Pérez-Mercado, Wanda I.

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    New ferrocene chemotherapeutic drugs and early detection of breast cancer using a nanostructured gold biosensor
    (2015) Pérez-Mercado, Wanda I.; Meléndez, Enrique; College of Arts and Sciences - Sciences; Cádiz, Mayra E.; Torres, Jessica; Department of Chemistry; Calcagno, Bárbara
    Three new ferrocene complexes were synthesized with 4-(1H-pyrrol-1-yl)phenol group appended to the cyclopentadienyl (Cp) rings. These are: 1,1’-4-(1H-pyrrol-1- yl)phenyl ferrocenedicarboxylate, (‘Fc-(CO2-Ph-4-Py)2’), 1,4-(1H-pyrrol-1-yl)phenyl, 1’- carboxyl ferrocenecarboxylate (‘Fc-(CO2-Ph-4-Py)CO2H’) and 4-(1H-pyrrol-1-yl)phenyl ferroceneacetylate (‘Fc-CH2CO2-Ph-4-Py’). The new species were full characterized by spectroscopic methods (FT-IR, 1HNMR, 13CNMR, and MS), and by electrochemistry. Additionally, the X-ray single crystal structure of Fc-(CO2-Ph-4-Py)2 was resolved. The Fc- (CO2-Ph-4-Py)2 crystallizes in the orthorhombic space group Pbca with the Fe2+ cation positioned on an inversion center and the Cp rings adopted an anti conformation. Cyclic voltammetry experiments showed that Fc-CH2CO2-Ph-4-Py has a redox potential very similar to the Fc/Fc+ redox couple whereas Fc-(CO2-Ph-4-Py)2 and Fc-(CO2-Ph-4- Py)CO2H have redox potentials of over 400 mV higher than Fc/Fc+ redox couple. The in vitro studies of Fc-(CO2-Ph-4-Py)2 and Fc-(CO2-Ph-4-Py)CO2H revealed that the latter two compounds have moderate antiproliferative activity on MCF-7 breast cancer cell line with a IC50 values of 45.5(6) and 57(7) µM respectively. In contrast with Fc-CH2CO2-Ph-4-Py which displayed low anti-proliferative activity with an IC50 value of 103(6) µM. The genotoxic effects of the new synthesized ferrocenes were addressed with cytokinesis-block micronucleus assay (CBMN) and reactive oxygen species (ROS) induction assay. The Fc- (CO2-Ph-4-Py)2 showed with the higher genotoxic effects on the MCF-7 followed by Fc- (CO2-Ph-4-Py)CO2H, and Fc-CH2CO2-Ph-4-Py with the lower effects. There is a correlation between the IC50 values of the ferrocenes and the amount of micronucleus formation activity on binucleated cells and the reactive oxygen species (ROS) production on MCF-7 cell line. However, no correlation was found between the redox activity and the genotoxic effects. A nanostructured gold dsDNA biosensor for early detection of breast cancer was designed and fabricated. The nanostructured gold dsDNA biosensor is based on the detection of the binding event of the beta protein 1 (BP1) with dsDNA. A redox-active probe (methylene blue) was intercalated in dsDNA to monitor the electrochemical response of the binding event of BP1. A linear correlation of the electrochemical response by concentration of BP1 was obtained (R2 = 0.998) with a limit of detection of 1.2 nM. This nanostructured gold dsDNA sensor is shown to be sensitive, selective, stable, and reusable allowing for its potential clinical use.