Abstract
The current work shows a new synthetic methodology to obtain 21 naphthoquinones that have been evaluated against oral cavity cancer. The compounds were obtained by a three-component reaction involving lawsone, dimedone and aromatic aldehydes catalyzed by lithium chloride under microwave irradiation to produce families of 1,4- and 1,2-naphthoquinones. A clonogenic assay was performed on SCC9 cell line cultures with all compounds, revealing five very active compounds. In the 3,4,5-dimethylthiazol-2,5-diphenyltetrazolium bromide cell viability assay using three different cell lines (SCC9, SCC4 and SCC25), 8c had an average IC50 of approximately 1.45 μM capable of reducing tumor cell viability, approximately 90-times higher than carboplatin. Therefore, the xanthene-naphthoquinone derivatives show promising bioactivity for oral cavity cancer treatment.
References
Dec 1, 1990·Cell Biology International Reports·J M JamisonC C Tsai
Jan 1, 1991·Journal of Medicinal Chemistry·G W RewcastleW A Denny
Mar 10, 2001·Cancer Treatment Reviews·W T Bradner
Aug 29, 2003·Phytochemistry·Kyung-Hee LeeMaung Tin-Wa
Apr 24, 2004·Journal of Natural Products·Anne-Emmanuelle HayPascal Richomme
Nov 25, 2005·Assay and Drug Development Technologies·Robert J Turner, Steven J Charlton
Jan 6, 2006·Chemical & Pharmaceutical Bulletin·Anatole Guy Blaise AzebazeAugustin Ephrem Nkengfack
May 3, 2006·Chemical & Pharmaceutical Bulletin·Surat LaphookhieoKan Chantrapromma
Apr 5, 2007·Nature Protocols·Nicolaas A P FrankenChris van Bree
May 20, 2008·Lancet·Athanassios ArgirisRobert L Ferris
Dec 17, 2008·Journal of Natural Products·Si-Jia TaoDe-An Guo
Mar 20, 2009·Journal of Natural Products·Fabien ZelefackMarie-Geneviève Dijoux-Franca
Jul 25, 2009·Journal of Natural Products·Panawan MoosophonKasem Soytong
Apr 15, 2010·Journal of Asian Natural Products Research·Najihah HashimHazar B M Ismail
Apr 26, 2011·Oral Oncology·A L WattersM Agulnik
Sep 29, 2011·Annual Review of Pharmacology and Toxicology·Yoshito KumagaiArthur K Cho
Feb 14, 2012·Phytochemistry·Sheng-Li NiuHui-Ming Hua
Jan 3, 2013·The Journal of Pharmacy and Pharmacology·Oktay TacarCrispin R Dass
Feb 7, 2013·Medicina oral, patología oral y cirugía bucal·Shao-Hui Huang, Brian O'Sullivan
May 17, 2013·The Journal of Physical Chemistry. B·Christopher S CoatesK V Lakshmi
Sep 17, 2013·Planta medica·Thiago F DinizSteyner F Cortes
Feb 6, 2014·Australian Dental Journal·N BeechM Batstone
Feb 7, 2014·Journal of Natural Products·Gordon M CraggDavid J Newman
Mar 7, 2014·Journal of Clinical and Experimental Dentistry·Begonya Chaveli-López
May 6, 2014·Oral and Maxillofacial Surgery Clinics of North America·Nadarajah Vigneswaran, Michelle D Williams
Feb 6, 2015·CA: a Cancer Journal for Clinicians·Lindsey A TorreAhmedin Jemal
Jan 30, 2016·BMC Complementary and Alternative Medicine·Dayang Fredalina BasriKok Meng Chan
Jun 10, 2016·The Journal of Organic Chemistry·Paula F CarneiroVitor F Ferreira
Jun 14, 2016·Current Pharmaceutical Design·Vitor Francisco FerreiraFernando de Carvalho da Silva