Phosphinatophenylporphyrins tailored for high photodynamic efficacy

被引:14
作者
Hynek, Jan [1 ,2 ]
Koncosova, Martina [3 ]
Zelenka, Jaroslav [3 ]
Krizova, Ivana [4 ]
Ruml, Tomas [3 ]
Kubat, Pavel [5 ]
Demel, Jan [1 ]
Lang, Kamil [1 ]
机构
[1] Czech Acad Sci, Inst Inorgan Chem, Rez 25068, Czech Republic
[2] Charles Univ Prague, Dept Inorgan Chem, Fac Sci, Hlavova 2030, Prague 12843 2, Czech Republic
[3] Univ Chem & Technol Prague, Dept Biochem & Microbiol, Tech 5, Prague 16628, Czech Republic
[4] Univ Chem & Technol Prague, Dept Biotechnol, Tech 5, Prague 16628, Czech Republic
[5] Czech Acad Sci, J Heyrovsky Inst Phys Chem, Dolejskova 3, Prague 18223 8, Czech Republic
关键词
SINGLET OXYGEN; PORPHYRINS; MITOCHONDRIA; ACID;
D O I
10.1039/c8ob01984c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The development of effective photosensitizers is particularly attractive for photodynamic therapy of cancer. Three novel porphyrin photosensitizers functionalized with phosphinic groups were synthesized and their physicochemical, photophysical, and photobiological properties were collected. Phosphinic acid groups ((RRPOOH)-R-1-P-2) attached to the porphyrin moiety (R-1) contain different R-2 substituents (methyl, isopropyl, phenyl in this study). The presence of phosphinic groups does not influence absorption and photophysical properties of the porphyrin units, including the O-2((1)Delta(g)) productivity. In vitro studies show that these porphyrins accumulate in cancer cells, are inherently nontoxic, however, exhibit high phototoxicity upon irradiation with visible light with their phototoxic efficacy tuned by R-2 substituents on the phosphorus centre. Thus, phosphinatophenylporphyrin with isopropyl substituents has the strongest photodynamic efficacy due to the most efficient cellular uptake. We demonstrate that these porphyrins are attractive candidates for photodynamic applications since their photodynamic efficacy can be easily tuned by the R-2 substituent.
引用
收藏
页码:7274 / 7281
页数:8
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