Literature DB >> 23072504

Structure of FD-895 revealed through total synthesis.

Reymundo Villa1, Alexander L Mandel, Brian D Jones, James J La Clair, Michael D Burkart.   

Abstract

The total synthesis of FD-895 was completed through a strategy that featured the use of a tandem esterification ring-closing metathesis (RCM) process to construct the 12-membered macrolide and a modified Stille coupling to append the side chain. These studies combined with detailed analysis of all four possible C16-C17 stereoisomers were used to confirm the structure of FD-895 and identify an analog with an enhanced subnanomolar bioactivity.

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Year:  2012        PMID： 23072504      PMCID： PMC3518397          DOI： 10.1021/ol3023006

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  19 in total

1.  Total synthesis of the potent antitumor macrolides pladienolide B and D.

Authors:  Regina M Kanada; Daisuke Itoh; Mitsuo Nagai; Jun Niijima; Naoki Asai; Yoshiharu Mizui; Shinya Abe; Yoshihiko Kotake
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

2.  Spliceostatin A targets SF3b and inhibits both splicing and nuclear retention of pre-mRNA.

Authors:  Daisuke Kaida; Hajime Motoyoshi; Etsu Tashiro; Takayuki Nojima; Masatoshi Hagiwara; Ken Ishigami; Hidenori Watanabe; Takeshi Kitahara; Tatsuhiko Yoshida; Hidenori Nakajima; Tokio Tani; Sueharu Horinouchi; Minoru Yoshida
Journal:  Nat Chem Biol       Date:  2007-07-22       Impact factor: 15.040

3.  Biological validation that SF3b is a target of the antitumor macrolide pladienolide.

Authors:  Akira Yokoi; Yoshihiko Kotake; Kentaro Takahashi; Tadashi Kadowaki; Yoshiko Matsumoto; Yukinori Minoshima; Naoko H Sugi; Koji Sagane; Makoto Hamaguchi; Masao Iwata; Yoshiharu Mizui
Journal:  FEBS J       Date:  2011-10-31       Impact factor: 5.542

4.  Highly efficient ruthenium catalysts for the formation of tetrasubstituted olefins via ring-closing metathesis.

Authors:  Ian C Stewart; Thay Ung; Alexandre A Pletnev; Jacob M Berlin; Robert H Grubbs; Yann Schrodi
Journal:  Org Lett       Date:  2007-03-23       Impact factor: 6.005

5.  Isolation and characterization of a new 12-membered macrolide FD-895.

Authors:  M Seki-Asano; T Okazaki; M Yamagishi; N Sakai; Y Takayama; K Hanada; S Morimoto; A Takatsuki; K Mizoue
Journal:  J Antibiot (Tokyo)       Date:  1994-12       Impact factor: 2.649

6.  Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays.

Authors:  T Mosmann
Journal:  J Immunol Methods       Date:  1983-12-16       Impact factor: 2.303

7.  Highly selective asymmetric acetate aldol reactions of an N-acetyl thiazolidinethione reagent.

Authors:  Yingchao Zhang; Andrew J Phillips; Tarek Sammakia
Journal:  Org Lett       Date:  2004-01-08       Impact factor: 6.005

8.  Pladienolides, new substances from culture of Streptomyces platensis Mer-11107. III. In vitro and in vivo antitumor activities.

Authors:  Yoshiharu Mizui; Takashi Sakai; Masao Iwata; Toshimitsu Uenaka; Kiyoshi Okamoto; Hajime Shimizu; Takao Yamori; Kentaro Yoshimatsu; Makoto Asada
Journal:  J Antibiot (Tokyo)       Date:  2004-03       Impact factor: 2.649

9.  Splicing factor SF3b as a target of the antitumor natural product pladienolide.

Authors:  Yoshihiko Kotake; Koji Sagane; Takashi Owa; Yuko Mimori-Kiyosue; Hajime Shimizu; Mai Uesugi; Yasushi Ishihama; Masao Iwata; Yoshiharu Mizui
Journal:  Nat Chem Biol       Date:  2007-07-22       Impact factor: 15.040

10.  A simple and advantageous protocol for the oxidation of alcohols with O-iodoxybenzoic acid (IBX).

Authors:  Jesse D More; Nathaniel S Finney
Journal:  Org Lett       Date:  2002-08-22       Impact factor: 6.005
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  12 in total

1.  Splice Modulation Synergizes Cell Cycle Inhibition.

Authors:  Kelsey A Trieger; James J La Clair; Michael D Burkart
Journal:  ACS Chem Biol       Date:  2020-02-17       Impact factor: 5.100

2.  Aberrant RNA splicing and mutations in spliceosome complex in acute myeloid leukemia.

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Journal:  Stem Cell Investig       Date:  2017-02-09

Review 3.  A Challenging Pie to Splice: Drugging the Spliceosome.

Authors:  Brian León; Manoj K Kashyap; Warren C Chan; Kelsey A Krug; Januario E Castro; James J La Clair; Michael D Burkart
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4.  Optimization of antitumor modulators of pre-mRNA splicing.

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5.  RNA Splicing Modulation Selectively Impairs Leukemia Stem Cell Maintenance in Secondary Human AML.

Authors:  Leslie A Crews; Larisa Balaian; Nathaniel P Delos Santos; Heather S Leu; Angela C Court; Elisa Lazzari; Anil Sadarangani; Maria A Zipeto; James J La Clair; Reymundo Villa; Anna Kulidjian; Rainer Storb; Sheldon R Morris; Edward D Ball; Michael D Burkart; Catriona H M Jamieson
Journal:  Cell Stem Cell       Date:  2016-08-25       Impact factor: 24.633

Review 6.  Modulating splicing with small molecular inhibitors of the spliceosome.

Authors:  Kerstin A Effenberger; Veronica K Urabe; Melissa S Jurica
Journal:  Wiley Interdiscip Rev RNA       Date:  2016-07-21       Impact factor: 9.957

7.  Stabilized cyclopropane analogs of the splicing inhibitor FD-895.

Authors:  Reymundo Villa; Manoj Kumar Kashyap; Deepak Kumar; Thomas J Kipps; Januario E Castro; James J La Clair; Michael D Burkart
Journal:  J Med Chem       Date:  2013-08-21       Impact factor: 7.446

8.  Coherence between cellular responses and in vitro splicing inhibition for the anti-tumor drug pladienolide B and its analogs.

Authors:  Kerstin A Effenberger; David D Anderson; Walter M Bray; Beth E Prichard; Nianchun Ma; Matthew S Adams; Arun K Ghosh; Melissa S Jurica
Journal:  J Biol Chem       Date:  2013-12-03       Impact factor: 5.157

9.  Pre-mRNA splicing-modulatory pharmacophores: the total synthesis of herboxidiene, a pladienolide-herboxidiene hybrid analog and related derivatives.

Authors:  Chandraiah Lagisetti; Maria V Yermolina; Lalit Kumar Sharma; Gustavo Palacios; Brett J Prigaro; Thomas R Webb
Journal:  ACS Chem Biol       Date:  2013-12-30       Impact factor: 5.100

10.  Total Synthesis of the Spliceosome Modulator Pladienolide B via Asymmetric Alcohol-Mediated syn- and anti-Diastereoselective Carbonyl Crotylation.

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Journal:  Angew Chem Int Ed Engl       Date:  2021-05-11       Impact factor: 16.823
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