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Synthesis and DNA‐Recognition and ‐Cleavage Properties of Multiply Charged Porphyrin Esters
Author(s) -
Wu Lin,
Hu Peng,
Xiao Ying,
Zhang Ming,
Zhang Lixia,
Weng Xiaocheng,
Wu Xiaojun,
Zhou Xiang,
Cao Xiaoping
Publication year - 2008
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200890005
Subject(s) - porphyrin , chemistry , cleavage (geology) , dna , singlet oxygen , plasmid , gel electrophoresis , stereochemistry , photochemistry , biochemistry , oxygen , organic chemistry , geotechnical engineering , fracture (geology) , engineering
A series of systematically modified porphyrin esters, compounds 1 – 6 , with multiple, permanent positive charges introduced at the meso ‐positions via N ‐methylated 4‐, 3‐, or 2‐pyridyl moieties, were prepared and characterized. Their singlet‐oxygen production, CT‐DNA‐binding properties, and plasmid‐DNA photocleavage propensities were determined spectroscopically and by gel electrophoresis, and compared to those of the known, fourfold‐charged parent porphyrin 4,4′,4″,4′′′‐porphyrin‐5,10,15,20‐tetrayltetrakis(1‐methylpyridinium) (TMPyP4). Some interesting structure–activity relationships could be established to rationalize effects affecting DNA binding mode and cleavage ability.