Book of abstracts version 5

Book of abstracts SPOC 2018
Synthesis of a terpyridine ligand for tumor-targeting ruthenium complexes
of a terpyridine Author ligand for tumor-targeting ruthenium complexes
Ward van den Berg
Academy of Technology for Health and Environment
Avans Hogeschool, Breda
Radboud University
Abstract
Terpyridine is a ligand that can form a coordinating bond with a central metal atom and form a complex. Complexes of
terpyrydine with ruthenium can be used for PhotoDynamic Therapy(PDT). PDT is a way of treatment for diseases like, skin
cancer and Bowen’s disease [1]. It consists of 3 parts: a photosensitizer(PS), oxygen and laser light. The laser light excites
the photosensitizer after which the excited electron falls back to its lower energy state and creates Reactive Oxygen
Species(ROS) [2]. After the ROS cause enough damage to the cellular structure, it induces apoptosis and dies. The goal of
this research is to synthesize the desired terpyridine ligand, tpy-MeCl and to analyze the intermediates and end product
with 1 H-NMR, 13 C-NMR, MS and EA analyses. To reach this goal 2 synthetic routes were taken. Route 1 esterificates tpy-
COOH with H 2SO 4 and MeOH to form tpy-COOMe which is then reduced with LiAlH 4 to tpy-MeOH. Route 2 directly
reduces tpy-COOH with LiAlH 4 to form tpy-MeOH. However difficulties were described with the direct reduction of tpy-
COOH by Willem Aarts [3]. The last step in both routes is the chlorination of tpy-MeOH to get tpy-MeCl. To follow the
progress of the reaction it will be monitored with TLC.
Keywords: Photodynamic therapy, Ruthenium complex, Terpyridine ligand, tpy-COOH, tpy-COOMe, tpy-MeOH, tpy-MeCl
Table of content
Figure 1: Reaction route for tpy-MeCl.
[1] C. Robertson, D. Hawkins and H. Abrahamse, "Photodynamic therapy (PDT): A short review on cellular mechan isms
and cancer research applications for PDT," Journal of Photochemistry and Photobiology B: Biology, pp. 2 -3, 2009.
[2] R. Boyle en L. Josefson, „Photodynamic Therapy and the Development of Metal-Based Photosensitisers,” Metal-Based
Drugs, p. 1, 2008.
[3] W. Aarts, „Synthesis of a terpyridine ligand for ruthenium complexes; Application in photodynamic therapy of cancer,”
2017
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