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Literature summary for 2.3.1.286 extracted from

  • Di Fruscia, P.; Zacharioudakis, E.; Liu, C.; Moniot, S.; Laohasinnarong, S.; Khongkow, M.; Harrison, I.F.; Koltsida, K.; Reynolds, C.R.; Schmidtkunz, K.; Jung, M.; Chapman, K.L.; Steegborn, C.; Dexter, D.T.; Sternberg, M.J.; Lam, E.W.; Fuchter, M.J.
    The discovery of a highly selective 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one SIRT2 inhibitor that is neuroprotective in an in vitro Parkinson's disease model (2015), ChemMedChem, 10, 69-82.
    View publication on PubMed
Search for more literature for 2.3.1.286

Application

Application Comment Organism
medicine 3-((2-methoxynaphthalen-1-yl)methyl)-7-((pyridin-3-ylmethyl)amino)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one (ICL-SIRT078) has a significant neuroprotective effect in a lactacystin-induced model of Parkinsonian neuronal cell death in the N27 cell line and an optimised derivative thereof, is a candidate neuroprotective agent in in vivo models of Parkinson's disease Homo sapiens

Cloned(Commentary)

Cloned (Comment) Organism
recombinant human SIRT2 (43-356) is expressed as a His-Sumo fusion protein in Escherichia coli Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
3-((2-methoxynaphthalen-1-yl)methyl)-7-((2-methylbenzyl)amino)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
3-((2-methoxynaphthalen-1-yl)methyl)-7-((pyridin-3-ylmethyl)amino)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one i.e. ICL-SIRT078, a substrate-competitive SIRT2 inhibitor with more than 50fold selectivity against SIRT1, 3 and 5. Treatment of MCF-7 breast cancer cells with ICL-SIRT078 results in hyperacetylation of alpha-tubulin, an established SIRT2 biomarker, at doses comparable with the biochemical IC50 data, while suppressing MCF-7 proliferation at higher concentrations Homo sapiens
3-((2-methoxynaphthalen-1-yl)methyl)-7-((thiophen-2-ylmethyl)-amino)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
3-((2-methoxynaphthalen-1-yl)methyl)-7-(neopentylamino)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
7-((3-fluorobenzyl)amino)-3-((2-methoxynaphthalen-1-yl)methyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
7-((3-methoxybenzyl)amino)-3-((2-methoxynaphthalen-1-yl)-methyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
7-(benzylamino)-3-((2-methoxynaphthalen-1-yl)methyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens

Organism

Organism UniProt Comment Textmining
Homo sapiens Q8IXJ6
-
-

Purification (Commentary)

Purification (Comment) Organism
-
 Homo sapiens

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
NAD+ + [alpha-tubulin peptide]-N6-acetyl-L-lysine
-
 Homo sapiens nicotinamide + [alpha-tubulin peptide]-L-lysine + 2'-O-acetyl-ADP-ribose
-
 ?

Synonyms

Synonyms Comment Organism
SIRT2
-
 Homo sapiens

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
 assay at Homo sapiens

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.00062
-
 3-((2-methoxynaphthalen-1-yl)methyl)-7-((pyridin-3-ylmethyl)amino)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one pH 7.5, temperature not specified in the publication Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00145
-
 pH 7.5, temperature not specified in the publication Homo sapiens 3-((2-methoxynaphthalen-1-yl)methyl)-7-((pyridin-3-ylmethyl)amino)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one
0.0019
-
 pH 7.5, temperature not specified in the publication Homo sapiens 7-((3-methoxybenzyl)amino)-3-((2-methoxynaphthalen-1-yl)-methyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one
0.004
-
 pH 7.5, temperature not specified in the publication Homo sapiens 7-((3-fluorobenzyl)amino)-3-((2-methoxynaphthalen-1-yl)methyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one
0.006
-
 pH 7.5, temperature not specified in the publication Homo sapiens 3-((2-methoxynaphthalen-1-yl)methyl)-7-((thiophen-2-ylmethyl)-amino)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one
0.00652
-
 pH 7.5, temperature not specified in the publication Homo sapiens 3-((2-methoxynaphthalen-1-yl)methyl)-7-(neopentylamino)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one
0.0172
-
 pH 7.5, temperature not specified in the publication Homo sapiens 3-((2-methoxynaphthalen-1-yl)methyl)-7-((2-methylbenzyl)amino)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one
0.0211
-
 pH 7.5, temperature not specified in the publication Homo sapiens 7-(benzylamino)-3-((2-methoxynaphthalen-1-yl)methyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one