Adenine Derivatives for Regenerable Antibacterial Surface Applications Based on A−T Base Pairing. Issue 32 (27th August 2020)

• Record Type: Journal Article
• Authors: Kinali‐Demirci, Selin; Idil, Onder; Disli, Ali; Demirci, Serkan
• Is Part Of: ChemistrySelect. Volume 5:Issue 32(2020)
• Page Start: 10128
• Page End: 10134
• Publication Date: 2020-08-27
• Subjects: adenine -- antibacterial surface -- DNA interaction -- tetrazole; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202002238
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Surface contamination is a major concern in the design, fabrication, and application of biomaterials. In this work, a series of new adenine derivatives were synthesized in a three‐step method with the goal of protecting the functional materials against microbial adhesion. Initially, 9‐(chloroalkyl)‐9H‐purin‐6‐amine compounds were synthesized from adenine. Then, these compounds were reacted with potassium thiocyanate or potassium selenocyanate. In the last step, adenine derivatives incorporating a tetrazole ring were synthesized via the cycloaddition of sodium azide with thiocyano or selenocyano derivatives. The antimicrobial activity of the compounds was evaluated by using the minimal inhibitory concentration method. Furthermore, the effect of the compounds on pBR322 plasmid DNA was studied using gel electrophoretic mobility measurements. The antimicrobial assay showed that some of the synthesized compounds exerted vigorous antibacterial and antifungal activities. Further experiments indicated that seleno‐adenine derivatives have higher antimicrobial and DNA effect than other derivatives. The surfaces activated by the adenine derivative demonstrated antibacterial activity resisting bacterial attachment in order to remove dead bacteria from the surface. All results showed that some of these adenine derivatives have an antibacterial activity and the potential for further applications, for example as a smart surface coating that prevents bacterial adhesion to biomaterials. Abstract : Surface contamination is a major concern in the design, fabrication, and application of biomaterials. In this work, a series of new adenine derivatives were synthesized with the goal of protecting the functional materials against microbial adhesion. This concept study showed that activated surfaces with adenine derivatives could be used as a reusable platform with repetitive bacterial killing and release functionality.