Specific and non-specific interactions of two carcinogenic mycotoxins, luteoskyrin and rugulosin with nucleic acids.
(-) Luteoskyrin and (+) Rugulosin are 2 hepatotoxic and carcinogenic anthraquinone-like pigments from Penicillia which contaminate rice and other foodstuffs. They inhibit in vivo and in vitro replication, transcription and DNA repair of Protocaryots and Eucaryots presumably by forming chelate-complexes with nucleic acids. In the present work, characterization, specificity and structure of binary polychelates (pigment-metal)n and ternary complexes (pigment-metal-nucleic acids) are successively reported: whereas, unspecific complex II with double-stranded polynucleotides is shown to result from simple adsorption of polychelate onto the double helix, complex I is specific for single-stranded DNA (or polypurine nucleotides) and results from electrostatic association of separate pigment-metal units with the polyphosphate chain. Additional stabilization is obtained by hydrophobic interaction between stacked aromatic moieties of pigment and purine units. A model of interaction is proposed for both complexes I and II.
D002273:Carcinogens; D002942:Circular Dichroism; D004247:DNA; D007700:Kinetics; D008958:Models, Molecular; D008968:Molecular Conformation; D009183:Mycotoxins; D009285:Naphthoquinones / Q000031:analogs & derivatives; D009690:Nucleic Acid Conformation; D010407:Penicillium; D010860:Pigments, Biological; D013053:Spectrophotometry
D002273:Carcinogens; D009183:Mycotoxins; D009285:Naphthoquinones; D010860:Pigments, Biological; D004247:DNA