Design of Therapeutic Self-Assembled Monolayers of Thiolated Abiraterone

Abstract

The aim of our work was to synthetize of a new analogue of abiraterone—thiolated abiraterone (HS-AB) and design a gold surface monolayer, bearing in mind recent advances in tuning monolayer structures and using them as efficient drug delivery systems. Therapeutic self-assembled monolayers (TSAMs) were prepared by chemically attaching HS-AB to gold surfaces. Their properties were studied by voltammetry and atomic force microscopy (AFM). A gold electrode with immobilized thioglycolic acid (HS-GA) was used for comparison. The surface concentration of HS-AB on the gold surface was 0.572 nmol/cm2, determined from the area of the voltammetric reduction peaks (desorption process). The area per one molecule estimated from the voltammetry experiments was 0.291 nmol/cm2. The capacity of thus prepared electrode was also tested. The calculated capacity for the HS-AB modified electrode is 2.90 μF/cm2. The obtained value indicates that the monolayer on the gold electrode is quite well ordered and well-packed. AFM images show the formation of gold nanoparticles as a result of immersing the HS-AB modified gold electrode in an aqueous solution containing 1 mM HAuCl4·3H2O. These structures arise as a result of the interaction between the HS-AB compound adsorbed on the electrode and the AuCl4− ions. The voltammetric experiments also confirm the formation of gold structures with specific catalytic properties in the process of oxygen reduction.

Keywords

• self-assembled monolayer
• thiolated abiraterone
• thioglycolic acid (GA)
• electrochemistry
• gold electrode
• capacity
• oxygen reduction