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 language | English |
|---|---|
| Pages (from-to) | 2877-2879 |
| Number of pages | 3 |
| Journal | Bioorganic and Medicinal Chemistry Letters |
| Volume | 19 |
| Issue number | 10 |
| DOIs | |
| Publication status | Published - May 15 2009 |
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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 journal › Article
}
TY - JOUR
T1 - Enhanced activity or resistance of adenosine derivatives towards adenosine deaminase-catalyzed deamination
T2 - Influence of ribose modifications
AU - Vistoli, Giulio
AU - Pedretti, Alessandro
AU - Alessandrini, Laura
AU - Casati, Silvana
AU - Ciuffreda, Pierangela
AU - Meroni, Giuseppe
AU - Santaniello, Enzo
PY - 2009/5/15
Y1 - 2009/5/15
N2 - 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.
AB - 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.
KW - Adenosine analogues
KW - Adenosine deaminase
KW - Adenosine derivatives
KW - Molecular docking
UR - http://www.scopus.com/inward/record.url?scp=65349150113&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=65349150113&partnerID=8YFLogxK
U2 - 10.1016/j.bmcl.2009.03.084
DO - 10.1016/j.bmcl.2009.03.084
M3 - Article
VL - 19
SP - 2877
EP - 2879
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
SN - 0960-894X
IS - 10
ER -