Instituto Canario Of Investigacion Del Cancer Icic

Canary Islands, Spain

Instituto Canario Of Investigacion Del Cancer Icic

Canary Islands, Spain
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Rudys S.,Vilnius University | Rios-Luci C.,University of La Laguna | Perez-Roth E.,University of La Laguna | Cikotiene I.,Vilnius University | And 2 more authors.
Bioorganic and Medicinal Chemistry Letters | Year: 2010

A series of 2-substituted 1,2-dihydro-3-phenyl-1-(trichloromethyl)benzo[b][1,6]naphthyridines were synthesized and their in vitro antiproliferative activities were examined against human solid tumor cell lines and relevant strains of bacteria and Candida. The compounds induced considerably growth inhibition in all cancer cell lines, whilst showed inactive against microbial strains. Furthermore, we found analog 2-ethoxy-1H-pyrano[4,3-b]quinoline as selective inhibitor of microbial strains. © 2010 Elsevier Ltd. All rights reserved.


Bonifazi E.L.,University of Buenos Aires | Rios-Luci C.,University of La Laguna | Rios-Luci C.,Instituto Canario Of Investigacion Del Cancer Icic | Leon L.G.,University of La Laguna | And 5 more authors.
Bioorganic and Medicinal Chemistry | Year: 2010

A series of 5-hydroxy-1,4-naphthoquinones analogues was synthesized from juglone (6) and their antiproliferative activity against a representative panel of six human solid tumor cell lines has been investigated. The 2,5-dihydroxy-3-(3-methylbut-2-enyl)naphthalene-1,4-dione (4) and 2,3-dihydro-5-hydroxy-2-(prop-1-en-2-yl)naphtho[2,3-b]furan-4,9-dione (27) were the most potent antiproliferative agents with GI50 values of 0.42-8.1 and 0.80-2.2 μM, respectively. The results provide insight into the correlation between some structural properties of 5-hydroxynaphthoquinones and their antiproliferative activity. © 2010 Elsevier Ltd. All rights reserved.


Gutierrez-Nicolas F.,University of La Laguna | Gutierrez-Nicolas F.,Instituto Canario Of Investigacion Del Cancer Icic | Gordillo-Roman B.,National Polytechnic Institute of Mexico | Oberti J.C.,University of La Laguna | And 6 more authors.
Journal of Natural Products | Year: 2012

Lupane triterpenoids 2 and 5-12 and oleanene derivatives 13 and 14 were prepared from lupeol (1), betulin (3), and germanicol (4). They were tested for anti-HIV activity, and some structure-activity relationships were outlined. The 20-(S) absolute configuration of epoxylupenone (8) was assessed by comparison of the observed and DFT-calculated vibrational circular dichroism spectra. The CompareVOA algorithm was employed to support the C-20 configuration assignment. The 20,29 double bond in lupenone (2) and 3-epilupeol (15) was stereoselectively epoxidized to produce 20-(S)-8 and 20-(S)-16, respectively, an assignment in agreement with their X-ray diffraction structures. © 2012 The American Chemical Society and American Society of Pharmacognosy.


Miguelez J.,CSIC - Institute of Natural Products and Agrobiology | Boto A.,CSIC - Institute of Natural Products and Agrobiology | Marin R.,University of La Laguna | Marin R.,Instituto Canario Of Investigacion Del Cancer Icic | And 2 more authors.
European Journal of Medicinal Chemistry | Year: 2013

Hydroxylated seco-analogs of cytotoxic phenanthroindolizidine alkaloids were prepared in good yields from inexpensive 4-hydroxyproline derivatives, in just two steps. Thus, a sequential oxidative radical scission - oxidation was used for the direct conversion of the proline derivative into a 2-(2-aryl-oxoethyl) pyrrolidine with a variety of aryl and heteroaryl groups. The 4R-stereogenic center allowed ready isomer separation, and stereocontrol in the introduction of new chains (interestingly, the 2,4-cis isomers predominated). In the second step, a cyclization reaction afforded alkaloid analogs with an indolizidinone core; a partial isomerization took place but the isomers were readily purifi ed. Then the cytotoxic activity of the bicyclic indolizidinones and the simpler pyrrolidine derivatives was compared against tumorogenic human neuronal SHSY-5Y and breast cancer MCF7 cells. All the biphenyl derivatives displayed a potent activity (one derivative caused >80% cell death in both tumor lines at micromolar dosis), being comparable in the pyrrolidine and indolizidinone series. © 2013 Elsevier Masson SAS. All rights reserved.


Boto A.,CSIC - Institute of Natural Products and Agrobiology | Miguelez J.,CSIC - Institute of Natural Products and Agrobiology | Marin R.,University of La Laguna | Marin R.,Instituto Canario Of Investigacion Del Cancer Icic | And 2 more authors.
Bioorganic and Medicinal Chemistry Letters | Year: 2012

Readily available proline derivatives can be transformed in just two steps into analogues of cytotoxic phenanthroindolizidine alkaloids. The key step uses a sequential radical scission-oxidation-alkylation process, which yields 2-substituted pyrrolidine amides. A second process effects the cyclization to give the desired alkaloid analogues, which possess an indolizidine core. The major and minor isomers (dr 3:2 to 3:1) can be easily separated, allowing their use to study structure-activity relationships (SAR). The process is versatile and allows the introduction of aryl and heteroaryl groups (including biphenyl, halogenated phenyl, and pyrrole rings). Some of these alkaloid analogues displayed a selective cytotoxic activity against tumorogenic human neuronal and mammary cancer cells, and one derivative caused around 80% cell death in both tumor lines at micromolar doses. The cytotoxicity of some monocyclic precursors was also studied, being comparable or superior to the bicyclic derivatives. © 2012 Elsevier Ltd. All rights reserved.


Luzardo O.P.,University of Las Palmas de Gran Canaria | Luzardo O.P.,Instituto Canario Of Investigacion Del Cancer Icic | Almeida-Gonzalez M.,University of Las Palmas de Gran Canaria | Almeida-Gonzalez M.,Instituto Canario Of Investigacion Del Cancer Icic | And 7 more authors.
Chemosphere | Year: 2012

The population of the Spanish archipelago of the Canary Islands has been studied in depth regarding its levels of contamination by organochlorine pesticides (OCs) and polychlorinated biphenyls (PCBs). Foodstuffs of animal origin, such as milk, are prominent contributors to the body burden of these contaminants. As this population presents one of the highest milk-intake in Spain and Europe, we evaluated the level of OCs and PCBs in 26 commercially available brands of milk (16 conventional and 10 organic brands) present in the market of these Islands, in order to estimate the relevance of milk as a source of these chemicals for the Canary population. Our findings showed that hexachlorobenzene, trans-chlordane, and PCB153 were present in almost all the samples with independence of the type of milk. For both types of milks, the concentration of OCs was very low, showing organic milks lower levels than conventional ones. As a consequence, the estimated daily intake for OCs was lower than the tolerable daily intake (TDI) established by International Agencies. The levels of PCBs in milk were also found to be very low, but, in this case, the situation was the opposite: there were higher levels of PCBs in organic than in conventional brands of milk. Unexpectedly, levels of dioxin-like PCBs (DL-PCBs) reached values higher than 25pg WHO-TEQ g -1 fat in percentile 75 for both types of milk indicating the existence of a number of brands of milk highly contaminated by these toxicants. Consequently, the population who consume the most contaminated milk brands could have estimated daily intakes well above the recommended TDI (2pg WHO-TEQ kg -1b.w.d -1) established by European Union Authorities. These results are of concern if we consider the well known adverse health effects exerted by dioxin-like compounds. © 2012 Elsevier Ltd.


Leon L.G.,University of La Laguna | Leon L.G.,Instituto Canario Of Investigacion Del Cancer Icic | Rios-Luci C.,University of La Laguna | Tejedor D.,CSIC - Institute of Natural Products and Agrobiology | And 8 more authors.
Journal of Medicinal Chemistry | Year: 2010

A small structure-focused library of propargylic enol ethers was prepared by means of a modular and efficient chemodifferentiating organocatalyzed multicomponent reaction. The most active compound (GI50 0.25 μM) against solid tumor cells was selected as lead. Cell cycle analysis and immunoblotting demonstrated arrest at the metaphase, pointing out human topoisomerase II as plausible molecular target. In vitro assays were carried out, showing that the lead behaves as a catalytic inhibitor of the enzyme. © 2010 American Chemical Society.


Amesty A.,University of La Laguna | Amesty A.,Instituto Canario Of Investigacion Del Cancer Icic | Burgueno-Tapia E.,National Polytechnic Institute of Mexico | Joseph-Nathan P.,National Polytechnic Institute of Mexico | And 4 more authors.
Journal of Natural Products | Year: 2011

Three new benzodihydrofurans (1-3) and seven known aromatic compounds (4-10) were isolated from the roots of Cyperus teneriffae. Vibrational circular dichroism spectroscopy was used to define the absolute configuration of 1. (Chemical Equation Presented). © 2011 The American Chemical Society and American Society of Pharmacognosy.


Cedron J.C.,Instituto Universitario Of Bio Organica Antonio Gonzalez | Cedron J.C.,Instituto Canario Of Investigacion Del Cancer Icic | Gutierrez D.,Higher University of San Andrés | Flores N.,Higher University of San Andrés | And 4 more authors.
Bioorganic and Medicinal Chemistry | Year: 2010

Twenty seven lycorine derivatives were prepared and evaluated for their in vitro antimalarial activity against chloroquine-sensitive strains of Plasmodium falciparum. The best antiplasmodial activities were achieved with lycorine derivatives that present free hydroxyl groups at C-1 and C-2 or esterified as acetates or isobutyrates. The double bond C-2-C-3 is also important for the activity. Concerning to the antiplasmodial activity of the secolycorines, the higher values were obtained with the replacement of the methylenedioxy moiety by hydroxyl or acetate groups and with methyl substituent attached to the nitrogen atom. © 2010 Elsevier Ltd. All rights reserved.


Luzardo O.P.,University of Las Palmas de Gran Canaria | Luzardo O.P.,Instituto Canario Of Investigacion Del Cancer Icic | Ruiz-Suarez N.,University of Las Palmas de Gran Canaria | Almeida-Gonzalez M.,University of Las Palmas de Gran Canaria | And 6 more authors.
Analytical and Bioanalytical Chemistry | Year: 2013

Human breast milk represents the best choice for the nutrition of infants. However, in addition to containing beneficial nutrients and antibodies, it can also be considered the best indicator of infant exposure to contaminants. We developed a multi-residue method using a modified QuEChERS (quick, easy, cheap, effective, rugged, and safe) procedure and capillary gas chromatography-triple quadrupole mass spectrometry for the determination of 57 persistent organic pollutants, including 23 organochlorine pesticides, 18 polychlorinated biphenyl (PCB) congeners, and 16 polycyclic aromatic hydrocarbons in human milk and colostrum samples. We have used primary secondary amine in the clean-up step as it gave a more efficient separation of the analytes from fat and superior removal of the co-extracted substances compared with gel permeation chromatography. No significant matrix effect was observed for the tested pollutants, and therefore matrix-matched calibration was not necessary. The average recoveries from spiked samples were in the range of 74.8-113.0 %. The precision was satisfactory, with relative standard deviations below 16 %, while values of 0.1-0.4 μg L-1 were established as the limit of quantification for all the target analytes (0.05 and 100 μg L-1). The method was successfully applied to the analysis of 18 human colostrum and 23 mature milk samples. All the samples tested were positive for at least nine different residues, with some samples containing up to 24 contaminants. Remarkably, the contaminants hexachlorobenzene, p,p'-DDE, PCB 138, PCB 180, phenanthrene, fluoranthene, and pyrene were present in 100 % of the colostrum and mature milk samples analyzed. © 2013 Springer-Verlag Berlin Heidelberg.

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