelen; Helen F Barker; Peter C Taylor; Aisling O'Driscoll; Fabio Benedetti; Cornelia Rudolph; Hans-Jochem Kolb; Andreas Hochhaus; Rüdiger Hehlmann; Andrew Chase; Nicholas C P Cross
Journal:  Cancer Res       Date:  2005-04-01       Impact factor: 12.701

Review 7.  Resveratrol and breast cancer chemoprevention: molecular mechanisms.

Authors:  Ludovic Le Corre; N Chalabi; L Delort; Yves-Jean Bignon; D J Bernard-Gallon
Journal:  Mol Nutr Food Res       Date:  2005-05       Impact factor: 5.914

8.  JAK2 V617F tyrosine kinase mutation in cell lines derived from myeloproliferative disorders.

Authors:  H Quentmeier; R A F MacLeod; M Zaborski; H G Drexler
Journal:  Leukemia       Date:  2006-03       Impact factor: 11.528

9.  A gain-of-function mutation of JAK2 in myeloproliferative disorders.

Authors:  Robert Kralovics; Francesco Passamonti; Andreas S Buser; Soon-Siong Teo; Ralph Tiedt; Jakob R Passweg; Andre Tichelli; Mario Cazzola; Radek C Skoda
Journal:  N Engl J Med       Date:  2005-04-28       Impact factor: 91.245

10.  Antiangiogenic and vascular-targeting activity of the microtubule-destabilizing trans-resveratrol derivative 3,5,4'-trimethoxystilbene.

Authors:  Mirella Belleri; Domenico Ribatti; Stefania Nicoli; Franco Cotelli; Luca Forti; Vanio Vannini; Lucia Anna Stivala; Marco Presta
Journal:  Mol Pharmacol       Date:  2005-02-09       Impact factor: 4.436

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  7 in total

1.  A46, a benzothiophene-derived compound, suppresses Jak2-mediated pathologic cell growth.

Authors:  Anurima Majumder; Andrew T Magis; Sung O Park; Nicholas C Figueroa; Rebekah Baskin; Annet Kirabo; Robert W Allan; Zhizhuang Joe Zhao; Kirpal S Bisht; György M Keseru; Peter P Sayeski
Journal:  Exp Hematol       Date:  2011-10-20       Impact factor: 3.084

2.  Cell death induced by the Jak2 inhibitor, G6, correlates with cleavage of vimentin filaments.

Authors:  Anurima Majumder; Annet Kirabo; Kanchana Karrupiah; Shigeharu Tsuda; Jennifer Caldwell-Busby; Arturo J Cardounel; György M Keseru; Peter P Sayeski
Journal:  Biochemistry       Date:  2011-08-17       Impact factor: 3.162

3.  The stilbenoid tyrosine kinase inhibitor, G6, suppresses Jak2-V617F-mediated human pathological cell growth in vitro and in vivo.

Authors:  Annet Kirabo; Jennifer Embury; Róbert Kiss; Tímea Polgár; Meghanath Gali; Anurima Majumder; Kirpal S Bisht; Christopher R Cogle; György M Keseru; Peter P Sayeski
Journal:  J Biol Chem       Date:  2010-12-02       Impact factor: 5.157

4.  The Jak2 inhibitor, G6, alleviates Jak2-V617F-mediated myeloproliferative neoplasia by providing significant therapeutic efficacy to the bone marrow.

Authors:  Annet Kirabo; Sung O Park; Anurima Majumder; Meghanath Gali; Mary K Reinhard; Heather L Wamsley; Zhizhuang Joe Zhao; Christopher R Cogle; Kirpal S Bisht; György M Keserü; Peter P Sayeski
Journal:  Neoplasia       Date:  2011-11       Impact factor: 5.715

5.  Identification of novel SAR properties of the Jak2 small molecule inhibitor G6: significance of the para-hydroxyl orientation.

Authors:  Rebekah Baskin; Meghanath Gali; Sung O Park; Zhizhuang Joe Zhao; György M Keseru; Kirpal S Bisht; Peter P Sayeski
Journal:  Bioorg Med Chem Lett       Date:  2011-12-21       Impact factor: 2.823

6.  The small molecule inhibitor G6 significantly reduces bone marrow fibrosis and the mutant burden in a mouse model of Jak2-mediated myelofibrosis.

Authors:  Annet Kirabo; Sung O Park; Heather L Wamsley; Meghanath Gali; Rebekah Baskin; Mary K Reinhard; Zhizhuang J Zhao; Kirpal S Bisht; György M Keserű; Christopher R Cogle; Peter P Sayeski
Journal:  Am J Pathol       Date:  2012-07-13       Impact factor: 4.307

7.  The Jak2 small molecule inhibitor, G6, reduces the tumorigenic potential of T98G glioblastoma cells in vitro and in vivo.

Authors:  Rebekah Baskin; Sung O Park; György M Keserű; Kirpal S Bisht; Heather L Wamsley; Peter P Sayeski
Journal:  PLoS One       Date:  2014-08-27       Impact factor: 3.240

  7 in total

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