The synthesis of new potential photosensitizers [1-3]. Part 4. Photophysical properties of some monophenyltripyridyl-porphyrin derivatives

被引:0
作者
Kus, Piotr [1 ]
Pasewicz-Sokol, Anna [2 ]
Ratuszna, Alicja [2 ,3 ]
Rojkiewicz, Marcin [1 ]
机构
[1] Univ Silesia, Dept Chem, 9 Szkolna St, PL-40006 Katowice, Poland
[2] Univ Silesia, Chelkowski Inst Phys, PL-40007 Katowice, Poland
[3] Silesian Ctr Educ & Interdisciplinary Res, PL-41500 Chorzow, Poland
关键词
photosensitizers; porphyrins; fluorescence; UV-vis; singlet oxygen; tetrapyrroles; ENANTIOSELECTIVE RECOGNITION; DNA; TETRAPHENYLPORPHYRIN; CONJUGATE; DESIGN; AGENTS;
D O I
10.1142/S1088424615501047
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Six monophenyltripyridylporphyrin derivatives were synthesized and characterized by spectroscopy in order to demonstrate their potential usefulness as photosensitizers for anticancer therapy purposes. Compounds 1 and 3-5 are amphiphilic, thus they may be suitable for transfer inside cells. Photochemical parameters such as fluorescence yield and singlet oxygen yield were determined. The former parameter does not exceed 10% which makes them unsuitable for photodynamic diagnosis (PDD). However, singlet oxygen yields are high and sufficient for these compounds to be considered as potential photodynamic therapy (PDT) photosensitizers.
引用
收藏
页码:1204 / 1211
页数:8
相关论文
共 27 条
[1]   Lead structures for applications in photodynamic therapy. Part 2: Synthetic studies for photo-triggered release systems of bioconjugate porphyrin photosensitizers [J].
Bakar, Mohd Bakri ;
Oelgemoeller, Michael ;
Senge, Mathias O. .
TETRAHEDRON, 2009, 65 (34) :7064-7078
[2]   Synthesis of cationic porphyrin modified amino acids [J].
Biron, E ;
Voyer, N .
CHEMICAL COMMUNICATIONS, 2005, (37) :4652-4654
[3]   Towards sequence selective DNA binding: design, synthesis and DNA binding studies of novel bis-porphyrin peptidic nanostructures [J].
Biron, Eric ;
Voyer, Normand .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (14) :2507-2515
[4]   PHOTOPHYSICAL PROPERTIES OF MESO-TETRAPHENYLPORPHYRIN AND SOME MESO-TETRA(HYDROXYPHENYL)PORPHYRINS [J].
BONNETT, R ;
MCGARVEY, DJ ;
HARRIMAN, A ;
LAND, EJ ;
TRUSCOTT, TG ;
WINFIELD, UJ .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1988, 48 (03) :271-276
[5]   SYNTHESIS OF CATIONIC METALLOPORPHYRIN PRECURSORS RELATED TO THE DESIGN OF DNA CLEAVERS [J].
CASAS, C ;
SAINTJALMES, B ;
LOUP, C ;
LACEY, CJ ;
MEUNIER, B .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (10) :2913-2917
[6]   Metalloporphyrins as chemical shift reagents:: the unambiguous NMR characterization of the cis- and trans-isomers of meso-(bis)4′-pyridyl-(bis)-4′-carboxymethylphenylporphyrins [J].
Gianferrara, Teresa ;
Giust, Davide ;
Bratsos, Ioannis ;
Alessio, Enzo .
TETRAHEDRON, 2007, 63 (23) :5006-5013
[7]   Highly enantioselective recognition of dicarboxylic acid substrates by the control of nonlinear responses [J].
Ikeda, Tomohiro ;
Hirata, Osamu ;
Takeuchi, Masayuki ;
Shinkai, Seiji .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (50) :16008-16009
[8]   Enantioselective recognition of dicarboxylic acid guests based on an allosteric effect of a chiral double-decker porphyrin which changes the stoichiometry upon the guest binding [J].
Ikeda, Tomohiro ;
Sada, Kazuki ;
Shinkai, Seiji ;
Takeuchi, Masayuki .
SUPRAMOLECULAR CHEMISTRY, 2011, 23 (1-2) :59-64
[9]   Efficient photocleavage of DNA by cationic porphyrin-acridine hybrids with the effective length of diamino alkyl linkage [J].
Ishikawa, Y ;
Yamashita, A ;
Uno, T .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2001, 49 (03) :287-293
[10]   Spectroscopic properties and photodynamic effects of new lipophilic porphyrin derivatives: Efficacy, localisation and cell death pathways [J].
Kramer-Marek, Gabriela ;
Serpa, Carlos ;
Szurko, Agnieszka ;
Widel, Maria ;
Sochanik, Aleksander ;
Snietura, Miroslaw ;
Kus, Piotr ;
Nunes, Rui M. D. ;
Arnaut, Luis G. ;
Ratuszna, Alicja .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, 2006, 84 (01) :1-14