engleski

Novel polycyclic heteroaromatic - quinoline hybrids for the interaction with the DNA

In the last two decades, the most extensively studied ligands that bind to the DNA/RNA, were those containing an intercalator (molecule that can fit between base pairs of the DNA), a nucleobase, and a linker between them.1 Although polycyclic heteroaromatic derivatives have been recognized as good intercalators, potential carcinogenic and mutagenic properties as well as low water solubility hamper their wider application in bio-medically oriented studies. However, recent studies have shown that amino acid derivatives of these intercalators (for example, peptide-based phenanthridines) lower their toxicity, and increase solubility and DNA-binding affinity.2 As a part of our ongoing research, we prepared hybrid molecules containing three structural units: (a) an intercalator unit (phenanthridine and pyrene polycylic heteroaromates), (b) easily accessible and functionalizable quinoline core, and (c) an amino acid linker of suitable length and flexibility connecting the intercalator and the quinoline group. The design was governed towards molecules possessing groups with synergistic properties. Namely, the quinolone core can act as an intercalator by itself, while the nitrogen atom can form hydrogen bond with the DNA/RNA. The quinoline core also contains protonated amino-alifatic chain that improves solubility and acts as a carrier/recognition moiety for the DNA. Such structures may represent attractive building blocks to elaborate synthetic mimics of tertiary structural motifs of proteins.

Pyrene ; quinoline ; fluorescence ; DNA recognition ; excimer emission

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