Literature DB >> 34778772

It takes two to tango: synthesis of cytotoxic quinones containing two redox active centers with potential antitumor activity.

Daisy J B Lima1,2, Renata G Almeida3, Guilherme A M Jardim3,4, Breno P A Barbosa2,3, Augusto C C Santos3, Wagner O Valença3, Marcos R Scheide4, Claudia C Gatto5, Guilherme G C de Carvalho1, Pedro M S Costa1, Claudia Pessoa1, Cynthia L M Pereira3, Claus Jacob2, Antonio L Braga4, Eufrânio N da Silva Júnior3.   

Abstract

We report the synthesis of 47 new quinone-based derivatives via click chemistry and their subsequent evaluation against cancer cell lines and the control L929 murine fibroblast cell line. These compounds combine two redox centers, such as an ortho-quinone/para-quinone or quinones/selenium with the 1,2,3-triazole nucleus. Several of these compounds present IC50 values below 0.5 μM in cancer cell lines with significantly lower cytotoxicity in the control cell line L929 and good selectivity index. Hence, our study confirms the use of a complete and very diverse range of quinone compounds with potential application against certain cancer cell lines. This journal is © The Royal Society of Chemistry.

Entities:  

Year:  2021        PMID: 34778772      PMCID: PMC8528272          DOI: 10.1039/d1md00168j

Source DB:  PubMed          Journal:  RSC Med Chem        ISSN: 2632-8682


  53 in total

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Authors:  Rebecca C Taylor; Sean P Cullen; Seamus J Martin
Journal:  Nat Rev Mol Cell Biol       Date:  2008-03       Impact factor: 94.444

2.  Ruthenium-catalyzed C-H oxygenation of quinones by weak O-coordination for potent trypanocidal agents.

Authors:  Gleiston G Dias; Torben Rogge; Rositha Kuniyil; Claus Jacob; Rubem F S Menna-Barreto; Eufrânio N da Silva Júnior; Lutz Ackermann
Journal:  Chem Commun (Camb)       Date:  2018-11-13       Impact factor: 6.222

3.  Growth inhibitory effects of 3'-nitro-3-phenylamino nor-beta-lapachone against HL-60: a redox-dependent mechanism.

Authors:  A J Araújo; A A de Souza; E N da Silva Júnior; J D B Marinho-Filho; M A B F de Moura; D D Rocha; M C Vasconcellos; C O Costa; C Pessoa; M O de Moraes; V F Ferreira; F C de Abreu; A V Pinto; R C Montenegro; L V Costa-Lotufo; M O F Goulart
Journal:  Toxicol In Vitro       Date:  2012-02-22       Impact factor: 3.500

4.  Natural product-inspired profluorophores for imaging NQO1 activity in tumour tissues.

Authors:  Zhiming Cheng; Wagner O Valença; Gleiston G Dias; Jamie Scott; Nicole D Barth; Fabio de Moliner; Gabriela B P Souza; Richard J Mellanby; Marc Vendrell; Eufrânio N da Silva Júnior
Journal:  Bioorg Med Chem       Date:  2019-07-15       Impact factor: 3.641

5.  Cytochrome c and dATP-dependent formation of Apaf-1/caspase-9 complex initiates an apoptotic protease cascade.

Authors:  P Li; D Nijhawan; I Budihardjo; S M Srinivasula; M Ahmad; E S Alnemri; X Wang
Journal:  Cell       Date:  1997-11-14       Impact factor: 41.582

Review 6.  Cytochrome c: functions beyond respiration.

Authors:  Yong-Ling P Ow; Douglas R Green; Zhenyue Hao; Tak W Mak
Journal:  Nat Rev Mol Cell Biol       Date:  2008-07       Impact factor: 94.444

7.  Direct sequential C-H iodination/organoyl-thiolation for the benzenoid A-ring modification of quinonoid deactivated systems: a new protocol for potent trypanocidal quinones.

Authors:  Guilherme A M Jardim; Willian X C Oliveira; Rossimiriam P de Freitas; Rubem F S Menna-Barreto; Thaissa L Silva; Marilia O F Goulart; Eufrânio N da Silva Júnior
Journal:  Org Biomol Chem       Date:  2018-03-07       Impact factor: 3.876

8.  Overcoming naphthoquinone deactivation: rhodium-catalyzed C-5 selective C-H iodination as a gateway to functionalized derivatives.

Authors:  Guilherme A M Jardim; Eufrânio N da Silva Júnior; John F Bower
Journal:  Chem Sci       Date:  2016-03-02       Impact factor: 9.825

9.  Synthesis of Selenium-Quinone Hybrid Compounds with Potential Antitumor Activity via Rh-Catalyzed C-H Bond Activation and Click Reactions.

Authors:  Guilherme A M Jardim; Daisy J B Lima; Wagner O Valença; Daisy J B Lima; Bruno C Cavalcanti; Claudia Pessoa; Jamal Rafique; Antonio L Braga; Claus Jacob; Eufrânio N da Silva Júnior; Eduardo H G da Cruz
Journal:  Molecules       Date:  2017-12-30       Impact factor: 4.411

10.  Cardiolipin provides an essential activating platform for caspase-8 on mitochondria.

Authors:  Francois Gonzalvez; Zachary T Schug; Riekelt H Houtkooper; Elaine D MacKenzie; David G Brooks; Ronald J A Wanders; Patrice X Petit; Frédéric M Vaz; Eyal Gottlieb
Journal:  J Cell Biol       Date:  2008-11-10       Impact factor: 10.539

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