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Título : | Synthesis of Novel Quaternary Ammonium Salts and Their in Vitro Antileishmanial Activity and U-937 Cell Cytotoxicity |
Autor : | Robledo Restrepo, Sara María Vélez Bernal, Iván Darío Ríos Vásquez, Luz Amalia Ocampo Cardona, Rogelio Duque Benítez, Sandra Milena Cedeño, David L. Jones, Marjorie A. |
metadata.dc.subject.*: | Leishmania Leishmaniasis Compuestos de Amonio Ammonium Compounds Antiprotozoarios Antiprotozoal Agents Compuestos de Amonio Cuaternario Quaternary Ammonium Compounds Sales (Química) Salts Relación Estructura-Actividad Structure-Activity Relationship Células U937 Citotoxicidad Cytotoxicity U937 Cells http://aims.fao.org/aos/agrovoc/c_34251 https://id.nlm.nih.gov/mesh/D007891 https://id.nlm.nih.gov/mesh/D007896 https://id.nlm.nih.gov/mesh/D064751 https://id.nlm.nih.gov/mesh/D000981 https://id.nlm.nih.gov/mesh/D000644 https://id.nlm.nih.gov/mesh/D012492 https://id.nlm.nih.gov/mesh/D013329 https://id.nlm.nih.gov/mesh/D020298 |
Fecha de publicación : | 2016 |
Editorial : | MDPI |
Citación : | Duque-Benítez SM, Ríos-Vásquez LA, Ocampo-Cardona R, Cedeño DL, Jones MA, Vélez ID, Robledo SM. Synthesis of Novel Quaternary Ammonium Salts and Their in Vitro Antileishmanial Activity and U-937 Cell Cytotoxicity. Molecules. 2016 Mar 29;21(4):381. doi: 10.3390/molecules21040381. |
Resumen : | ABSTRACT: This work describes the synthesis of a series of quaternary ammonium salts and the assessment of their in vitro antileishmanial activity and cytotoxicity. A preliminary discussion on a structure-activity relationship of the compounds is also included. Three series of quaternary ammonium salts were prepared: (i) halomethylated quaternary ammonium salts (series I); (ii) non-halogenated quaternary ammonium salts (series II) and (iii) halomethylated choline analogs (series III). Assessments of their in vitro cytotoxicity in human promonocytic cells U-937 and antileishmanial activity in axenic amastigotes of L. (Viannia) panamensis (M/HOM/87/UA140-pIR-eGFP) were carried out using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide) micromethod. Antileishmanial activity was also tested in intracellular amastigotes of L. (V) panamensis using flow cytometry. High toxicity for human U937 cells was found with most of the compounds, which exhibited Lethal Concentration 50 (LC50) values in the range of 9 to 46 μg/mL. Most of the compounds evidenced antileishmanial activity. In axenic amastigotes, the antileishmanial activity varied from 14 to 57 μg/mL, while in intracellular amastigotes their activity varied from 17 to 50 μg/mL. N-Chloromethyl-N,N-dimethyl-N-(4,4-diphenylbut-3-en-1-yl)ammonium iodide (1a), N-iodomethyl-N,N-dimethyl-N-(4,4-diphenylbut-3-en-1-yl)ammonium iodide (2a), N,N,N-trimethyl-N-(4,4-diphenylbut-3-en-1-yl)ammonium iodide (3a) and N,N,N-trimethyl-N-(5,5-diphenylpent-4-en-1-yl)ammonium iodide (3b) turned out to be the most active compounds against intracellular amastigotes of L. (V) panamensis, with EC50 values varying between 24.7 for compound 3b and 38.4 μg/mL for compound 1a. Thus, these compounds represents new "hits" in the development of leishmanicidal drugs. |
ISSN : | 1420-3049 |
metadata.dc.identifier.doi: | 10.3390/molecules21040381 |
Aparece en las colecciones: | Artículos de Revista en Ciencias Médicas |
Ficheros en este ítem:
Fichero | Descripción | Tamaño | Formato | |
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VelezIvan_2016_Synthesis_Novel_Quaternary.pdf | Artículo de investigación | 992.42 kB | Adobe PDF | Visualizar/Abrir |
VelezIvan_2016_Synthesis_Novel_Quaternary.epub | Artículo de investigación | 458.73 kB | EPUB | Visualizar/Abrir |
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