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Statements

Subject Item
n2:RIV%2F00216208%3A11310%2F11%3A10100517%21RIV12-GA0-11310___
rdf:type
n16:Vysledek skos:Concept
rdfs:seeAlso
http://dx.doi.org/10.1016/j.bbapap.2010.05.016
dcterms:description
An antineoplastic alkaloid ellipticine is a prodrug, whose pharmacological efficiency is dependent on its cytochrome P450 (CYP)- and/or peroxidase-mediated activation in target tissues. The aim of this review was to summarize our knowledge on the molecular mechanisms of ellipticine action in the cancer cells. The CYP-mediated ellipticine metabolites 9-hydroxy- and 7-hydroxyellipticine and the product of ellipticine oxidation by peroxidases, the ellipticine dimer, are the detoxication metabolites of this compound. In contrast, two carbenium ions, ellipticine-13-ylium and ellipticine-12-ylium, derived from two activation ellipticine metabolites, 13-hydroxyellipticine and 12-hydroxyellipticine, generate two major deoxyguanosine adducts in DNA found in the human breast adenocarcinoma MCF-7 cells, leukemia HL-60 and CCRF-CEM cells, neuroblastoma IMR-32, UKF-NB-3, and UKF-NB-4 cells and glioblastoma U87MG cells in vitro and in rat breast carcinoma in vivo. Formation of these covalent DNA adducts by ellipticine is the predominant mechanism of its cytotoxicity and anti-tumor activity to these cancer cell lines. Ellipticine is also an inducer of CYP1A, 1B1, and 3A4 enzymes in the cancer cells and/or in vivo in rats exposed to this compound, thus modulating its own pharmacological efficiencies. The study forms the basis to further predict the susceptibility of human cancers to ellipticine and suggests that this alkaloid for treatment in combination with CYP and/or peroxidase gene transfer increasing the anticancer potential of this prodrug. It also suggests ellipticine reactive metabolites 13-hydroxyellipticine and 12-hydroxyellipticine to be good candidates for targeting to tumors absent from the CYP and peroxidase activation enzymes. (C) 2010 Elsevier B.V. All rights reserved. An antineoplastic alkaloid ellipticine is a prodrug, whose pharmacological efficiency is dependent on its cytochrome P450 (CYP)- and/or peroxidase-mediated activation in target tissues. The aim of this review was to summarize our knowledge on the molecular mechanisms of ellipticine action in the cancer cells. The CYP-mediated ellipticine metabolites 9-hydroxy- and 7-hydroxyellipticine and the product of ellipticine oxidation by peroxidases, the ellipticine dimer, are the detoxication metabolites of this compound. In contrast, two carbenium ions, ellipticine-13-ylium and ellipticine-12-ylium, derived from two activation ellipticine metabolites, 13-hydroxyellipticine and 12-hydroxyellipticine, generate two major deoxyguanosine adducts in DNA found in the human breast adenocarcinoma MCF-7 cells, leukemia HL-60 and CCRF-CEM cells, neuroblastoma IMR-32, UKF-NB-3, and UKF-NB-4 cells and glioblastoma U87MG cells in vitro and in rat breast carcinoma in vivo. Formation of these covalent DNA adducts by ellipticine is the predominant mechanism of its cytotoxicity and anti-tumor activity to these cancer cell lines. Ellipticine is also an inducer of CYP1A, 1B1, and 3A4 enzymes in the cancer cells and/or in vivo in rats exposed to this compound, thus modulating its own pharmacological efficiencies. The study forms the basis to further predict the susceptibility of human cancers to ellipticine and suggests that this alkaloid for treatment in combination with CYP and/or peroxidase gene transfer increasing the anticancer potential of this prodrug. It also suggests ellipticine reactive metabolites 13-hydroxyellipticine and 12-hydroxyellipticine to be good candidates for targeting to tumors absent from the CYP and peroxidase activation enzymes. (C) 2010 Elsevier B.V. All rights reserved.
dcterms:title
Cytochrome P450-and peroxidase-mediated oxidation of anticancer alkaloid ellipticine dictates its anti-tumor efficiency Cytochrome P450-and peroxidase-mediated oxidation of anticancer alkaloid ellipticine dictates its anti-tumor efficiency
skos:prefLabel
Cytochrome P450-and peroxidase-mediated oxidation of anticancer alkaloid ellipticine dictates its anti-tumor efficiency Cytochrome P450-and peroxidase-mediated oxidation of anticancer alkaloid ellipticine dictates its anti-tumor efficiency
skos:notation
RIV/00216208:11310/11:10100517!RIV12-GA0-11310___
n16:predkladatel
n21:orjk%3A11310
n3:aktivita
n8:P n8:Z
n3:aktivity
P(1M0505), P(GAP301/10/0356), Z(MSM0021620808)
n3:cisloPeriodika
1
n3:dodaniDat
n19:2012
n3:domaciTvurceVysledku
n11:2146851 n11:8486573
n3:druhVysledku
n22:J
n3:duvernostUdaju
n20:S
n3:entitaPredkladatele
n17:predkladatel
n3:idSjednocenehoVysledku
192626
n3:idVysledku
RIV/00216208:11310/11:10100517
n3:jazykVysledku
n10:eng
n3:klicovaSlova
deoxyguanosine adducts; covalent binding; drug ellipticine; human brain-tumors; human-breast-cancer; carcinogen aristolochic acid; cell-cycle arrest; xenobiotic-metabolizing enzymes; polycyclic aromatic-hydrocarbons; Dna adduct formation
n3:klicoveSlovo
n4:covalent%20binding n4:deoxyguanosine%20adducts n4:carcinogen%20aristolochic%20acid n4:human%20brain-tumors n4:cell-cycle%20arrest n4:human-breast-cancer n4:drug%20ellipticine n4:polycyclic%20aromatic-hydrocarbons n4:Dna%20adduct%20formation n4:xenobiotic-metabolizing%20enzymes
n3:kodStatuVydavatele
NL - Nizozemsko
n3:kontrolniKodProRIV
[335C920877F2]
n3:nazevZdroje
Biochimica et Biophysica Acta - Proteins and Proteomics
n3:obor
n13:CE
n3:pocetDomacichTvurcuVysledku
2
n3:pocetTvurcuVysledku
3
n3:projekt
n9:GAP301%2F10%2F0356 n9:1M0505
n3:rokUplatneniVysledku
n19:2011
n3:svazekPeriodika
1814
n3:tvurceVysledku
Stiborová, Marie Rupertová, Martina Frei, Eva
n3:wos
000285277900022
n3:zamer
n14:MSM0021620808
s:issn
1570-9639
s:numberOfPages
11
n15:doi
10.1016/j.bbapap.2010.05.016
n18:organizacniJednotka
11310