Adenosine analogs bearing phosphate isosteres as human MDO1 ligands

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Zhang , Y , Jumppanen , A M , Maksimainen , M M , Auno , A S , Awol , Z , Ghemtio , L , Venkannagari , H , Lehtiö , L , Yli-Kauhaluoma , J , Xhaard , H & Boije af Gennäs , G 2018 , ' Adenosine analogs bearing phosphate isosteres as human MDO1 ligands ' , Bioorganic & Medicinal Chemistry , vol. 26 , no. 8 , pp. 1588-1597 . https://doi.org/10.1016/j.bmc.2018.02.006

Title: Adenosine analogs bearing phosphate isosteres as human MDO1 ligands
Author: Zhang, Yuezhou; Jumppanen, Antti Mikael; Maksimainen, Mirko M.; Auno, Atte Samuli; Awol, Zulfa; Ghemtio, Leo; Venkannagari, Harikanth; Lehtiö, Lari; Yli-Kauhaluoma, Jari; Xhaard, Henri; Boije af Gennäs, Gustav
Contributor: University of Helsinki, Faculty of Pharmacy
University of Helsinki, Faculty of Pharmacy
University of Helsinki, Faculty of Pharmacy
University of Helsinki, Faculty of Pharmacy
University of Helsinki, Faculty of Pharmacy
University of Helsinki, Faculty of Pharmacy
University of Helsinki, Faculty of Pharmacy
Date: 2018-05-01
Language: eng
Number of pages: 10
Belongs to series: Bioorganic & Medicinal Chemistry
ISSN: 0968-0896
URI: http://hdl.handle.net/10138/311575
Abstract: The human O-acetyl-ADP-ribose deacetylase MDO1 is a mono-ADP-ribosylhydrolase involved in the reversal of post-translational modifications. Until now MDO1 has been poorly characterized, partly since no ligand is known besides adenosine nucleotides. Here, we synthesized thirteen compounds retaining the adenosine moiety and bearing bioisosteric replacements of the phosphate at the ribose 50-oxygen. These compounds are composed of either a squaryldiamide or an amide group as the bioisosteric replacement and/or as a linker. To these groups a variety of substituents were attached such as phenyl, benzyl, pyridyl, carboxyl, hydroxy and tetrazolyl. Biochemical evaluation showed that two compounds, one from both series, inhibited ADP-ribosyl hydrolysis mediated by MDO1 in high concentrations. (C) 2018 Elsevier Ltd. All rights reserved.
Subject: 317 Pharmacy
Adenosine analogs
Adenosine diphosphate ribose
Mono-ADP-ribosylhydrolase
Human macrodomain-containing protein 1
MDO1
Macrodomain
Phosphate isosteres
MACRO DOMAIN
BINDING
LRP16
CARCINOMA
PROTEINS
RECEPTOR
FAMILY
CELLS
MODEL
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