A current area of interest in anti-cancer research is the G-quadruplex DNA located in oncogenes. The guanine-rich promoter regions of many oncogenes contain the sequence which forms a G-quadruplex structure. Molecules with a high affinity for the G-quadruplex are of interest as possible anti-cancer drugs. Previous research has found that the cationic porphyrin, Tetra-N-methylpyridinium porphyrin, TMPyP4, successfully binds to the G-quadruplex. The high affinity of TMPyP4 to both end-stack and intercalate with the G-quadruplex is due to the extended aromatic characteristic of the molecule. Therefore, TMPyP4 may be used as a model ligand for observing the interactions occurring in the G-quadruplex. The interactions of the TMPyP4 have been previously studied . We are focusing on synthesizing various porphyrins with cationic substituents and studying their interactions with the G-quadruplex through ITC, and CD instrumentation. In particular, the synthesis of 5,10,15-tri-(N-methyl-4-pyridyl)porphyrin, 5,15-trans-di(N-methyl-4-pyridyl)porphyrin, and 5,10-cis-di(N-methyl-4-pyridyl)porphyrin. 

Synthesis and binding studies of cationic porphyrins with G-quadruplex DNA

245th National Meeting (2013)

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