Literature DB >> 32071675

Reinvestigation of Mycothiazole Reveals the Penta-2,4-dien-1-ol Residue Imparts Picomolar Potency and 8S Configuration.

Tyler A Johnson1,2, Joseph D Morris1, David A Coppage2, Colon V Cook1, Lauren N Persi1, Marcos A Ogarrio1, Taylor C Garcia1, Nicole L McIntosh1, Erin P McCauley2, Joseph Media3, Mani Maheshwari3, Frederick A Valeriote3, Jiajiu Shaw4, Phillip Crews2.   

Abstract

Reinvestigation of mycothiazole (1) revealed picomolar potency (IC50 = 0.00016, 0.00027, 0.00035 μM) against pancreatic, (PANC-1), liver (HepG2), and colon (HCT-116) tumor cell lines. Reevaluation of 1 provided [α]D data indicating Vanuatu specimens of C. mycofijiensis contain the 8S enantiomer of 1 and not the 8R configuration previously reported. Semisynthesis provided 8-O-acetylmycothiazole (2), 8-oxomycothiazole (8), mycothiazole nitrosobenzene derivatives (MND1, MND2: 9a, 9b), and MND3 (10) with IC50 = 0.00129, >1.0, >1.0, >1.0, >1.0 μM, respectively, against PANC-1 cell lines. These results highlight the significance of the penta-2,4-dien-1-ol residue as a key structural feature of 1 required for its cytotoxicty against tumor cell lines.
Copyright © 2020 American Chemical Society.

Entities:  

Year:  2020        PMID： 32071675      PMCID： PMC7025380          DOI： 10.1021/acsmedchemlett.9b00302

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


  15 in total

1.  Lomaiviticins A and B, potent antitumor antibiotics from Micromonospora lomaivitiensis.

Authors:  H He; W D Ding; V S Bernan; A D Richardson; C M Ireland; M Greenstein; G A Ellestad; G T Carter
Journal:  J Am Chem Soc       Date:  2001-06-06       Impact factor: 15.419

2.  Total Synthesis of the Potent HIF-1 Inhibitory Antitumor Natural Product, (8R)-Mycothiazole, via Baldwin-Lee CsF/CuI sp(3)-sp(2)-Stille Cross-Coupling. Confirmation of the Crews Reassignment.

Authors:  Liping Wang; Karl J Hale
Journal:  Org Lett       Date:  2015-08-14       Impact factor: 6.005

3.  Synthesis and biological evaluation of simplified mycothiazole analogues.

Authors:  Graciela Mahler; Gloria Serra; Sylvia Dematteis; Jenny Saldaña; Laura Domínguez; Eduardo Manta
Journal:  Bioorg Med Chem Lett       Date:  2005-12-27       Impact factor: 2.823

4.  Asymmetric total synthesis of (-)-mycothiazole.

Authors:  H Sugiyama; F Yokokawa; T Shioiri
Journal:  Org Lett       Date:  2000-07-13       Impact factor: 6.005

5.  A reassignment of (-)-mycothiazole and the isolation of a related diol.

Authors:  Rachel N Sonnenschein; Tyler A Johnson; Karen Tenney; Frederick A Valeriote; Phillip Crews
Journal:  J Nat Prod       Date:  2006-01       Impact factor: 4.050

6.  The marine sponge metabolite mycothiazole: a novel prototype mitochondrial complex I inhibitor.

Authors:  J Brian Morgan; Fakhri Mahdi; Yang Liu; Veena Coothankandaswamy; Mika B Jekabsons; Tyler A Johnson; Koneni V Sashidhara; Phillip Crews; Dale G Nagle; Yu-Dong Zhou
Journal:  Bioorg Med Chem       Date:  2010-06-25       Impact factor: 3.641

7.  Discovery and development of anticancer agents from marine sponges: perspectives based on a chemistry-experimental therapeutics collaborative program.

Authors:  Frederick A Valeriote; Karen Tenney; Joseph Media; Halina Pietraszkiewicz; Matthew Edelstein; Tyler A Johnson; Taro Amagata; Phillip Crews
Journal:  J Exp Ther Oncol       Date:  2012

Review 8.  A selective account of effective paradigms and significant outcomes in the discovery of inspirational marine natural products.

Authors:  Koneni V Sashidhara; Kimberly N White; Phillip Crews
Journal:  J Nat Prod       Date:  2009-03-27       Impact factor: 4.050

9.  Mitochondrial genome-knockout cells demonstrate a dual mechanism of action for the electron transport complex I inhibitor mycothiazole.

Authors:  Kirsten J Meyer; A Jonathan Singh; Alanna Cameron; An S Tan; Dora C Leahy; David O'Sullivan; Praneta Joshi; Anne C La Flamme; Peter T Northcote; Michael V Berridge; John H Miller
Journal:  Mar Drugs       Date:  2012-04-16       Impact factor: 6.085

Review 10.  Tubulin Inhibitor-Based Antibody-Drug Conjugates for Cancer Therapy.

Authors:  Hao Chen; Zongtao Lin; Kinsie E Arnst; Duane D Miller; Wei Li
Journal:  Molecules       Date:  2017-08-01       Impact factor: 4.411
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  2 in total

1.  In Vivo Evaluation of (-)-Zampanolide Demonstrates Potent and Persistent Antitumor Efficacy When Targeted to the Tumor Site.

Authors:  Leila Takahashi-Ruiz; Joseph D Morris; Phillip Crews; Tyler A Johnson; April L Risinger
Journal:  Molecules       Date:  2022-07-01       Impact factor: 4.927

2.  Re-evaluation of the Fijianolide/Laulimalide Chemotype Suggests an Alternate Mechanism of Action for C-15/C-20 Analogs.

Authors:  Joseph D Morris; Leila Takahashi-Ruiz; Lauren N Persi; Jonathan C Summers; Erin P McCauley; Peter Y W Chan; Gabriella Amberchan; Itzel Lizama-Chamu; David A Coppage; Phillip Crews; April L Risinger; Tyler A Johnson
Journal:  ACS Omega       Date:  2022-03-07
  2 in total

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