Supramolecular architectures involving DNA bases can have a strong impact in several fields such as nanomedicine and nanodevice manufacturing. To date, in addition to the four canonical nucleobases (adenine, thymine, guanine and cytosine), four other forms of cytosine modified at the 5 position have been identified in DNA. Among these four new cytosine derivatives, 5-carboxylcytosine has been recently discovered in mammalian stem cell DNA, and proposed as the final product of the oxidative epigenetic demethylation pathway on the 5 position of cytosine. In this work, a calcium salt of 5-carboxylcytosine has been synthesized and deposited on graphite surface, where it forms self-assembled features as long range monolayers and up to one micron long filaments. These structures have been analyzed in details combining different theoretical and experimental approaches: X-ray single-crystal diffraction data were used to simulate the molecule-graphite interaction, first using molecular dynamics and then refining the results using density functional theory (DFT); finally, data obtained with DFT were used to rationalize atomic force microscopy (AFM) results.

Self-assembling of calcium salt of the new DNA base 5-carboxylcytosine / Irrera, Simona; Ruiz Hernandez, Sergio E.; Reggente, Melania; Passeri, Daniele; Natali, Marco; Gala, Fabrizio; Zollo, Giuseppe; Rossi, Marco; Portalone, Gustavo. - In: APPLIED SURFACE SCIENCE. - ISSN 0169-4332. - STAMPA. - 407:(2017), pp. 297-306. [10.1016/j.apsusc.2017.02.171]

Self-assembling of calcium salt of the new DNA base 5-carboxylcytosine

IRRERA, SIMONA;REGGENTE, MELANIA;PASSERI, Daniele;NATALI, MARCO;GALA, FABRIZIO;ZOLLO, Giuseppe;ROSSI, Marco;PORTALONE, Gustavo
2017

Abstract

Supramolecular architectures involving DNA bases can have a strong impact in several fields such as nanomedicine and nanodevice manufacturing. To date, in addition to the four canonical nucleobases (adenine, thymine, guanine and cytosine), four other forms of cytosine modified at the 5 position have been identified in DNA. Among these four new cytosine derivatives, 5-carboxylcytosine has been recently discovered in mammalian stem cell DNA, and proposed as the final product of the oxidative epigenetic demethylation pathway on the 5 position of cytosine. In this work, a calcium salt of 5-carboxylcytosine has been synthesized and deposited on graphite surface, where it forms self-assembled features as long range monolayers and up to one micron long filaments. These structures have been analyzed in details combining different theoretical and experimental approaches: X-ray single-crystal diffraction data were used to simulate the molecule-graphite interaction, first using molecular dynamics and then refining the results using density functional theory (DFT); finally, data obtained with DFT were used to rationalize atomic force microscopy (AFM) results.
5-carboxylcytosine; ab initio calculation; atomic force microscopy (AFM); molecular dynamics; nanomedicine; X-ray diffraction (XRD)
01 Pubblicazione su rivista::01a Articolo in rivista
Self-assembling of calcium salt of the new DNA base 5-carboxylcytosine / Irrera, Simona; Ruiz Hernandez, Sergio E.; Reggente, Melania; Passeri, Daniele; Natali, Marco; Gala, Fabrizio; Zollo, Giuseppe; Rossi, Marco; Portalone, Gustavo. - In: APPLIED SURFACE SCIENCE. - ISSN 0169-4332. - STAMPA. - 407:(2017), pp. 297-306. [10.1016/j.apsusc.2017.02.171]
File allegati a questo prodotto
File Dimensione Formato  
Irrera_Self-assembling_2017.pdf

solo gestori archivio

Note: full text - editor PDF
Tipologia: Versione editoriale (versione pubblicata con il layout dell'editore)
Licenza: Tutti i diritti riservati (All rights reserved)
Dimensione 2.76 MB
Formato Adobe PDF
2.76 MB Adobe PDF   Visualizza/Apri   Richiedi una copia
Irrera_preprint_selfassembling_2017.pdf

solo gestori archivio

Tipologia: Documento in Pre-print (manoscritto inviato all'editore, precedente alla peer review)
Licenza: Tutti i diritti riservati (All rights reserved)
Dimensione 685.06 kB
Formato Adobe PDF
685.06 kB Adobe PDF   Visualizza/Apri   Richiedi una copia

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/11573/939775
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 3
  • ???jsp.display-item.citation.isi??? 3
social impact