Synthesis and cytotoxic activity of metallic complexes of lawsone

In the present study, a series of metallic complexes of the 1,4-naphthoquinone lawsone (2–6) were synthesized and evaluated for potential cytotoxicity in a mouse leukemic macrophagic RAW 264.7 cell line. Cell viability was determined by the MTT assay. Significant growth inhibition was observed for t...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2013-05, Vol.21 (9), p.2471-2477
Main Authors: Oramas-Royo, Sandra, Torrejón, Concepción, Cuadrado, Irene, Hernández-Molina, Rita, Hortelano, Sonsoles, Estévez-Braun, Ana, de las Heras, Beatriz
Format: Article
Language:English
Subjects:
adenocarcinoma
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Apoptosis
Apoptosis - drug effects
caspases
Cell Proliferation - drug effects
Cell Survival - drug effects
cell viability
chemistry
Crystallography, X-Ray
Cytotoxicity
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
growth retardation
HeLa Cells
Hep G2 Cells
hepatoma
HepG2
HT29 Cells
human cell lines
Humans
inhibitory concentration 50
Lawsone
Macrophages - drug effects
Metallic complexes
mice
Models, Molecular
Molecular Structure
Naphthoquinones - chemistry
Organometallic Compounds - chemical synthesis
Organometallic Compounds - chemistry
Organometallic Compounds - pharmacology
proteins
Structure-Activity Relationship
Tumor Cells, Cultured
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Summary:In the present study, a series of metallic complexes of the 1,4-naphthoquinone lawsone (2–6) were synthesized and evaluated for potential cytotoxicity in a mouse leukemic macrophagic RAW 264.7 cell line. Cell viability was determined by the MTT assay. Significant growth inhibition was observed for the copper complex (4) with an IC50 value of 2.5μM. This compound was selected for further evaluation of cytotoxic activity on several human cancer cells including HT-29 (human colorectal adenocarcinoma), HepG2 (human hepatocellular carcinoma) and HeLa, (human cervical adenocarcinoma cells). Significant cell viability decrease was also observed in HepG2 cells. The apoptotic potential of this complex was evaluated in these cells. Compound 4 induced apoptosis by a mechanism that involves the activation of caspases 3, 8 and 9 and modulation of apoptotic-related proteins such as Bax, Bad, and p53. These results indicate that metal complexes of lawsone derivatives, in particular compound 4, might be used for the design of new antitumoral agents.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2013.03.002