Enhanced activity or resistance of adenosine derivatives towards adenosine deaminase-catalyzed deamination

Influence of ribose modifications

Giulio Vistoli, Alessandro Pedretti, Laura Alessandrini, Silvana Casati, Pierangela Ciuffreda, Giuseppe Meroni, Enzo Santaniello

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The effect of the presence of the 1′-C-methyl group and 2′,3′-O-substitution in the adenosine structure on ADA activity has been investigated by modeling studies. Results show that the 2′- and 3′-O- substituents are harbored in a quite large cavity of intermediate polarity, whereas the 1′-C-substituent clashes against Ala180 distorting the architecture of the catalytic centre. Globally, the study emphasizes the ability of ADA to transform a large set of 2′,3′-O-substituted adenosine analogues as well as the opportunity to design 1′-C-substituted adenosine derivatives resistant to ADA-catalyzed deamination.

Original languageEnglish
Pages (from-to)2877-2879
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Volume19
Issue number10
DOIs
Publication statusPublished - May 15 2009

Fingerprint

Deamination
Adenosine Deaminase
Ribose
Adenosine
Derivatives
Substitution reactions

Keywords

  • Adenosine analogues
  • Adenosine deaminase
  • Adenosine derivatives
  • Molecular docking

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry

Cite this

Enhanced activity or resistance of adenosine derivatives towards adenosine deaminase-catalyzed deamination : Influence of ribose modifications. / Vistoli, Giulio; Pedretti, Alessandro; Alessandrini, Laura; Casati, Silvana; Ciuffreda, Pierangela; Meroni, Giuseppe; Santaniello, Enzo.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 19, No. 10, 15.05.2009, p. 2877-2879.

Research output: Contribution to journalArticle

Vistoli, Giulio ; Pedretti, Alessandro ; Alessandrini, Laura ; Casati, Silvana ; Ciuffreda, Pierangela ; Meroni, Giuseppe ; Santaniello, Enzo. / Enhanced activity or resistance of adenosine derivatives towards adenosine deaminase-catalyzed deamination : Influence of ribose modifications. In: Bioorganic and Medicinal Chemistry Letters. 2009 ; Vol. 19, No. 10. pp. 2877-2879.
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