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ISSN 1998-9539

Cyano-aryl Porphyrazine Pigments with Polycyclic Substituents as the Promising Agents of Photodynamic Therapy and Potential Sensors of Local Viscosity

Svetlana A. Lermontova,a Ilya S. Grigoryev,a Nina N. Peskova,b Elena Yu. Ladilina,a Tatyana S. Lyubova,a Vladimir I. Plekhanov,c Ivan D. Grishin,b Irina V. Balalaeva,b and Larisa G. Klapshinaa,b@

aG.A. Razuvaev Institute of Organometallic Chemistry of RAS, 603950 Nizhny Novgorod, Russia

bLobachevsky State University of Nizhny Novgorod, 603950 Nizhny Novgorod, Russia

cInstitute of Applied Physics of RAS, 603950 Nizhny Novgorod, Russia

@Corresponding author E-mail: klarisa@iomc.ras.ru

 

The unique cyanoporphyrazine pigment with four bulky phenanthryl peripheral substituents has been prepared. It demonstrates the noticeable shift of Q-band to longer wavelengths due to phenanthryl aromatic system extension. The compound showed very strong predominance of photoinduced cytotoxicity over cytotoxicity in the dark. The presented results indicate the enhancement of photodynamic properties of porphyrazine containing polycyclic aryl substituents in peripheral framing. It is confirmed that the chemical design of the peripheral aryl groups is an efficient toolkit for a fine tuning of photodynamic properties. Furthermore, we have shown that in spite of the presence of bulky substituents new cyano-aryl porphyrazine demonstrates the properties of fluorescent molecular rotors, i.e. the segmental intramolecular mobility in environment of low viscosity. Previously using related cyano-aryl porphyrazines combining the properties of fluorescent molecular rotors and photosensitizers we had demonstrated high potential of these compounds as the sensors of local viscosity and rigidity of biological submicrometer environment within a living cell. So, in respect to PDT it can be a significant expansion of photosensitizer functionality as a potential agent of optical theranostics.