Photodynamic therapy (PDT) is a form of phototherapy that works by producing reactive oxygen species (ROS) from the irradiation, with a specific lightweight, of a photosensitizer in the presence of Oxygen. This mechanism makes PDT applicable in areas such as tumor detection and treatment of cancer and other non-malignant diseases (viruses and bacteria). This thesis continues the work of Tessari Francesco, an older colleague from my university, that found a potentially useful set of molecules for PDT: a 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin (TPFPP) conjugated with 1,8-diazabiciclo[5.4.0]undec-7-ene (DBU). The use of azabicyclic amidines and guanidines, aims at the exploitation of their nucleophilic behaviour, rather than their more commonly known basicity. DBU has proved to undergo nucleophilic substitution reaction with TPFPP, leading to the obtainment of mono-, di-, tri- or tetrasubstituted conjugates. The reaction involves the ring opening of DBU, leading to the formation of an ε-caprolactam derivative. In this project I also used another base, 1,5-Diazabicyclo[4.3.0]non-5-ene (DBN), another azabicyclic amidines, to have another set of molecules to use as comparison to the DBU set. The aim of this work is to show the whole characterization process of those two compound sets: from the choice of the solvent in which to conduct the synthesis, to the singlet oxygen generation capabilities. This is to show which process had better results than the others.
La Photodynamic therapy (PDT) è una metodologia fototerapica che funziona attraverso la produzione di specie radicaliche dell’ossigeno (ROS) in seguito a irradiazione, con corretta lunghezza d’onda, di un foto sensibilizzatore in presenza di ossigeno. Questo meccanismo rende la PDT una tecnica utilizzabile in aree come l’identificazione e cura delle forme tumorali oltre che alla possibilità di debellare malattie causate da agenti patogeni, come virus e batteri. Questa tesi riprende il lavoro di Tessari Francesco, un ex collega proveniente dalla mia università, che trovò un set di molecole potenzialmente utili per la PDT: dei derivati dell’unione tra 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin (TPFPP) e 1,8-diazabiciclo[5.4.0]undec-7-ene (DBU). L’uso di amidine e guanidine azabicicliche, ha come scopo quello di sfruttare il loro comportamento nucleofilo, piuttosto che la loro basicità. DBU ha dimostrato di intraprendere una reazione di sostituzione nucleofila aromatica con TPFPP, portando all’ottenimento di coniugati mono-, di-, tri-, tetra-sostituiti. Tale reazione prevede l’apertura dell’anello del DBU, per formare un derivato dell’ε-caprolattame. In questo progetto è stata usata anche 1,5-Diazabicyclo[4.3.0]non-5-ene (DBN), un’altra amidina azabiciclica, per poter avere un altro set di molecole da confrontare con il set di molecole ottenute dalla reazione con il DBU. L’obiettivo di questa tesi è quello di mostrare l’intero processo di caratterizzazione dei due set di molecole: dalla scelta del solvente migliore in cui svolgere la reazione, alle capacità dei due set di molecole di generare radicali liberi dell’ossigeno, per mostrare quali processi siano stati più efficaci rispetto ad altri.
Sintesi e fotocaratterizzazione di nuovi coniugati azabiciclo-porfirinici per la terapia antibiotica e PDT
FRENDO, FEDERICO
2021/2022
Abstract
Photodynamic therapy (PDT) is a form of phototherapy that works by producing reactive oxygen species (ROS) from the irradiation, with a specific lightweight, of a photosensitizer in the presence of Oxygen. This mechanism makes PDT applicable in areas such as tumor detection and treatment of cancer and other non-malignant diseases (viruses and bacteria). This thesis continues the work of Tessari Francesco, an older colleague from my university, that found a potentially useful set of molecules for PDT: a 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin (TPFPP) conjugated with 1,8-diazabiciclo[5.4.0]undec-7-ene (DBU). The use of azabicyclic amidines and guanidines, aims at the exploitation of their nucleophilic behaviour, rather than their more commonly known basicity. DBU has proved to undergo nucleophilic substitution reaction with TPFPP, leading to the obtainment of mono-, di-, tri- or tetrasubstituted conjugates. The reaction involves the ring opening of DBU, leading to the formation of an ε-caprolactam derivative. In this project I also used another base, 1,5-Diazabicyclo[4.3.0]non-5-ene (DBN), another azabicyclic amidines, to have another set of molecules to use as comparison to the DBU set. The aim of this work is to show the whole characterization process of those two compound sets: from the choice of the solvent in which to conduct the synthesis, to the singlet oxygen generation capabilities. This is to show which process had better results than the others.File | Dimensione | Formato | |
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https://hdl.handle.net/20.500.12608/36015