Please use this identifier to cite or link to this item: http://hdl.handle.net/10316/45095
DC FieldValueLanguage
dc.contributor.authorSerafim, Teresa L.-
dc.contributor.authorCarvalho, Filipa S.-
dc.contributor.authorMarques, Maria P. M.-
dc.contributor.authorCalheiros, Rita-
dc.contributor.authorSilva, Tiago-
dc.contributor.authorGarrido, Jorge-
dc.contributor.authorMilhazes, Nuno-
dc.contributor.authorBorges, Fernanda-
dc.contributor.authorRoleira, Fernanda-
dc.contributor.authorSilva, Elisiário T.-
dc.contributor.authorHoly, Jon-
dc.contributor.authorOliveira, Paulo J.-
dc.date.accessioned2017-12-15T17:45:34Z-
dc.date.available2017-12-15T17:45:34Z-
dc.date.issued2011-
dc.identifier.urihttp://hdl.handle.net/10316/45095-
dc.description.abstractIn the present work, lipophilic caffeic and ferulic acid derivatives were synthesized, and their cytotoxicity on cultured breast cancer cells was compared. A total of six compounds were initially evaluated: caffeic acid (CA), hexyl caffeate (HC), caffeoylhexylamide (HCA), ferulic acid (FA), hexyl ferulate (HF), and feruloylhexylamide (HFA). Cell proliferation, cell cycle progression, and apoptotic signaling were investigated in three human breast cancer cell lines, including estrogen-sensitive (MCF-7) and insensitive (MDA-MB-231 and HS578T). Furthermore, direct mitochondrial effects of parent and modified compounds were investigated by using isolated liver mitochondria. The results indicated that although the parent compounds presented no cytotoxicity, the new compounds inhibited cell proliferation and induced cell cycle alterations and cell death, with a predominant effect on MCF-7 cells. Interestingly, cell cycle data indicates that effects on nontumor BJ fibroblasts were predominantly cytostatic and not cytotoxic. The parent compounds and derivatives also promoted direct alterations on hepatic mitochondrial bioenergetics, although the most unexpected and never before reported one was that FA induces the mitochondrial permeability transition. The results show that the new caffeic and ferulic acid lipophilic derivatives show increased cytotoxicity toward human breast cancer cell lines, although the magnitude and type of effects appear to be dependent on the cell type. Mitochondrial data had no direct correspondence with effects on intact cells suggesting that this organelle may not be a critical component of the cellular effects observed. The data provide a rational approach to the design of effective cytotoxic lipophilic hydroxycinnamic derivatives that in the future could be profitably applied for chemopreventive and/or chemotherapeutic purposes.por
dc.language.isoengpor
dc.rightsopenAccesspor
dc.subjectAntineoplastic Agentspor
dc.subjectAntioxidantspor
dc.subjectApoptosispor
dc.subjectBreast Neoplasmspor
dc.subjectCaffeic Acidspor
dc.subjectCell Cyclepor
dc.subjectCell Line, Tumorpor
dc.subjectCell Proliferationpor
dc.subjectCoumaric Acidspor
dc.subjectFemalepor
dc.subjectHumanspor
dc.subjectMitochondriapor
dc.titleLipophilic Caffeic and Ferulic Acid Derivatives Presenting Cytotoxicity against Human Breast Cancer Cellspor
dc.typearticle-
degois.publication.firstPage763por
degois.publication.lastPage774por
degois.publication.issue5por
degois.publication.titleChemical Research in Toxicologypor
dc.peerreviewedyespor
dc.identifier.doi10.1021/tx200126rpor
dc.identifier.doi10.1021/tx200126r-
degois.publication.volume24por
uc.controloAutoridadeSim-
item.fulltextCom Texto completo-
item.grantfulltextopen-
item.languageiso639-1en-
crisitem.author.deptFaculty of Sciences and Technology-
crisitem.author.deptFaculty of Pharmacy-
crisitem.author.parentdeptUniversity of Coimbra-
crisitem.author.researchunitCNC - Center for Neuroscience and Cell Biology-
crisitem.author.researchunitQFM-UC – Molecular Physical-Chemistry R&D Unit-
crisitem.author.researchunitCNC - Center for Neuroscience and Cell Biology-
crisitem.author.orcid0000-0003-4924-5204-
crisitem.author.orcid0000-0002-8391-0055-
crisitem.author.orcid0000-0001-8981-231X-
crisitem.author.orcid0000-0003-4229-5882-
Appears in Collections:FCTUC Ciências da Vida - Artigos em Revistas Internacionais
Files in This Item:
File Description SizeFormat
ChemResTox_11_24.pdf3.2 MBAdobe PDFView/Open
Show simple item record

SCOPUSTM   
Citations

80
checked on Feb 18, 2020

WEB OF SCIENCETM
Citations 1

87
checked on Sep 2, 2021

Page view(s)

297
checked on Sep 24, 2021

Download(s) 50

316
checked on Sep 24, 2021

Google ScholarTM

Check

Altmetric

Altmetric


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.