Synthesis and Antiproliferative Activity of New Cyclodiprenyl Phenols against Select Cancer Cell Lines

Synthesis and Antiproliferative Activity of New Cyclodiprenyl Phenols against Select Cancer Cell Lines

Six new cyclodiprenyl phenols were synthesized by direct coupling of perillyl alcohol and the appropriate phenol. Their structures were established by IR, HRMS and mainly NMR. Three human cancer cell lines—breast (MCF-7), prostate (PC-3) and colon (HT-29)—were used in antiprolife...

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Main Authors: Bastián Said, Iván Montenegro, Manuel Valenzuela, Yusser Olguín, Nelson Caro, Enrique Werner, Patricio Godoy, Joan Villena, Alejandro Madrid
Format: Article
Language:English
Published: MDPI AG 2018-09-01
Series:Molecules
Subjects:
perillyl alcohol
synthesis
cyclodiprenyl phenols
antiproliferative agents
Online Access:http://www.mdpi.com/1420-3049/23/9/2323
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spelling doaj-83b5eec7c9de4344a9e224d590509e812020-11-25T01:13:33ZengMDPI AGMolecules1420-30492018-09-01239232310.3390/molecules23092323molecules23092323Synthesis and Antiproliferative Activity of New Cyclodiprenyl Phenols against Select Cancer Cell LinesBastián Said0Iván Montenegro1Manuel Valenzuela2Yusser Olguín3Nelson Caro4Enrique Werner5Patricio Godoy6Joan Villena7Alejandro Madrid8Departamento de Química, Universidad Técnica Federico Santa María, Av. Santa María 6400, Vitacura 7630000, Santiago, ChileEscuela de Obstetricia y Puericultura, Facultad de medicina, Campus de la Salud, Universidad de Valparaíso, Angamos 655, Reñaca, Viña del Mar 2520000, ChileLaboratorio de Microbiología Celular, Instituto de Investigación e Innovación en Salud, Facultad de Ciencias de la Salud, Universidad Central de Chile, Santiago 8320000, ChileCenter for Integrative Medicine and Innovative Science (CIMIS), Facultad de Medicina, Universidad Andrés Bello, Santiago 8320000, ChileCentro de Investigación Australbiotech, Universidad Santo Tomás, Avda. Ejército 146, Santiago 8320000, ChileDepartamento De Ciencias Básicas, Campus Fernando May Universidad del Biobío, Avda. Andrés Bello s/n casilla 447, Chillán 3780000, ChileInstituto de Microbiología Clínica, Facultad de Medicina, Universidad Austral de Chile, Los Laureles s/n, Isla Teja, Valdivia 5090000, ChileCentro de Investigaciones Biomedicas (CIB), Facultad de Medicina, Campus de la Salud, Universidad de Valparaíso, Angamos 655, Reñaca, Viña del Mar 2520000, ChileLaboratorio de Productos Naturales y Síntesis Orgánica, Departamento de Química, Facultad de Ciencias Naturales y Exactas, Universidad de Playa Ancha, Avda. Leopoldo Carvallo 270, Playa Ancha, Valparaíso 2340000, ChileSix new cyclodiprenyl phenols were synthesized by direct coupling of perillyl alcohol and the appropriate phenol. Their structures were established by IR, HRMS and mainly NMR. Three human cancer cell lines—breast (MCF-7), prostate (PC-3) and colon (HT-29)—were used in antiproliferative assays, with daunorubicin and dunnione as positive controls. Results described in the article suggest that dihydroxylated compounds 2–4 and monohydroxylated compound 5 display selectivity against cancer cell lines, cytotoxicity, apoptosis induction, and mitochondrial membrane impairment capacity. Compound 2 was identified as the most effective of the series by displaying against all cancer cell lines a cytotoxicity close to dunnione antineoplastic agent, suggesting that the cyclodiprenyl phenols from perillyl alcohol deserve more extensive investigation of their potential medicinal applications.http://www.mdpi.com/1420-3049/23/9/2323perillyl alcoholsynthesiscyclodiprenyl phenolsantiproliferative agents
collection DOAJ
language English
format Article
sources DOAJ
author Bastián Said
Iván Montenegro
Manuel Valenzuela
Yusser Olguín
Nelson Caro
Enrique Werner
Patricio Godoy
Joan Villena
Alejandro Madrid
spellingShingle Bastián Said
Iván Montenegro
Manuel Valenzuela
Yusser Olguín
Nelson Caro
Enrique Werner
Patricio Godoy
Joan Villena
Alejandro Madrid
Synthesis and Antiproliferative Activity of New Cyclodiprenyl Phenols against Select Cancer Cell Lines
Molecules
perillyl alcohol
synthesis
cyclodiprenyl phenols
antiproliferative agents
author_facet Bastián Said
Iván Montenegro
Manuel Valenzuela
Yusser Olguín
Nelson Caro
Enrique Werner
Patricio Godoy
Joan Villena
Alejandro Madrid
author_sort Bastián Said
title Synthesis and Antiproliferative Activity of New Cyclodiprenyl Phenols against Select Cancer Cell Lines
title_short Synthesis and Antiproliferative Activity of New Cyclodiprenyl Phenols against Select Cancer Cell Lines
title_full Synthesis and Antiproliferative Activity of New Cyclodiprenyl Phenols against Select Cancer Cell Lines
title_fullStr Synthesis and Antiproliferative Activity of New Cyclodiprenyl Phenols against Select Cancer Cell Lines
title_full_unstemmed Synthesis and Antiproliferative Activity of New Cyclodiprenyl Phenols against Select Cancer Cell Lines
title_sort synthesis and antiproliferative activity of new cyclodiprenyl phenols against select cancer cell lines
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2018-09-01
description Six new cyclodiprenyl phenols were synthesized by direct coupling of perillyl alcohol and the appropriate phenol. Their structures were established by IR, HRMS and mainly NMR. Three human cancer cell lines—breast (MCF-7), prostate (PC-3) and colon (HT-29)—were used in antiproliferative assays, with daunorubicin and dunnione as positive controls. Results described in the article suggest that dihydroxylated compounds 2–4 and monohydroxylated compound 5 display selectivity against cancer cell lines, cytotoxicity, apoptosis induction, and mitochondrial membrane impairment capacity. Compound 2 was identified as the most effective of the series by displaying against all cancer cell lines a cytotoxicity close to dunnione antineoplastic agent, suggesting that the cyclodiprenyl phenols from perillyl alcohol deserve more extensive investigation of their potential medicinal applications.
topic perillyl alcohol
synthesis
cyclodiprenyl phenols
antiproliferative agents
url http://www.mdpi.com/1420-3049/23/9/2323
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