Document Detail


New tungstenocenes containing 3-hydroxy-4-pyrone ligands: antiproliferative activity on HT-29 and MCF-7 cell lines and binding to human serum albumin studied by fluorescence spectroscopy and molecular modeling methods.
MedLine Citation:
PMID:  23212785     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Three new water-soluble tungstenocene derivatives were synthesized and characterized using 3-hydroxy-4-pyrone ligands, which provide aqueous stability to the complexes. The antiproliferative activities of the complexes on HT-29 colon cancer and MCF-7 breast cancer cell lines were evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay and showed the new tungstenocene derivatives have higher antiproliferative action than tungstenocene dichloride (Cp(2)WCl(2), where Cp is cyclopentadienyl). The binding interactions of the tungstenocenes with human serum albumin (HSA) were investigated using fluorescence spectroscopy and molecular modeling methods. Analysis of the fluorescence quenching spectra indicates that the tungstenocene complexes bind HSA by hydrophobic interactions and hydrogen bonding at fatty acid binding site 6 and drug binding site II. Docking studies provided a description of the hydrophobic interactions and hydrogen bonding by which the tungstenocenes become engaged with HSA. It was determined that the binding affinity of the tungstenoecenes for HSA is in the order Cp(2)WCl(2) < [Cp(2)W(ethyl maltolato)]Cl < [Cp(2)W(maltolato)]Cl < [Cp(2)W(kojato)]Cl, consistent with the hydrophobic interactions and the number of hydrogen bonds involved.
Authors:
Moralba Domínguez-García; Carlos Ortega-Zúñiga; Enrique Meléndez
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2012-12-05
Journal Detail:
Title:  Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry     Volume:  18     ISSN:  1432-1327     ISO Abbreviation:  J. Biol. Inorg. Chem.     Publication Date:  2013 Feb 
Date Detail:
Created Date:  2013-02-05     Completed Date:  2013-07-23     Revised Date:  2014-02-04    
Medline Journal Info:
Nlm Unique ID:  9616326     Medline TA:  J Biol Inorg Chem     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  195-209     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Antineoplastic Agents / chemistry,  pharmacology*
Binding Sites
Cell Proliferation / drug effects*
Cell Survival / drug effects
Coordination Complexes / chemistry,  pharmacology*
HT29 Cells
Humans
Hydrogen Bonding
Hydrophobic and Hydrophilic Interactions
Inhibitory Concentration 50
MCF-7 Cells
Models, Molecular
Molecular Docking Simulation
Organometallic Compounds / chemistry,  pharmacology
Protein Binding
Serum Albumin
Solubility
Spectrometry, Fluorescence
Tungsten*
Grant Support
ID/Acronym/Agency:
S06 GM008103/GM/NIGMS NIH HHS; S06 GM008103-37./GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Antineoplastic Agents; 0/Coordination Complexes; 0/Organometallic Compounds; 0/Serum Albumin; 1271-29-0/titanocene; V9306CXO6G/Tungsten
Comments/Corrections

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