Tag: M.W=200-250

Abdelkader, Elwy H. published the artcileGenetic Encoding of N⁶-(((Trimethylsilyl)methoxy)carbonyl)-L-lysine for NMR Studies of Protein-Protein and Protein-Ligand Interactions, Related Products of amides-buliding-blocks, the publication is Journal of the American Chemical Society (2021), 143(2), 1133-1143, database is CAplus and MEDLINE.

Trimethylsilyl (TMS) groups present outstanding NMR probes of biol. macromols. as they produce intense singlets in ¹H NMR spectra near 0 ppm, where few other proton resonances occur. We report a system for genetic encoding of N⁶-(((trimethylsilyl)methoxy)carbonyl)-L-lysine (TMSK) for site-specific incorporation into proteins. The system is based on pyrrolysyl-tRNA synthetase mutants, which deliver proteins with high yield and purity in vivo and in cell-free protein synthesis. As the TMS signal can readily be identified in 1D ¹H NMR spectra of high-mol. weight systems without the need of isotopic labeling, TMSK delivers an excellent site-specific NMR probe for the study of protein structure and function, which is both inexpensive and convenient. We demonstrate the utility of TMSK to detect ligand binding, measure the rate of conformational change, and assess protein dimerization by paramagnetic relaxation enhancement. In addition, we present a system for dual incorporation of two different unnatural amino acids (TMSK and O-tert-butyl-tyrosine) in the same protein in quantities sufficient for NMR spectroscopy. Close proximity of the TMS and tert-Bu groups was readily detected by nuclear Overhauser effects.

Journal of the American Chemical Society published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C11H22N2O4, Related Products of amides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Hu, Liming published the artcileThermophilic pyrrolysyl-tRNA synthetase mutants for enhanced mammalian genetic code expansion, Quality Control of 2418-95-3, the publication is ACS Synthetic Biology (2020), 9(10), 2723-2736, database is CAplus and MEDLINE.

Genetic code expansion (GCE) is a powerful technique for site-specific incorporation of noncanonical amino acids (ncAAs) into proteins in living cells, which is achieved through evolved aminoacyl-tRNA synthetase mutants. Stability is important for promoting enzyme evolution, and we found that many of the evolved synthetase mutants have reduced thermostabilities. In this study, we characterized two novel pyrrolysyl-tRNA synthetases (PylRSs) derived from thermophilic archaea: Methanosarcina thermophila (Mt) and Methanosarcina flavescens (Mf). Further study demonstrated that the wild-type PylRSs and several mutants were orthogonal and active in both Escherichia coli and mammalian cells and could thus be used for GCE. Compared with the commonly used M. barkeri PylRS, the wild-type thermophilic PylRSs displayed reduced GCE efficiency; however, some of the mutants, as well as some chimeras, outperformed their mesophilic counterparts in mammalian cell culture at 37°C. Their better performance could at least partially be attributed to the fact that these thermophilic synthetases exhibit a threshold of enhanced stability against destabilizing mutations to accommodate structurally diverse substrate analogs. These were indicated by the higher melting temperatures (by 3-6°C) and the higher expression levels that were typically observed for the MtPylRS and MfPylRS mutants relative to the Mb equivalent Using histone H3 as an example, we demonstrated that one of the thermophilic synthetase mutants promoted the incorporation of multiple acetyl-lysine residues in mammalian cells. The enzymes developed in this study add to the PylRS toolbox and provide potentially better scaffolds for PylRS engineering and evolution, which will be necessary to meet the increasing demands for expanded substrate repertoire with better efficiency and specificity in mammalian systems.

ACS Synthetic Biology published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C11H22N2O4, Quality Control of 2418-95-3.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Madeira, Mila F. M. published the artcileThe role of 5-lipoxygenase in Aggregatibacter actinomycetemcomitans-induced alveolar bone loss, Quality Control of 321673-30-7, the publication is Journal of Clinical Periodontology (2017), 44(8), 793-802, database is CAplus and MEDLINE.

Leukotrienes (LTs) are pro-inflammatory lipid mediators formed by the enzyme 5-lipoxygenase (5-LO). The involvement of 5-LO metabolites in periodontal disease (PD) is not well defined. This study aimed to assess the role of 5-LO in exptl. PD induced by Aggregatibacter actinomycetemcomitans (Aa). In vivo experiments were carried out using SV129 wild-type (WT) and 5-LO-deficient (5lo^-/-) mice inoculated with Aa. Osteoclasts were stimulated in vitro with AaLPS in the presence or not of selective inhibitors of the 5-LO pathway, or LTB4 or platelet-activating factor (PAF), as PAF has already been shown to increase osteoclast activity. In 5lo^-/- mice, there were no loss of alveolar bone and less TRAP-pos. osteoclasts in periodontal tissues, after Aa inoculation, despite local production of TNF-α and IL-6. The differentiation and activity of osteoclasts stimulated with AaLPS were diminished in the presence of BLT1 antagonist or 5-LO inhibitor, but not in the presence of cysteinyl leukotriene receptor antagonist. The osteoclast differentiation induced by PAF was impaired by the BLT1 antagonism. In conclusion, LTB4 but not CysLTs is important for Aa-induced alveolar bone loss. Overall, LTB4 affects osteoclast differentiation and activity and is a key intermediate of PAF-induced osteoclastogenesis.

Journal of Clinical Periodontology published new progress about 321673-30-7. 321673-30-7 belongs to amides-buliding-blocks, auxiliary class Immunology/Inflammation,Scavenger receptor, name is [(2-Hexylcyclopentylidene)amino]thiourea, and the molecular formula is C12H23N3S, Quality Control of 321673-30-7.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Ramalho, Theresa published the artcileLeukotriene-B4 modulates macrophage metabolism and fat loss in type 1 diabetic mice, Product Details of C12H23N3S, the publication is Journal of Leukocyte Biology (2019), 106(3), 665-675, database is CAplus and MEDLINE.

Serum levels of leukotriene-B4 (LTB4) are increased in type 1 diabetes (T1D) and it mediates systemic inflammation and macrophage reprogramming associated with this condition. Herein, investigated the involvement of LTB4 in adiposity loss, hyperlipidemia, and changes in macrophage metabolism in a mouse model of streptozotocin-induced T1D. LTB4 receptor (BLT1) antagonist u75302 was employed to block LTB4 effects. As expected, hypoinsulinemia in T1D was associated with hyperglycemia, low levels of glucagon, hyperlipidemia, significant body fat loss, and increased white adipose tissue expression of Fgf21, a marker for lipolysis. With the exception of hyperglycemia and hypoglucagonemia, blockade of LTB4 signaling reverted these parameters in T1D mice. Along with hyperlipidemia, macrophages from T1D mice exhibited higher lipid uptake and accumulation. These cells also had enhanced glycolysis and oxidative metabolism and these parameters were dependent on the mitochondrial uncoupling respiration, as evidenced by elevated expression of oxidation markers carnitine palmitoyltransferase and uncoupling protein 1. Interestingly, all these parameters were at least partially reverted in T1D mice treated with u75302. Altogether, these findings suggest that in T1D mice LTB4/BLT1 is involved in the fat loss, hyperlipidemia, and increased macrophage lipid uptake and metabolism with an important involvement of mitochondrial uncoupling activity. These previously unrecognized LTB4/BLT1 functions may be explored in future to therapeutically alleviate severity of hyperlipidemia and systemic inflammation in T1D.

Journal of Leukocyte Biology published new progress about 321673-30-7. 321673-30-7 belongs to amides-buliding-blocks, auxiliary class Immunology/Inflammation,Scavenger receptor, name is [(2-Hexylcyclopentylidene)amino]thiourea, and the molecular formula is C12H23N3S, Product Details of C12H23N3S.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Fang, Danxuan published the artcileStable, Bioresponsive, and Macrophage-Evading Polyurethane Micelles Containing an Anionic Tripeptide Chain Extender, HPLC of Formula: 2418-95-3, the publication is ACS Omega (2019), 4(15), 16551-16563, database is CAplus and MEDLINE.

Polymeric nanocarriers have been extensively used in medicinal applications for drug delivery. However, i.v. nanocarriers circulating in the blood will be rapidly cleared from the mononuclear macrophage system. The surface physicochem. characterizations of nanocarriers are the primary factors to determine their fate in vivo, such as evading the reticuloendothelial system, exhibiting long blood circulation times, and accumulating in the targeted site. In this work, we develop a series of polyurethane micelles containing segments of an anionic tripeptide, hydrophilic mPEG, and disulfide bonds. It is found that the long hydrophilic mPEG can shield the micellar surface and have a synergistic effect with the neg. charged tripeptide to minimize macrophage phagocytosis. Meanwhile, the disulfide bond can rapidly respond to the intracellular reduction environment, leading to the acceleration of drug release and improvement of the therapeutic effect. Our results verify that these anionic polyurethane micelles hold great potential in the development of the stealth immune system and controllable intracellular drug transporters.

ACS Omega published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C11H22N2O4, HPLC of Formula: 2418-95-3.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Huang, Sheng-Yin published the artcileA turn-on luminescent europium probe for cyanide detection in water, Category: amides-buliding-blocks, the publication is Chemical Communications (Cambridge, United Kingdom) (2018), 54(66), 9210-9213, database is CAplus and MEDLINE.

A luminescent europium probe that responds to cyanide directly in water with a large nine-fold turn-on of the Eu^III centered time-gated luminescence is presented. Unlike other CN^– probes reported, the mechanism of action of Eu^III-Lys-HOPO does not rely on reaction of CN^– with the probe, but on direct coordination of CN^– to the Eu^III ion concomitant with displacement of three inner-sphere water mols. This unusual coordination of CN^– with a lanthanide ion in aqueous solution was confirmed by luminescence lifetime measurements.

Chemical Communications (Cambridge, United Kingdom) published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C11H22N2O4, Category: amides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Pazos, Michael A. published the artcileDistinct Cellular Sources of Hepoxilin A₃ and Leukotriene B₄ Are Used To Coordinate Bacterial-Induced Neutrophil Transepithelial Migration, Safety of [(2-Hexylcyclopentylidene)amino]thiourea, the publication is Journal of Immunology (2015), 194(3), 1304-1315, database is CAplus and MEDLINE.

Neutrophilic infiltration is a leading contributor to pathol. in a number of pulmonary disease states, including cystic fibrosis. Hepoxilin A₃ (HXA₃) is a chemotactic eicosanoid shown to mediate the transepithelial passage of neutrophils in response to infection in several model systems and at multiple mucosal surfaces. Another well-known eicosanoid mediating general neutrophil chemotaxis is leukotriene B₄ (LTB₄). We sought to distinguish the roles of each eicosanoid in the context of infection of lung epithelial monolayers by Pseudomonas aeruginosa. Using human and mouse in vitro transwell model systems, we used a combination of biosynthetic inhibitors, receptor antagonists, as well as mutant sources of neutrophils to assess the contribution of each chemoattractant in driving neutrophil transepithelial migration. We found that following chemotaxis to epithelial-derived HXA₃ signals, neutrophil-derived LTB₄ is required to amplify the magnitude of neutrophil migration. LTB₄ signaling is not required for migration to HXA₃ signals, but LTB₄ generation by migrated neutrophils plays a significant role in augmenting the initial HXA₃-mediated migration. We conclude that HXA₃ and LTB₄ serve independent roles to collectively coordinate an effective neutrophilic transepithelial migratory response.

Journal of Immunology published new progress about 321673-30-7. 321673-30-7 belongs to amides-buliding-blocks, auxiliary class Immunology/Inflammation,Scavenger receptor, name is [(2-Hexylcyclopentylidene)amino]thiourea, and the molecular formula is C12H23N3S, Safety of [(2-Hexylcyclopentylidene)amino]thiourea.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Kaye, Irving Allan published the artcilePreparation of secondary and tertiary 2-thiazolylamines, Computed Properties of 2451-91-4, the publication is Journal of the American Chemical Society (1952), 2271-3, database is CAplus.

cf. C.A. 46, 9094b. Basically mono- or disubstituted derivatives of 2-aminothiazole (I) were prepared by the condensation of an appropriately substituted thiourea with di-Me chloroacetal (II). The reaction of 2-bromothiazole (IIA) with either a primary or secondary amine was a less satisfactory method. N,N-Diethyl-N’-benzyl-N’-(2-thiazolyl)ethylenediamine (III), tested for antihistaminic activity on the isolated guinea-pig ileum strip, showed 1.5% of the activity of pyribenzamine (IV). The N,N-di-Me analog (V) of III was 20% as active as IV. Against acetylcholine, V had 0.15% the activity of atropine. The method of Ganapathi and Venkataraman (C.A. 40, 4059.5) gave 67% IIA. The method of Campbell, et al. (C.A. 43, 1340g), gave 93% PhCH:NEt (VI). VI with Pd-C gave 94% PhCH₂NHEt (VII), b₈₂ 124-5°. The method of Moore and Crossley (Organic Syntheses, 21, 81(1941); C.A. 35, 6241.4) yielded 91 and 89%, resp., of PhCH₂NCS, b₃ 105-7°, and EtNCS, b₁₂₀ 60-70°. The method of Frank and Smith (Ibid. 28, 89(1948); C.A. 43, 1734h) yielded 71% BzNHCSNHCH₂Ph (VIII), m. 124-4.5°. Alk. cleavage of VIII gave 92% H₂NCSNHCH₂Ph (IX). PhCH₂NCS and NH₄OH gave IX. EtNCS and NH₄OH gave 70% EtNHCSNH₂. The method of Frank and Smith, loc. cit., gave 79.5% BzNHCSN(CH₂Ph)₂ (X), m. 142-3°. Et₂NCH₂CH₂NHCH₂Ph (XI) (82.5 g.) in 100 cc. C₆H₆ added dropwise (cooling) to 21.2 g. BrCN in 100 cc. C₆H₆, the solution heated 4 h. on the steam bath, cooled, treated with 20 g. NaOH in 150 cc. water, extracted with C₆H₆, and the extract fractionated yielded 37.1 g. XI, b₅ 128-34°; and 41.3 g. benzyl(2-diethylaminoethyl)cyanamide (XII), b₅ 179-80°. The same procedure, except for filtration of the HBr salts of excess amines, yielded 95% NCNEtCH₂Ph (XIII), b₁₂ 157-8°; and 100% NCN(CH₂Ph)₂ (XIV), m. 60-2°, b₃ 180-5°. Gaseous NH₃ and H₂S passed rapidly into 17.6 g. XIII in 125 cc. MeOH saturated with NH₃ (temperature held below 35°), the flow of NH₃ stopped after 1 h., that of H₂S 1 h. later, ice and water added, and the precipitate filtered yielded 15.8 g. PhCH₂EtNCSNH₂, m. 122.5-3.5°. XIV yielded 73% (PhCH₂)₂NCSNH₂. XII gave an oil which was cyclized in 45% yield to III, b_0.9 135-9°, m. 147.5-8.5°. V, 34% yield, b_0.04 118-25°, m. 158.5-9.5°. Method A: PhCH₂NHCSNH₂ (74.8 g.), 67.3 g. II, and 250 cc. water heated 18 h. on the steam bath, diluted with 1 l. water, and made alk. with NaOH yielded 80.0 g. 2-benzylaminothiazole (XV), m. 126-7.5°. IIA (16.4 g.) and 21.4 g. PhCH₂NH₂ refluxed 72 h. in cumene or xylene yielded 1.8 g. XV, m. 127.5-8.5. B: IIA (8.2 g.), 11.6 g. Et₂NCH₂CH₂NH₂, and 12 g. pyridine refluxed 3.5 h., cooled to room temperature, 100 cc. water added, and the solution saturated with K₂CO₃ and extracted with Et₂O yielded 6.0 g. N,N-diethyl-N’-(2-thiazolyl)ethylenediamine, b_0.4 112-15°; di-HCl salt, m. 181.5-2.5°. The following N,N-disubstituted 2-aminothiazoles were also prepared (substituents, method, b.p./mm., % yield, and m.p. given): Et, H, A, -, 70, 49-50° (picrate, m. 182-3°); Et, benzyl, A, 119-22°/0.10, 28, 153.5-54°; benzyl, benzyl, A, 116-20°/0.05, 57, 167-7.5°.

Journal of the American Chemical Society published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Computed Properties of 2451-91-4.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Nieland, Thomas J. F. published the artcileDiscovery of chemical inhibitors of the selective transfer of lipids mediated by the HDL receptor SR-BI, Recommanded Product: [(2-Hexylcyclopentylidene)amino]thiourea, the publication is Proceedings of the National Academy of Sciences of the United States of America (2002), 99(24), 15422-15427, database is CAplus and MEDLINE.

The high-d. lipoprotein (HDL) receptor, scavenger receptor, class B, type I (SR-BI), mediates both the selective uptake of lipids, mainly cholesterol esters, from HDL to cells and the efflux of cholesterol from cells to lipoproteins. The mechanism underlying these lipid transfers is distinct from classic receptor-mediated endocytosis, but it remains poorly understood. To investigate SR-BI’s mechanism of action and in vivo function, the authors developed a high-throughput screen to identify small mol. inhibitors of SR-BI-mediated lipid transfer in intact cells. The authors identified five compounds that in the low nanomolar to micromolar range block lipid transport (BLTs), both selective uptake and efflux. The effects of these compounds were highly specific to the SR-BI pathway, because they did not interfere with receptor-mediated endocytosis or with other forms of intracellular vesicular traffic. Surprisingly, all five BLTs enhanced, rather than inhibited, HDL binding by increasing SR-BI’s binding affinity for HDL (decreased dissociation rates). Thus, the BLTs provide strong evidence for a mechanistic coupling between HDL binding and lipid transport and may serve as a starting point for the development of pharmacol. useful modifiers of SR-BI activity and, thus, HDL metabolism

Proceedings of the National Academy of Sciences of the United States of America published new progress about 321673-30-7. 321673-30-7 belongs to amides-buliding-blocks, auxiliary class Immunology/Inflammation,Scavenger receptor, name is [(2-Hexylcyclopentylidene)amino]thiourea, and the molecular formula is C12H23N3S, Recommanded Product: [(2-Hexylcyclopentylidene)amino]thiourea.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Stanke-Labesque, Francoise published the artcileLeukotriene B₄ pathway activation and atherosclerosis in obstructive sleep apnea, Product Details of C12H23N3S, the publication is Journal of Lipid Research (2012), 53(9), 1944-1951, database is CAplus and MEDLINE.

Leukotriene B₄ (LTB₄) production increases in obstructive sleep apnea syndrome (OSA) and is linked to early vascular remodeling, the mechanism of which is unknown. The objective of this study was to to determine the mol. mechanisms of LTB₄ pathway activation in polymorphonuclear cells (PMNs) and early vascular remodeling in OSA and the specific contribution of intermittent hypoxia (IH). PMNs were isolated from 120 OSA patients and 33 healthy subjects and used for measurements of LTB₄ production, determination of mRNA and protein expression levels, or exposed for four cycles of in vitro IH. PMNs derived from OSA patients exhibited increased LTB₄ production, for which apnea-hypopnea index was an independent predictor (P = 0.042). 5-Lipoxygenase-activating protein (FLAP) mRNA and protein increased significantly in PMNs from OSA patients vs. controls and were associated with carotid luminal diameter and intima-media thickness. LTB₄ (10 ng/mL) increased IL-6 (P = 0.006) and MCP-1 (P = 0.002) production in OSA patient monocytes. In vitro exposure of PMNs from controls to IH enhanced FLAP mRNA levels (P = 0.027) and induced a 2.7-fold increase (P = 0.028) in LTB₄ secretion compared with PMNs exposed to normoxia. In conclusion, upregulation of FLAP in PMNs in response to IH may participate in early vascular remodeling in OSA patients, suggesting FLAP as a potential therapeutic target for the cardiovascular morbidity associated with OSA.

Journal of Lipid Research published new progress about 321673-30-7. 321673-30-7 belongs to amides-buliding-blocks, auxiliary class Immunology/Inflammation,Scavenger receptor, name is [(2-Hexylcyclopentylidene)amino]thiourea, and the molecular formula is C6H5NO, Product Details of C12H23N3S.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics