Design of Therapeutic Self-Assembled Monolayers of Thiolated Abiraterone

• Main Authors: Elżbieta U. Stolarczyk, Katarzyna Sidoryk, Marcin Cybulski, Marek Kubiszewski, Krzysztof Stolarczyk
• Format: Article
• Language: English
• Published: MDPI AG 2018-12-01
• Series: Nanomaterials
• Subjects: self-assembled monolayer; thiolated abiraterone; thioglycolic acid (GA); electrochemistry; gold electrode; capacity; oxygen reduction
• Online Access: https://www.mdpi.com/2079-4991/8/12/1018
• ISSN: 2079-4991

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.