Synthesis & Evaluation of novel Phenazine dyes for use in Amina Tariq - Supervisor Dr. Natalia Sergeeva MSc Polymers, Colourants and Fine Chemicals 1. Introduction Dyes as photosensitizors are in use in a myriad of applications across all disciplines. Currently; one of the most investigated applications of dyes is in PDT. Photodynamic therapy is a sophisticated light driven oncological treatment. 2. Synthetic Route 6. References Allison, R.R. and Moghissi, K. Photodynamic Therapy (PDT): PDT Mechanisms. Clinical Endoscopy. 2013, 46(1), pp.24-29. Robertson, C.A., Evans, D.H. and Abrahamse, H. Photodynamic therapy (PDT): A short review on cellular mechanisms and cancer research applications for PDT. Journal of Photochemistry and Photobiology B: Biology. 2009, 96(1), pp.1-8. Sharman, W.M., Allen, C.M. and van Lier, J.E. Photodynamic therapeutics: basic principles and clinical applications. Drug Discovery Today. 1999, 4(11), pp.507-517. 3. Mechanism of dye excitation by Jablonski Diagram 4. Photochemical and photophysical principles of PDT Sensitizer hᶹ 1 Sensitizer * 1 Sensitizer * 3 Sensitizer * Type I Mechanism 3 Sensitizer* + 3 Sensitizer * Sensitizer +. +Sensitizer -. 3 Sensitizer * + Substrate Substrate +. + Sensitizer -. Sensitizer -. + O 2 ( 3 Σ g - ) Sensitizer + O 2 -. Substrate +. + O 2 ( 3 Σ g - ) Oxidative damage Substrate + O 2 -. Oxidative damage Type II Mechanism 3 Sensitizer * + O 2 ( 3 Σ g - ) Sensitizer + O 2 ( 1 ∆ g ) O 2 ( 1 ∆ g ) +Substrate Oxidative damage 5 Analytical Testing 1. UV-Vis 2. LC-MS 3. NMR 4. Spectroscopy N N N NH 2 THF,HCl (0-5C), NaNO2 N N N N N 2 N X N X X = Cl Br I KX +

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Page 1: Synthesis and evaluation of novel phenazine dyes for use in PDT

Synthesis & Evaluation of novel Phenazine dyes for use in PDTAmina Tariq - Supervisor Dr. Natalia SergeevaMSc Polymers, Colourants and Fine Chemicals1. Introduction

Dyes as photosensitizors are in use in a myriad of applications across all disciplines. Currently; one of the most investigated applications of dyes is in PDT. Photodynamic therapy is a sophisticated light driven oncological treatment.

2. Synthetic Route

NN NH2 THF, HCl(0-5C), NaNO2

NN2N X N X

X = Cl Br I

KX +

6. ReferencesAllison, R.R. and Moghissi, K. Photodynamic Therapy (PDT): PDT Mechanisms. Clinical Endoscopy. 2013, 46(1), pp.24-29.Robertson, C.A., Evans, D.H. and Abrahamse, H. Photodynamic therapy (PDT): A short review on cellular mechanisms and cancer research applications for PDT. Journal of Photochemistry and Photobiology B: Biology. 2009, 96(1), pp.1-8.Sharman, W.M., Allen, C.M. and van Lier, J.E. Photodynamic therapeutics: basic principles and clinical applications. Drug Discovery Today. 1999, 4(11), pp.507-517.

3. Mechanism of dye excitation by Jablonski Diagram4. Photochemical and photophysical principles of PDT Sensitizer hᶹ 1Sensitizer*

1Sensitizer* 3Sensitizer*

Type I Mechanism 3Sensitizer* + 3Sensitizer* Sensitizer+. +Sensitizer-.

3Sensitizer* + Substrate Substrate+. + Sensitizer-.

Sensitizer-. + O2 (3Σg -) Sensitizer + O2 -.

Substrate+. + O2 (3Σg -) Oxidative damage

Substrate + O2-. Oxidative damage

Type II Mechanism 3Sensitizer* + O2 (3Σg

-) Sensitizer + O2 (1∆g) O2 (1∆g) +Substrate Oxidative damage

Analytical Testing

1. UV-Vis2. LC-MS3. NMR

4. Spectroscopy