Abstract
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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Binding Sites
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Circular Dichroism
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DNA / chemistry
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DNA / drug effects*
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DNA / radiation effects
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Electrophoresis, Agar Gel
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Esters / chemical synthesis
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Esters / chemistry
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Esters / pharmacology*
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Molecular Structure
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Photosensitizing Agents / chemical synthesis
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Photosensitizing Agents / chemistry
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Photosensitizing Agents / pharmacology*
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Plasmids / chemistry
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Plasmids / drug effects
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Plasmids / radiation effects
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Porphyrins / chemical synthesis
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Porphyrins / chemistry
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Porphyrins / pharmacology*
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Singlet Oxygen / chemistry
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Stereoisomerism
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Structure-Activity Relationship
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Ultraviolet Rays
Substances
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Esters
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Photosensitizing Agents
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Porphyrins
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Singlet Oxygen
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DNA