N-(3-(4-Hydroxyphenyl)-propenoyl)-amino acid tryptamides as SIRT2 inhibitors

Kiviranta, Päivi H.; Leppänen, Jukka; Rinne, Valtteri; Suuronen, Tiina; Kyrylenko, Olga; Kyrylenko, Sergiy; Kuusisto, Erkki; Tervo, Anu J.; Järvinen, Tomi; Salminen, Antero; Poso, Antti; Wallén, Erik A.A.

doi:10.1016/j.bmcl.2007.02.023

Cited by 46 publications

(36 citation statements)

References 25 publications

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“…Two of the eleven, CD03241 (52) and TRIPOS360702 (53) gave IC 50 values in the tens of micromolar range, while two others gave IC 50 values between 100 and 200 μM [55]. A later study showed that the activity of 53 was concentrated in a smaller pharmacophore, diamide 54 [56]. Another effort by the same group showed that 55, an analogue of 52, had improved activity over the screening hit while reducing the molecular weight [57].…”

Section: Sirtuin Inhibitorsmentioning

confidence: 93%

Sirtuin Modulators: Targets for Metabolic Diseases and Beyond

Bg¹,

Ng²

2008

CTMC

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Over the past ten years, sirtuins have emerged as an important class of drug targets. These enzymes play an important role in gene activation and silencing in all organisms from prokaryotes to humans. There is evidence that sirtuin modulation can be beneficial for a wide variety of diseases associated with aging. Among these conditions are diabetes, neurodegenerative diseases, and cancer. Agents that activate some sirtuins may be beneficial, while inhibitors of other sirtuins might represent treatment options. This review covers the chemical activators and inhibitors of the sirtuins that have appeared in the literature through the first half of 2008.

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Section: Sirtuin Inhibitorsmentioning

confidence: 93%

Sirtuin Modulators: Targets for Metabolic Diseases and Beyond

Bg¹,

Ng²

2008

CTMC

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“…GST-SIRT1 and GST-SIRT2 were produced as described previously [42,43]. His-SIRT3 (BML-SE270) was purchased from Enzo Life Sciences.…”

Section: Methodsmentioning

confidence: 99%

The Identification of a SIRT6 Activator from Brown Algae Fucus distichus

et al. 2017

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Brown seaweeds contain many bioactive compounds, including polyphenols, polysaccharides, fucosterol, and fucoxantin. These compounds have several biological activities, including anti-inflammatory, hepatoprotective, anti-tumor, anti-hypertensive, and anti-diabetic activity, although in most cases their mechanisms of action are not understood. In this study, extracts generated from five brown algae (Fucus dichitus, Fucus vesiculosus (Linnaeus), Cytoseira tamariscofolia, Cytoseira nodacaulis, Alaria esculenta) were tested for their ability to activate SIRT6 resulting in H3K9 deacetylation. Three of the five macroalgal extracts caused a significant increase of H3K9 deacetylation, and the effect was most pronounced for F. dichitus. The compound responsible for this in vitro activity was identified by mass spectrometry as fucoidan.

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“…As with all quaternary amino acids, it is well known that Aib reduces the conformational space of the peptide backbone and has a high preference to form peptides with α‐ or 3 10 ‐helical structures . As information of interest, it is known that Aib is contained in some peptide antibiotics of fungal origin and its presence in peptides is being continuously investigated to improve the treatment of some diseases . Furthermore, this molecule has been proven to exist in the errant solid bodies either within the solar system or outside of it.…”

Section: Introductionmentioning

confidence: 99%

The Shape of the Simplest Non‐proteinogenic Amino Acid α‐Aminoisobutyric Acid (Aib)

Alonso

Peña

López

et al. 2019

Chemistry A European J

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The simplest non‐proteinogenic amino acid α‐aminoisobutyric acid (Aib), an analogue of glycine and alanine, has been vaporized by laser ablation and probed by high‐resolution Fourier transform microwave spectroscopic techniques. Comparison of the experimental rotational and 14N nuclear quadrupole constants with that predicted ab initio has allowed the identification of three conformers of Aib exhibiting three types of hydrogen‐bond interactions I (NH⋅⋅⋅O=C, cis‐COOH), II (OH⋅⋅⋅N, trans‐COOH), and III (N−H⋅⋅⋅O−H, cis‐COOH) within the amino acid backbone. The observation of conformer III, not detected previously for related proteinogenic amino acids with a nonpolar side chain in a supersonic expansion, indicates that the presence of the methyl groups should restrict the conformational relaxation from conformer Aib‐III to Aib‐I. For conformer Aib‐II, the rotational spectra of the 13C isotopomers reveal a tunneling motion arising from the two equivalent methyl groups in the molecule. The observation of a single spectrum at the midpoint between those predicted for the two 13C of the methyl groups has been explained by considering a double‐minimum potential function with a low‐energy interconversion barrier for a large amplitude internal motion. This singular fact has been corroborated by the anomalous centrifugal distortion effects determined in conformer Aib‐II.

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N-(3-(4-Hydroxyphenyl)-propenoyl)-amino acid tryptamides as SIRT2 inhibitors

Cited by 46 publications

References 25 publications

Sirtuin Modulators: Targets for Metabolic Diseases and Beyond

Sirtuin Modulators: Targets for Metabolic Diseases and Beyond

The Identification of a SIRT6 Activator from Brown Algae Fucus distichus

The Shape of the Simplest Non‐proteinogenic Amino Acid α‐Aminoisobutyric Acid (Aib)

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