Β-1,2,3-triazolyl-nucleosides as nicotinamide riboside mimics

E. J. Amigues; E. Armstrong; M. Dvorakova; M. E. Migaud; M. Huang

doi:10.1080/15257770902865415

Β-1,2,3-triazolyl-nucleosides as nicotinamide riboside mimics

E. J. Amigues
, E. Armstrong
, M. Dvorakova
, M. E. Migaud
, M. Huang

Queen's University Belfast

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

Abstract

The synthesis of a series of pyridine- and piperidine-substituted 1,2,3-triazolides linked to a riboside moiety is described. The presence of a triazolide substituent on the pyridine moiety permitted the facile reduction of the latter under mild hydrogenation conditions. These analogues were modelled as to define their similarity to nicotinamide riboside and quantify their ability to bind NAD-dependent protein deacetylases.

Original language	English
Pages (from-to)	238-259
Number of pages	22
Journal	Nucleosides, Nucleotides and Nucleic Acids
Volume	28
Issue number	3
DOIs	https://doi.org/10.1080/15257770902865415
Publication status	Published - Mar 2009
Externally published	Yes

Keywords

Inhibition
Nucleoside
Nucleotide
Sirtuin

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10.1080/15257770902865415

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title = "Β-1,2,3-triazolyl-nucleosides as nicotinamide riboside mimics",

abstract = "The synthesis of a series of pyridine- and piperidine-substituted 1,2,3-triazolides linked to a riboside moiety is described. The presence of a triazolide substituent on the pyridine moiety permitted the facile reduction of the latter under mild hydrogenation conditions. These analogues were modelled as to define their similarity to nicotinamide riboside and quantify their ability to bind NAD-dependent protein deacetylases.",

keywords = "Inhibition, Nucleoside, Nucleotide, Sirtuin",

author = "Amigues, \{E. J.\} and E. Armstrong and M. Dvorakova and Migaud, \{M. E.\} and M. Huang",

note = "Funding Information: Received 3 February 2009; accepted 4 March 2009. M. E. Migaud and M. Huang share joint authorship this article. The authors thank Professor R. Marmorstein and Ms. B. Sanders (from the Wistar Institute, Philadelphia, USA) for carrying out the preliminary inhibition studies and extensive discussions, and the EPSRC/MRC GR0100461 and the EC-FP6-EST program, which financially supported this work. Address correspondence to M. E. Migaud and M. Huang, School of Chemistry and Chemical Engineering, David Keir Building, Queen{\textquoteright}s University Belfast, Stranmillis Road, Belfast, BT9 5AG, Northern Ireland. E-mail: m.migaud@qub.ac.uk and m.huang@qub.ac.uk",

year = "2009",

month = mar,

doi = "10.1080/15257770902865415",

language = "English",

volume = "28",

pages = "238--259",

journal = "Nucleosides, Nucleotides and Nucleic Acids",

issn = "1525-7770",

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}

TY - JOUR

T1 - Β-1,2,3-triazolyl-nucleosides as nicotinamide riboside mimics

AU - Amigues, E. J.

AU - Armstrong, E.

AU - Dvorakova, M.

AU - Migaud, M. E.

AU - Huang, M.

N1 - Funding Information: Received 3 February 2009; accepted 4 March 2009. M. E. Migaud and M. Huang share joint authorship this article. The authors thank Professor R. Marmorstein and Ms. B. Sanders (from the Wistar Institute, Philadelphia, USA) for carrying out the preliminary inhibition studies and extensive discussions, and the EPSRC/MRC GR0100461 and the EC-FP6-EST program, which financially supported this work. Address correspondence to M. E. Migaud and M. Huang, School of Chemistry and Chemical Engineering, David Keir Building, Queen’s University Belfast, Stranmillis Road, Belfast, BT9 5AG, Northern Ireland. E-mail: m.migaud@qub.ac.uk and m.huang@qub.ac.uk

PY - 2009/3

Y1 - 2009/3

N2 - The synthesis of a series of pyridine- and piperidine-substituted 1,2,3-triazolides linked to a riboside moiety is described. The presence of a triazolide substituent on the pyridine moiety permitted the facile reduction of the latter under mild hydrogenation conditions. These analogues were modelled as to define their similarity to nicotinamide riboside and quantify their ability to bind NAD-dependent protein deacetylases.

AB - The synthesis of a series of pyridine- and piperidine-substituted 1,2,3-triazolides linked to a riboside moiety is described. The presence of a triazolide substituent on the pyridine moiety permitted the facile reduction of the latter under mild hydrogenation conditions. These analogues were modelled as to define their similarity to nicotinamide riboside and quantify their ability to bind NAD-dependent protein deacetylases.

KW - Inhibition

KW - Nucleoside

KW - Nucleotide

KW - Sirtuin

UR - https://www.scopus.com/pages/publications/67651213428

U2 - 10.1080/15257770902865415

DO - 10.1080/15257770902865415

M3 - Article

C2 - 19333861

AN - SCOPUS:67651213428

SN - 1525-7770

VL - 28

SP - 238

EP - 259

JO - Nucleosides, Nucleotides and Nucleic Acids

JF - Nucleosides, Nucleotides and Nucleic Acids

IS - 3

ER -

Β-1,2,3-triazolyl-nucleosides as nicotinamide riboside mimics

Abstract

Keywords

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