A ferutinin analogue with enhanced potency and selectivity against ER-positive breast cancer cells in vitro

[Display omitted] •A hemi-synthetic analogue of the natural phytoestrogen ferutinin is designed to overcome its estrogenic activity.•Ferutinin analogue induces a cytotoxic effect 30 times higher than that of ferutinin towards MCF-7 cell line.•Treatment with ferutinin analogue (1 μM) produced signifi...

Full description

Saved in:
Bibliographic Details
Published inBiomedicine & pharmacotherapy Vol. 105; pp. 267 - 273
Main Authors Safi, Rémi, Hamade, Aline, Bteich, Najat, El Saghir, Jamal, Assaf, Mona Diab, El-Sabban, Marwan, Najjar, Fadia
Format Journal Article
LanguageEnglish
Published France Elsevier Masson SAS 01.09.2018
Subjects
Online AccessGet full text

Cover

Loading…
Abstract [Display omitted] •A hemi-synthetic analogue of the natural phytoestrogen ferutinin is designed to overcome its estrogenic activity.•Ferutinin analogue induces a cytotoxic effect 30 times higher than that of ferutinin towards MCF-7 cell line.•Treatment with ferutinin analogue (1 μM) produced significant accumulation of cells at the pre G0/G1 cell cycle phase.•Ferutinin analogue inhibit the proliferation of MCF-7 cell line and consistently target their stem cells. Estrogen is considered a risk factor for breast cancer since it promotes breast-cell proliferation. The jaesckeanadiol-3-p-hydroxyphenylpropanoate, a hemi-synthetic analogue of the natural phytoestrogen ferutinin (jaesckeanadiol-p-hydroxybenzoate), is designed to be devoid of estrogenic activity. This analogue induces a cytotoxic effect 30 times higher than that of ferutinin towards MCF-7 breast cancer cell line. We compared these two compounds with respect to their effect on proliferation, cell cycle distribution and cancer stem-like cells in the MCF-7 cell line. Treatment with ferutinin (30 μM) and its analogue (1 μM) produced significant accumulation of cells at the pre G0/G1 cell cycle phase and triggered apoptosis. Importantly, this compound retains its anti-proliferative activity against breast cancer stem/progenitor cells that are naturally insensitive to ferutinin at the same dose. These results position ferutinin analogue as an effective compound inhibiting the proliferation of estrogen-dependent breast cancer cells and consistently targeting their stem-like cells.
AbstractList Estrogen is considered a risk factor for breast cancer since it promotes breast-cell proliferation. The jaesckeanadiol-3-p-hydroxyphenylpropanoate, a hemi-synthetic analogue of the natural phytoestrogen ferutinin (jaesckeanadiol-p-hydroxybenzoate), is designed to be devoid of estrogenic activity. This analogue induces a cytotoxic effect 30 times higher than that of ferutinin towards MCF-7 breast cancer cell line. We compared these two compounds with respect to their effect on proliferation, cell cycle distribution and cancer stem-like cells in the MCF-7 cell line. Treatment with ferutinin (30 μM) and its analogue (1 μM) produced significant accumulation of cells at the pre G0/G1 cell cycle phase and triggered apoptosis. Importantly, this compound retains its anti-proliferative activity against breast cancer stem/progenitor cells that are naturally insensitive to ferutinin at the same dose. These results position ferutinin analogue as an effective compound inhibiting the proliferation of estrogen-dependent breast cancer cells and consistently targeting their stem-like cells.
[Display omitted] •A hemi-synthetic analogue of the natural phytoestrogen ferutinin is designed to overcome its estrogenic activity.•Ferutinin analogue induces a cytotoxic effect 30 times higher than that of ferutinin towards MCF-7 cell line.•Treatment with ferutinin analogue (1 μM) produced significant accumulation of cells at the pre G0/G1 cell cycle phase.•Ferutinin analogue inhibit the proliferation of MCF-7 cell line and consistently target their stem cells. Estrogen is considered a risk factor for breast cancer since it promotes breast-cell proliferation. The jaesckeanadiol-3-p-hydroxyphenylpropanoate, a hemi-synthetic analogue of the natural phytoestrogen ferutinin (jaesckeanadiol-p-hydroxybenzoate), is designed to be devoid of estrogenic activity. This analogue induces a cytotoxic effect 30 times higher than that of ferutinin towards MCF-7 breast cancer cell line. We compared these two compounds with respect to their effect on proliferation, cell cycle distribution and cancer stem-like cells in the MCF-7 cell line. Treatment with ferutinin (30 μM) and its analogue (1 μM) produced significant accumulation of cells at the pre G0/G1 cell cycle phase and triggered apoptosis. Importantly, this compound retains its anti-proliferative activity against breast cancer stem/progenitor cells that are naturally insensitive to ferutinin at the same dose. These results position ferutinin analogue as an effective compound inhibiting the proliferation of estrogen-dependent breast cancer cells and consistently targeting their stem-like cells.
Author Hamade, Aline
Assaf, Mona Diab
El-Sabban, Marwan
Najjar, Fadia
El Saghir, Jamal
Safi, Rémi
Bteich, Najat
Author_xml – sequence: 1
  givenname: Rémi
  surname: Safi
  fullname: Safi, Rémi
  organization: Departments of Chemistry–Biochemistry and Biology, Laboratoire d’Innovation Thérapeutique, Faculty of Sciences II, Lebanese University, Lebanon
– sequence: 2
  givenname: Aline
  surname: Hamade
  fullname: Hamade, Aline
  organization: Departments of Chemistry–Biochemistry and Biology, Laboratoire d’Innovation Thérapeutique, Faculty of Sciences II, Lebanese University, Lebanon
– sequence: 3
  givenname: Najat
  surname: Bteich
  fullname: Bteich, Najat
  organization: Departments of Chemistry–Biochemistry and Biology, Laboratoire d’Innovation Thérapeutique, Faculty of Sciences II, Lebanese University, Lebanon
– sequence: 4
  givenname: Jamal
  surname: El Saghir
  fullname: El Saghir, Jamal
  organization: Department of Anatomy, Cell Biology and Physiological Sciences, Faculty of Medicine, American University of Beirut, Beirut, Lebanon
– sequence: 5
  givenname: Mona Diab
  surname: Assaf
  fullname: Assaf, Mona Diab
  organization: Department of Chemistry and Biochemistry, Faculty of Sciences II, Lebanese University, Lebanon
– sequence: 6
  givenname: Marwan
  surname: El-Sabban
  fullname: El-Sabban, Marwan
  email: me00@aub.edu.lb
  organization: Department of Anatomy, Cell Biology and Physiological Sciences, Faculty of Medicine, American University of Beirut, Beirut, Lebanon
– sequence: 7
  givenname: Fadia
  surname: Najjar
  fullname: Najjar, Fadia
  email: fnajjar@ul.edu.lb, fadia.najjar@gmail.com
  organization: Departments of Chemistry–Biochemistry and Biology, Laboratoire d’Innovation Thérapeutique, Faculty of Sciences II, Lebanese University, Lebanon
BackLink https://www.ncbi.nlm.nih.gov/pubmed/29860218$$D View this record in MEDLINE/PubMed
BookMark eNp9kE1r3DAQhkVISTZp_0EpOvbi7UiyZPtSCCFpA4FCac9CksdZbb2SK9kJ-feR2bTHwIDQzPvOx3NBTkMMSMhHBlsGTH3Zb62P085sObB2C7JEe0I2rJNQKYDmlGygkaISgvNzcpHzHgCkEu0ZOeddq4CzdkP-XNEB0zL74AM1wYzxYUH65OcdxbAzwWFPpzhjcM-l3NOMI7rZP_q5_B-MD3mmNz-rKWZfskhtQlNSbnUm6nAcMy2diz7F9-TdYMaMH17fS_L79ubX9ffq_se3u-ur-8oJxefKQYuSG0QHpjENdLUchJK261vGVN3Y2jHXD3KwAqxUtYJa1MyqrjXAXW_FJfl87Dul-HfBPOuDz-sqJmBcsuZQd12xCFak9VHqUsw54aCn5A8mPWsGesWs9_qIWa-YNcgSbbF9ep2w2AP2_03_uBbB16MAy52PHpPOzuNK06fCT_fRvz3hBerVkxU
CitedBy_id crossref_primary_10_2174_1389450121666201005103521
crossref_primary_10_3390_ijms22157910
crossref_primary_10_2174_1389450120666191029155053
crossref_primary_10_3390_plants11151905
Cites_doi 10.1096/fj.07-8560rev
10.1016/j.lfs.2013.03.018
10.1021/np049652h
10.1248/bpb.32.1803
10.1210/mend.11.9.9983
10.1016/j.lfs.2011.11.001
10.1016/S0005-2736(01)00307-8
10.1056/NEJM200101253440407
10.1055/s-2008-1034293
10.1002/ptr.3311
10.7314/APJCP.2014.15.5.2123
10.1006/bbrc.2002.6446
10.1016/j.phymed.2009.05.020
10.1007/s00774-012-0366-0
10.1211/jpp.57.9.0017
10.1021/np0201671
10.1016/j.bcp.2004.05.016
10.1055/s-0031-1280319
10.1016/S0143-4160(02)00203-8
10.1002/ptr.1443
10.1016/j.lfs.2014.06.006
10.1016/j.bmc.2011.08.021
10.1038/sj.onc.1206937
10.1016/j.phytochem.2008.09.019
10.1007/s00774-009-0070-x
10.1007/s11010-011-1164-z
10.3322/caac.21203
10.1016/j.cbi.2003.10.008
10.1111/j.1469-7580.2010.01242.x
10.1016/j.canlet.2006.03.004
10.1016/j.bmcl.2009.05.104
10.1111/cbdd.12670
ContentType Journal Article
Copyright 2018 Elsevier Masson SAS
Copyright © 2018 Elsevier Masson SAS. All rights reserved.
Copyright_xml – notice: 2018 Elsevier Masson SAS
– notice: Copyright © 2018 Elsevier Masson SAS. All rights reserved.
DBID NPM
AAYXX
CITATION
7X8
DOI 10.1016/j.biopha.2018.05.058
DatabaseName PubMed
CrossRef
MEDLINE - Academic
DatabaseTitle PubMed
CrossRef
MEDLINE - Academic
DatabaseTitleList MEDLINE - Academic
PubMed

Database_xml – sequence: 1
  dbid: NPM
  name: PubMed
  url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed
  sourceTypes: Index Database
DeliveryMethod fulltext_linktorsrc
Discipline Medicine
Pharmacy, Therapeutics, & Pharmacology
EISSN 1950-6007
EndPage 273
ExternalDocumentID 10_1016_j_biopha_2018_05_058
29860218
S0753332218300775
Genre Journal Article
GroupedDBID ---
--K
--M
.1-
.FO
.GJ
.~1
0R~
1B1
1P~
1RT
1~.
1~5
23N
4.4
457
4CK
4G.
53G
5GY
5RE
5VS
7-5
71M
8P~
9JM
AABNK
AACTN
AAEDT
AAEDW
AAFWJ
AAIKJ
AAKOC
AALRI
AAOAW
AAQFI
AAQXK
AAXKI
AAXUO
ABBQC
ABFNM
ABMAC
ABMZM
ABXDB
ABZDS
ACDAQ
ACIUM
ACRLP
ADBBV
ADEZE
ADMUD
ADVLN
AEBSH
AEKER
AENEX
AEVXI
AFCTW
AFJKZ
AFKWA
AFPKN
AFRHN
AFTJW
AFXIZ
AGHFR
AGUBO
AGYEJ
AHHHB
AI.
AIEXJ
AIKHN
AITUG
AJOXV
AJRQY
AJUYK
AKRWK
ALCLG
ALMA_UNASSIGNED_HOLDINGS
AMFUW
AMRAJ
ANZVX
ASPBG
AVWKF
AXJTR
AZFZN
BKOJK
BLXMC
BNPGV
CS3
DU5
EBS
EFJIC
EJD
EO8
EO9
EP2
EP3
F5P
FDB
FEDTE
FGOYB
FIRID
FNPLU
FYGXN
G-2
G-Q
GBLVA
GROUPED_DOAJ
HMT
HVGLF
HZ~
IHE
J1W
KOM
M34
M41
MO0
N9A
NCXOZ
O-L
O9-
OAUVE
OD~
OGGZJ
OK1
OO0
OZT
P-8
P-9
P2P
PC.
Q38
R2-
RIG
ROL
RPZ
SDF
SDG
SDP
SEM
SES
SEW
SPT
SSH
SSP
SSZ
T5K
VH1
WUQ
Z5R
~02
~G-
0SF
NPM
AAYXX
ACRPL
ADNMO
CITATION
7X8
ID FETCH-LOGICAL-c362t-c08e52aeec0a7a70945f365b9d811647b4c1cdf5fb30b564604341b698a02cdb3
IEDL.DBID .~1
ISSN 0753-3322
IngestDate Wed Dec 04 08:04:49 EST 2024
Fri Dec 06 06:44:52 EST 2024
Wed Oct 16 00:58:16 EDT 2024
Sat Nov 16 16:00:20 EST 2024
IsPeerReviewed true
IsScholarly true
Keywords BC
Hemi-synthetic analogue
BCSCs
Estrogen
FRT
HRT
E2
SC
SD
Ferutinin
FBS
Stem/progenitor cells
IC50
p-ER
CSCs
SFU
Breast cancer
SERM
EDTA
ER
3D
Ca2
HAEC
PI
CTL
Language English
License Copyright © 2018 Elsevier Masson SAS. All rights reserved.
LinkModel DirectLink
MergedId FETCHMERGED-LOGICAL-c362t-c08e52aeec0a7a70945f365b9d811647b4c1cdf5fb30b564604341b698a02cdb3
Notes ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
PMID 29860218
PQID 2049934131
PQPubID 23479
PageCount 7
ParticipantIDs proquest_miscellaneous_2049934131
crossref_primary_10_1016_j_biopha_2018_05_058
pubmed_primary_29860218
elsevier_sciencedirect_doi_10_1016_j_biopha_2018_05_058
PublicationCentury 2000
PublicationDate 2018-09-01
PublicationDateYYYYMMDD 2018-09-01
PublicationDate_xml – month: 09
  year: 2018
  text: 2018-09-01
  day: 01
PublicationDecade 2010
PublicationPlace France
PublicationPlace_xml – name: France
PublicationTitle Biomedicine & pharmacotherapy
PublicationTitleAlternate Biomed Pharmacother
PublicationYear 2018
Publisher Elsevier Masson SAS
Publisher_xml – name: Elsevier Masson SAS
References Chen, Huang, Wu, Lin, Hsu, Hsieh (bib0135) 2007; 246
Cavani, Ferretti, Carnevale, Bertoni, Zavatti, Palumbo (bib0110) 2012; 30
Iranshahi, Kalategi, Rezaee, Shahverdi, Ito, Furukawa (bib0035) 2008; 74
Kuete, Wiench, Hegazy, Mohamed, Fankam, Shahat (bib0070) 2012; 78
Arghiani, Matin, Bahrami, Iranshahi, Sazgarnia, Rassouli (bib0080) 2014; 109
Choi, Seo, Choi, Choi, Kim, Shin (bib0150) 2012; 363
Tang, BT Ang, Pervaiz (bib0025) 2007; 21
Palumbo, Ferretti, Bertoni, Cavani, Resca, Casolari (bib0100) 2009; 27
Mansoor, Ramalho, Mulhovo, Rodrigues, Ferreira (bib0145) 2009; 19
Poli, Appendino, Sacchetti, Ballero, Maggiano, Ranelletti (bib0045) 2005; 19
Clemons, Goss (bib0010) 2001; 344
Clarke, Liu, Bouker, Gu, Lee, Zhu (bib0020) 2003; 22
Choi, Lee (bib0140) 2009; 32
Nazari, Iranshahi (bib0030) 2011; 25
Bocca, Gabriel, Bozzo, Miglietta (bib0155) 2004; 147
Appendino, Spagliardi, Cravotto, Pocock, Milligan (bib0085) 2002; 65
Zavatti, Resca, Bertoni, Maraldi, Guida, Carnevale (bib0115) 2013; 92
Abramov, Zamaraeva, Hagelgans, Azimov, Krasilnikov (bib0125) 2001; 1512
Lhuillier, Fabre, Cheble, Oueida, Maurel, Valentin (bib0055) 2005; 68
Ikeda, Arao, Otsuka, Nomoto, Horiguchi, Kato (bib0090) 2002; 291
Ferretti, Bertoni, Cavani, Benincasa, Sena, Carnevale (bib0095) 2012; 90
Ferretti, Bertoni, Cavani, Zavatti, Resca, Carnevale (bib0105) 2010; 217
Dall’Acqua, Linardi, Maggi, Nicoletti, Petitto, Innocenti (bib0065) 2011; 19
Macho, Blanco-Molina, Spagliardi, Appendino, Bremner, Heinrich (bib0050) 2004; 68
Jagetia, Baliga, Venkatesh, Ulloor, Mantena, Genebriera (bib0160) 2005; 57
Lazennec, Ediger, Petz, Nardulli, Katzenellenbogen (bib0015) 1997; 11
Iranshahi, Sahebkar, Hosseini, Takasaki, Konoshima, Tokuda (bib0040) 2010; 17
Abramov, MR Duchen (bib0130) 2003; 33
Safi, Rodriguez, Hilal, Diab-Assaf, Diab, El-Sabban (bib0120) 2016; 87
Alkhatib, Hennebelle, Joha, Idziorek, Preudhomme, Quesnel (bib0060) 2008; 69
Matin, Nakhaeizadeh, Bahrami, Iranshahi, Arghiani, Rassouli (bib0075) 2014; 15
DeSantis, Ma, Bryan, Jemal (bib0005) 2014; 64
Macho (10.1016/j.biopha.2018.05.058_bib0050) 2004; 68
Choi (10.1016/j.biopha.2018.05.058_bib0140) 2009; 32
Abramov (10.1016/j.biopha.2018.05.058_bib0130) 2003; 33
Tang (10.1016/j.biopha.2018.05.058_bib0025) 2007; 21
Alkhatib (10.1016/j.biopha.2018.05.058_bib0060) 2008; 69
Chen (10.1016/j.biopha.2018.05.058_bib0135) 2007; 246
Matin (10.1016/j.biopha.2018.05.058_bib0075) 2014; 15
Arghiani (10.1016/j.biopha.2018.05.058_bib0080) 2014; 109
Appendino (10.1016/j.biopha.2018.05.058_bib0085) 2002; 65
Ikeda (10.1016/j.biopha.2018.05.058_bib0090) 2002; 291
Clarke (10.1016/j.biopha.2018.05.058_bib0020) 2003; 22
Lhuillier (10.1016/j.biopha.2018.05.058_bib0055) 2005; 68
Poli (10.1016/j.biopha.2018.05.058_bib0045) 2005; 19
Nazari (10.1016/j.biopha.2018.05.058_bib0030) 2011; 25
Kuete (10.1016/j.biopha.2018.05.058_bib0070) 2012; 78
Palumbo (10.1016/j.biopha.2018.05.058_bib0100) 2009; 27
Iranshahi (10.1016/j.biopha.2018.05.058_bib0040) 2010; 17
Clemons (10.1016/j.biopha.2018.05.058_bib0010) 2001; 344
Cavani (10.1016/j.biopha.2018.05.058_bib0110) 2012; 30
Ferretti (10.1016/j.biopha.2018.05.058_bib0105) 2010; 217
DeSantis (10.1016/j.biopha.2018.05.058_bib0005) 2014; 64
Iranshahi (10.1016/j.biopha.2018.05.058_bib0035) 2008; 74
Abramov (10.1016/j.biopha.2018.05.058_bib0125) 2001; 1512
Dall’Acqua (10.1016/j.biopha.2018.05.058_bib0065) 2011; 19
Safi (10.1016/j.biopha.2018.05.058_bib0120) 2016; 87
Lazennec (10.1016/j.biopha.2018.05.058_bib0015) 1997; 11
Mansoor (10.1016/j.biopha.2018.05.058_bib0145) 2009; 19
Bocca (10.1016/j.biopha.2018.05.058_bib0155) 2004; 147
Zavatti (10.1016/j.biopha.2018.05.058_bib0115) 2013; 92
Choi (10.1016/j.biopha.2018.05.058_bib0150) 2012; 363
Jagetia (10.1016/j.biopha.2018.05.058_bib0160) 2005; 57
Ferretti (10.1016/j.biopha.2018.05.058_bib0095) 2012; 90
References_xml – volume: 25
  start-page: 315
  year: 2011
  end-page: 323
  ident: bib0030
  article-title: Biologically active sesquiterpene coumarins from Ferula species
  publication-title: Phytother.Res.
  contributor:
    fullname: Iranshahi
– volume: 90
  start-page: 161
  year: 2012
  end-page: 168
  ident: bib0095
  article-title: Structural and histomorphometric evaluations of ferutinin effects on the uterus of ovariectomized rats during osteoporosis treatment
  publication-title: Life Sci.
  contributor:
    fullname: Carnevale
– volume: 217
  start-page: 48
  year: 2010
  end-page: 56
  ident: bib0105
  article-title: Influence of ferutinin on bone metabolism in ovariectomized rats. II: role in recovering osteoporosis
  publication-title: J. Anat.
  contributor:
    fullname: Carnevale
– volume: 291
  start-page: 354
  year: 2002
  end-page: 360
  ident: bib0090
  article-title: Terpenoids found in the umbelliferae family act as agonists/antagonists for ER(alpha) and ERbeta: differential transcription activity between ferutinine-liganded ER(alpha) and ERbeta
  publication-title: Biochem. Biophys. Res. Commun.
  contributor:
    fullname: Kato
– volume: 27
  start-page: 538
  year: 2009
  end-page: 545
  ident: bib0100
  article-title: Influence of ferutinin on bone metabolism in ovariectomized rats. I: role in preventing osteoporosis
  publication-title: J. Bone Min. Metab.
  contributor:
    fullname: Casolari
– volume: 87
  start-page: 382
  year: 2016
  end-page: 397
  ident: bib0120
  article-title: Hemisynthesis, antitumoral effect, and molecular docking studies of ferutinin and its analogues
  publication-title: Chem. Biol. Drug Des.
  contributor:
    fullname: El-Sabban
– volume: 363
  start-page: 119
  year: 2012
  end-page: 128
  ident: bib0150
  article-title: Induction of Fas-mediated extrinsic apoptosis, p21WAF1-related G2/M cell cycle arrest and ROS generation by costunolide in estrogen receptor-negative breast cancer cells, MDA-MB-231
  publication-title: Mol. Cell. Biochem.
  contributor:
    fullname: Shin
– volume: 92
  start-page: 993
  year: 2013
  end-page: 1003
  ident: bib0115
  article-title: Ferutinin promotes proliferation and osteoblastic differentiation in human amniotic fluid and dental pulp stem cells
  publication-title: Life Sci.
  contributor:
    fullname: Carnevale
– volume: 147
  start-page: 79
  year: 2004
  end-page: 86
  ident: bib0155
  article-title: A sesquiterpene lactone, costunolide, interacts with microtubule protein and inhibits the growth of MCF-7 cells
  publication-title: Chem. Biol. Interact.
  contributor:
    fullname: Miglietta
– volume: 22
  start-page: 7316
  year: 2003
  end-page: 7339
  ident: bib0020
  article-title: Antiestrogen resistance in breast cancer and the role of estrogen receptor signaling
  publication-title: Oncogene
  contributor:
    fullname: Zhu
– volume: 15
  start-page: 2123
  year: 2014
  end-page: 2128
  ident: bib0075
  article-title: Ferutinin, an apoptosis inducing terpenoid from Ferula ovina
  publication-title: Asian Pac. J. Cancer Prev.
  contributor:
    fullname: Rassouli
– volume: 246
  start-page: 237
  year: 2007
  end-page: 252
  ident: bib0135
  article-title: Isocostunolide, a sesquiterpene lactone, induces mitochondrial membrane depolarization and caspase-dependent apoptosis in human melanoma cells
  publication-title: Cancer Lett.
  contributor:
    fullname: Hsieh
– volume: 69
  start-page: 2979
  year: 2008
  end-page: 2983
  ident: bib0060
  article-title: Activity of elaeochytrin A from Ferula elaeochytris on leukemia cell lines
  publication-title: Phytochemistry
  contributor:
    fullname: Quesnel
– volume: 78
  start-page: 193
  year: 2012
  end-page: 199
  ident: bib0070
  article-title: Antibacterial activity and cytotoxicity of selected Egyptian medicinal plants
  publication-title: Planta Med.
  contributor:
    fullname: Shahat
– volume: 68
  start-page: 468
  year: 2005
  end-page: 471
  ident: bib0055
  article-title: Daucane sesquiterpenes from Ferula hermonis
  publication-title: J. Nat. Prod.
  contributor:
    fullname: Valentin
– volume: 19
  start-page: 152
  year: 2005
  end-page: 157
  ident: bib0045
  article-title: Antiproliferative effects of daucane esters from Ferula communis and
  publication-title: Phytother. Res.
  contributor:
    fullname: Ranelletti
– volume: 33
  start-page: 101
  year: 2003
  end-page: 112
  ident: bib0130
  article-title: Actions of ionomycin, 4-BrA23187 and a novel electrogenic Ca2+ ionophore on mitochondria in intact cells
  publication-title: Cell Calcium
  contributor:
    fullname: MR Duchen
– volume: 17
  start-page: 269
  year: 2010
  end-page: 273
  ident: bib0040
  article-title: Cancer chemopreventive activity of diversin from Ferula diversivittata in vitro and in vivo
  publication-title: Phytomedicine
  contributor:
    fullname: Tokuda
– volume: 1512
  start-page: 98
  year: 2001
  end-page: 110
  ident: bib0125
  article-title: Influence of plant terpenoids on the permeability of mitochondria and lipid bilayers
  publication-title: Biochim. Biophys. Acta
  contributor:
    fullname: Krasilnikov
– volume: 32
  start-page: 1803
  year: 2009
  end-page: 1808
  ident: bib0140
  article-title: Costunolide-induced apoptosis in human leukemia cells: involvement of c-jun N-terminal kinase activation
  publication-title: Biol. Pharm. Bull.
  contributor:
    fullname: Lee
– volume: 64
  start-page: 52
  year: 2014
  end-page: 62
  ident: bib0005
  article-title: Breast cancer statistics, 2013
  publication-title: CA Cancer J. Clin.
  contributor:
    fullname: Jemal
– volume: 19
  start-page: 5876
  year: 2011
  end-page: 5885
  ident: bib0065
  article-title: Natural daucane sesquiterpenes with antiproliferative and proapoptotic activity against human tumor cells
  publication-title: Bioorg. Med. Chem.
  contributor:
    fullname: Innocenti
– volume: 65
  start-page: 1612
  year: 2002
  end-page: 1615
  ident: bib0085
  article-title: Daucane phytoestrogens: a structure-activity study
  publication-title: J. Nat. Prod.
  contributor:
    fullname: Milligan
– volume: 68
  start-page: 875
  year: 2004
  end-page: 883
  ident: bib0050
  article-title: Calcium ionophoretic and apoptotic effects of ferutinin in the human Jurkat T-cell line
  publication-title: Biochem. Pharmacol.
  contributor:
    fullname: Heinrich
– volume: 30
  start-page: 619
  year: 2012
  end-page: 629
  ident: bib0110
  article-title: Effects of different doses of ferutinin on bone formation/resorption in ovariectomized rats
  publication-title: J. Bone Min. Metab.
  contributor:
    fullname: Palumbo
– volume: 344
  start-page: 276
  year: 2001
  end-page: 285
  ident: bib0010
  article-title: Estrogen and the risk of breast cancer
  publication-title: N. Engl. J. Med.
  contributor:
    fullname: Goss
– volume: 57
  start-page: 1213
  year: 2005
  end-page: 1219
  ident: bib0160
  article-title: Evaluation of the cytotoxic effect of the monoterpene indole alkaloid echitamine in-vitro and in tumour-bearing mice
  publication-title: J. Pharm. Pharmacol.
  contributor:
    fullname: Genebriera
– volume: 74
  start-page: 147
  year: 2008
  end-page: 150
  ident: bib0035
  article-title: Cancer chemopreventive activity of terpenoid coumarins from Ferula species
  publication-title: Planta Med.
  contributor:
    fullname: Furukawa
– volume: 109
  start-page: 87
  year: 2014
  end-page: 94
  ident: bib0080
  article-title: Investigating anticancer properties of the sesquiterpene ferutinin on colon carcinoma cells, in vitro and in vivo
  publication-title: Life Sci.
  contributor:
    fullname: Rassouli
– volume: 11
  start-page: 1375
  year: 1997
  end-page: 1386
  ident: bib0015
  article-title: Mechanistic aspects of estrogen receptor activation probed with constitutively active estrogen receptors: correlations with DNA and coregulator interactions and receptor conformational changes
  publication-title: Mol. Endocrinol.
  contributor:
    fullname: Katzenellenbogen
– volume: 21
  start-page: 3777
  year: 2007
  end-page: 3785
  ident: bib0025
  article-title: Cancer stem cell: target for anti-cancer therapy
  publication-title: FASEB J.
  contributor:
    fullname: Pervaiz
– volume: 19
  start-page: 4255
  year: 2009
  end-page: 4258
  ident: bib0145
  article-title: Induction of apoptosis in HuH-7 cancer cells by monoterpene and beta-carboline indole alkaloids isolated from the leaves of Tabernaemontana elegans
  publication-title: Bioorg. Med. Chem. Lett.
  contributor:
    fullname: Ferreira
– volume: 21
  start-page: 3777
  year: 2007
  ident: 10.1016/j.biopha.2018.05.058_bib0025
  article-title: Cancer stem cell: target for anti-cancer therapy
  publication-title: FASEB J.
  doi: 10.1096/fj.07-8560rev
  contributor:
    fullname: Tang
– volume: 92
  start-page: 993
  year: 2013
  ident: 10.1016/j.biopha.2018.05.058_bib0115
  article-title: Ferutinin promotes proliferation and osteoblastic differentiation in human amniotic fluid and dental pulp stem cells
  publication-title: Life Sci.
  doi: 10.1016/j.lfs.2013.03.018
  contributor:
    fullname: Zavatti
– volume: 68
  start-page: 468
  year: 2005
  ident: 10.1016/j.biopha.2018.05.058_bib0055
  article-title: Daucane sesquiterpenes from Ferula hermonis
  publication-title: J. Nat. Prod.
  doi: 10.1021/np049652h
  contributor:
    fullname: Lhuillier
– volume: 32
  start-page: 1803
  year: 2009
  ident: 10.1016/j.biopha.2018.05.058_bib0140
  article-title: Costunolide-induced apoptosis in human leukemia cells: involvement of c-jun N-terminal kinase activation
  publication-title: Biol. Pharm. Bull.
  doi: 10.1248/bpb.32.1803
  contributor:
    fullname: Choi
– volume: 11
  start-page: 1375
  year: 1997
  ident: 10.1016/j.biopha.2018.05.058_bib0015
  article-title: Mechanistic aspects of estrogen receptor activation probed with constitutively active estrogen receptors: correlations with DNA and coregulator interactions and receptor conformational changes
  publication-title: Mol. Endocrinol.
  doi: 10.1210/mend.11.9.9983
  contributor:
    fullname: Lazennec
– volume: 90
  start-page: 161
  year: 2012
  ident: 10.1016/j.biopha.2018.05.058_bib0095
  article-title: Structural and histomorphometric evaluations of ferutinin effects on the uterus of ovariectomized rats during osteoporosis treatment
  publication-title: Life Sci.
  doi: 10.1016/j.lfs.2011.11.001
  contributor:
    fullname: Ferretti
– volume: 1512
  start-page: 98
  year: 2001
  ident: 10.1016/j.biopha.2018.05.058_bib0125
  article-title: Influence of plant terpenoids on the permeability of mitochondria and lipid bilayers
  publication-title: Biochim. Biophys. Acta
  doi: 10.1016/S0005-2736(01)00307-8
  contributor:
    fullname: Abramov
– volume: 344
  start-page: 276
  year: 2001
  ident: 10.1016/j.biopha.2018.05.058_bib0010
  article-title: Estrogen and the risk of breast cancer
  publication-title: N. Engl. J. Med.
  doi: 10.1056/NEJM200101253440407
  contributor:
    fullname: Clemons
– volume: 74
  start-page: 147
  year: 2008
  ident: 10.1016/j.biopha.2018.05.058_bib0035
  article-title: Cancer chemopreventive activity of terpenoid coumarins from Ferula species
  publication-title: Planta Med.
  doi: 10.1055/s-2008-1034293
  contributor:
    fullname: Iranshahi
– volume: 25
  start-page: 315
  year: 2011
  ident: 10.1016/j.biopha.2018.05.058_bib0030
  article-title: Biologically active sesquiterpene coumarins from Ferula species
  publication-title: Phytother.Res.
  doi: 10.1002/ptr.3311
  contributor:
    fullname: Nazari
– volume: 15
  start-page: 2123
  year: 2014
  ident: 10.1016/j.biopha.2018.05.058_bib0075
  article-title: Ferutinin, an apoptosis inducing terpenoid from Ferula ovina
  publication-title: Asian Pac. J. Cancer Prev.
  doi: 10.7314/APJCP.2014.15.5.2123
  contributor:
    fullname: Matin
– volume: 291
  start-page: 354
  year: 2002
  ident: 10.1016/j.biopha.2018.05.058_bib0090
  article-title: Terpenoids found in the umbelliferae family act as agonists/antagonists for ER(alpha) and ERbeta: differential transcription activity between ferutinine-liganded ER(alpha) and ERbeta
  publication-title: Biochem. Biophys. Res. Commun.
  doi: 10.1006/bbrc.2002.6446
  contributor:
    fullname: Ikeda
– volume: 17
  start-page: 269
  year: 2010
  ident: 10.1016/j.biopha.2018.05.058_bib0040
  article-title: Cancer chemopreventive activity of diversin from Ferula diversivittata in vitro and in vivo
  publication-title: Phytomedicine
  doi: 10.1016/j.phymed.2009.05.020
  contributor:
    fullname: Iranshahi
– volume: 30
  start-page: 619
  year: 2012
  ident: 10.1016/j.biopha.2018.05.058_bib0110
  article-title: Effects of different doses of ferutinin on bone formation/resorption in ovariectomized rats
  publication-title: J. Bone Min. Metab.
  doi: 10.1007/s00774-012-0366-0
  contributor:
    fullname: Cavani
– volume: 57
  start-page: 1213
  year: 2005
  ident: 10.1016/j.biopha.2018.05.058_bib0160
  article-title: Evaluation of the cytotoxic effect of the monoterpene indole alkaloid echitamine in-vitro and in tumour-bearing mice
  publication-title: J. Pharm. Pharmacol.
  doi: 10.1211/jpp.57.9.0017
  contributor:
    fullname: Jagetia
– volume: 65
  start-page: 1612
  year: 2002
  ident: 10.1016/j.biopha.2018.05.058_bib0085
  article-title: Daucane phytoestrogens: a structure-activity study
  publication-title: J. Nat. Prod.
  doi: 10.1021/np0201671
  contributor:
    fullname: Appendino
– volume: 68
  start-page: 875
  year: 2004
  ident: 10.1016/j.biopha.2018.05.058_bib0050
  article-title: Calcium ionophoretic and apoptotic effects of ferutinin in the human Jurkat T-cell line
  publication-title: Biochem. Pharmacol.
  doi: 10.1016/j.bcp.2004.05.016
  contributor:
    fullname: Macho
– volume: 78
  start-page: 193
  year: 2012
  ident: 10.1016/j.biopha.2018.05.058_bib0070
  article-title: Antibacterial activity and cytotoxicity of selected Egyptian medicinal plants
  publication-title: Planta Med.
  doi: 10.1055/s-0031-1280319
  contributor:
    fullname: Kuete
– volume: 33
  start-page: 101
  year: 2003
  ident: 10.1016/j.biopha.2018.05.058_bib0130
  article-title: Actions of ionomycin, 4-BrA23187 and a novel electrogenic Ca2+ ionophore on mitochondria in intact cells
  publication-title: Cell Calcium
  doi: 10.1016/S0143-4160(02)00203-8
  contributor:
    fullname: Abramov
– volume: 19
  start-page: 152
  year: 2005
  ident: 10.1016/j.biopha.2018.05.058_bib0045
  article-title: Antiproliferative effects of daucane esters from Ferula communis and F. arrigonii on human colon cancer cell lines
  publication-title: Phytother. Res.
  doi: 10.1002/ptr.1443
  contributor:
    fullname: Poli
– volume: 109
  start-page: 87
  year: 2014
  ident: 10.1016/j.biopha.2018.05.058_bib0080
  article-title: Investigating anticancer properties of the sesquiterpene ferutinin on colon carcinoma cells, in vitro and in vivo
  publication-title: Life Sci.
  doi: 10.1016/j.lfs.2014.06.006
  contributor:
    fullname: Arghiani
– volume: 19
  start-page: 5876
  year: 2011
  ident: 10.1016/j.biopha.2018.05.058_bib0065
  article-title: Natural daucane sesquiterpenes with antiproliferative and proapoptotic activity against human tumor cells
  publication-title: Bioorg. Med. Chem.
  doi: 10.1016/j.bmc.2011.08.021
  contributor:
    fullname: Dall’Acqua
– volume: 22
  start-page: 7316
  year: 2003
  ident: 10.1016/j.biopha.2018.05.058_bib0020
  article-title: Antiestrogen resistance in breast cancer and the role of estrogen receptor signaling
  publication-title: Oncogene
  doi: 10.1038/sj.onc.1206937
  contributor:
    fullname: Clarke
– volume: 69
  start-page: 2979
  year: 2008
  ident: 10.1016/j.biopha.2018.05.058_bib0060
  article-title: Activity of elaeochytrin A from Ferula elaeochytris on leukemia cell lines
  publication-title: Phytochemistry
  doi: 10.1016/j.phytochem.2008.09.019
  contributor:
    fullname: Alkhatib
– volume: 27
  start-page: 538
  year: 2009
  ident: 10.1016/j.biopha.2018.05.058_bib0100
  article-title: Influence of ferutinin on bone metabolism in ovariectomized rats. I: role in preventing osteoporosis
  publication-title: J. Bone Min. Metab.
  doi: 10.1007/s00774-009-0070-x
  contributor:
    fullname: Palumbo
– volume: 363
  start-page: 119
  year: 2012
  ident: 10.1016/j.biopha.2018.05.058_bib0150
  article-title: Induction of Fas-mediated extrinsic apoptosis, p21WAF1-related G2/M cell cycle arrest and ROS generation by costunolide in estrogen receptor-negative breast cancer cells, MDA-MB-231
  publication-title: Mol. Cell. Biochem.
  doi: 10.1007/s11010-011-1164-z
  contributor:
    fullname: Choi
– volume: 64
  start-page: 52
  year: 2014
  ident: 10.1016/j.biopha.2018.05.058_bib0005
  article-title: Breast cancer statistics, 2013
  publication-title: CA Cancer J. Clin.
  doi: 10.3322/caac.21203
  contributor:
    fullname: DeSantis
– volume: 147
  start-page: 79
  year: 2004
  ident: 10.1016/j.biopha.2018.05.058_bib0155
  article-title: A sesquiterpene lactone, costunolide, interacts with microtubule protein and inhibits the growth of MCF-7 cells
  publication-title: Chem. Biol. Interact.
  doi: 10.1016/j.cbi.2003.10.008
  contributor:
    fullname: Bocca
– volume: 217
  start-page: 48
  year: 2010
  ident: 10.1016/j.biopha.2018.05.058_bib0105
  article-title: Influence of ferutinin on bone metabolism in ovariectomized rats. II: role in recovering osteoporosis
  publication-title: J. Anat.
  doi: 10.1111/j.1469-7580.2010.01242.x
  contributor:
    fullname: Ferretti
– volume: 246
  start-page: 237
  year: 2007
  ident: 10.1016/j.biopha.2018.05.058_bib0135
  article-title: Isocostunolide, a sesquiterpene lactone, induces mitochondrial membrane depolarization and caspase-dependent apoptosis in human melanoma cells
  publication-title: Cancer Lett.
  doi: 10.1016/j.canlet.2006.03.004
  contributor:
    fullname: Chen
– volume: 19
  start-page: 4255
  year: 2009
  ident: 10.1016/j.biopha.2018.05.058_bib0145
  article-title: Induction of apoptosis in HuH-7 cancer cells by monoterpene and beta-carboline indole alkaloids isolated from the leaves of Tabernaemontana elegans
  publication-title: Bioorg. Med. Chem. Lett.
  doi: 10.1016/j.bmcl.2009.05.104
  contributor:
    fullname: Mansoor
– volume: 87
  start-page: 382
  year: 2016
  ident: 10.1016/j.biopha.2018.05.058_bib0120
  article-title: Hemisynthesis, antitumoral effect, and molecular docking studies of ferutinin and its analogues
  publication-title: Chem. Biol. Drug Des.
  doi: 10.1111/cbdd.12670
  contributor:
    fullname: Safi
SSID ssj0005638
Score 2.2934678
Snippet [Display omitted] •A hemi-synthetic analogue of the natural phytoestrogen ferutinin is designed to overcome its estrogenic activity.•Ferutinin analogue induces...
Estrogen is considered a risk factor for breast cancer since it promotes breast-cell proliferation. The jaesckeanadiol-3-p-hydroxyphenylpropanoate, a...
SourceID proquest
crossref
pubmed
elsevier
SourceType Aggregation Database
Index Database
Publisher
StartPage 267
SubjectTerms Breast cancer
Estrogen
Ferutinin
Hemi-synthetic analogue
Stem/progenitor cells
Title A ferutinin analogue with enhanced potency and selectivity against ER-positive breast cancer cells in vitro
URI https://dx.doi.org/10.1016/j.biopha.2018.05.058
https://www.ncbi.nlm.nih.gov/pubmed/29860218
https://search.proquest.com/docview/2049934131
Volume 105
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3da9RAEF9KC-KLaP06tWUE6VPX23xsNnk8SsuptBRtoW9hv2KjkBx3V-Fe_Nud2U3aCoog5CXZSbLszO7M7M7Mj7F3aaKt0oXjQmrBc60qrlPleU7ORpoKIwPy3OlZMb_MP17Jqy12NObCUFjlsPbHNT2s1sOT6TCa00XbTr-gsssylEcUylDIjTLYpSAUg_c_74V5FAHNmog5UY_pcyHGy7Q9FWVCJViG-p0E_P5n9fQ38zOooZPH7NFgP8IsdvEJ2_LdLntwOpyQ77KD81iLenMIF3epVatDOIDzuyrVm6fs-wwav8TGru1Ad3EPB2hbFnx3HeICYNGTRb3BZgerAJgToCZAf9UtmpVw_JnHoK8fHgxFt6_B0ptLoPOAFeCXkX7ZP2OXJ8cXR3M-IC9wiwptza0ovUy191ZopRW6gLLJCmkqVyZUgMzkNrGukY3JkJtFXogctaEpqlKL1DqTPWfbXd_5lwyUTZ0SrimVzXKXFLrKpEGnrsG5b13eTBgfB7xexAIb9Rh59q2ODKqJQbWQeJUTpkau1L8JSo064B9vvh2ZWOMcooHQne9vVkiEfh-p82TCXkTu3vYlrQilKylf_fd_X7OHdBcD096w7fXyxu-hJbM2-0FU99nO7MOn-dkvxN7y6g
link.rule.ids 314,780,784,4502,24116,27924,27925,45585,45679
linkProvider Elsevier
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1La9wwEB7SFNpcSps-sk0fKpScoq5sS5Z9DCFh22ZDaDeQm9HLqROwl91NYS_97RlJdtNCS6HgkyXZQjPSNyN9mgF4nybKSJVbyoRilCtZUpVKR7l3NtKUaREyz01P88k5_3QhLjbgcLgL42mV_dof1_SwWvdvxv1ojudNM_6KYJdlqI-olCGQ2z24zwVav6jUH378wvPIQzprX5v66sP9uUDy0k3nozIhChYhgKfP_P5nfPqb_Rlw6PgxPOoNSHIQ-_gENly7DQ-m_RH5NuydxWDU630yu7tbtdwne-TsLkz1-ilcH5DaLbCwbVqi2riJQ_y-LHHtt0AMIPPOm9RrLLZkGTLmhFwTRF2qBu1KcvSFRtbXd0e0p7eviPEtF8QfCCwJfhnrL7pncH58NDuc0D71AjWIaCtqWOFEqpwzTEkl0QcUdZYLXdoi8RHINDeJsbWodYbizHnOOMKhzstCsdRYnT2HzbZr3Q4QaVIrma0LaTJuk1yVmdDo1dU4-Y3l9QjoMODVPEbYqAbq2VUVBVR5AVVM4FOMQA5SqX7TlApB4B8t3w1CrHAS-YFQretullgJHT-P58kIXkTp_uxLWvo0XUnx8r__-xYeTmbTk-rk4-nnXdjyJZGl9go2V4sb9xrNmpV-E9T2FnuB9Ic
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=A+ferutinin+analogue+with+enhanced+potency+and+selectivity+against+ER-positive+breast+cancer+cells+in+vitro&rft.jtitle=Biomedicine+%26+pharmacotherapy&rft.au=Safi%2C+R%C3%A9mi&rft.au=Hamade%2C+Aline&rft.au=Bteich%2C+Najat&rft.au=El+Saghir%2C+Jamal&rft.date=2018-09-01&rft.eissn=1950-6007&rft.volume=105&rft.spage=267&rft_id=info:doi/10.1016%2Fj.biopha.2018.05.058&rft_id=info%3Apmid%2F29860218&rft.externalDocID=29860218
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0753-3322&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0753-3322&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0753-3322&client=summon