Literature DB >> 28666736

Synthesis and biological evaluation of novel steroidal 5α,8α-epidioxyandrost-6-ene-3β-ol-17-(O-phenylacetamide)oxime derivatives as potential anticancer agents.

Ming Bu1, Tingting Cao2, Hongxia Li2, Mingzhou Guo3, Burton B Yang4, Chengchu Zeng2, Yue Zhou2, Na Zhang2, Liming Hu5.   

Abstract

Inspired by the significant anti-cancer activity of our previously screened natural ergosterol peroxide (EP, 1), we synthesized and characterized a series of novel 5α,8α-epidioxyandrost-3β-ol-17-(O-phenylacetamide)oxime derivatives (9a-o). The anti-proliferative activity of the synthesized compounds against human hepatocellular carcinoma cells (HepG2, Sk-Hep1) and human breast cancer cells (MCF-7, MDA-MB231) were investigated. Compounds 9d, 9f, 9h, 9j and 9m displayed good anti-proliferative activity (most IC50<20μM) in vitro. Furthermore, fluorescence imaging showed that the designed coumarin-9d conjugate (12) localized mainly in mitochondria, leading to enhanced anticancer activities over the parent structure.
Copyright © 2017 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Cytotoxic activities; Endoperoxide; Ergosterol peroxide; Photooxygenation; Steroidal derivatives

Mesh：

Substances：

Year:  2017        PMID： 28666736     DOI： 10.1016/j.bmcl.2017.06.048

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


  8 in total

1.  Structure-Based Design of Inhibitors with Improved Selectivity for Steroidogenic Cytochrome P450 17A1 over Cytochrome P450 21A2.

Authors:  Charlie Fehl; Caleb D Vogt; Rahul Yadav; Kelin Li; Emily E Scott; Jeffrey Aubé
Journal:  J Med Chem       Date:  2018-05-24       Impact factor: 7.446

2.  Development of ergosterol peroxide probes for cellular localisation studies.

Authors:  Taotao Ling; Walter H Lang; Michelle M Martinez-Montemayor; Fatima Rivas
Journal:  Org Biomol Chem       Date:  2019-05-29       Impact factor: 3.876

3.  Research and study of 2-((4,6 dimethyl pyrimidine-2-yle) thio)-N-phenyl acetamide derivatives as inhibitors of sirtuin 2 protein for the treatment of cancer using QSAR, molecular docking and molecular dynamic simulation.

Authors:  Sahar Ilaghi-Hoseini; Zahra Garkani-Nejad
Journal:  J Mol Model       Date:  2022-10-06       Impact factor: 2.172

4.  Synthesis of Ergosterol Peroxide Conjugates as Mitochondria Targeting Probes for Enhanced Anticancer Activity.

Authors:  Ming Bu; Hongling Li; Haijun Wang; Jing Wang; Yu Lin; Yukun Ma
Journal:  Molecules       Date:  2019-09-11       Impact factor: 4.411

5.  Ergosterol Peroxide from the Medicinal Mushroom Ganoderma lucidum Inhibits Differentiation and Lipid Accumulation of 3T3-L1 Adipocytes.

Authors:  Yong-Un Jeong; Young-Jin Park
Journal:  Int J Mol Sci       Date:  2020-01-10       Impact factor: 5.923

Review 6.  Antiprotozoal and Antitumor Activity of Natural Polycyclic Endoperoxides: Origin, Structures and Biological Activity.

Authors:  Valery M Dembitsky; Ekaterina Ermolenko; Nick Savidov; Tatyana A Gloriozova; Vladimir V Poroikov
Journal:  Molecules       Date:  2021-01-28       Impact factor: 4.411

7.  Insights into Ergosterol Peroxide's Trypanocidal Activity.

Authors:  Thuluz Meza-Menchaca; Angel Ramos-Ligonio; Aracely López-Monteon; Abraham Vidal Limón; Leonid A Kaluzhskiy; Tatjana V Shkel; Natallia V Strushkevich; Luis Felipe Jiménez-García; Lourdes Teresa Agredano Moreno; Verónica Gallegos-García; Jorge Suárez-Medellín; Ángel Trigos
Journal:  Biomolecules       Date:  2019-09-12

8.  Novel Steroidal 5α,8α-Endoperoxide Derivatives with Semicarbazone/Thiosemicarbazone Side-chain as Apoptotic Inducers through an Intrinsic Apoptosis Pathway: Design, Synthesis and Biological Studies.

Authors:  Liwei Ma; Haijun Wang; Jing Wang; Lei Liu; Song Zhang; Ming Bu
Journal:  Molecules       Date:  2020-03-07       Impact factor: 4.411
  8 in total

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