title: Combination of two chromophores: synthesis and PDT application of porphyrin-pentamethinium conjugate.
abstract: A general method for the synthesis of a novel porphyrin with pentamethine periphery substitution is described. The combination of two chromophoric systems, a porphyrin macrocycle and a polymethine moiety was achieved by transformation of tetrapyridyl porphyrin. The synthetic strategy included conversion of the tetrapyridyl porphyrin to its corresponding 2,4-dinitrophenylpyridinuim salt, which was subsequently converted to tetrakis(meso-pentamethinium salt) on the porphyrin core. This novel porphyrin exhibited PDT properties as manifested by the induction of apoptosis in the myeloid cell line HL-60 and the effective reduction of amelanotic melanoma in nude mice.
authors.affiliation: Institute of Chemical Technology, Technicka 5, 16628 Prague 6, Czech Republic; First Faculty of Medicine, Charles University in Prague, Katerinska 32, 12108 Prague 2, Czech Republic.
authors.forename: Tomáš
authors.initials: T
authors.lastname: Bříza
authors.forename: Jarmila
authors.initials: J
authors.lastname: Králová
authors.forename: Petr
authors.initials: P
authors.lastname: Cígler
authors.forename: Zdeněk
authors.initials: Z
authors.lastname: Kejík
authors.forename: Pavla
authors.initials: P
authors.lastname: Poučková
authors.forename: Petr
authors.initials: P
authors.lastname: Vašek
authors.forename: Irena
authors.initials: I
authors.lastname: Moserová
authors.forename: Pavel
authors.initials: P
authors.lastname: Martásek
authors.forename: Vladimír
authors.initials: V
authors.lastname: Král
mesh_terms: D000818:Animals; D017209:Apoptosis; D008725:Bis-Trimethylammonium Compounds / Q000737:chemistry*; D016923:Cell Death; D053938:DNA Fragmentation; D015195:Drug Design; D018922:HL-60 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D008545:Melanoma / Q000188:drug therapy*; D051379:Mice; D008819:Mice, Nude; D008956:Models, Chemical; D009369:Neoplasms / Q000188:drug therapy*; D010778:Photochemotherapy / Q000295:instrumentation* / Q000379:methods; D011166:Porphyrins / Q000737:chemistry*; D012492:Salts / Q000737:chemistry; D013997:Time Factors
chemical_list: D008725:Bis-Trimethylammonium Compounds; D011166:Porphyrins; D012492:Salts; C014147:pentamethonium