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Interactions of porphyrinyl‐nucleosides with DNA using the example of porphyrinyl‐thymidine
Author(s) -
Trumble William R.,
Wandrekar Vinay,
Czuchajowski Leszek
Publication year - 1996
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570330638
Subject(s) - chemistry , nucleobase , thymidine , porphyrin , intercalation (chemistry) , dna , steric effects , pyridinium , molecule , stereochemistry , base pair , photochemistry , medicinal chemistry , biochemistry , organic chemistry
meso ‐Tri( N ‐memyl‐4‐pyridinium)porphyrinyl‐ p ‐phenylene‐5′‐ O ‐thymidine, interacting with plasmid ds DNA showed an 8 nm red‐shift of the Soret band. The observed Soret band shift was 4 run less than the shift of the respective meso ‐tetra( N ‐methyl‐4‐pyridinium)porphyrin, which is usually assumed to indicate intercalation. Experimental spectra and the MMX‐ and AM‐1 calculations of a series of model structures further suggest that the investigated porphyrinyl‐thymidine also interacts with adenine due to its nucleobase. The possibility of intercalation was also viewed based on interaction of immobilized porphyrin with ds DNA. Theoretical considerations suggested that there are no steric limitations to the formation of a system in which the porphyrinyl‐thymidine in question interacts with a molecule of porphyrinyl‐adenosine, via A‐T base pairing, to join two ds DNA molecules.