Oxaliplatin analogues with carboxy derivatives of boldine with enhanced antioxidant activity

Marco Mellado; Carlos Jara; David Astudillo; Joan Villena; Patricio G. Reveco; Franz A. Thomet

doi:10.1155/2015/920143

Oxaliplatin analogues with carboxy derivatives of boldine with enhanced antioxidant activity

Marco Mellado, Carlos Jara, David Astudillo, Joan Villena, Patricio G. Reveco, Franz A. Thomet

Research output: Contribution to journal › Article › peer-review

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Abstract

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.

Original language	English
Article number	920143
Journal	Bioinorganic Chemistry and Applications
Volume	2015
DOIs	https://doi.org/10.1155/2015/920143
State	Published - 28 Feb 2015
Externally published	Yes

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title = "Oxaliplatin analogues with carboxy derivatives of boldine with enhanced antioxidant activity",

abstract = "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.",

author = "Marco Mellado and Carlos Jara and David Astudillo and Joan Villena and Reveco, {Patricio G.} and Thomet, {Franz A.}",

note = "Publisher Copyright: {\textcopyright} 2015 Marco Mellado et al.",

year = "2015",

month = feb,

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doi = "10.1155/2015/920143",

language = "English",

volume = "2015",

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T1 - Oxaliplatin analogues with carboxy derivatives of boldine with enhanced antioxidant activity

AU - Mellado, Marco

AU - Jara, Carlos

AU - Astudillo, David

AU - Villena, Joan

AU - Reveco, Patricio G.

AU - Thomet, Franz A.

PY - 2015/2/28

Y1 - 2015/2/28

N2 - 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.

AB - 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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DO - 10.1155/2015/920143

M3 - Article

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VL - 2015

JO - Bioinorganic Chemistry and Applications

JF - Bioinorganic Chemistry and Applications

M1 - 920143

ER -

Oxaliplatin analogues with carboxy derivatives of boldine with enhanced antioxidant activity

Abstract

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