14379-56-7Relevant articles and documents
Synthetic ceramide analogues as skin permeation enhancers: Structure-Activity relationships
Vavrova, Katerina,Hrabalek, Alexandr,Dolezal, Pavel,Samalova, Lucie,Palat, Karel,Zbytovska, Jarmila,Holas, Tomas,Klimentova, Jana
, p. 5381 - 5390 (2003)
The study presents new information about the structure-activity relationships of the skin permeation enhancers. A series of ceramide analogues including eight different polar head groups and six different chain lengths was synthesised. The compounds were evaluated as permeation enhancers in vitro using porcine skin. The physico-chemical parameters of the tested compounds obtained by computer modelling were used to evaluate, by multiple linear regression, the enhancement ratios (ERs) of the compounds. The regression analysis suggests that the hydrogen bonding ability of the compounds is inversely related to the ER values and that the molecular size and lipophilicity must be well balanced. In the studied enhancers having the same chain length, the enhancement activity is dependent only on their permeability coefficients. This finding confirms the Warner's hypothesis that the polar head of an enhancer is responsible for the permeation and anchoring of the molecule into the stratum corneum lipids and that it does not influence the mechanism of action. For the specific action of enhancers, that is disordering of the intercellular lipid packing, the length of the hydrophobic chain(s) and not the lipophilicity is important. Furthermore, the examination of the FTIR spectra indicated that the most active substances possess the most ordered chains. The described relationships could bring more rational approaches in designing new potent enhancers for transdermal formulations.
Hydrogen-bonding networks involving water in amphiphilic N-dodecanoyl-L-serine monohydrate
Schade,Fuhrhop,Hubert,Weber,Luger
, p. 1070 - 1073 (1997)
The amphiphilic title compound, C15H29NO4.H2O, forms a head-to-tail bilayer packing arrangement in the crystal. The crystal structure shows an entangled network of hydrogen bonds in which the water molecule has a central position. A rarely observed methine donor hydrogen bridge was found.
The relationship between the structure and properties of amino acid surfactants based on glycine and serine
Qiao, Weihong,Qiao, Yangyang
, p. 821 - 828 (2013/11/06)
Two series of surfactants based on glycine and serine were synthesized with aproic acid, octanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid and hexadecanoic acid. All the surfactants were characterized by MS and 1H NMR, the structures of the synthesized surfactants are correct and the signals in MS and 1H NMR can be explained. The reaction conditions, surface properties and foam properties were studied. For the two series of surfactants, critical micelle concentration (CMC) and γ CMC (surface tension at CMC) decrease and surface activity is enhanced as the length of carbon chain increases. The surfactants with tetradecanoyl and hexadecanoyl groups show a good foaming property and especially, the long-chain acyl-serine performs better. These are all related to the hydromethyl group in the serine.
The effect of unsaturation on the formation of self-assembled gels from fatty acid L-serine amides and their cytotoxicity towards caco-2 cancer cells
Lim, Li Yun Grace,Su, Yingying,Braet, Filip,Thordarson, Pall
scheme or table, p. 653 - 656 (2010/01/16)
A series of saturated and unsaturated fatty acid l-serines 3 were synthesized and their ability to form self-assembled gels was investigated. The saturated (lauroyl 3a and steraoyl 3b) and monounsaturated (oleoyl 3c) fatty acid l-serines form gels in both water and organic solvent, whereas the diunsaturated linoleyl-l-serine 3d does not form gels in these solvents, indicating that unsaturation adversely affects the gelation process. Cytotoxicity studies on these compounds with Caco-2 cancer cells in vitro show that these gels are only moderately cytotoxic at concentrations up to 0.5 mM, making them a promising candidate for applications such as drug delivery. CSIRO 2009.
A novel acylase from Streptomyces mobaraensis that efficiently catalyzes hydrolysis/synthesis of capsaicins as well as N-acyl-L-amino acids and N-acyl-peptides
Koreishi, Mayuko,Zhang, Demin,Imanaka, Hiroyuki,Imamura, Koreyoshi,Adachi, Shuji,Matsuno, Ryuichi,Nakanishi, Kazuhiro
, p. 72 - 78 (2007/10/03)
A novel enzyme that catalyzes efficient hydrolysis of capsaicin (8-methyl-N-vanillyl-6-nonenamide) was isolated from the culture broth of Streptomyces mobaraensis. The enzyme consisted of two dissimilar subunits with molecular masses of 61 and 19 KDa. The enzyme was activated and stabilized in the presence of Co2+. It showed a pH optimum of about 8 and was stable at temperatures of up to 55°C for 1 h at pH 7.8. The specific activity of the enzyme for the hydrolysis of capsaicin was 10 2-104 times higher than those for the enzymes reported to date. In an aqueous/n-hexane biphasic system, capsaicin analogues such as octanoyl, decanoyl, and lauroyl vanillylamides were synthesized from the corresponding fatty acids and vanillylamine at yields of 50% or greater. In addition, the enzyme catalyzed the deacylation of N-lauroyl-L-amino acids and N-lauroyl-L-dipeptides and the efficient synthesis of Nα-lauroyl-L-lysine, Nε-lauroyl-L-lysine, and various N-lauroyl-peptides in aqueous solution in both the absence and the presence of glycerol.
CHIRAL SURFACTANT AND METHOD FOR USING THE SAME IN CHIRAL SEPARATION
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Page/Page column 14, (2010/02/11)
PROBLEM TO BE SOLVED: To provide a method for separating chiral compounds by using a micelle electrodynamic capillary chromatography. SOLUTION: This method of chiral separation is provided by bringing the chiral compound in contact with a chiral surfactant expressed by the general formula (wherein, R1=a 4-18C alkyl, a 4-18C halogen-substituted alkyl, a 4-18C polyether hydrocarbon, a 4-18C alkyl having a chiral center, in which the above alkyl groups may have unsaturated bond, or a cholesterol hydrocarbon; Y =CH2; A=NH; X=CO; C=carbon: Z=COO-, SO4-, SO3-, PO3-, PO4-, NR'3+, PR'3+, OH, a polyether, an ampho-ion or a polyalcohol; and R'=H or a 1-4C hydrocarbon and may be halogenated or may have unsaturated bond) of an effective amount under a condition of an electrophoretic capillary chromatography.
Isolation and total synthesis of gymnastatin N, a POLO-like kinase 1 active constituent from the fungus Arachniotus punctatus
Phoon, Chee Wee,Somanadhan, Brinda,Heng, Sabrina Cher Hui,Ngo, Anna,Ng, Siew Bee,Butler, Mark S.,Buss, Antony D.,Sim, Mui Mui
, p. 11619 - 11628 (2007/10/03)
A high throughput screen against POLO-like kinase 1 (Plk1), an anti-cancer target, identified an active extract from the fungus Arachniotus punctatus. Bioassay guided fractionation led to the isolation of the new natural product, gymnastatin N (1) and the known compound aranorosinol A (2) with IC50 values of 13 and 118 μM, respectively. A 12′-hydroxy analog of gymnastatin N, 3, was also isolated as a minor component. Gymnastatin N (1) was found to be a 52:48 mixture of (1S,6′R) and (1R,6′R) diastereomers, by synthesis of the four possible diastereomers and comparison of the optical rotation and chiral HPLC profile of each diastereoisomer with the natural product. Analogues of 1 were synthesized and evaluated against the Plk1 assay and these SAR studies suggested that the diene and free carboxylic acid moieties might be responsible for its bioactivity. Graphical Abstract.
Synthesis and antitumor activities of glycine-exchanged analogs of spicamycin
Sakai,Kawai,Kamishohara,Odagawa,Suzuki,Uchida,Kawasaki,Tsuruo,Otake
, p. 504 - 508 (2007/10/02)
A series of SPM VIII analogs were synthesized to investigate the effect of the amino acid moiety on the antitumor activity. The L-threonine analog and the glycylglycine analog of SPM VIII showed much higher cytotoxity to P388 murine leukemia cells (IC50 5.8 nM and 0.11 nM, respectively) than SPM VIII (IC50 25 nM). However, replacement of the glycine moiety with other amino acids greatly reduced the antitumor activity against COL-1 human colon cancer xenograft model. This study indicated that the glycine moiety of SPM VIII is crucial for the antitumor effect.
