engleski

Photo induced switch of DNA/RNA inactive substance into classical intercalator

Intercalation of aromatic compounds in double stranded (ds) nucleic acids is of paramount significance for many biologically and medicinally important interactions. On the other hand, amidine derivatives are among the very few small molecules that efficiently inhibit of Rev-RRE binding. Therefore, the new amidino substituted compound 1 was prepared by Pinner reaction converted into naphtho[2, 1-b]furan derivative 2 by photodehydrocyclization. Novel compounds 1 and 2 were fully spectroscopicaly characterized. Interactions of compounds 1 and 2 with ds-DNA and RNA were studied by spectroscopic titrations (UV/Vis and fluorimetric) and thermal denaturation experiments. Obtained results show that 'Opened' analogue 1 does not bind to ds-DNA while 'closed' 2 under the same conditions strongly interacts with DNA and RNA, very likely by intercalation into double helix. We have shown that it is possible efficiently convert 'DNA inactive' compound 1 into 'DNA active' compound 2 by light irradiation of the aqueous solutions of the former. This possibility offers the new and attractive approach to photodynamic anticancer therapy.

intercalation; intercalators; naphtho[2; 1-b]furan

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