Design, Synthesis and Biological Applications of Polypeptoids and Boron Dipyrromethenes

Abstract

The dissertation is about the design, synthesis and biological applications of polypeptoids and boron dipyrromethenes (BODIPYs). The dissertation is divided into seven chapters reporting various aspects of the background to my field of study and the results obtained during my PhD program. Chapter 1 is a concise overview of the fundamental concepts of polypeptoids and hydrogels, as well as their recent developments on synthetic strategies, property investigations, and biological applications in different fields. Chapter 2 presents the design, synthesis and potential application as tissue engineering scaffold of thermoreversible ABC polypeptoid hydrogels. A series of ABC copolypeptoids were synthesized and their gelation behavior were investigated in water and biological media. The potential use of the hydrogel as tissue engineering scaffold to induce chondrogenesis of human stem cells was also investigated. Chapter 3 describes the synthesis and characterization of a series of highly water soluble PEGylated polypeptoids bearing oligomeric ethylene glycol side chains. Their potential use as antifouling material was investigated. Chapter 4 reports the solution self-assembly of coil-crystalline diblock copolypeptoids (PNMG-b-PNDG). The relationship between polymer compositions and micelle morphologies was investigated. Chapter 5 is a brief introduction of BNCT and a concise overview of BODIPYs on their synthetic methodologies, functionalization strategies, and potential applications. Chapter 6 describes the design, synthesis and in vitro biological studies of a series of carborane-containing BODIPYs. Their ability to cross the BBB was investigated. Chapter 7 reports the design and synthesis of a series of push-pull BODIPYs. Their spectroscopic and electrochemical properties were investigated by UV-Vis and fluorescence spectroscopy, cyclic voltammetry and DFT calculation.