Barbero, N.

Chinig&#242

Dereje, D. M.

Fiorio Pla, A.

Moran Plata, M. J.

Pontremoli, C.

Sansone, E.

Visentin, S.

English

Chinigò, G.

Institutional Research Information System University of Turin

SIFB Meeting on Photobiology23rd-24th June 2021The Effect of Substitutions on Cyanine dyes on their Photodynamic ActivityC. Pontremoli1, M.J. Moran Plata1, D.M. Dereje1, E. Sansone2, G. Chinigò2, A. Fiorio Pla2, S. Visentin3, N. Barbero11University of Torino, Department of Chemistry, NIS Interdepartmental and INSTM Reference Centre, Via P. Giuria 7, 10125 Torino, Italy.2University of Torino, Department of Life Sciences and Systems Biology, Via Accademia Albertina 13, 10123 Turin, Italy3University of Torino, Department of Molecular Biotechnology and Health Sciences, Via G. Quarello 15A, 10135 Torino, Italy.Over the recent years, extensive efforts have been devoted to the development of near-infrared (NIR) dyes for biological applications, especially for photodynamic therapy (PDT). In this context, polymethine dyes can be considered as innovative photosensitizers (PS) due to the easy and low-cost synthesis along with remarkable absorption property in the far-red NIR region, perfectly matching the biological tissues’ transparency window (600-900 nm) [1]. In particular, NIR polymethine cyanines (CY) are well suited for this purpose and have been extensively studied for many biomedical applications [2], thanks to their high molar absorption coefficients, remarkable brightness, fluorescence and photostability, especially in organic media [3]. However, despite their excellent photodynamic activity, their chemical instability and self-aggregation properties when in contact with biological media still limit their effective clinical application. To overcome these drawbacks, the incorporation of these dyes in nanoparticles (NPs) is extremely important to prevent the formation of dye aggregates in aqueous environment.The present contribution deals with the design and synthesis of a new series of CY polymethine dyes based on indolenine ring and with different substitution groups synthetized by microwave irradiation and photophysically characterized by UV-Vis and fluorescence spectroscopy, with the aim to highlight a structure-activity relationship. 	Afterwards, to assess the suitability of these dyes to be used in PDT, the Reactive Oxygen Species (ROS) production ability of the CY samples has been evaluated by using the 1,3-diphenylisobenzofuran (DPBF) probe and compared with standards PS well-known in literature (i.e Methylene Blue and Bengal Rose). 	In addition, the in vitro biological assessments were examined by exposing the MCF-7 cells to increasing concentration of each PSs to select the maximum non-cytotoxic concentration suitable for performing the in vitro PDT. The potential photocytotoxicity of each cyanine dyes was evaluated by performing an in vitro photodynamic treatment, showing low cytotoxicity in dark, but promoting phototoxic effect upon irradiation.	Finally, these dyes have been also encapsulated into Solid Lipid Nanoparticles (SLNs) and Human Serum Albumin (HSA) NPs to increase their solubility and improve their photochemical properties. References[1]	Avirah R.R., Jayaram D.T., Adarsh N., Ramaiah D., (2012) Squaraine dyes in PDT: From basic design to in vivo demonstration, Org. Biomol. Chem. 10, 911–920.[2]	Ciubini B., Visentin S., Serpe L., Canaparo R., Fin A., Barbero N., (2019) Design and synthesis of symmetrical pentamethine cyanine dyes as NIR photosensitizers for PDT, Dye. Pigment. 160, 806–813.[3]	Barbero N., Butnarasu C., Visentin S., Barolo C., (2019) Squaraine Dyes: Interaction with Bovine Serum Albumin to Investigate Supramolecular Adducts with Aggregation-Induced Emission (AIE) Properties, Chem. - An Asian J. 14, 896 –903.[2]	Ciubini B., Visentin S., Serpe L., Canaparo R., Fin A., Barbero N., (2019) Design and synthesis of symmetrical pentamethine cyanine dyes as NIR photosensitizers for PDT, Dye. Pigment. 160, 806–813.[3]	Barbero N., Butnarasu C., Visentin S., Barolo C., (2019) Squaraine Dyes: Interaction with Bovine Serum Albumin to Investigate Supramolecular Adducts with Aggregation-Induced Emission (AIE) Properties, Chem. - An Asian J. 14, 896 –903.

The Effect of Substitutions on Cyanine dyes on their Photodynamic Activity

https://iris.unito.it/bitstream/2318/1801727/1/Oral.PONTREMOLI.Carlotta.doc

The Effect of Substitutions on Cyanine dyes on their Photodynamic Activity

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