The present work deals with the synthesis and characterization of a novel nucleoamino acid derivative based on a L-tyrosine moiety to which a thymine nucleobase was anchored by means of an amide bond to the N-alpha group. This derivative, denominated by us TyrT, belongs to the family of the nucleobase-amino acid conjugates that show a wide range of biological activities, frequently associated with their ability to interact with nucleic acids. In this respect, the interaction of TyrT with poly(A), a proposed RNA target for anticancer strategies, was studied by circular dichroism (CD) which suggested its ability to bind this RNA. Moreover, the modification of the morphology of a sample of TyrT in the presence of poly(A) was visualised by scanning electron microscopy (SEM) which was in agreement with the evidence that the thyminyl L-tyrosine interacts with poly(A). Finally, computational analyses have been performed to hypothesize the binding mode from a structural point of view, suggesting that the binding is mainly kept via hydrophobic contacts, reproducing a stacking-like interaction between the thymine ring of TyrT and the two successive adenine rings of a poly(A) model.

Solid phase synthesis of TyrT, a thymine-tyrosine conjugate with poly(A) RNA-binding ability / Roviello, Gn; Roviello, V; Autiero, I; Saviano, M. - In: RSC ADVANCES. - ISSN 2046-2069. - 6:33(2016), pp. 27607-27613. [10.1039/c6ra00294c]

Solid phase synthesis of TyrT, a thymine-tyrosine conjugate with poly(A) RNA-binding ability

Roviello V;Saviano M
2016

Abstract

The present work deals with the synthesis and characterization of a novel nucleoamino acid derivative based on a L-tyrosine moiety to which a thymine nucleobase was anchored by means of an amide bond to the N-alpha group. This derivative, denominated by us TyrT, belongs to the family of the nucleobase-amino acid conjugates that show a wide range of biological activities, frequently associated with their ability to interact with nucleic acids. In this respect, the interaction of TyrT with poly(A), a proposed RNA target for anticancer strategies, was studied by circular dichroism (CD) which suggested its ability to bind this RNA. Moreover, the modification of the morphology of a sample of TyrT in the presence of poly(A) was visualised by scanning electron microscopy (SEM) which was in agreement with the evidence that the thyminyl L-tyrosine interacts with poly(A). Finally, computational analyses have been performed to hypothesize the binding mode from a structural point of view, suggesting that the binding is mainly kept via hydrophobic contacts, reproducing a stacking-like interaction between the thymine ring of TyrT and the two successive adenine rings of a poly(A) model.
2016
Solid phase synthesis of TyrT, a thymine-tyrosine conjugate with poly(A) RNA-binding ability / Roviello, Gn; Roviello, V; Autiero, I; Saviano, M. - In: RSC ADVANCES. - ISSN 2046-2069. - 6:33(2016), pp. 27607-27613. [10.1039/c6ra00294c]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/819122
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