112-67-4Relevant articles and documents
Analysis of Intact Cholesteryl Esters of Furan Fatty Acids in Cod Liver
Hammann, Simon,Wendlinger, Christine,Vetter, Walter
, p. 611 - 620 (2015)
Furan fatty acids (F-acids) are a class of natural antioxidants with a furan moiety in the acyl chain. These minor fatty acids have been reported to occur with high proportions in the cholesteryl ester fraction of fish livers. Here we present a method for the direct analysis of intact cholesteryl esters with F-acids and other fatty acids in cod liver lipids. For this purpose, the cholesteryl ester fraction was isolated by solid phase extraction (SPE) and subsequently analyzed by gas chromatography with mass spectrometry (GC/MS) using a cool-on-column inlet. Pentadecanoic acid esterified with cholesterol was used as an internal standard. GC/MS spectra of F-acid cholesteryl esters featured the molecular ion along with characteristic fragment ions for both the cholesterol and the F-acid moiety. All investigated cod liver samples (n = 8) showed cholesteryl esters of F-acids and, to a lower degree, of conventional fatty acids. By means of GC/MS-SIM up to ten F-acid cholesteryl esters could be determined in the samples. The concentrations of cholesteryl esters with conventional fatty acids amounted to 78-140 mg/100 g lipids (mean 97 mg/100 g lipids), while F-acid cholesteryl esters were present at 47-270 mg/100 g lipids (mean 130 mg/100 g lipids).
Antitumor liposomes bearing a prodrug of combretastatin A-4 and a tetrasaccharide ligand of selectins
Sitnikov,Boldyrev,Moiseeva,Shavyrin,Beletskaya,Combes,Bovin,Fedorov,Vodovozova
, p. 2290 - 2296 (2010)
Therapeutic liposomes with an average diameter of 100 nm based on natural phospholipids (phosphatidylcholine and phosphatidylinositol) containing palmitoyl or oleoyl derivatives of the antimitotic agent combretastatin A-4 were constructed. The cytotoxicity of liposomes with the oleoyl derivative in the human breast cancer cell culture turned out to be only three times lower than that of combretastatin A-4, thus indicating the probability of facile intracellular hydrolysis of the prodrug. To achieve selective drug delivery to the tumor tissue in vivo, the diglyceride conjugate of the tetrasaccharide ligand of selectins, viz., Sialyl-Lewis X (SiaLeX, 2 mol.%) was incorporated into the liposomes. The SiaLeX-equipped liposomes loaded with the lipophilic prodrug showed a reliable inhibition of tumor growth on the model of spontaneous breast cancer in mice.
Odd-even effect in a thiazole based organogelator: Understanding the interplay of non-covalent interactions on property and applications
Yadav, Priyanka,Ballabh, Amar
, p. 721 - 730 (2015)
New series of thiazole based amides, namely, 1e [N-(thiazol-2-yl)pentadecamide] to 1h [N-(thiazol-2-yl)stearamide], 2e [N-(4-methylthiazol-yl)pentadecamide] to 2h [N-(4-methylthiazol-yl)stearamide], 3e [N-(5-methylthiazol-yl)pentadecamide] to 3h [N-(5-methylthiazol-yl)stearamide] were synthesized, characterized and investigated for their gelation properties. Interestingly, out of three series of thiazole amides synthesized, two (1e-1h and 3e-3h) had displayed odd-even effect on gelation property with an increase in the methylene functional group of alkyl chain attached with thiazole moiety. The gelation-non-gelation of solvents was found to be more significant for the series of compounds 1e-1h, whereas a subtle effect was observed in the series of compounds 3e-3h. A single crystal study of non-gelator (2d) highlighted the crucial role of the methyl group and its position on the thiazole moiety in bringing about a change in supramolecular synthon from a robust cyclic N-H...N interaction to the combination of N-H...N and N-H...O interactions. Self-assembly of four molecules of 2d led to the formation of a zero-dimensional (0-D) hydrogen bonded network instead of a one-dimensional hydrogen bonded network observed in gelling compounds mediated by (methyl)C-H...N, C-H...O and van der Waals interaction. Various gelling agents (3e-3h) were used for the synthesis of nearly spherical silver and ZnO nanoparticles using a sol-gel method, through encapsulation and stabilization of nanoparticles in the gel network. Interestingly, the alkyl chain lengths of thiazole amides were found to affect the size of synthesized Ag and ZnO nanoparticles.
Tryptamine-derived alkaloids from Annonaceae exerting neurotrophin-like properties on primary dopaminergic neurons
Schmidt, Fanny,Douaron, Gael Le,Champy, Pierre,Amar, Majid,Seon-Meniel, Blandine,Raisman-Vozari, Rita,Figadere, Bruno
, p. 5103 - 5113 (2010)
N-fatty acyl tryptamines constitute a scarce group of natural compounds mainly encountered in Annonaceous plants. No biological activity was reported so far for these rare molecules. This study investigated the neurotrophic properties of these natural tryptaminic derivatives on dopaminergic (DA) neurons in primary mesencephalic cultures. A structure-activity relationships study led us to precise the role of a nitrogen atom into the aliphatic chain conferring to the compounds a combined neuroprotective and neuritogenic activity in the nanomolar range. The potent antioxidant activity of these natural products seems to be involved in part of their mechanism of action. This study provides the first description of natural neurotrophin mimetics present in Annonaceae extracts, and led to the biological characterization of compounds, which present a potential interest in neurodegenerative diseases such as Parkinson's disease.
Quadruple helix formation of a photoresponsive peptide amphiphile and its light-triggered dissociation into single fibers
Muraoka, Takahiro,Cui, Honggang,Stupp, Samuel I.
, p. 2946 - 2947 (2008)
Using a peptide amphiphile having a bulky photolabile 2-nitrobenzyl group between the alkyl chain and the peptide segment, we demonstrated quadruple helical fiber formation and its dissociation into single fibrils in response to light. Putting the bulky g
Synthesis and characterization of allyl fatty acid derivatives as reactive coalescing agents for latexes
Barbosa, Joana V.,Oliveira, Fernanda,Moniz, Jorge,Magalhaes, Fernao D.,Bastos, Margarida M. S. M.
, p. 2215 - 2226 (2012)
This work evaluated the use of allyl fatty acid esters derived from vegetable oil (palmitic acid, soybean and sunflower oils) as reactive coalescing agents in a waterborne latex system. Allyl fatty acid derivatives (AFAD) from vegetable oils were synthesized by two different processes. The synthesis was monitored by IR-spectroscopy and the final product characterized by FT-IR, GC-MS, 1H and 13C NMR. The presence of conjugated double bonds in the aliphatic chain was confirmed, which is a determinant for the proposed autoxidative latexes drying mechanism. Each of the AFAD were subsequently added to a standard acrylic emulsion, in order to study its potential as reactive coalescing agent. The minimum film-forming temperature (MFT), glass transition temperature (Tg), drying time and rubbing resistance to solvents were evaluated. The results showed that, when added to water-borne acrylic resins, an AFAD acts as a non-volatile plasticizer capable of autoxidative crosslinking with itself. AOCS 2012.
A General Approach to Intermolecular Olefin Hydroacylation through Light-Induced HAT Initiation: An Efficient Synthesis of Long-Chain Aliphatic Ketones and Functionalized Fatty Acids
Guin, Joyram,Paul, Subhasis
supporting information, p. 4412 - 4419 (2021/02/05)
Herein, an operationally simple, environmentally benign and effective method for intermolecular radical hydroacylation of unactivated substrates by employing photo-induced hydrogen atom transfer (HAT) initiation is described. The use of commercially available and inexpensive photoinitiators (Ph2CO and NHPI) makes the process attractive. The olefin hydroacylation protocol applies to a wide array of substrates bearing numerous functional groups and many complex structural units. The reaction proves to be scalable (up to 5 g). Different functionalized fatty acids, petrochemicals and naturally occurring alkanes can be synthesized with this protocol. A radical chain mechanism is implicated in the process.
Synthesis and self-assembly of Salen type Schiff based on o-phenylenediamine organogels in response to Zn2+
Niu, Wei-Ya,Shang, Qi,Xue, Ji-Jun,Yang, Yun-Shang,Zhang, Ying-Peng
, (2020/12/29)
Two Salen type Schiff based on o-phenylenediamine were synthesized. The prepared organogelators demonstrated excellent gel properties in some selected solvents, such as n-pentanol, chloroform, and 1,2-dichloroethane. The results for thermal stability showed that under concentrations increasing of the gel molecules and then the gel-to-sol transition temperature value is increased. Through various techniques found that the hydrogen bonding between molecules, the van der Waals force, and the π-π stacking provide multiple driving forces for gel self-assembly. The morphology of the xerogel was investigated by Scanning Electron Microscope (SEM). The metal ions responsiveness experiment is completed by adding the metal ions solution dropwise to the gel surface and confirmed by the UV spectrum.
