Impact of the carbon chain length of novel platinum complexes derived from N-alkyl-propanediamines on their cytotoxic activity and cellular uptake

This work describes the synthesis and characterization of four new ligands derived from 1,3-propanediamine in addition to the preparation and characterization of their respective platinum(II) complexes by reaction with K2PtCl4. These ligands were obtained by the reaction of the corresponding alkyl m...

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Bibliographic Details
Published in:Journal of inorganic biochemistry 2008-04, Vol.102 (4), p.767-772
Main Authors: Silva, Heveline, Valério Barra, Carolina, França da Costa, Cristiane, de Almeida, Mauro Vieira, César, Eloi Teixeira, Silveira, Josianne N., Garnier-Suillerot, Arlette, Silva de Paula, Flávia Cristina, Pereira-Maia, Elene Cristina, Fontes, Ana Paula Soares
Format: Article
Language:English
Subjects:
Amines
Antitumor agents
Carbon - chemistry
Cell Line, Tumor
Cellular uptake
Diamines - chemistry
Diamines - pharmacology
Drug Screening Assays, Antitumor
Humans
Lipophilicity
Magnetic Resonance Spectroscopy
Platinum
Platinum Compounds - chemistry
Platinum Compounds - pharmacology
Spectrophotometry, Infrared
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Summary:This work describes the synthesis and characterization of four new ligands derived from 1,3-propanediamine in addition to the preparation and characterization of their respective platinum(II) complexes by reaction with K2PtCl4. These ligands were obtained by the reaction of the corresponding alkyl mesylate with 1,3-propanediamine. We have prepared compounds having different carbon chains lengths in an attempt to correlate this factor, which influences the lipophilicity of the compounds, with cytotoxic activity. Octanol/water partition coefficients, the effect of the four complexes on the growth of two tumoral cell lines, and their cellular uptake were investigated. Increasing lipophilicity enhances the rate of cellular uptake and, consequently, the cytotoxic activity.
ISSN:0162-0134
1873-3344
DOI:10.1016/j.jinorgbio.2007.11.013