Literature DB >> 27107948

Synthesis of a stable and orally bioavailable englerin analogue.

David M Fash1, Cody J Peer2, Zhenwu Li1, Ian J Talisman1, Sima Hayavi3, Florian J Sulzmaier4, Joe W Ramos4, Carole Sourbier5, Leonard Neckers5, W Douglas Figg2, John A Beutler6, William J Chain7.   

Abstract

Synthesis of analogues of englerin A with a reduced propensity for hydrolysis of the glycolate moiety led to a compound which possessed the renal cancer cell selectivity of the parent and was orally bioavailable in mice.
Copyright © 2016 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Bioavailability; Cancer; Englerins; Sesquiterpenes

Mesh：

Substances：

Year:  2016        PMID： 27107948      PMCID： PMC4862412          DOI： 10.1016/j.bmcl.2016.04.016

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  23 in total

1.  Chlorinated englerins with selective inhibition of renal cancer cell growth.

Authors:  Rhone K Akee; Tanya Ransom; Ranjala Ratnayake; James B McMahon; John A Beutler
Journal:  J Nat Prod       Date:  2012-01-26       Impact factor: 4.050

2.  The past, present, and future of cancer incidence in the United States: 1975 through 2020.

Authors:  Hannah K Weir; Trevor D Thompson; Ashwini Soman; Bjørn Møller; Steven Leadbetter
Journal:  Cancer       Date:  2015-02-03       Impact factor: 6.860

3.  Stereocontrolled total synthesis of (-)-englerin A.

Authors:  Keisuke Takahashi; Keita Komine; Yuichi Yokoi; Jun Ishihara; Susumi Hatakeyama
Journal:  J Org Chem       Date:  2012-08-17       Impact factor: 4.354

4.  A short enantioselective total synthesis of (-)-englerin A.

Authors:  Martin Zahel; Anton Kessberg; Peter Metz
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-15       Impact factor: 15.336

5.  A brief synthesis of (-)-englerin A.

Authors:  Zhenwu Li; Mika Nakashige; William J Chain
Journal:  J Am Chem Soc       Date:  2011-04-08       Impact factor: 15.419

6.  Englerin A stimulates PKCθ to inhibit insulin signaling and to simultaneously activate HSF1: pharmacologically induced synthetic lethality.

Authors:  Carole Sourbier; Bradley T Scroggins; Ranjala Ratnayake; Thomas L Prince; Sunmin Lee; Min-Jung Lee; Peter Literati Nagy; Young H Lee; Jane B Trepel; John A Beutler; W Marston Linehan; Len Neckers
Journal:  Cancer Cell       Date:  2013-01-23       Impact factor: 31.743

7.  A formal synthesis of (-)-englerin A by relay ring closing metathesis and transannular etherification.

Authors:  Jungyong Lee; Kathlyn A Parker
Journal:  Org Lett       Date:  2012-05-07       Impact factor: 6.005

8.  (-)-Englerin A is a potent and selective activator of TRPC4 and TRPC5 calcium channels.

Authors:  Yasemin Akbulut; Hannah J Gaunt; Katsuhiko Muraki; Melanie J Ludlow; Mohamed S Amer; Alexander Bruns; Naveen S Vasudev; Lea Radtke; Matthieu Willot; Sven Hahn; Tobias Seitz; Slava Ziegler; Mathias Christmann; David J Beech; Herbert Waldmann
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-23       Impact factor: 15.336

9.  Englerin a selectively induces necrosis in human renal cancer cells.

Authors:  Florian J Sulzmaier; Zhenwu Li; Mika L Nakashige; David M Fash; William J Chain; Joe W Ramos
Journal:  PLoS One       Date:  2012-10-22       Impact factor: 3.240

10.  Englerin A Agonizes the TRPC4/C5 Cation Channels to Inhibit Tumor Cell Line Proliferation.

Authors:  Cheryl Carson; Pichai Raman; Jennifer Tullai; Lei Xu; Martin Henault; Emily Thomas; Sarita Yeola; Jianmin Lao; Mark McPate; J Martin Verkuyl; George Marsh; Jason Sarber; Adam Amaral; Scott Bailey; Danuta Lubicka; Helen Pham; Nicolette Miranda; Jian Ding; Hai-Ming Tang; Haisong Ju; Pamela Tranter; Nan Ji; Philipp Krastel; Rishi K Jain; Andrew M Schumacher; Joseph J Loureiro; Elizabeth George; Giuliano Berellini; Nathan T Ross; Simon M Bushell; Gül Erdemli; Jonathan M Solomon
Journal:  PLoS One       Date:  2015-06-22       Impact factor: 3.240
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  7 in total

Review 1.  Englerins: A Comprehensive Review.

Authors:  Zhenhua Wu; Senzhi Zhao; David M Fash; Zhenwu Li; William J Chain; John A Beutler
Journal:  J Nat Prod       Date:  2017-02-07       Impact factor: 4.050

2.  Biological Effects of Modifications of the Englerin A Glycolate.

Authors:  Sarath P D Seenadera; Sarah A Long; Rhone Akee; Gabriela Bermudez; Gregory Parsonage; Jonathan Strope; Cody Peer; W Douglas Figg; Kathlyn A Parker; David J Beech; John A Beutler
Journal:  ACS Med Chem Lett       Date:  2022-08-22       Impact factor: 4.632

3.  Bridgehead Modifications of Englerin A Reduce TRPC4 Activity and Intravenous Toxicity but not Cell Growth Inhibition.

Authors:  Zhenhua Wu; Jean-Simon Suppo; Sarka Tumova; Jonathan Strope; Fernando Bravo; Melody Moy; Ethan S Weinstein; Cody J Peer; William D Figg; William J Chain; Antonio M Echavarren; David J Beech; John A Beutler
Journal:  ACS Med Chem Lett       Date:  2020-08-03       Impact factor: 4.345

Review 4.  The Role of Compounds Derived from Natural Supplement as Anticancer Agents in Renal Cell Carcinoma: A Review.

Authors:  Inamul Haque; Arvind Subramanian; Chao H Huang; Andrew K Godwin; Peter J Van Veldhuizen; Snigdha Banerjee; Sushanta K Banerjee
Journal:  Int J Mol Sci       Date:  2017-12-31       Impact factor: 5.923

5.  (-)-Englerin A-evoked Cytotoxicity Is Mediated by Na+ Influx and Counteracted by Na+/K+-ATPase.

Authors:  Melanie J Ludlow; Hannah J Gaunt; Hussein N Rubaiy; Katie E Musialowski; Nicola M Blythe; Naveen S Vasudev; Katsuhiko Muraki; David J Beech
Journal:  J Biol Chem       Date:  2016-11-14       Impact factor: 5.157

Review 6.  Natural products targeting cancer cell dependency.

Authors:  Changxiang Shi; Eun Ju Yang; Shishi Tao; Guowen Ren; Pui Kei Mou; Joong Sup Shim
Journal:  J Antibiot (Tokyo)       Date:  2021-06-23       Impact factor: 2.649

Review 7.  Remarkable Progress with Small-Molecule Modulation of TRPC1/4/5 Channels: Implications for Understanding the Channels in Health and Disease.

Authors:  Aisling Minard; Claudia C Bauer; David J Wright; Hussein N Rubaiy; Katsuhiko Muraki; David J Beech; Robin S Bon
Journal:  Cells       Date:  2018-06-01       Impact factor: 6.600
  7 in total

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