Synthesis and DNA-binding properties of bisdiazoliumylporphyrins

Daryono H. Tjahjono, Tomoko Yamamoto, Sumito Ichimoto, Naoki Yoshioka, Hidenari Inoue

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Abstract

A pair of 5,15-bisdiazoliumylporphyrins with only two meso-substituents, 5,15-bis(1,3-dimethylimidazolium-2-yl)-porphyrin 1b and 5,15-bis(1,2-dimethylpyrazolium-4-yl)porphyrin 2b, has been synthesized. The crowded porphyrin 1b intercalates between base pairs of DNA to stabilize the duplex DNA to thermal denaturation due to its high affinity for DNA. The binding of porphyrin 1b to DNA is an exothermic interaction and enthalpically driven. Porphyrin 1b interacts more strongly with poly(dA-dT)2 than with poly(dG-dC)2, and the interaction is more favorable or selective to AT-rich sites than to GC-rich sites.

Original languageEnglish
Pages (from-to)3077-3081
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number18
DOIs
Publication statusPublished - 2000

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ASJC Scopus subject areas

  • Chemistry(all)

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