In thepresentwork,we report thesynthesis andthe characterizationofdabPNAhexamerswithdiaminobutyricacidbackboneof D-or/andL-configuration. In particular, thefournucleo-amino acidswe synthesized,D-andL-diaminobutyryl adenines andD-and L-diaminobutyryl thymines, were used in various combinations to assemble the following oligomers: H-G-(tL-dab)6-K-NH2, HG-( tD-dab)6-K-NH2, H-G-(aL-dab)6-K-NH2, H-G-(tL-dab-tD-dab)3-K-NH2, H-G-(aL-dab-aD-dab)3-K-NH2, H-G-(aL-dab-tD-dab)3-K-NH2. By using CD and UV spectroscopies, we investigated the ability of complementary dab PNA strands to bind to each other. We found that binding occurs only between oligomers with backbone of alternate configuration [(tL-dab-tD-dab)3/(aL-dabaD- dab)3 and (aL-dab-tD-dab)3/(aL-dab-tD-dab)3] and implies cooperative hydrogen bonds and base stacking. Furthermore, interesting properties relative to the self-complementary oligomer (aL-dab-tD-dab)3 forming palindromic complexes emerged from preliminary dynamic light-scattering experiments that suggested the formation of multimeric aggregates. These results, together with the high serum stability of the DABA-based oligomers, as shown by HPLC analysis, encourage us to further study dab PNAs as new self-recognizing bio-inspired polymers, to develop new nanomaterials in biotechnological and biomedical applications.

Evidences of complex formation between DABA-based nucleo-gamma-peptides with alternate configuration backbone

Moccia M;Saviano M;Pedone C;
2009

Abstract

In thepresentwork,we report thesynthesis andthe characterizationofdabPNAhexamerswithdiaminobutyricacidbackboneof D-or/andL-configuration. In particular, thefournucleo-amino acidswe synthesized,D-andL-diaminobutyryl adenines andD-and L-diaminobutyryl thymines, were used in various combinations to assemble the following oligomers: H-G-(tL-dab)6-K-NH2, HG-( tD-dab)6-K-NH2, H-G-(aL-dab)6-K-NH2, H-G-(tL-dab-tD-dab)3-K-NH2, H-G-(aL-dab-aD-dab)3-K-NH2, H-G-(aL-dab-tD-dab)3-K-NH2. By using CD and UV spectroscopies, we investigated the ability of complementary dab PNA strands to bind to each other. We found that binding occurs only between oligomers with backbone of alternate configuration [(tL-dab-tD-dab)3/(aL-dabaD- dab)3 and (aL-dab-tD-dab)3/(aL-dab-tD-dab)3] and implies cooperative hydrogen bonds and base stacking. Furthermore, interesting properties relative to the self-complementary oligomer (aL-dab-tD-dab)3 forming palindromic complexes emerged from preliminary dynamic light-scattering experiments that suggested the formation of multimeric aggregates. These results, together with the high serum stability of the DABA-based oligomers, as shown by HPLC analysis, encourage us to further study dab PNAs as new self-recognizing bio-inspired polymers, to develop new nanomaterials in biotechnological and biomedical applications.
2009
Istituto di Biostrutture e Bioimmagini - IBB - Sede Napoli
nucleo-? -peptides; dabPNA; alternate-configuration backbone; multimeric aggregates
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.14243/123160
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 4
  • ???jsp.display-item.citation.isi??? ND
social impact