Synthesis and DNA-recognition and -cleavage properties of multiply charged porphyrin esters.
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.
Wu
Lin
L
College of Chemistry and Molecular Sciences, Wuhan University, Hubei, Wuhan 430072, PR of China.
Hu
Peng
P
Xiao
Ying
Y
Zhang
Ming
M
Zhang
Lixia
L
Weng
Xiaocheng
X
Wu
Xiaojun
X
Zhou
Xiang
X
Cao
Xiaoping
X
D001665:Binding Sites; D002942:Circular Dichroism; D004247:DNA / Q000737:chemistry / Q000187:drug effects* / Q000528:radiation effects; D004587:Electrophoresis, Agar Gel; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D017319:Photosensitizing Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D010957:Plasmids / Q000737:chemistry / Q000187:drug effects / Q000528:radiation effects; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D026082:Singlet Oxygen / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014466:Ultraviolet Rays
D004952:Esters; D017319:Photosensitizing Agents; D011166:Porphyrins; D026082:Singlet Oxygen; D004247:DNA