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Literature DB >> 18788726

Antitumor compounds based on a natural product consensus pharmacophore.

Chandraiah Lagisetti¹, Alan Pourpak, Qin Jiang, Xiaoli Cui, Tinopiwa Goronga, Stephan W Morris, Thomas R Webb.

Abstract

We report the design and highly enantioselective synthesis of a potent analogue of the spliceosome inhibitor FR901464, based on a non-natural product scaffold. The design of this compound was facilitated by a pharmacophore hypothesis that assumed key interaction types that are common to FR901464 and an otherwise unrelated natural product (pladienolide). The synthesis allows for the preparation of numerous novel analogues. We present results on the in vitro activity for this compound against several tumor cell lines.

Entities: CellLine Chemical Disease Gene Species

Mesh：

Substances：

Year: 2008 PMID： 18788726 PMCID： PMC2701350 DOI： 10.1021/jm8006195

Source DB: PubMed Journal: J Med Chem ISSN： 0022-2623 Impact factor: 7.446

14 in total

1. FR901464: total synthesis, proof of structure, and evaluation of synthetic analogues.

Authors: C F Thompson; T F Jamison; E N Jacobsen
Journal: J Am Chem Soc Date: 2001-10-17 Impact factor: 15.419

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. Targeting the spliceosome.

Authors: Brian Rymond
Journal: Nat Chem Biol Date: 2007-09 Impact factor: 15.040

4. Total syntheses, fragmentation studies, and antitumor/antiproliferative activities of FR901464 and its low picomolar analogue.

Authors: Brian J Albert; Ananthapadmanabhan Sivaramakrishnan; Tadaatsu Naka; Nancy L Czaicki; Kazunori Koide
Journal: J Am Chem Soc Date: 2007-02-06 Impact factor: 15.419

5. New antitumor substances, FR901463, FR901464 and FR901465. III. Structures of FR901463, FR901464 and FR901465.

Authors: H Nakajima; S Takase; H Terano; H Tanaka
Journal: J Antibiot (Tokyo) Date: 1997-01 Impact factor: 2.649

6. New antitumor substances, FR901463, FR901464 and FR901465. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities.

Authors: H Nakajima; B Sato; T Fujita; S Takase; H Terano; M Okuhara
Journal: J Antibiot (Tokyo) Date: 1996-12 Impact factor: 2.649

7. Organocatalytic transfer hydrogenation of cyclic enones.

Authors: Jamison B Tuttle; Stéphane G Ouellet; David W C MacMillan
Journal: J Am Chem Soc Date: 2006-10-04 Impact factor: 15.419

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

Review 10. Enantioselective organocatalytic transfer hydrogenation reactions using Hantzsch esters.

Authors: Stéphane G Ouellet; Abbas M Walji; David W C MacMillan
Journal: Acc Chem Res Date: 2007-12 Impact factor: 22.384

26 in total

1. A triple exon-skipping luciferase reporter assay identifies a new CLK inhibitor pharmacophore.

Authors: Yihui Shi; Jaehyeon Park; Chandraiah Lagisetti; Wei Zhou; Lidia C Sambucetti; Thomas R Webb
Journal: Bioorg Med Chem Lett Date: 2016-12-24 Impact factor: 2.823

2. Synthetic mRNA splicing modulator compounds with in vivo antitumor activity.

Authors: Chandraiah Lagisetti; Alan Pourpak; Tinopiwa Goronga; Qin Jiang; Xiaoli Cui; Judith Hyle; Jill M Lahti; Stephan W Morris; Thomas R Webb
Journal: J Med Chem Date: 2009-11-26 Impact factor: 7.446

3. Genome-wide RNAi screens in human brain tumor isolates reveal a novel viability requirement for PHF5A.

Authors: Christopher G Hubert; Robert K Bradley; Yu Ding; Chad M Toledo; Jacob Herman; Kyobi Skutt-Kakaria; Emily J Girard; Jerry Davison; Jason Berndt; Philip Corrin; Justin Hardcastle; Ryan Basom; Jeffery J Delrow; Thomas Webb; Steven M Pollard; Jeongwu Lee; James M Olson; Patrick J Paddison
Journal: Genes Dev Date: 2013-05-01 Impact factor: 11.361

Antitumor compounds based on a natural product consensus pharmacophore.

1. FR901464: total synthesis, proof of structure, and evaluation of synthetic analogues.

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

3. Targeting the spliceosome.

4. Total syntheses, fragmentation studies, and antitumor/antiproliferative activities of FR901464 and its low picomolar analogue.

5. New antitumor substances, FR901463, FR901464 and FR901465. III. Structures of FR901463, FR901464 and FR901465.

6. New antitumor substances, FR901463, FR901464 and FR901465. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities.

7. Organocatalytic transfer hydrogenation of cyclic enones.

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

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

Review 10. Enantioselective organocatalytic transfer hydrogenation reactions using Hantzsch esters.

1. A triple exon-skipping luciferase reporter assay identifies a new CLK inhibitor pharmacophore.

2. Synthetic mRNA splicing modulator compounds with in vivo antitumor activity.

3. Genome-wide RNAi screens in human brain tumor isolates reveal a novel viability requirement for PHF5A.

4. Sudemycins, novel small molecule analogues of FR901464, induce alternative gene splicing.

5. Design, synthesis and initial biological evaluation of a novel pladienolide analog scaffold.

6. Effects of thailanstatins on glucocorticoid response in trabecular meshwork and steroid-induced glaucoma.

7. Optimization of antitumor modulators of pre-mRNA splicing.

Review 8. Splicing factor gene mutations in hematologic malignancies.

Review 9. Modulating splicing with small molecular inhibitors of the spliceosome.

Review 10. The development and application of small molecule modulators of SF3b as therapeutic agents for cancer.