Peptide nucleic acids (PNA) are a class of non-ionic DNA mimics, in which the sugar-phosphate backbone is replaced by ethylenediamine-glycine backbone. They bind complementary DNA or RNA with high affinity and selectivity. Hence they promised to be potential therapeutic agents. However they have serious drawbacks in terms of their aqueous solubility and cell penetration ability. Further their equal affinity for iso-sequential DNA / RNA decreases their target specificity by half. In order to overcome these drawbacks, we have designed, synthesized and evaluated several PNA analogues, which are conformationally constrained, in backbone. These include pyrrolidine, cyclopentyl and cyclohexyl moieties that are chiral and recently acyclic PNA analogues that possess cationic (amino and guanidine) groups to make them more soluble in water. These have been labeled with fluorescence groups to examine their cell membrane permeability properties. This lecture presents a comparison of the biophysical properties such as their differential complementation with iso-sequential DNA / RNA, selectivity in binding parallel and antiparrallel sequences and their cell permeation abilities.

Peptide nucleic acid analogs: Designs for selective binding with DNA/RNA and cell permeation

248th National Meeting (2014)

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