112-13-0Relevant articles and documents
Unexpected stereoselective exchange of straight-chain fatty acyl-CoA α-protons by human α-methylacyl-CoA racemase 1A (P504S)
Sattar, Fouzia A.,Darley, Daniel J.,Politano, Francesco,Woodman, Timothy J.,Threadgill, Michael D.,Lloyd, Matthew D.
, p. 3348 - 3350 (2010)
α-Methylacyl-CoA racemase (AMACR; P504S) catalysed exchange of straight-chain fatty acyl-CoA α-protons. One α-proton was removed in each catalytic cycle, with the pro-S proton preferred. This reaction was most efficient for straight-chain substrates with longer side-chains. 2-Methyldecanoyl-CoA underwent α-proton exchange 3× more efficiently (as judged by Kcat/Km) than decanoyl-CoA.
Synthesis, characterization, and properties of copolyanhydrides based on 2-octylsuccinic acid and sebacic acid
Hamdan, Yousef M.,Fu, Shitao,Jiang, Xiangmei,Cheng, Yinhua,Huang, Kaixun,Yu, Kaichao
, p. 762 - 767 (2008)
2-Octylsuccinic acid and its copolyanhydrides with sebacic acid have been synthesized by melt polycondensation, and were characterized by Fourier transform infrared spectroscopy, 1H NMR, gel permeation chromatography, differential scanning calorimetry, and thermal gravimetric analysis. In vitro studies showed that all copolymers are degradable in phosphate buffer at 37°C. The release profiles of the hydrophilic model drug ciprofloxacin hydrochloride follow first-order release kinetics. CSIRO 2008.
The effect of vicinal di-halo substituents on the organogelling properties of aromatic supramolecular gelators and their application as soft templates
Busch, Verónica M.,Di Chenna, Pablo H.,Di Salvo, Florencia,Giovanetti, Lisandro,Japas, M. Laura,MacCormack, Andrea S.
, p. 8198 - 8208 (2020)
A pronounced effect of vicinal dihalogen substituents on the gelling properties of aromatic low molecular weight organogelators is reported. A new family of N,N′-(4,5-dihalogen-1,2-phenylene)dialkylamides with fluorine, chlorine, bromine and iodine was designed and synthesized. A systematic investigation of their organogelling ability, thermic stability, mechanical properties and self-assembled structure was performed to elucidate the effect that the vicinal di-halo substituents have on the organogels. It was found that the presence of two halogen atoms (X) has a determinant effect as the brominated compounds are generally the most efficient organogelators. In hydrocarbons, the gelling ability increased from fluorine to iodine following the halogen bond donor ability trend. SAXS results were in agreement with a fibrillar self-assembly where the halogens are located at the surface of the fibers. Multiple cooperative interactions are involved in the self-assembly of the gels: π-π stacking, hydrogen bonds and X?X contacts. Thus, this work provides a new strategy for the design of new gelators or to improve the efficiency of known organogelators by introducing two vicinal halogen substituents into the aromatic rings. An ethanolic gel was also successfully used as a template to prepare silica and titania nanotubes. Hence, such organogels are promising materials for future research and development.
Selective reduction of barbituric acids using SmI2/H 2O: Synthesis, reactivity, and structural analysis of tetrahedral adducts
Szostak, Michal,Sautier, Brice,Spain, Malcolm,Behlendorf, Maike,Procter, David J.
, p. 12559 - 12563 (2013)
Making a mark: Since the 1864 landmark discovery by Adolf von Baeyer, barbituric acids have played a prominent role in organic synthesis. Herein, the first chemoselective monoreduction of barbituric acids to the corresponding hemiaminals is described. The method delivers mono- and bicyclic hemiaminal products by a general single-electron-transfer polarity reversal mechanism. Re-use of this article is permitted in accordance with the Terms and Conditions set out at http://angewandte.org/open.
L-ascorbyl 6-palmitate as lead compound targeting SphK1: an in silico and in vitro investigation
Chen, HaiJiao,Liu, Bo,Sun, Peng,Yang, Xinmei,Yao, Qingqiang,Zhi, Ying
, p. 781 - 787 (2021)
Sphingosine kinases (SphKs) are a class of lipid kinases, that have received extensive attention as important rate-limiting enzyme in tumor. Inhibition of the activity of SphK1 can lead to an anticancer effect. Herein, we describe the discovery process and biological characteristics of a new SphK1 inhibitor, ascorbyl palmitate, discovered through computer-aided drug design. Biochemical experiments show that ascorbyl palmitate has a strong inhibitory effect on SphK1, with an IC50 value of 6.4 μM. The MTT experiment showed that ascorbyl palmitate had anti-cancer effects toward the U87, A549, 22RV1, and A375 cell lines. Among them, ascorbyl palmitate has prominent inhibitory activity against the 22RV1 cell line, with an IC50 value of 41.57 μM. To explore the structure–activity relationship, four ascorbyl palmitate derivatives were synthesized and tested for kinase activity. The outstanding effect of ascorbyl palmitate toward SphK1 and its known non-toxicity suggest that ascorbyl palmitate may be a lead compound for the development of effective SphK1 anti-cancer inhibitors.
Synthesis, calorimetric studies, and crystal structures of N, O-diacylethanolamines with matched chains
Kamlekar, Ravi Kanth,Tarafdar, Pradip K.,Swamy, Musti J.
, p. 42 - 52 (2010)
Recent studies show that N-, O -diacylethanolamines (DAEs) can be derived by the O -acylation of N-acylethanolamines (NAEs) under physiological conditions. Because the content of NAEs in a variety of organisms increases in response to stress, it is likely that DAEs may also be present in biomembranes. In view of this, a homologous series of DAEs with matched acyl chains (n = 10-20) have been synthesized and characterized. Transition enthalpies and entropies obtained from differential scanning calorimetry show that dry DAEs with even and odd acyl chains independently exhibit linear dependence on the chainlength. Linear least-squares analyses yielded incremental values contributed by each methylene group to the transition enthalpy and entropy and the corresponding end contributions. N-, O-Didecanoylethanolamine (DDEA), N-, O-dilauroylethanolamine (DLEA), and N-, O-dimyristoylethanolamine (DMEA) crystallized in the orthorhombic space group Pbc21 with four symmetry-related molecules in the unit cell. Single-crystal X-ray diffraction studies show that DDEA, DLEA, and DMEA are isostructural and adopt an L-shaped structure with the N-acyl chain and the central ethanolamine moiety being essentially identical to the structure of N-acylethanolamines, whereas the O-acyl chain is linear with all-trans conformation. In all three DAEs, the lipid molecules are organized in a bilayer fashion wherein the N-acyl and O-acyl chains from adjacent layers oppose each other. Copyright
Neutrophil-Selective Fluorescent Probe Development through Metabolism-Oriented Live-Cell Distinction
Gao, Min,Lee, Sun Hyeok,Park, Sang Hyuk,Ciaramicoli, Larissa Miasiro,Kwon, Haw-Young,Cho, Heewon,Jeong, Joseph,Chang, Young-Tae
supporting information, p. 23743 - 23749 (2021/10/14)
Human neutrophils are the most abundant leukocytes and have been considered as the first line of defence in the innate immune system. Selective imaging of live neutrophils will facilitate the in situ study of neutrophils in infection or inflammation events as well as clinical diagnosis. However, small-molecule-based probes for the discrimination of live neutrophils among different granulocytes in human blood have yet to be reported. Herein, we report the first fluorescent probe NeutropG for the specific distinction and imaging of active neutrophils. The selective staining mechanism of NeutropG is elucidated as metabolism-oriented live-cell distinction (MOLD) through lipid droplet biogenesis with the help of ACSL and DGAT. Finally, NeutropG is applied to accurately quantify neutrophil levels in fresh blood samples by showing a high correlation with the current clinical method.