Research group: Photochemistry and Supramolecular Chemistry of Porphyrinoids Head of the group: Assoc. Prof. RNDr. Jiří Mosinger, Ph.D.

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1 Research group: Photochemistry and Supramolecular Chemistry of Porphyrinoids Head of the group: Assoc. Prof. RNDr. Jiří Mosinger, Ph.D. Supervisor and consultant of undergraduates and Ph.D. students; author or co-author of ca 40 scientific papers (over 500 citations). Lectures: C240P41 Inorganic Chemistry for Clinic and Toxicological Analysis C240P17 Inorganic Chemistry IV (Mechanism of Inorganic Reactions) C240P48 Introduction to Coordination and Supramolecular Chemistry Students and PhD Students of the group: Mgr. Lukáš Plíštil (Ph.D. student) Ing. Eva Káfuňková (Ph.D. student) Bc. Soňa Jesenská Bc.Veronika Hrdinková Bc. Martin Perlík Bc. Petr Henke Martin Valný Main scientific interest: Chemistry and Photochemistry of Porphyrins and Metalloporphyrins, Singlet Oxygen ( 1 O 2 ) Production/Detection, Host-Guest Interaction, Supramolecular Photoactive Systems, New Photoactive Nanomaterials, Applications in Photodynamic Therapy and Photodisinfection Recent research topics The recent research of the group lays in chemistry and photophysics of porphyrin-type sensitizers, in the formulation of new photofunctional materials and self-assembled structures with potential impact in medicine, light-harvesting, and sensing. The research focuses on two areas: (1) Photophysics and photochemistry of sensitizers, self-assembled systems and (2) Design, preparation, photophysical characterization, and testing of novel photoactive materials. (1) The topic includes the characterization of sensitizers suitable for photodynamic therapy, self-aggregation, the formation of complexes with biologically relevant (DNA, proteins) and transport (cyclodextrins, calixarenes) molecules and solution-phase self-

2 assemblies. We also study photoinduced electron/energy transfer processes within these systems and the formation and reactivity of singlet oxygen in solutions. (2) The materials are based on singlet oxygen producing sensitizers embedded in polymeric nanofibers. The topic includes the characterization of photophysical properties in solid matrices (fluorescence, excited stated, singlet oxygen). We have found that functionalized nanofabrics based on polymeric nanofibers are well suited for the fabrication of textiles with bactericidal and virucidal surfaces after irradiation by visible light. A B Cell line G361 human melanoma with porhyrin sensitizer before A and after B the white light irradiation. Example of photodynamic effect. Porphyrin- cyclodextrin host-guest interaction (Example of supramolecular sensitizer).

3 A novel approach for obtaining photofunctional nanofabrics based on immobilization of the porphyrin sensitizer in polymeric nanofibres. The nanofabrics produce singlet oxygen after irradiation by visible light causing that these materials have bactericidal and virocidal properties and can be used for photooxidation reactions and oxygen sensing. Photodisinfection effect of the polymer nanofabrics doped by sensitizer (A) on bacteria E. coli: Agar plates with pieces of A and a control nanofabric B without sensitizer inoculated with E. coli (dark dots) exposed to light (left Petri dishes, 1), and kept in the dark (right Petri dishes, 2). Selected publications: Mosinger J., Lang K.,, Plíštil L. Jesenská S.,Hostomský J., Zelinger Z., Kubát P,.:Fluorescent Polyurethane nanofabrics: A source of Singlet Oxygen and Oxygen Sensing. Langmuir (2010) in press. Mosinger, J., Slavetinska, L., Lang, K., Coufal, P., Kubat, P.: Cyclodextrin Carriers of Positively Charged Porphyrin Sensitizers. Organic & Biomolecular Chem. 7: 3797 (2009). Tomankova, K., Kolarova, H., Bajgar, R., Jirova, D., Kejlova, K., Mosinger, J.: Study of the Photodynamic Effect on the A549 Cell Line by Atomic Force Microscopy and the Influence of Green Tea Extract on the Production of Reactive Oxygen Species. Natural Compouds and Their Role in Apoptotic Cell Signaling Pathways 1171: 549 (2009). Mosinger J., Lang K., Kubát P., Sýkora J, Hof M., Plíštil L., Mosinger B.: Photofunctional Polyurethane Nanofabrics Doped by Zinc Tetraphenylporphyrin and Zinc Phthalocyanine Photosensitizers. J. Fluoresc. 19: 705 (2009). Kolar, P., Kolarova, H., Tomankova, K., Mosinger, J.: Photodynamic Activity Study of Palladium(II) meso-tetrakis(4-sulfonatophenyl)porphyrin Sensitizer on Cancer Cell Line A549. Metal Ions in Biology and Medicine 10: 500 (2008).

4 Tomankova, K., Kolarova, H,, Mosinger, J. : Photodamage Study of Zinc-5,10,15,20- tetrakis(4-sulphonatophenyl)porphyrine on A549 Cell Lines by Atomic Force Microscopy. Metal Ions in Biology and Medicine, 10: 478 (2008). Kolarova H., Nevrelova P., Tomankova K., Kolar P., Bajgar R.,, Mosinger J.: Production of Oxygen Species after Photodynamic Therapy by Porphyrin Sensitizers. Gen Physiol. Biophys. 27: 101 (2008). Lang K., Kubát P., Mosinger J., Bujdák J., Hof M., Janda P., Sýkora J., Iyi. N.: Photoactive Oriented Films of Layered Double Hydroxides. Phys. Chem. Chem. Phys. 10: 4429 (2008). Slavětínská L., Mosinger J., Dračínský M., Pošta M.: NMR study of Host-Guest Complexes of Disulfonated Derivatives of 9, 10-diphenylanthracene and Corresponding Endoperoxides with Cyclodextrins. J. Incl. Phenom. Macrocycl. Chem. 61: 241 (2008). Slavětínská L., Mosinger J., Kubát P.: Supramolecular Carriers of Singlet Oxygen: Photosensitized Formation and Thermal Decomposition of Endoperoxides in the Presence of Cyclodextrins. J. Photochem. Photobiol. 195: 1 (2008). Lang K., Bezdička P., Bourdelande J.L., Hernando J., Jirka I., Káfuňková E., Kovanda F., Kubát P., Mosinger J., Wágnerová D.M.: Layered Double Hydroxides with Intercalated Porphyrins as Photofunctional Materials: Subtle Structural Changes Modify Singlet Oxygen Production. Chem. Mater. 19: 3822 (2007). Kolarova H., Bajgar R., Tomankova K., Nevrelova P., Mosinger J.: Comparison of Sensitizers by Detecting Reactive Oxygen Species after Photodynamic Reaction in Vitro. Toxicology in Vitro 21: 1287 (2007). Mosinger J., Jirsák O., Lang K, Kubát P.: Baktericidal Nanofabrics Based on Photoproduction of Singlet Oxygen. J.Mater.Chem., 17: 164 (2007). Mosinger J., Janošková M., Lang K, Kubát P..: Light-Induced Aggregation of Cationic Porphyrins. J. Photochem. Photobiol. A: Chem 181: 283 (2006). Singlet oxygen in the practice; the present state and prospects Chem. Listy 100: 169 (2006). Progress in the Photochemistry of Singlet Oxygen Chem. Listy 99: 211 (2005). Kolářová H., Maceček J., Nevřelová P., Huf M., Tomečka M., Bajgar R., Mosinger J., Strnad M.: Photodynamic Therapy with Zinc-tetra(p-sulfophenyl)porphyrin Bound to Cyclodextrin Induces Single Strand Breaks of Cellular DNA in G361 Melanoma Cells. Toxicology in Vitro 19: 971 (2005).

5 Photophysical Properties of Porhyrinoid Sensitizers Noncovalently Bound to Host Molecules; Models for Photodynamic Therapy. Coordination Chemistry Review 248: 321 (2004). Kolárová H., Mosinger J., Lenobel R., Kejlová K., Jirová D. Strnad M.: In Vitro Toxicity Testing of Supramolecular Sensitizers for Photodynamic Therapy. Toxicology in vitro 17: 775 (2003). Mosinger J., Kliment V. Jr., Sejbal J., Kubát P., Lang K.: Host-Guest Complexes of Anionic Porphyrin Sensitizers with Cyclodextrins. J. Porphyrin Phthalocyanines 6: 514 (2002). Mosinger J., Tománková V., Němcová I., Zýka J.: Cyclodextrins in Analytical Chemistry Anal. Lett. 34: 1979 (2001). Lang K., Kubát P., Lhoták P., Mosinger J., Wagnerová D.M.: Photophysical Properties and Photoinduced Electron Transfer within Host-Guest Complexes of 5,10,15,20-tetrakis(4-Nmethylpyridyl)porphyrin with Water-Soluble Calixarenes and Cyclodextrins. Photochem. Photobiol. 74: 558 (2001). Mosinger J., Losinská K., Abrhamová T., Veiserová S., Mička Z., Němcová I., Mosinger B.: Determination of Singlet Oxygen Production and Antibacterial Effect of Nonpolar Porphyrins in Heterogeneous Systems. Anal. Lett. 33: 1091 (2000). Mosinger J., Deumie M., Lang K., Kubát P., Wagnerová D.M.: Supramolecular Sensitizer: Complexation of meso-tetrakis(4-sulfonatophenyl)porphyrin with 2-hydroxypropyl-cyclodextrins. J. Photochem. Photobiol. A 130: 13 (2000). Patent application: Mosinger J., Jirsák O., Mosinger B., Mareš L. System containing at least one layer of nanofibers and the method of nanofibers production. PV , PS3477 CZ (2006).