Month: January 2023

Piceatannol antagonizes lipolysis by promoting autophagy-lysosome-dependent degradation of lipolytic protein clusters in adipocytes was written by Kwon, Jung Yeon;Kershaw, Jonathan;Chen, Chih-Yu;Komanetsky, Susan M.;Zhu, Yuyan;Guo, Xiaoxuan;Myer, Phillip R.;Applegate, Bruce;Kim, Kee-Hong. And the article was included in Journal of Nutritional Biochemistry in 2022.HPLC of Formula: 10083-24-6 This article mentions the following:

Overly elevated circulating non-esterified fatty acids (NEFAs) is an emerging health concern of obesity-associated energy disorders. However, methods to reduce circulating NEFAs remain elusive. The present study determined the effect of piceatannol, a naturally occurring stilbene, on adipocyte lipolysis and its underlying mechanism. Differentiated 3T3-L1 adipocytes, brown adipocytes and isolated white adipose tissue were treated with various concentrations of piceatannol for 1.5-h both in the basal and stimulated lipolysis conditions. Piceatannol significantly inhibited NEFAs and glycerol release with a concomitant reduction of ATGL, CGI-58 and PLIN1 expression in adipocytes. Using a series of inhibitor assays, piceatannol-induced degradation of these proteins was found to be mediated by upregulation of the autophagy-lysosome pathway. Moreover, we demonstrated that piceatannol is capable of stimulating autophagy in vitro. Importantly, piceatannol administration tended to lower fasting-induced serum glycerol levels in healthy mice. Furthermore, piceatannol administration lowered lipolysis, central adiposity and hyperinsulinemia in diet-induced obese mice. Our study provides profound evidence of a novel inhibitory role of piceatannol in lipolysis through autophagy-lysosome-dependent degradation of the key lipolytic proteins in adipocytes. This study offers a mechanistic foundation for investigating the potential of piceatannol-containing foods in reducing lipolysis and its associated metabolic disorders. In the experiment, the researchers used many compounds, for example, (E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol (cas: 10083-24-6HPLC of Formula: 10083-24-6).

(E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol (cas: 10083-24-6) belongs to alcohols. Alcohols are weak acids. The most acidic simple alcohols (methanol and ethanol) are about as acidic as water, and most other alcohols are somewhat less acidic. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.HPLC of Formula: 10083-24-6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthesis of cinnamic acid ester derivatives with antiproliferative and antimetastatic activities on murine melanoma cells was written by Vale, Juliana Alves do;Rodrigues, Michelle Peixoto;Lima, Angela Maria Almeida;Santiago, Samira Soares;Lima, Graziela Domingues de Almeida;Almeida, Alisson Andrade;Oliveira, Leandro Licursi de;Bressan, Gustavo Costa;Teixeira, Robson Ricardo;Machado-Neves, Mariana. And the article was included in Biomedicine & Pharmacotherapy in 2022.Application of 873-76-7 This article mentions the following:

The synthesis of seventeen compounds I [R = Bn, Ph, 4-ClC₆H₄CH₂, etc.] was derived from cinnamic acid and their bioactivity evaluation against melanoma cells. The compound Ph 2,3-dibromo-3-phenylpropanoate II was the most effective against murine B16-F10 cells, as observed in cytotoxicity and cell migration assays. Simultaneously, this compound showed low cytotoxic activity on non-tumor cells. At the highest concentration, the compound II was able to trigger apoptosis, whereas at lower concentrations, it affected the cell cycle and melanoma cell proliferation. Furthermore, cinnamate II impaired cell invasion, adhesion, colonization, and actin polymerization In conclusion, these results highlight the antiproliferative and antimetastatic potential of cinnamic acid derivatives on melanoma. In the experiment, the researchers used many compounds, for example, (4-Chlorophenyl)methanol (cas: 873-76-7Application of 873-76-7).

(4-Chlorophenyl)methanol (cas: 873-76-7) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Application of 873-76-7

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Chocolates with Brazilian cocoa: Tracking volatile compounds according to consumers’ preference was written by Cemin, Paloma;Reis Ribeiro, Stephanie;de Candido de Oliveira, Fernanda;Leal Leaes, Fernanda;Regina dos Santos Nunes, Marta;Wagner, Roger;Sant’Anna, Voltaire. And the article was included in Food Research International in 2022.Related Products of 3391-86-4 This article mentions the following:

This study aimed to evaluate the volatile compounds of chocolates made of Brazilian cocoas and statistically track them according to the products sensorial profile in order to relate them to consumers’ acceptance by preference map methodol. The intensity of the chocolate, acidity, woody, smoked, green, floral, burned, musty, and cocoa notes from chocolates produced with cocoa from different Brazilian states were analyzed by a trained panel and by 128 consumers. Samples from Cote dIvoire, which is known for its high-quality chocolate, were evaluated for comparison. Solid-phase microextraction headspace sampling/gas chromatog.-mass spectrometry was employed to evaluate the samples volatile compounds One hundred volatile compounds were identified within the samples. The results from the preference maps showed that the maximum preference was found for chocolate made of cocoa from Rondonia, Bahia, and Espirito Santo and Cote dIvoire and organic samples from Para. The ideal sample point was characterized by intense chocolate, floral, and woody notes and mild green and burned notes. The presence of furfural, 3-Me butanal, phenethyl acetate, 2-phenyl-5-methyl-2-hexenal, Me pyrazine, phenethyl acetate, 2-phenyl-5-methyl-2-hexenal, and tetra-Me pyrazine were shown to be important for consumer acceptance in the ideal product, whereas the presence of (Z)-2-heptenal and 2-pentyl furan may increase consumer rejection. 2,3-Me pyrazine, Me pyrazine, and 2,3-butanediol, which are important volatile compounds previously reported in the literature, were statistically tracked to both pos. and neg. sample attributes and must be better explored concerning consumers acceptance of chocolates. In the experiment, the researchers used many compounds, for example, Oct-1-en-3-ol (cas: 3391-86-4Related Products of 3391-86-4).

Oct-1-en-3-ol (cas: 3391-86-4) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Related Products of 3391-86-4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Benzosultam Synthesis by Gold(I)-Catalyzed Ammonium Formation/Nucleophilic Substitution was written by Pertschi, Romain;Weibel, Jean-Marc;Pale, Patrick;Blanc, Aurelien. And the article was included in Organic Letters in 2019.Application of 142253-56-3 This article mentions the following:

The synthesis of benzosultams was achieved through a gold(I)-catalyzed ammonium formation strategy. Starting from easily available N-(2-alkynyl)phenylsulfonyl azetidine derivatives, a cyclization reaction generated a spiroammonium gold intermediate that was ring-opened by nucleophilic alc. or indole. This new methodol. is compatible with the large variation in the substrates and nucleophiles and gave benzosultams in high yield (18-98%, 20 examples). This strategy also gave benzosultam analogs via iododeauration and subsequent cross-coupling reactions. In the experiment, the researchers used many compounds, for example, 1-Boc-Azetidine-3-yl-methanol (cas: 142253-56-3Application of 142253-56-3).

1-Boc-Azetidine-3-yl-methanol (cas: 142253-56-3) belongs to alcohols. Under appropriate conditions, inorganic acids also react with alcohols to form esters. To form these esters, a wide variety of specialized reagents and conditions can be used. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Application of 142253-56-3

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Thieno[3,2-b]pyrrole-5-carboxamides as New Reversible Inhibitors of Histone Lysine Demethylase KDM1A/LSD1. Part 2: Structure-Based Drug Design and Structure-Activity Relationship was written by Vianello, Paola;Sartori, Luca;Amigoni, Federica;Cappa, Anna;Faga, Giovanni;Fattori, Raimondo;Legnaghi, Elena;Ciossani, Giuseppe;Mattevi, Andrea;Meroni, Giuseppe;Moretti, Loris;Cecatiello, Valentina;Pasqualato, Sebastiano;Romussi, Alessia;Thaler, Florian;Trifiro, Paolo;Villa, Manuela;Botrugno, Oronza A.;Dessanti, Paola;Minucci, Saverio;Vultaggio, Stefania;Zagarri, Elisa;Varasi, Mario;Mercurio, Ciro. And the article was included in Journal of Medicinal Chemistry in 2017.SDS of cas: 224309-64-2 This article mentions the following:

The balance of methylation levels at histone H3 lysine 4 (H3K4) is regulated by KDM1A (LSD1). KDM1A is overexpressed in several tumor types, thus representing an emerging target for the development of novel cancer therapeutics. The authors have previously described the identification of thieno[3,2-b]pyrrole-5-carboxamides, as novel reversible inhibitors of KDM1A, whose preliminary exploration resulted in compound (I) with biochem. IC₅₀ = 160 nM. The authors now report the structure-guided optimization of this chem. series, based on multiple ligand/KDM1A-CoRest co-crystal structures, which led to several extremely potent inhibitors. In particular, compounds N-[3-(methoxymethyl)-2-[[4-[[(3R)-pyrrolidin-3-yl]- methoxy]phenoxy]methyl]phenyl]-4-methyl-thieno[3,2-b]-pyrrole-5-carboxamide hydrochloride (46), 4-ethyl-N-[3-(methoxymethyl)-2-[[4-[[(3R)-pyrrolidin-3-yl]-methoxy]phenoxy]methyl]phenyl]thieno[3,2-b]pyrrole-5-carboxamide (49) and N-[3-(ethoxymethyl)-2-[[4-[[(3R)-pyrrolidin-3-yl]methoxy]-phenoxy]methyl]phenyl]-4-methyl-thieno[3,2-b]pyrrole-5-carboxamide hydrochloride (50) showed single digit nanomolar IC₅₀ values for in vitro inhibition of KDM1A, with high selectivity in secondary assays. In THP-1 cells these compounds transcriptionally affected the expression of genes regulated by KDM1A, such as CD14, CD11b, and CD86. Moreover, 49 and 50 showed a remarkable anti-clonogenic cell growth effect on MLL-AF9 human leukemia cells. In the experiment, the researchers used many compounds, for example, tert-Butyl (4-hydroxycyclohexyl)carbamate (cas: 224309-64-2SDS of cas: 224309-64-2).

tert-Butyl (4-hydroxycyclohexyl)carbamate (cas: 224309-64-2) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.SDS of cas: 224309-64-2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Interactions of dietary eicosapentaenoic acid and vitamin C on growth performance, anti-oxidation and muscle quality of abalone Haliotis discus hannai Ino was written by Rao, Wanxiu;Chen, Peng;Liu, Chang;Cui, Zhengyi;Lei, Keke;Luo, Kai;Zhang, Wenbing;Mai, Kangsen. And the article was included in Aquaculture in 2022.Category: alcohols-buliding-blocks This article mentions the following:

A 93-day feeding trial was conducted to investigate the effects of dietary eicosapentaenoic acid (EPA) and vitamin C (VC) on the growth performance, anti-oxidation and muscle quality of abalone Haliotis discus hannai (initial body weight: 26.89 ± 0.26 g; initial shell length: 60.36 ± 0.25 mm). Six exptl. diets in a 3 x 2 two-factor design were formulated with graded levels of dietary EPA (0.25%, 0.75% and 1.25%) and dietary VC (0 and 1260 mg/kg). Results showed that the weight gain rate (WGR) of abalone was significantly increased with the increasing dietary EPA levels (P < 0.05), but there was no significant effect of dietary VC on the WGR. The significant highest superoxide dismutase (SOD) activity was observed in the group with 1.25% of dietary EPA and 1260 mg/kg of dietary VC, and there was a significant interaction between dietary EPA and VC (P < 0.05). Dietary EPA supplementation significantly improved muscle hardness and the content of ∑n-3 polyunsaturated fatty acids, volatile compounds, adenosine-5-monophosphate (AMP) and inosine-5-monophosphate (IMP) in muscle. Dietary VC supplementation significantly improved the muscle hardness, springiness, chewiness, and the contents of volatile compounds, hydroxyproline and IMP in muscle (P < 0.05). Significant interactions between dietary EPA and VC were observed on volatile compounds, AMP and IMP (P < 0.05). In conclusion, dietary EPA and VC interactively influence the anti-oxidative capability and muscle quality of abalone. In the experiment, the researchers used many compounds, for example, Calcium (R)-3-(2,4-dihydroxy-3,3-dimethylbutanamido)propanoate (cas: 137-08-6Category: alcohols-buliding-blocks).

Calcium (R)-3-(2,4-dihydroxy-3,3-dimethylbutanamido)propanoate (cas: 137-08-6) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Alcohols may be oxidized to give ketones, aldehydes, and carboxylic acids. These functional groups are useful for further reactions. Oxidation of organic compounds generally increases the number of bonds from carbon to oxygen (or another electronegative element, such as a halogen), and it may decrease the number of bonds to hydrogen.Category: alcohols-buliding-blocks

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Off-critical wetting layer divergence at the liquid/vapor interface of binary liquid mixtures was written by Williamson, J. Charles;Weatherford, Emily E.;DenBeste, Makayla M.;Riley, K. Caroline;Yee, Estella F.;Rogers, Sawyer T.;Tibbetts, Clara A.. And the article was included in Journal of Chemical Physics in 2022.Application In Synthesis of 1,2-Propanediol This article mentions the following:

Surface wetting phenomena impact chem., physics, biol., and engineering. The wetting behaviors of partially miscible binary liquid systems are especially complex. Here, we report evidence of universal behavior in the divergence of wetting layer growth at liquid-vapor interfaces of the cyclohexane + aniline, hexane + o-toluidine, and methanol + carbon disulfide systems. Layer growth on the micron scale was followed using visible light scattering from stirred samples. The layer thicknesses were found to diverge with decreasing temperature when coexistence was approached from the one-phase region, but only for solutions richer in the higher d./higher surface tension component. The onset of divergence was <1 K above the bulk coexistence temperature; nearer the critical composition, the onset temperature was the critical temperature itself. All three systems showed identical divergent wetting properties after variable normalization. In contrast, no divergent wetting layer formation was seen in the benzene + 1,2-propanediol or water + phenol systems. The math. sign of the Hamaker constant correlates with the contrasting behaviors. Collectively, these results have implications for theor. descriptions of adsorption layer growth and crossover behavior, for measurements of complete wetting temperatures, and for practical applications. (c) 2022 American Institute of Physics. In the experiment, the researchers used many compounds, for example, 1,2-Propanediol (cas: 57-55-6Application In Synthesis of 1,2-Propanediol).

1,2-Propanediol (cas: 57-55-6) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. Tertiary alcohols cannot be oxidized at all without breaking carbon-carbon bonds, whereas primary alcohols can be oxidized to aldehydes or further oxidized to carboxylic acids.Application In Synthesis of 1,2-Propanediol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthesis and evaluation of arylalkoxy- and biarylalkoxy-phenylamide and phenylimidazoles as potent and selective sphingosine-1-phosphate receptor subtype-1 agonists was written by Evindar, Ghotas;Satz, Alexander L.;Bernier, Sylvie G.;Kavarana, Malcolm J.;Doyle, Elisabeth;Lorusso, Jeanine;Taghizadeh, Nazbeh;Halley, Keith;Hutchings, Amy;Kelley, Michael S.;Wright, Albion D.;Saha, Ashis K.;Hannig, Gerhard;Morgan, Barry A.;Westlin, William F.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2009.Electric Literature of C9H9F3O This article mentions the following:

In a search for potent and selective sphingosine-1-phosphate receptor agonists, the previously reported phenylamide and phenylimidazole scaffolds were utilized to explore extensive side-chain modifications to generate new mol. entities. A number of designed mols. demonstrated good selectivity and excellent in vitro and in vivo potency in both mouse and rat models. Oral administration of the lead mol. I (PPI-4667) demonstrated potent and dose-responsive lymphopenia. In the experiment, the researchers used many compounds, for example, 2-(4-(Trifluoromethyl)phenyl)ethanol (cas: 2968-93-6Electric Literature of C9H9F3O).

2-(4-(Trifluoromethyl)phenyl)ethanol (cas: 2968-93-6) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Converting an alcohol to an alkene requires removal of the hydroxyl group and a hydrogen atom on the neighbouring carbon atom. Dehydrations are most commonly carried out by warming the alcohol in the presence of a strong dehydrating acid, such as concentrated sulfuric acid.Electric Literature of C9H9F3O

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Photocleavable Supramolecular Polysaccharide Nanoparticles for Targeted Drug Release in Cancer Cells was written by Liu, Jiang-Hua;Wu, Xianjing;Zhang, Ying-Ming;Liu, Yu. And the article was included in Asian Journal of Organic Chemistry in 2018.COA of Formula: C7H7NO4 This article mentions the following:

Photocontrolled, targeted and biocompatible supramol. nanoparticles were constructed through the host-guest interactions of 2-nitrobenzyl ester-linked β-cyclodextrin and adamantane-grafted hyaluronic acid (HA). In this system, we used HA and 2-nitrobenzyl ester as targeting and photoresponsive groups, resp. Moreover, the introduction of β-cyclodextrin further enhanced the biocompatibility of the supramol. nanoparticles. Benefiting from the light-responsive capability of a 2-nitrobenzyl ester moiety, the hydrophobic anticancer drug camptothecin was loaded in the internal hydrophobic microenvironment of the supramol. nanoparticle and could be specifically released in the cancer cells. These results demonstrated that supramol. polysaccharide drug nanocarriers with targeting ability and intelligent light-stimulus responsiveness may have excellent potential in the clin. cancer treatments. In the experiment, the researchers used many compounds, for example, 3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9COA of Formula: C7H7NO4).

3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.COA of Formula: C7H7NO4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

How Does the Quality of Phospholipidosis Data Influence the Predictivity of Structural Alerts? was written by Przybylak, Katarzyna R.;Alzahrani, Abdullah Rzgallah;Cronin, Mark T. D.. And the article was included in Journal of Chemical Information and Modeling in 2014.COA of Formula: C10H22O3 This article mentions the following:

The ability of drugs to induce phospholipidosis (PLD) is linked directly to their mol. substructures: hydrophobic, cyclic moieties with hydrophilic, peripheral amine groups. These structural properties can be captured and coded into SMILES arbitrary target specification (SMARTS) patterns. Such structural alerts, which are capable of identifying potential PLD inducers, should ideally be developed on a relatively large but reliable data set. We had previously developed a model based on SMARTS patterns consisting of 32 structural fragments using information from 450 chems. In the present study, addnl. PLD structural alerts have been developed based on a newer and larger data set combining two data sets published recently by the United States Food and Drug Administration (US FDA). To assess the predictive performance of the updated SMARTS model, two publicly available data sets were considered. These data sets were constructed using different criteria and hence represent different standards for overall quality. In the first data set high quality was assured as all neg. chems. were confirmed by the gold standard method for the detection of PLD-transmission electron microscopy (EM). The second data set was constructed from seven previously published data sets and then curated by removing compounds where conflicting results were found for PLD activity. Evaluation of the updated SMARTS model showed a strong, pos. correlation between predictive performance of the alerts and the quality of the data set used for the assessment. The results of this study confirm the importance of using high quality data for modeling and evaluation, especially in the case of PLD, where species, tissue, and dose dependence of results are addnl. confounding factors. In the experiment, the researchers used many compounds, for example, rel-(1s,4s)-4-(2-Hydroxypropan-2-yl)-1-methylcyclohexanol hydrate (cas: 2451-01-6COA of Formula: C10H22O3).

rel-(1s,4s)-4-(2-Hydroxypropan-2-yl)-1-methylcyclohexanol hydrate (cas: 2451-01-6) belongs to alcohols. Alcohols are weak acids. The most acidic simple alcohols (methanol and ethanol) are about as acidic as water, and most other alcohols are somewhat less acidic. A multistep synthesis may use Grignard-like reactions to form an alcohol with the desired carbon structure, followed by reactions to convert the hydroxyl group of the alcohol to the desired functionality.COA of Formula: C10H22O3

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts