title: Hierarchical Self-Assembly of Bile-Acid-Derived Dicationic Amphiphiles and Their Toxicity Assessment on Microbial and Mammalian Systems.
abstract: A thiol-yne click chemistry approach was adopted for the first time to prepare highly water-soluble bile acid derived dicationic amphiphiles. The synthesized amphiphiles dicationic cysteamine conjugated cholic acid (DCaC), dicationic cysteamine conjugated deoxycholic acid (DCaDC), and dicationic cysteamine conjugated lithocholic acid (DCaLC) exhibited hierarchically self-assembled microstructures at various concentrations in an aqueous medium. Interestingly at below critical micellar concentration (CMC) the amphiphiles showed distinct fractal patterns such as fractal grass, microdendrites and fern leaf like fractals for DCaC, DCaDC and DCaLC respectively. The fractal dimension (Df) analysis indicated that the formation of fractal like aggregates is a diffusion limited aggregation (DLA) process. The preliminary aggregation studies such as determination of CMC, fluorescence quenching, wettability and contact angle measurements were elaborately investigated. The morphology of the aggregates were analyzed by SEM and OPM techniques. Further, we demonstrated the antimicrobial and hemolytic activity for the cationic amphiphiles. DCaC had potent antimicrobial activity and showed no toxicity on human RBCs indicating that DCaC could be used in biomedical applications, in addition to their industrial and laboratory applications such as detergency, surface cleaning, and disinfection agent.
authors: Department of Polymer Science, University of Madras , Guindy Campus, Chennai 600025, Tamil Nadu, India.
authors: Thangavel
authors: T
authors: Muthukumarasamyvel
authors: Department of Biotechnology, University of Madras , Guindy Campus, Chennai 600025, Tamil Nadu, India.
authors: Raju
authors: R
authors: Baskar
authors: Department of Polymer Science, University of Madras , Guindy Campus, Chennai 600025, Tamil Nadu, India.
authors: Shanmugam
authors: S
authors: Chandirasekar
authors: Department of Biotechnology, University of Madras , Guindy Campus, Chennai 600025, Tamil Nadu, India.
authors: Kesavachandran
authors: K
authors: Umamaheswari
authors: Department of Polymer Science, University of Madras , Guindy Campus, Chennai 600025, Tamil Nadu, India.
authors: Nagappan
authors: N
authors: Rajendiran
mesh_terms: D000818:Animals; D001647:Bile Acids and Salts / Q000737:chemistry*; D019826:Cholic Acid; D003840:Deoxycholic Acid; D006801:Humans; D008823:Micelles
chemical_list: D001647:Bile Acids and Salts; D008823:Micelles; D003840:Deoxycholic Acid; D019826:Cholic Acid
keywords: amphiphiles; cysteamine hydrochloride; dicationic bile salts; fractals; hierarchical self-assembly; surfactant; thiol-yne; wettability