Literature DB >> 23791367

Anticancer activity and SAR studies of substituted 1,4-naphthoquinones.

Deepak Bhasin1, Somsundaram N Chettiar, Jonathan P Etter, May Mok, Pui-Kai Li.   

Abstract

In this paper, we report the structure-activity relationship studies of substituted 1,4-naphthoquinones for its anticancer properties. 1,4-Naphthoquinone, Juglone, Menadione, Plumbagin and LLL12.1 were used as lead molecules to design PD compounds. Most of the PD compounds showed improved antiproliferative activity in comparison to the lead molecule in prostate (DU-145), breast (MDA-MB-231) and colon (HT-29) cancer cell lines. PD9, PD10, PD11, PD13, PD14 and PD15 were found to be the most potent compound with an IC₀ value of 1-3 μM in all cancer cell lines. Fluorescent polarization assay was employed to study the inhibition of STAT3 dimerization by PD compounds. PD9 and PD18 were found to be potent STAT3 dimerization inhibitors.
Copyright © 2013. Published by Elsevier Ltd.

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Year:  2013        PMID： 23791367      PMCID： PMC4304211          DOI： 10.1016/j.bmc.2013.05.017

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  29 in total

1.  Studies in the juglone series; hydroxy and hydroxyhalogeno derivatives.

Authors:  R H THOMSON
Journal:  J Org Chem       Date:  1948-11       Impact factor: 4.354

2.  Synthesis and antiplatelet, antiinflammatory, and antiallergic activities of substituted 3-chloro-5,8-dimethoxy-1,4-naphthoquinone and related compounds.

Authors:  L J Huang; F C Chang; K H Lee; J P Wang; C M Teng; S C Kuo
Journal:  Bioorg Med Chem       Date:  1998-12       Impact factor: 3.641

3.  In vitro antifungal activity of naphthoquinone derivatives.

Authors:  Kenroh Sasaki; Hidetomo Abe; Fumihiko Yoshizaki
Journal:  Biol Pharm Bull       Date:  2002-05       Impact factor: 2.233

4.  Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents.

Authors:  Julio Benites; Jaime A Valderrama; Karina Bettega; Rozangela Curi Pedrosa; Pedro Buc Calderon; Julien Verrax
Journal:  Eur J Med Chem       Date:  2010-10-14       Impact factor: 6.514

5.  Inhibition of Nox-4 activity by plumbagin, a plant-derived bioactive naphthoquinone.

Authors:  Yaxian Ding; Zi-Jiang Chen; Shiguo Liu; Danian Che; Michael Vetter; Chung-Ho Chang
Journal:  J Pharm Pharmacol       Date:  2005-01       Impact factor: 3.765

6.  Efficient synthesis of 'redox-switched' naphthoquinone thiol-crown ethers and their biological activity evaluation.

Authors:  Sheng Tung Huang; Hsien Shou Kuo; Chiao Long Hsiao; Yuh Ling Lin
Journal:  Bioorg Med Chem       Date:  2002-06       Impact factor: 3.641

7.  Plumbagin, a plant derived natural agent inhibits the growth of pancreatic cancer cells in in vitro and in vivo via targeting EGFR, Stat3 and NF-κB signaling pathways.

Authors:  Bilal Bin Hafeez; Mohammad Sarwar Jamal; Joseph W Fischer; Ala Mustafa; Ajit Kumar Verma
Journal:  Int J Cancer       Date:  2012-03-20       Impact factor: 7.396

8.  Inhibitory effects of plumbagin and juglone on azoxymethane-induced intestinal carcinogenesis in rats.

Authors:  S Sugie; K Okamoto; K M Rahman; T Tanaka; K Kawai; J Yamahara; H Mori
Journal:  Cancer Lett       Date:  1998-05-15       Impact factor: 8.679

9.  Synthesis and preliminary pharmacological evaluation of new (+/-) 1,4-naphthoquinones structurally related to lapachol.

Authors:  Alcides J M da Silva; Camilla D Buarque; Flávia V Brito; Laure Aurelian; Luciana F Macedo; Linda H Malkas; Robert J Hickey; Daniele V S Lopes; François Noël; Yugo L B Murakami; Noelson M V Silva; Paulo A Melo; Rodrigo R B Caruso; Newton G Castro; Paulo R R Costa
Journal:  Bioorg Med Chem       Date:  2002-08       Impact factor: 3.641

10.  A novel small-molecule disrupts Stat3 SH2 domain-phosphotyrosine interactions and Stat3-dependent tumor processes.

Authors:  Xiaolei Zhang; Peibin Yue; Steven Fletcher; Wei Zhao; Patrick T Gunning; James Turkson
Journal:  Biochem Pharmacol       Date:  2010-01-11       Impact factor: 5.858
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  10 in total

1.  Synthesis, anticancer activity, and molecular modeling of 1,4-naphthoquinones that inhibit MKK7 and Cdc25.

Authors:  Igor A Schepetkin; Alexander S Karpenko; Andrei I Khlebnikov; Marina O Shibinska; Igor A Levandovskiy; Liliya N Kirpotina; Nadezhda V Danilenko; Mark T Quinn
Journal:  Eur J Med Chem       Date:  2019-09-18       Impact factor: 6.514

2.  Novel 2-Carbonylbenzo[b]thiophene 1,1-Dioxide Derivatives as Potent Inhibitors of STAT3 Signaling Pathway.

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Journal:  ACS Med Chem Lett       Date:  2015-07-27       Impact factor: 4.345

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Journal:  ACS Omega       Date:  2022-05-18

4.  Analysis of quinolinequinone reactivity, cytotoxicity, and anti-HIV-1 properties.

Authors:  Ayna Alfadhli; Andrew Mack; Logan Harper; Sam Berk; Christopher Ritchie; Eric Barklis
Journal:  Bioorg Med Chem       Date:  2016-09-12       Impact factor: 3.641

5.  Biologically active metabolites produced by the basidiomycete Quambalaria cyanescens.

Authors:  Eva Stodůlková; Ivana Císařová; Miroslav Kolařík; Milada Chudíčková; Petr Novák; Petr Man; Marek Kuzma; Barbora Pavlů; Jan Černý; Miroslav Flieger
Journal:  PLoS One       Date:  2015-02-27       Impact factor: 3.240

6.  In Vitro Inhibition of Helicobacter pylori Growth by Redox Cycling Phenylaminojuglones.

Authors:  Julio Benites; Héctor Toledo; Felipe Salas; Angélica Guerrero; David Rios; Jaime A Valderrama; Pedro Buc Calderon
Journal:  Oxid Med Cell Longev       Date:  2018-04-24       Impact factor: 6.543

7.  Synthesis and antimicrobial activity of N-substituted-β-amino acid derivatives containing 2-hydroxyphenyl, benzo[b]phenoxazine and quinoxaline moieties.

Authors:  Kristina Mickevičienė; Rūta Baranauskaitė; Kristina Kantminienė; Maryna Stasevych; Olena Komarovska-Porokhnyavets; Volodymyr Novikov
Journal:  Molecules       Date:  2015-02-13       Impact factor: 4.411

8.  The combination therapy of meglumine antimoniate and oxiranes (epoxy-α-lapachone and epoxymethyl-lawsone) enhance the leishmanicidal effect in mice infected by Leishmania (Leishmania) amazonensis.

Authors:  Luiz Filipe Gonçalves-Oliveira; Franklin Souza-Silva; Luzia Monteiro de Castro Côrtes; Laura Barral Veloso; Bernardo Acácio Santini Pereira; Lea Cysne-Finkelstein; Guilherme Curty Lechuga; Saulo Cabral Bourguignon; Fernando Almeida-Souza; Kátia da Silva Calabrese; Vitor Francisco Ferreira; Carlos Roberto Alves
Journal:  Int J Parasitol Drugs Drug Resist       Date:  2019-08-12       Impact factor: 4.077

9.  Synthesis and Biological Screening of New Lawson Derivatives as Selective Substrate-Based Inhibitors of Cytochrome bo3 Ubiquinol Oxidase from Escherichia coli.

Authors:  Isam Elamri; Melanie Radloff; Katharina F Hohmann; Vijaykumar D Nimbarte; Hamid R Nasiri; Michael Bolte; Schara Safarian; Hartmut Michel; Harald Schwalbe
Journal:  ChemMedChem       Date:  2020-04-14       Impact factor: 3.466

10.  Characterization and Trypanocidal Activity of a Novel Pyranaphthoquinone.

Authors:  Elen Diana Dantas; Fabia Julliana Jorge de Souza; William Nascimento Litaiff Nogueira; Cláudia Cândida Silva; Pedro Henrique Antunes de Azevedo; Cícero Flávio Soares Aragão; Patricia Danielle Oliveira de Almeida; Mariana Filomena do Carmo Cardoso; Fernando de Carvalho da Silva; Eduardo Pereira de Azevedo; Euzébio Guimarães Barbosa; Emerson Silva Lima; Vitor Francisco Ferreira; Ádley Antonini Neves de Lima
Journal:  Molecules       Date:  2017-09-30       Impact factor: 4.411
  10 in total

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