Naslov
Synthesis of 13 1-[2-(2-pyridyl)ethylamine] chlorin e6 derivative

Autori
Srdanović, Sonja

Vrsta, podvrsta i kategorija rada
Ocjenski radovi, diplomski rad, diplomski

Fakultet
Odjel za biotehnologiju

Mjesto
Rijeka

Datum
Podatak o recenziji nije dostupan

Godina
2015

Stranica
66

Mentor
Margetić, Davor

Ključne riječi
organic synthesis, medicinal chemistry, porphyrins

Sažetak
Derivatives of chlorin e6, the class of porphyrins, is considered to be second generation of photosensitizers used in photodynamic therapy (PDT). Novel derivates have been synthesized for the purpose of creating photosensibilisator that is more soluble in water and absorb light at longer wavelengths. Naturally occurring chlorophyll a was isolated from blue-green algae Spirulina Pacifica and Chlorella and transformed to chlorin e6. Dimethyl pheophorbide a was used as a starting reactant for further synthesis. 173, 152-dimethyl-131-(2-pyridyl)ethylamino chlorin e6 1 was synthesized by reaction of reverse Dieckmann condensation after treating dimethyl pheophorbide a with 2-(2-pyridyl)ethylamine. Product 1 was then tried to methylate to give derivate that is more soluble in water. In a similar way, 173, 152-dimethyl-131-2-(1H-indol-3-yl)ethylamino chlorin e6 3 was obtained, by treating methyl pheophorbide a with tryptamine. Isocyclic ring of methyl pheophorbide a was opened by nucleophilic attack to give 1 and 3. When ring E maintained preserved 173-methyl-152-(2-pyridyl)ethylamino pheophorbide a 2 and and 17 3-methyl-15 2-2-(1H-indol-3-yl)ethylamino pheophorbide a 4 were obtained in smaller amounts. Structure of all novel derivates of chlorin e6 were confirmed by spectroscopic methods: 1H NMR, 13C NMR, UV-VIS and IR.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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