Oxaliplatin Analogues with Carboxy Derivatives of Boldine with Enhanced Antioxidant Activity

A new oxaliplatin analog [Pt(dach)(L5)] (1) was synthesized and characterized as a continuation of a study of the previously reported [Pt(dach)(L6)] (2), where dach = (1R,2R)-diaminocyclohexane, L5 = 3-carboxyboldine, and L6 = 3-carboxypredicentrine. Compounds 1 and 2 exhibited a substantially enhan...

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Main Authors: Marco Mellado, Carlos Jara, David Astudillo, Joan Villena, Patricio G. Reveco, Franz A. Thomet
Format: Article
Language:English
Published: Wiley 2015-01-01
Series:Bioinorganic Chemistry and Applications
Online Access:http://dx.doi.org/10.1155/2015/920143
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author Marco Mellado
Carlos Jara
David Astudillo
Joan Villena
Patricio G. Reveco
Franz A. Thomet
author_facet Marco Mellado
Carlos Jara
David Astudillo
Joan Villena
Patricio G. Reveco
Franz A. Thomet
author_sort Marco Mellado
collection DOAJ
description A new oxaliplatin analog [Pt(dach)(L5)] (1) was synthesized and characterized as a continuation of a study of the previously reported [Pt(dach)(L6)] (2), where dach = (1R,2R)-diaminocyclohexane, L5 = 3-carboxyboldine, and L6 = 3-carboxypredicentrine. Compounds 1 and 2 exhibited a substantially enhanced antioxidant activity compared to oxaliplatin (130 and 30 times for 1 and 13 and 4 times for 2 using the DPPH and FRAP assays, resp.). In addition, 1 and 2 exhibited cytotoxic activity in the same range as oxaliplatin toward the two human tumor cell lines (MCF-7 and HT-29) studied and two to four times lower activity in the human colon nontumor cell line (CCD-841). Preadministration of L5 or L6 to the colon tumor (HT-29) and the colon nontumor (CCD-841) cell lines prior to oxaliplatin addition increased the viability of the nontumor cell line to a greater extent than that of the tumor cell line.
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language English
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series Bioinorganic Chemistry and Applications
spelling doaj-art-38027ebbb9fd44bfba87a423ab4468822025-02-03T01:23:25ZengWileyBioinorganic Chemistry and Applications1565-36331687-479X2015-01-01201510.1155/2015/920143920143Oxaliplatin Analogues with Carboxy Derivatives of Boldine with Enhanced Antioxidant ActivityMarco Mellado0Carlos Jara1David Astudillo2Joan Villena3Patricio G. Reveco4Franz A. Thomet5Departamento de Química, Universidad Técnica Federico Santa María, Avenida España 1680, 2390123 Valparaíso, ChileCentro de Investigaciones Biomédicas (CIB), Escuela de Medicina, Universidad de Valparaiso, Avenida Hontaneda 2664, 2340000 Valparaíso, ChileLaboratorio de Investigación-Estrés Oxidativo, Escuela de Medicina, Universidad de Valparaiso, Avenida Brasil 1560, 2340000 Valparaíso, ChileLaboratorio de Investigación-Estrés Oxidativo, Escuela de Medicina, Universidad de Valparaiso, Avenida Brasil 1560, 2340000 Valparaíso, ChileDepartamento de Química, Universidad Técnica Federico Santa María, Avenida España 1680, 2390123 Valparaíso, ChileDepartamento de Química, Universidad Técnica Federico Santa María, Avenida España 1680, 2390123 Valparaíso, ChileA new oxaliplatin analog [Pt(dach)(L5)] (1) was synthesized and characterized as a continuation of a study of the previously reported [Pt(dach)(L6)] (2), where dach = (1R,2R)-diaminocyclohexane, L5 = 3-carboxyboldine, and L6 = 3-carboxypredicentrine. Compounds 1 and 2 exhibited a substantially enhanced antioxidant activity compared to oxaliplatin (130 and 30 times for 1 and 13 and 4 times for 2 using the DPPH and FRAP assays, resp.). In addition, 1 and 2 exhibited cytotoxic activity in the same range as oxaliplatin toward the two human tumor cell lines (MCF-7 and HT-29) studied and two to four times lower activity in the human colon nontumor cell line (CCD-841). Preadministration of L5 or L6 to the colon tumor (HT-29) and the colon nontumor (CCD-841) cell lines prior to oxaliplatin addition increased the viability of the nontumor cell line to a greater extent than that of the tumor cell line.http://dx.doi.org/10.1155/2015/920143
spellingShingle Marco Mellado
Carlos Jara
David Astudillo
Joan Villena
Patricio G. Reveco
Franz A. Thomet
Oxaliplatin Analogues with Carboxy Derivatives of Boldine with Enhanced Antioxidant Activity
Bioinorganic Chemistry and Applications
title Oxaliplatin Analogues with Carboxy Derivatives of Boldine with Enhanced Antioxidant Activity
title_full Oxaliplatin Analogues with Carboxy Derivatives of Boldine with Enhanced Antioxidant Activity
title_fullStr Oxaliplatin Analogues with Carboxy Derivatives of Boldine with Enhanced Antioxidant Activity
title_full_unstemmed Oxaliplatin Analogues with Carboxy Derivatives of Boldine with Enhanced Antioxidant Activity
title_short Oxaliplatin Analogues with Carboxy Derivatives of Boldine with Enhanced Antioxidant Activity
title_sort oxaliplatin analogues with carboxy derivatives of boldine with enhanced antioxidant activity
url http://dx.doi.org/10.1155/2015/920143
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