Book of abstracts version 5

Book of abstracts SPOC 2018
The synthesis of a terpyridine for the use of photo dynamic therapy
Author
Kevin van Eekelen
of a terpyridine for the use of photo dynamic therapy
Academy of Technology for Health and Environment
Avans Hogeschool, Breda
University of Leiden
Abstract
Photo dynamic therapy (PDT) is a new way to treat cancer. In contrast to chemo - and radio therapy, PDT is a very targeted
method to cure cancer. While chemo- and radio therapy also damage healthy cells in the body, the PDT only affects the
cancer cells. To use PDT a photosensitizer is needed. This photosensitizer will be exposed to light of the right wavelength
and undergo a reaction which will produce oxygen radicals. Those oxygen radicals will destroy the cancer cell [1]. In this
research [2,2':6',2''-terpyridin]-4'-ylmethanol (Tpy-MeOH) will be synthesized, which can be used as a photosensitizer in a
ruthenium complex. This molecule can be seen at the bottom left side of Figure 1. The goal of this research is to
synthesize Tpy-MeOH in a 4-steps synthesis from 2-acetylpyridine, in which a minimum reaction yield is achieved of 50%.
In these syntheses different reactions are done among which; aldol condensation, Michael addition, oxidat ion with
KMnO 4, Fischer esterification and a reduction with NaBH 4. This can be shown in Figure 1 [2]. To purify the products after
synthesis recrystallisation is applied. To characterize the synthesized products, the following techniques were applied; 1 H-
NMR, 13 C-NMR, FTIR and MS.
Keywords: photo dynamic therapy and terpyridine derivative synthesis.
Table of content
Figure 15: Synthesis route to Tpy-MeOH.
[1] A. Y. Pawel Mroz, „Cell Death Pathways in Photodynamic Therapy o f Cancer,” cancers, vol. 3, pp. 2516-2539, 2011.
[2] B. M. Katarzyna Czerwińska, „Copper(II) complexes of functionalized 2,2’:6’,2’’- terpyridines and 2,6-di(thiazol-2-
yl)pyridine: structure, spectroscopy, cytotoxicity and catalytic activity,” Dalton Tran s., vol. 46, p. 9591–9604, 2017.
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