Synthesis and biological evaluations of novel pillar[5]arene conjugates

Student thesis: Doc typesDoctor of Sciences


Pillar[5]arenes, a new class of synthetic macrocycles, consist of five 1,4-dialkoxylhydroquinones linked by methylene bridges at the para position. These characteristics endow pillars[5]arenes a rigid pillar shape, an intrinsic 4.7 Å electron-rich cavity and two fine-tunable rims. Benefiting these unique features, pillar[5]arenes have been successfully applied in life science to construct artificial trans-membrane transport systems, develop antibacterial agents and drug delivery systems and so on. However, applications in life science are still limited mainly due to their intrinsic poor water solubility as well as lack of known scaffolds that allow the precise modification with different functional groups at both rims.
To address these issues, we first developed a co-oligomerization methodology to synthesize copillar[4+1]arenes as heteromultivalent scaffolds. We thus obtained two novel clickable copillar[4+1]arenes that could be readily modified with different functional groups in a controlled manner through orthogonal CuAAC reaction. We then generated several families of glycoclusters designed: 1) as antiadhesion and antibiofilm agents of P. aeruginosa biofilms; 2) as artificial water transport channels; 3) as novel SARS-CoV-2 antiadhesion agents. For comparison, homo-conjugates with different topologies and valencies have been also prepared. This work further expands the application scope of copillar[4+1]arenes in life sciences as we showed that these glycoconjugates can help to clarify some fundamental scientific questions in several therapeutic relevant areas.
Date of Award27 Oct 2021
Original languageEnglish
Awarding Institution
  • University of Namur
SponsorsChina Scholarship Council
SupervisorStephane Vincent (Supervisor), Carmela Aprile (President), Guillaume Berionni (Jury), Eric Doris (Jury) & Annemieke MADDER (Jury)

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