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Digital archive of theses discussed at the University of Pisa

 

Thesis etd-06302022-113452


Thesis type
Tesi di dottorato di ricerca
Author
IACOPINI, DALILA
URN
etd-06302022-113452
Thesis title
New Glycoconjugation Synthetic Approaches for Therapeutic and Diagnostic Applications
Academic discipline
CHIM/06
Course of study
SCIENZE CHIMICHE E DEI MATERIALI
Supervisors
tutor Prof.ssa Di Bussolo, Valeria
relatore Dott. Biancalana, Lorenzo
Keywords
  • altered cellular metabolism
  • coumarin-based fluorescent probes
  • glycal derived vinyl epoxides
  • glycoconjugation
  • pyran-dioxane moieties.
Graduation session start date
11/07/2022
Availability
Withheld
Release date
11/07/2025
Summary
Glycoconjugation is currently a very investigated and applied procedure in the field of synthetic chemistry and clinical research and it has a key role in carbohydrate-based drugs and vaccines design. In the chemotherapy field it leads to molecules with therapeutic or diagnostic action mostly directed towards cancer cells, in consideration of an enhanced selectivity.
In this context, the present PhD thesis reports the stereoselective derivatization of therapeutic and/or diagnostic agents with carbohydrates, and the synthesis of new glycomimetics as potential bioactive compounds. In particular, the connection of carbohydrate-based ligands to antiproliferative Ruthenium(II)-arene complexes
and diiron bis(cyclopentadienyl) complexes is extensively studied. The glycoconjugation approach was also used for the development of specific diagnostic agents, able to detect the increased level and activity that hydrolytic enzymes, such as α- and β-glucosidases show in presence of tumor pathology. In addition, this thesis, also reports the synthesis of new interesting glyco-mimetics as potential antiviral agents and the development of a new completely stereoselective intramolecular version of a O-glycosylation process for the construction of polycyclic systems containing pyran-dioxane moieties.
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