Sequence Specific Interaction of the Photoactive Drug Hypericin Depends on the Structural Arrangement and the Stability of the Structure Containing its Specific 5′AG3′ Target: A Resonance Raman Spectroscopy Study

Abstract

The resonance Raman spectra of three oligonucleotides with different lengths containing a specific 5'AG3' target doublet for hypericin - a potent antiretroviral and anticancer photoactive agent, and their 1:1 and 1:2 (oligonucleotide: hypericin) complexes are reported. It is shown that the structural arrangement of the oligonucleotides, their structural stability and the local structural arrangement around the 5'AG3' hypericin target, are the factors which determine the formation of a stable, specifically bounded DNA-hypericin complexes.

Interaction of a Potential Anticancer Agent Hypericin and its Model Compound Emodin with DNA and Bovine Serum Albumin

“…Comparing the structure of hypericin and emodin molecules considering their binding characteristics during complex formation with DNA, we hypothesize that hypericin binds into the major DNA groove, this is supported by results obtained by Kočišová et al (23).…”

“…The most probable binding sites in the DNA structure for hypericin molecule were found by Raman spectroscopy (23). Vibrational spectra for hypericin in complex with polynucleotides show that N7 of purines, preferentially guanine, is included in the interaction.…”

Biophysical Characterization and Anticancer Activities of Photosensitive Phytoanthraquinones Represented by Hypericin and Its Model Compounds

“…As a representative of highly hydrophobic PSs, hypericin binds to DNA by means of a large groove [203,204]. A binding constant, whose value was also determined, is 4.0 × 10 4 L/mol [204].…”