Phthalocyanines Promising, Exciting and Versatile Photosensitisers for Photodynamic Therapy


Fabienne Dumoulin, Gebze Technical University, Chemistry Department

Photodynamic therapy is based on the combined action of light activating a photosensitiser to convert molecular

oxygen into its highly reactive singlet form. This therapeutic modality is mainly known as an alternative cancer treatment

but is actually most widely used to cure age-related macular degeneration (AMD), and is extremely promising as a

valuable alternative to antibiotics against antimicrobial issues.

Porphyrinoids such as porphyrins and phthalocyanines must be appropriately metalated and/or substituted to

exert efficient photodynamic action thanks to the tailoring of desired properties.

Being specialized in the development of substitution patterns ensuring water-solubility and biocompatibility, we explored

several ways to produce better photosensitising systems, by:

– combining the photodynamic effect with an antivascular effect [1]

– promoting their excitation at near-infra-red wavelengths [2]

– inserting them into nanoparticles to benefit from the Enhanced and Permeation Retention effect [3]

– targeting tumours which over express specific receptors, by introducing carbohydrates [4] or vitamins [5]

– investigating the recent interest of more hydrophobic substitution pattern [6]

– optimizing the singlet oxygen generation thanks to the heavy atom effect [7]

– playing with the amphiphilicity and hydrophobicity of the photosensitisers [8]

– among others….

All these works concomitant of more fundamental studies [9] allowing systematic structure-properties and

structure-activities relationships investigations will be presented after a brief introduction on photodynamic therapy and of

the different types of photosensitisers.

These works are and have been funded by several TUBITAK projects (106T376, 109T523, 111M386, 111T031,

112T670, 113Z595 and 214Z099) and acknowledged by the Turkish Academy of Sciences (TÜBA-GEBIP 2015), the

Bilim Akademisi (BAGEP-2016) and the METU Prof. Dr. Mustafa Parlar Foundation for Research and education

(Incentive Award 2016).



[1] Tuncel, S.; Trivella, A.; Atilla, D.; Bennis, K.; Savoie, H.; Albrieux, F.; Delort, L.; Billard, H.; Dubois, V.; Ahsen, V.;

Caldefie-Chézet, F.; Richard, C.; Boyle, R.W.; Ducki, S.; Dumoulin, F. Mol. Pharm. 201310, 3706-3716.

[2] Aydın Tekdaş, D.; Kumru, U.; Gürek, A.G.; Durmuş, M.; Ahsen, V.; Dumoulin, F. Tetrahedron Lett. 201253, 5227-


[3] Giuntini, F.; Dumoulin, F.; Daly, R.; Ahsen V.; Scanlan E. M.; Lavado A.; Aylott J. W.; Rosser G.; Beeby, A.; Boyle, R.

  1. Nanoscale 20124, 2034-2045.

[4] (a) Zorlu, Y.; Dumoulin, F.; Bouchu, D.; Ahsen, V.; Lafont, D. Tetrahedron Lett. 201051, 6615-6618; (b) Lafont D.,

Zorlu, Y.; Savoie, H.; Albrieux, F.; Ahsen, V.; Boyle R. W.; F. Dumoulin, F. Photodiagn. Photodyn. Ther. 201310, 252-


[5] Tarakci, D. K.; Berber S.; Zorlu Y.; Atilla D.; Ahsen V.; Dumoulin, F. New. J. Chem 201539, 3929-3935

[6] Işci, Ü.; Beyreis, M.; Tortik, N.; Topal, S. Z.; Glueck, M.; Ahsen, V.; Dumoulin, F.; Kiesslich, T.; Plaetzer, K. Photodiag.

Photodyn. Ther., 201613, 40-47.

[7] (a) Topkaya, D.; Arnoux, P.; Dumoulin, F. J. Porphyrins Phthalocyanines. 201519, 1081-1087; (b) Chin, Y.; Lim, S.

H.; Zorlu, Y.; Ahsen, V.; Kiew, L. V.; Chung, L. Y.; Dumoulin, F.; Lee, H. B. PlosOne, 2014, 9(5): e97894.

doi:10.1371/journal.pone.0097894; (c) Zorlu, Y.; Dumoulin, F.; Durmus, M.; Ahsen, V. Tetrahedron 201066, 3248-3258.

[8] B. Pucelik, Il. Gürol, V. Ahsen, F. Dumoulin, J. M. Dąbrowski Eur. J. Med. Chem. 2016124, 284-298

[9] (a) Zorlu, Y.; Kumru, U.; İşci, Ü.; Divrik, B.; Jeanneau, E.; Albrieux, F.; Dede, Y.; Ahsen, V.; Dumoulin, F. Chem

Commun, 20155, 6580-6583; (b) Topal, S. Z.; İşci, Ü.; Kumru, U.; Atilla, D.; Gürek, A. G.; Hirel, C.; Durmuş, M.;

Tommasino, J.-B.; Luneau, D.; Berber, S.; Dumoulin, F.; Ahsen, V. Dalton Trans201443, 6897-6908