<?xml version="1.0" encoding="ISO-8859-1"?><article xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance">
<front>
<journal-meta>
<journal-id>2340-9894</journal-id>
<journal-title><![CDATA[Ars Pharmaceutica (Internet)]]></journal-title>
<abbrev-journal-title><![CDATA[Ars Pharm]]></abbrev-journal-title>
<issn>2340-9894</issn>
<publisher>
<publisher-name><![CDATA[Universidad de Granada]]></publisher-name>
</publisher>
</journal-meta>
<article-meta>
<article-id>S2340-98942017000400003</article-id>
<article-id pub-id-type="doi">10.30827/ars.v58i4.6441</article-id>
<title-group>
<article-title xml:lang="en"><![CDATA[Synthesis and cytotoxic activity of per-acetylated and halogenated derivatives of nucleosides in breast cancer cells]]></article-title>
<article-title xml:lang="es"><![CDATA[Síntesis y evaluación citotoxica de derivados halogenados y peracetylados de nucleósidos en celulas de cáncer de mama]]></article-title>
</title-group>
<contrib-group>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Berrío Escobar]]></surname>
<given-names><![CDATA[JF]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Pastrana Restrepo]]></surname>
<given-names><![CDATA[MH]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Galeano Jaramillo]]></surname>
<given-names><![CDATA[E]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Márquez Fernández]]></surname>
<given-names><![CDATA[DM]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Márquez Fernández]]></surname>
<given-names><![CDATA[ME]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Martínez Martínez]]></surname>
<given-names><![CDATA[A]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
</contrib-group>
<aff id="Af1">
<institution><![CDATA[,Universidad de Antioquia UdeA Facultad de Ciencias Farmacéuticas y Alimentarias Grupo Productos Naturales Marinos]]></institution>
<addr-line><![CDATA[Calle 70 No 52-21, Medellín ]]></addr-line>
<country>Colombia</country>
</aff>
<aff id="Af2">
<institution><![CDATA[,Universidad Nacional Sede Medellín Facultad de Ciencias Grupo Biotecnología Animal]]></institution>
<addr-line><![CDATA[Medellín ]]></addr-line>
<country>Colombia</country>
</aff>
<pub-date pub-type="pub">
<day>00</day>
<month>12</month>
<year>2017</year>
</pub-date>
<pub-date pub-type="epub">
<day>00</day>
<month>12</month>
<year>2017</year>
</pub-date>
<volume>58</volume>
<numero>4</numero>
<fpage>145</fpage>
<lpage>154</lpage>
<copyright-statement/>
<copyright-year/>
<self-uri xlink:href="http://scielo.isciii.es/scielo.php?script=sci_arttext&amp;pid=S2340-98942017000400003&amp;lng=en&amp;nrm=iso"></self-uri><self-uri xlink:href="http://scielo.isciii.es/scielo.php?script=sci_abstract&amp;pid=S2340-98942017000400003&amp;lng=en&amp;nrm=iso"></self-uri><self-uri xlink:href="http://scielo.isciii.es/scielo.php?script=sci_pdf&amp;pid=S2340-98942017000400003&amp;lng=en&amp;nrm=iso"></self-uri><abstract abstract-type="short" xml:lang="en"><p><![CDATA[ABSTRACT  Objectives: To make the synthesis of halogenated derivatives on the nitrogenous base and their respective acyl ester and amide type derivatives for all hydroxyl and amine groups of the uridine and cytarabine nucleosides, and evaluate cytotoxicity against breast cancer cell line.  Methods: First, it was accomplished the halogenation reaction on the 5-position of the nitrogenous base, subsequently, the ester and amide derivatives were performed for all hydroxyl and amine group present in the nucleosides. Besides, the uridine acetonide derivatives as prepared by acid catalysis. The products were characterized by nuclear magnetic resonance spectroscopy (1H RMN y 13C RMN) and mass spectrometry in positive mode by direct injection. Derivatives were evaluated in Chinese hamster ovary (CHO-K1) and human breast cancer (MCF-7) cell lines.  Results: The four derivatives were obtained with chlorine and bromine for the uridine and cytarabine, respectively, their respective per-acetylated derivatives, the per-acetylated nucleoside and the uridine acetonide; the compounds were obtained with efficiency over 90%. The per-acetylated nucleosides and the halogenated and per-acetylated derivatives did not show inhibitory effects on cell viability in MCF-7 cell line. However, the per-acetylated and halogenated derivatives presented a higher cytotoxic activity than their respective per-acetylated nucleoside. The uridine 3&#8217;,4&#8217;-acetonide showed a significant cytotoxicity on both cell lines.  Conclusions: The per-acetylated nucleoside, and the respective halogenated derivatives with chlorine and bromine were obtained with high yields, nevertheless, these compounds did not exhibit a significant anti-proliferative activity (p&lt;0.05), possibly due to a low intra-cellular activation.]]></p></abstract>
<abstract abstract-type="short" xml:lang="es"><p><![CDATA[RESUMEN  Objetivos: Sintetizar derivados halogenados sobre la base nitrogenada, sus respectivos derivados tipo éster o amida de todos los grupos hidroxilo y amina presentes en los nucleósidos uridina y citarabina, y evaluar su actividad citotóxica sobre una línea celular de cáncer de mama.  Metodología: primero se realizó la reacción de halogenación en la posición 5 de la base nitrogenada, posteriormente se formaron los ésteres y amidas de todos los grupos hidroxilos y amino presentes en los nucleósidos. Además, se preparó el derivado acetónido con catálisis ácida. Los compuestos se caracterizaron por espectroscopía de resonancia magnética nuclear (RMN 1H y RMN 13C) y espectrometría de masas por inyección directa en modo positivo. Los derivados se evaluaron sobre líneas celulares de tumor de Ovario de Hámster Chino (CHO) y de cáncer de mamá (MCF-7).  Resultados: Se obtuvieron 4 derivados mono-halogenados con cloro y bromo de la uridina y citarabina, respectivamente, sus respectivos derivados per-acetilados, los nucleósidos per-acetilados y el acetónido de la uridina; los compuestos se obtuvieron con rendimientos superiores a 90%. Los nucleósidos per-acetilados, y los derivados per-acetilados y halogenados no exhibieron una inhibición significativa de la viabilidad celular en ambas líneas celulares, sin embargo, de estos, los derivados per-acetilados y halogenados presentaron mayor actividad citotóxica que los respectivos nucleósidos per-acetilados. El derivado acetónido de la uridina mostró citotoxicidad significativa sobre ambas líneas celulares.  Conclusiones: se obtuvieron los nucleósidos per-acetilados y los respectivos derivados clorados y bromados de estos, con rendimientos altos, sin embargo, estos compuestos no exhibieron una actividad anti-proliferativa significativa (p&lt;0,05), posiblemente debido a una baja activación intra-celular de los nucleósidos.]]></p></abstract>
<kwd-group>
<kwd lng="en"><![CDATA[anticancer nucleoside]]></kwd>
<kwd lng="en"><![CDATA[breast cancer]]></kwd>
<kwd lng="en"><![CDATA[cytotoxic activity]]></kwd>
<kwd lng="en"><![CDATA[esterification and halogenation reactions]]></kwd>
<kwd lng="en"><![CDATA[uridine and cytarabine]]></kwd>
<kwd lng="es"><![CDATA[actividad citotóxica]]></kwd>
<kwd lng="es"><![CDATA[cáncer de mama]]></kwd>
<kwd lng="es"><![CDATA[nucleósidos anticancerosos]]></kwd>
<kwd lng="es"><![CDATA[reacciones de esterificación y halogenación]]></kwd>
<kwd lng="es"><![CDATA[uridina y citarabina]]></kwd>
</kwd-group>
</article-meta>
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