Enabling Single-Chain Surfactants to Form Vesicles by Nonamphiphilic Liquid Crystals in Water AND Controlling Attachment and Ligand-Mediated Adherence of Candida albicans on Monolayers

Date of Award

May 2014

Degree Type


Degree Name

Doctor of Philosophy (PhD)




Yan-Yeung Luk


Attachment behavior of fungi Candida albicans, Odd and even effect by surfactants in water, Vesicles by surfactants and bolaamphiphiles

Subject Categories

Physical Sciences and Mathematics


This dissertation describes a fundamental study of weak noncovalent interactions and surface forces that exist at the interfaces of various interacting moieties (small molecules or microbes), and its relevance to colloidal and material chemistry.

Chapter 1 presents an emulsion system that enables single-chain anionic or nonionic surfactants to sequester and encapsulate certain water-soluble organic salts, leading to the formation of vesicles in water. The water-soluble organic salt in the system comprises of disodium cromoglycate crystals that are emulsified by surfactants in water to form stable liquid crystal droplets. The work provides an exception to the rule of geometric packing factor that dictates formation of micelles by the surfactants in water.

Chapter 2 shows that the odd or even number of carbon atoms present in the aliphatic chain of surfactants affect the ability of surfactants to emulsify aqueous-based liquid crystals of disodium cromoglycate. Such an odd-even effect is frequently observed for solid state properties like melting point, heat of fusion and refractive index but is rarely observed for molecules present in solution. When mixed in water, anionic single-chain surfactants with odd number of carbon atoms emulsifies disodium cromoglycate to form liquid crystal droplets, while surfactants with even number of carbon atoms fail to emulsify disodium cromoglycate.

Chapter 3 Bolaamphiphiles usually form vesicles only in extreme conditions or in the presence of surfactants. Here, we explore the co-assembly system of synthesized bolaamphiphiles and disodium cromoglycate in water. The combination of the self-assembly forces of the bolaamphiphile and self-associating property of disodium cromoglycate liquid crystals act together at the interface form a unique microemulsion of liquid crystal droplets of disodium cromoglycate embedded in liquid crystal phase.

Chapter 4 describes a key event (adhesion) that precedes infections caused by "Candida albicans". Adhesion of "C. albicans " to a surface is a complex process and is governed by nonspecific attachment or multiple ligand-receptor interactions. The work demonstrates that the multiple ligand-receptor interactions used by "C. albicans" for adherence to a surface can be individually studied using self-assembled monolayers (SAMs) decorated with minimal motif of the ligands. The SAMs were also used to differentiate between the interactions of the two different morphological forms of"C. albicans".

Chapter 5 presents a study on small molecules that were used to inhibit biofilm formed by "C. albicans". The acyclic triazoles used in the study were not toxic to the "C. albicans" and were capable of inhibiting biofilm formed by "C. albicans". The acyclic triazole can be used as promising candidates to design new antifungal agents. The chapter also reports the synthesis of squarylated homoserine lactones (SHLs) structural mimics of bacterial acyl homoserine lactones (AHLs) to study the inhibitory effects of SHLs on fungal biofilm. The bacterial AHLs are known to repress the growth of "C. albicans"and control fungal biofilm in native host environment. The synthesized SHLs were non-toxic to "C. albicans"and failed to inhibit biofilm formed by "C. albicans".

Chapter 6 uses gradient nanotopography combined with controlled surface chemistry to confine bacterial biofilm formed by " Escherichia coli ". The "E. coli " biofilm were confined within micrometer sized regions of hydrophobic SAMs surrounded by polyol-terminated SAMs. The study reveals that surface with higher topography enhances the ability of the bioinert SAMs to resist bacterial adherence to surface.


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