Literature DB >> 32551017

Design and Synthesis of 1,2-Deoxy-pyranose Derivatives of Spliceostatin A toward Prostate Cancer Treatment.

Yusuke Yoshikawa1, Airi Ishibashi2, Tsunayoshi Takehara3, Takeyuki Suzuki3, Kenichi Murai1, Yasufumi Kaneda2, Keisuke Nimura2, Mitsuhiro Arisawa1.   

Abstract

We designed and synthesized a novel 1,2-deoxy-pyranose and terminal epoxide methyl substituted derivatives of spliceostatin A using Julia-Kocienski olefination as a key step. With respect to the biological activity, the 1,2-deoxy-pyranose analogue of spliceostatin A suppressed AR-V7 expression at the nano level (IC50 = 3.3 nM). In addition, the in vivo toxicity test showed that the 1,2-deoxy-pyranose analogue was able to avoid severe toxicity compared to spliceostatin A.
Copyright © 2020 American Chemical Society.

Entities:  

Year:  2020        PMID： 32551017      PMCID： PMC7294732          DOI： 10.1021/acsmedchemlett.0c00153

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


  40 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.  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

3.  Gold-catalyzed Hosomi-Sakurai type reaction for the total synthesis of herboxidiene.

Authors:  Barla Thirupathi; Debendra K Mohapatra
Journal:  Org Biomol Chem       Date:  2016-05-19       Impact factor: 3.876

4.  A phase I, open-label, single-arm, dose-escalation study of E7107, a precursor messenger ribonucleic acid (pre-mRNA) splicesome inhibitor administered intravenously on days 1 and 8 every 21 days to patients with solid tumors.

Authors:  D S Hong; R Kurzrock; A Naing; J J Wheler; G S Falchook; J S Schiffman; N Faulkner; M J Pilat; J O'Brien; P LoRusso
Journal:  Invest New Drugs       Date:  2013-11-22       Impact factor: 3.850

5.  Abiraterone in metastatic prostate cancer without previous chemotherapy.

Authors:  Charles J Ryan; Matthew R Smith; Johann S de Bono; Arturo Molina; Christopher J Logothetis; Paul de Souza; Karim Fizazi; Paul Mainwaring; Josep M Piulats; Siobhan Ng; Joan Carles; Peter F A Mulders; Ethan Basch; Eric J Small; Fred Saad; Dirk Schrijvers; Hendrik Van Poppel; Som D Mukherjee; Henrik Suttmann; Winald R Gerritsen; Thomas W Flaig; Daniel J George; Evan Y Yu; Eleni Efstathiou; Allan Pantuck; Eric Winquist; Celestia S Higano; Mary-Ellen Taplin; Youn Park; Thian Kheoh; Thomas Griffin; Howard I Scher; Dana E Rathkopf
Journal:  N Engl J Med       Date:  2012-12-10       Impact factor: 91.245

6.  Phase I pharmacokinetic and pharmacodynamic study of the first-in-class spliceosome inhibitor E7107 in patients with advanced solid tumors.

Authors:  Ferry A L M Eskens; Francisco J Ramos; Herman Burger; James P O'Brien; Adelaida Piera; Maja J A de Jonge; Yoshiharu Mizui; Erik A C Wiemer; Maria Josepa Carreras; José Baselga; Josep Tabernero
Journal:  Clin Cancer Res       Date:  2013-08-27       Impact factor: 12.531

Review 7.  The spliceosome as a target of novel antitumour drugs.

Authors:  Sophie Bonnal; Luisa Vigevani; Juan Valcárcel
Journal:  Nat Rev Drug Discov       Date:  2012-11       Impact factor: 84.694

8.  Pladienolides, new substances from culture of Streptomyces platensis Mer-11107. I. Taxonomy, fermentation, isolation and screening.

Authors:  Takashi Sakai; Tomohiro Sameshima; Motoko Matsufuji; Naoto Kawamura; Kazuyuki Dobashi; Yoshiharu Mizui
Journal:  J Antibiot (Tokyo)       Date:  2004-03       Impact factor: 2.649

9.  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

10.  Pladienolides, new substances from culture of Streptomyces platensis Mer-11107. II. Physico-chemical properties and structure elucidation.

Authors:  Takashi Sakai; Naoki Asai; Akifumi Okuda; Naoto Kawamura; Yoshiharu Mizui
Journal:  J Antibiot (Tokyo)       Date:  2004-03       Impact factor: 2.649
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  3 in total

Review 1.  Regulation of RNA Splicing: Aberrant Splicing Regulation and Therapeutic Targets in Cancer.

Authors:  Koji Kitamura; Keisuke Nimura
Journal:  Cells       Date:  2021-04-16       Impact factor: 6.600

2.  Herboxidiene Features That Mediate Conformation-Dependent SF3B1 Interactions to Inhibit Splicing.

Authors:  Adriana Gamboa Lopez; Srinivasa Rao Allu; Patricia Mendez; Guddeti Chandrashekar Reddy; Hannah M Maul-Newby; Arun K Ghosh; Melissa S Jurica
Journal:  ACS Chem Biol       Date:  2021-02-22       Impact factor: 5.100

3.  Structural basis of intron selection by U2 snRNP in the presence of covalent inhibitors.

Authors:  Constantin Cretu; Patricia Gee; Xiang Liu; Anant Agrawal; Tuong-Vi Nguyen; Arun K Ghosh; Andrew Cook; Melissa Jurica; Nicholas A Larsen; Vladimir Pena
Journal:  Nat Commun       Date:  2021-07-23       Impact factor: 14.919
  3 in total

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