- Enzymic synthesis, physicochemical, and cell activity of glucosyl ester derivatives based on N-fatty acyl amino acid
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Series of glucosyl esters derivatives were synthesized by enzymatic acylation and some surface properties, and cell activity were calculated and tested. The antitumor activity in vitro against three cancer cells, human colon carcinoma (K562), human hepatoma (HepG2), and human breast adenocarcinoma (MCF-7) of compounds, were evaluated using MTT methods. The glucosyl esters could significantly displayed high anticancer activity. Thereinto, compounds 12 and 12′ showed higher inhibition effect to cancer cells than others. Several compounds were more active than control drug 5-FU. The structure–activity relationship analysis revealed that lipophilic properties might be essential parameter for their activity.
- An, Dong,Feng, Dexin
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p. 653 - 662
(2019/02/25)
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- HUMAN MICROBIOTA DERIVED N-ACYL AMIDES FOR THE TREATMENT OF HUMAN DISEASE
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The present invention provides compositions and methods for the modulation of G protein-coupled receptors (GPCRs). The invention provides a genetically engineered cell, wherein the cell expresses a human microbial N-acyl synthase (hm-NAS) gene. In one embodiment, the hm-NAS gene is N-acyl serinol synthase. The invention provides a probiotic composition, the probiotic composition comprises a genetically engineered cell of the invention. The invention provides a method for modulating a G protein-coupled receptor (GPCR) activity in a subject, the method comprises administering to the subject an effective amount of a composition comprising at least one selected from the group consisting of a genetically engineered cell, an hm-NAS gene, and a N-acyl amide.
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Page/Page column 87-88
(2019/01/17)
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- Long-acting entecavir prodrug and preparation method and application thereof
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The invention relates to a long-acting entecavir prodrug and a preparation method and application thereof. The long-acting entecavir prodrug has a structure shown as formula I that is shown in the description; the long-acting entecavir prodrug can release slowly, continuously and stably in vivo and convert into an entecavir material technical, so that long acting is achieved. In the formula I, R1,R2 and R3 are defined the same as in the description.
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Paragraph 0081; 0082; 0084
(2019/04/17)
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- Lipid dipeptide and gel
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A gelator that includes a lipid peptide of Formula (1) wherein R1 is a C9-23 aliphatic group, R2 is a hydrogen atom or a C1-4 alkyl group optionally having a C1-2 branched chain, R3 is a —(CH2)n—X group, n is a number from 1 to 4, and X is an amino group, a guanidino group, a —CONH2 group, or a 5-membered ring optionally having 1 to 3 nitrogen atoms, a 6-membered ring optionally having 1 to 3 nitrogen atoms, or a fused heterocycle including a 5-membered ring and a 6-membered ring that optionally has 1 to 3 nitrogen atoms; or a pharmaceutically usable salt of the lipid peptide.
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Page/Page column 25
(2016/05/19)
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- Method for synthesizing fatty acyl glycocoll
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The invention discloses a method for synthesizing fatty acyl glycocoll. The method comprises the steps that an oxidant, a catalyst promoter and an alkali solution are mixed into an aqueous solution, the aqueous solution is added into an organic solvent system formed by mixing fatty acid monoethanolamide and a catalyst, a reaction is carried out for 0.5-3 h under the condition of maintaining the pH of the whole mixed system to be 6.0-12.0 and the temperature to be 20-40 DEG C, then a reaction is carried out for 0.5-2 h under stirring, and a product containing fatty acyl glycocoll is obtained. According to the method for synthesizing fatty acyl glycocoll, the reaction speed and the product yield are high, the reaction condition is mild and easy to control, and the method for synthesizing fatty acyl glycocoll is efficient, conforms to environment-friendly chemistry and is capable of facilitating industrialized production.
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Paragraph 0027; 0028
(2017/01/02)
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- Enzymatic synthesis and characterization of galactosyl monoesters
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Enzyme-catalyzed synthesis of several fatty acyl-amino acid esters based on d-galactose, as well as their chemical evaluation, was performed. These novel galactosyl fatty acyl-amino acid monoesters were synthesized by utilizing lipase from lipozyme TL IM in tert-butanol with d-galactose and fatty acyl-amino acids as starting materials. The products were characterized by 1H NMR, 13C NMR and MS analysis. In addition, their primary physical properties, such as hydrophilic-lipophilic balance (HLB), critical micellar concentration (CMC), solubility in water, maximum surface excess (Γmax), and minimal surface tension (Amin) were measured. The experimental results showed that their CMC values are between 5 and 0.4 mM. The HLB values of galactosyl esters 15-17 indicate that they are useful as oil-in-water emulsions or detergents, whereas 18-22 can be employed as water-in-oil emulsifiers or wetting agents.
- An, Dong,Zhao, Xiaohui,Ye, Zhiwen
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- N-Alkylamido-d-glucamine-based gelators for the generation of thixotropic gels
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Hydrogels made from new gelators, composed of the alkyl chain and a d-glucamine moiety linked together with glycine(s), exhibit thixotropic properties, whereas the hydrogels formed with structurally similar N-alkyl-d-glucamide, which do not contain the glycine moiety, have a tendency to crystallize and do not show thixotropic behaviour.
- Ohsedo, Yutaka,Oono, Masashi,Saruhashi, Kowichiro,Watanabe, Hisayuki
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p. 48554 - 48558
(2014/12/10)
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- Structure and thermotropic phase behavior of a homologous series of n -Acylglycines: Neuroactive and antinociceptive constituents of biomembranes
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N-Acylglycines (NAGs) with different acyl chains have been found in the mammalian brain and other tissues. They exhibit significant biological and pharmacological properties and appear to play important roles in communication and signaling pathways within and between cells. In view of this, a homologous series of NAGs have been synthesized and characterized in the present study. Differential scanning calorimetric (DSC) studies show that the transition enthalpies and entropies of dry as well as hydrated NAGs exhibit a linear dependence on the acyl chain length. Most of the NAGs show a minor transition below the chain-melting phase transition, suggesting the presence of polymorphism in the solid state. Structures of N-myristoylglycine (NMG) and N-palmitoylglycine (NPG) were solved in monoclinic system with C2/c and P21 space groups, respectively. Analysis of the crystal structures show that NAGs are organized in a bilayer fashion, with head-to-head (and tail-to-tail) arrangement of molecules. The acyl chains in both structures are essentially perpendicular to the bilayer plane, which is consistent with a lack of odd-even alternation in the thermodynamic properties. The bilayer is stabilized by strong hydrogen bonding interactions between COOH groups of the molecules from opposite leaflets as well as N-H···O hydrogen bonds between the amide groups of adjacent molecules in the same leaflet and dispersion interactions among the acyl chains. Powder X-ray diffraction data show that the d-spacings for the NAGs with different acyl chains (n = 8-20) exhibit a linear dependence on the chain length, suggesting that all the NAGs investigated here adopt a similar packing arrangement in the crystal lattice. These observations are relevant for understanding the role of N-acylglycines in biological membranes.
- Reddy, S. Thirupathi,Krovi, Krishna Prasad,Swamy, Musti J.
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p. 4944 - 4954
(2014/12/10)
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- The relationship between the structure and properties of amino acid surfactants based on glycine and serine
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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.
- Qiao, Weihong,Qiao, Yangyang
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p. 821 - 828
(2013/11/06)
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- SPRAY BASE MATERIAL INCLUDING LOW-MOLECULAR GELATOR
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There is provided a spray base material that can be safely used with a sense of security, that prevents leakage of liquid from a spray container, that is sprayable under any condition (when inverted, for example), that is sprayable to achieve uniform coat
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Page/Page column 9
(2012/02/15)
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- New N-acylamino acids and derivatives from renewable fatty acids: Gelation of hydrocarbons and thermal properties
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This work reports the synthesis of new fatty N-acylamino acids and N-acylamino esters from the C16:0, C18:0, C18:1, and C18:1(OH) fatty acid families and demonstrates the activity of these compounds as organogel agents. Compounds were heated and dissolved in various solvents (n-hexane, toluene, and gasoline). Only saturated C16:0 and C18:0 derived from alanine were able to form gels in toluene, and saturated C16:0 derived from phenylalanine showed gelation in n-hexane. This is the first evidence that fatty N-acylamino esters and N-acylamino acid derivatives of l-serine and fatty acids C16:0, C18:0, and C18:1 are able to form gels with hexane. This observation confirms the importance of the hydroxyl group in the segment derivative of l-serine in forming good gels.
- Duarte, Rodrigo Da Costa,Ongaratto, Renata,Piovesan, Luciana Almeida,De Lima, Vania Rodrigues,Soldi, Valdir,Merlo, Aloir Ant?nio,D'Oca, Marcelo G. Montes
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p. 2454 - 2460
(2012/06/01)
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- Evaluation of endogenous fatty acid amides and their synthetic analogues as potential anti-inflammatory leads
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A series of endogenous fatty acid amides and their analogues (1-78) were prepared, and their inhibitory effects on pro-inflammatory mediators (NO, IL-1β, IL-6, and TNF-α) in LPS-activated RAW264.7 cells were evaluated. Their inhibitory activity on the pro-inflammatory chemokine MDC in IFN-γ-activated HaCaT cells was also examined. The results showed that the activity is strongly dependent on the nature of the fatty acid part of the molecules. As expected, the amides derived from enone fatty acids showed significant activity and were more active than those derived from other types of fatty acids. A variation of the amine headgroup also altered bioactivity profile remarkably, possibly by modulating cell permeability. Regarding the amine part of the molecules, N-acyl dopamines exhibited the most potent activity (IC50 ~2 μM). This is the first report of the inhibitory activity of endogenous fatty acid amides and their analogues on the production of nitric oxide, cytokines (IL-1β, IL-6, and TNF-α) and the chemokine MDC. This study suggests that the enone fatty acid-derived amides (such as N-acyl ethanolamines and N-acyl amino acids) and N-acyl dopamines may be potential anti-inflammatory leads.
- Dang, Hung The,Kang, Gyeoung Jin,Yoo, Eun Sook,Hong, Jongki,Choi, Jae Sue,Kim, Hyung Sik,Chung, Hae Young,Jung, Jee H.
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experimental part
p. 1520 - 1527
(2011/03/23)
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- Process for converting primary amidoalcohols to amidocarboxylic acids in high yield
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The invention relates to an improved process for oxidizing a primary amidoalcohol to the corresponding amidocarboxylic acid in high yield.
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Page/Page column 5-6; 7
(2008/06/13)
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- A comparative study on the surface activity and micellar behaviour of some N-acylamino acid based surfactants
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N-Hexadecanoyl derivatives of amino acids viz alanine, sarcosine, glycine, aspartic acid, glutamic acid and dioctanoyl derivative of lysine and their sodium salts have been synthesised and characterised spectrophotometrically and by elemental analysis. Activation energy for thermal decomposition of these surfactants has been obtained using thermogravimetric analysis. Studies on surface activity and micellization of these N-acylamino acid based surfactants using surface tension and dye-solubilization techniques reveal specific relationship between their structural characteristics and solution behaviour. The observed trend of CMC for these amphiphiles are explained in terms of varying hydrophobicity with changes in their molecular architecture. Dioctanoyllysinate displays high CMC value by virtue of two short C8-chains compared to the single and more hydrophobic C16-chain of the other surfactants. Hexadecanoylaspartate and glutamate, with their hydrophilicity enhanced by the presence of two carboxylate head groups, also display relatively higher CMCs. Solubilizing properties for these surfactants follow an order similar to that observed for their CMCs. Areas per molecule calculated indicate the influence of molecular structure on the packing of these surfactants at the air-water interface.
- George, Alex,Modi, Jayesh,Jain, Nirmesh,Bahadur, Pratap
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p. 985 - 992
(2007/10/03)
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- Cosmetic composition
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A composition suitable for topical application to mammalian skin and hair for inducing, maintaining or increasing hair growth comprises a hair growth promoter chosen from glutamine derivatives and salts thereof. The composition preferably also comprises an activity enhancer which may be chosen from hair growth stimulants, penetration enhancers and cationic polymers.
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- Determination of N-terminal myristoylation of proteins using a combined gas chromatographic/mass spectrometric assay of derived myristoylglycine: Electron impact-induced fragmentation of acylglycine derivatives
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A method based on gas chromatography/mass spectrometry is described for the detection of N-terminal myristoylation of proteins. Myristoylglycine, derivatized as its trimethylsily (TMS) ester, gave an electron impact mass spectrum containing abundant molecular and [M - CH3]+ ions, together with several ions diagnostic of the acyl glycine moiety, namely at m/z 145, 158, 172 and 189. The compositions of these ions and the mechanism that produced them were investigated by high-resolution mass measurements, deuterium labelling and the preparation of analogons compounds. As these ions were present in the spectra of all acylglycines examined, they could be used as markers for these compounds. A selected-ion monitoring method for the detection of myristoylglycine was set up using the above ions and was used to confirm the presence of N-terminal myristoylation in three referenee peptides. A series of ions produced by radical-induced cleavage of the alkyl chain following TMS group migration and elimination of carbon dioxide gave information on the structure of the chain and could be used to determine the structure of other potential acylglycines such as those with unsaturated acyl chains. Thus the derivatives could be used not only to detect myristoylation of protein, but also to detect and determine the structures of other acyl substituents.
- McIlhinney,Harvey
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p. 900 - 910
(2007/10/02)
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- Cosmetic composition containing DOPA derivatives
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A composition for topical application to human hair or skin contains a chemical analogue of dihydroxyphenyl alanine (DOPA). This chemical analogue can be absorbed by skin or by a hair follicle and metabolised in-vivo, thus leading to the formation of melanin in skin or to the growth of melanin-pigmented hair. Consequently the composition can give controlled skin darkening to mimic sun-induced tanning or can bring about the growth of dar hair in place of the grey or white hair.
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- Cosmestic composition
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A composition suitable for topical application to mammalian skin and hair for inducing, maintaining or increasing hair growth comprises a hair growth promoter chosen from glutamic acid derivatives and salts thereof. The composition preferably also comprises an activity enhancer which may be chosen from hair growth stimulants, penetration enhancers and cationic polymers.
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- Hair growth composition containing citric acid esters
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Triesters of citric acid are used for inducing, maintaining or increasing hair growth. Compositions for topical application to mammalian hair or scalp comprise an effective amount of from 1% to 99% by weight of an ester of citric acid having the structure (1): where, R1, R2 and R3 each independently represent a branched or unbranched alkyl, alkenyl, aryl, alkylaryl or arylalkyl group, each said group having from 1 to 18 carbon atoms, R4 represents -H, or a branched or unbranched saturated or unsaturated acyl, alkyl, aryl, alkylaryl or aylalkyl group having from 1 to 18 carbon atoms, in the presence of a cosmetically acceptable vehicle for the citric acid ester and in the absence of solid absorbent for the ester;, said effective amount of said ester being sufficient to increase hair growth in the rat, when said composition is applied topically thereto over a period of no more than three months, by at least 10% more than that obtainable using a control composition from which the said ester has been omitted, in accordance with the Rat Hair Growth Test.
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- Cosmetic composition
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A composition suitable for topical application to mammalian skin and hair for inducing, maintaining or increasing hair growth comprises a hair growth promoter chosen from N-acylated amino-acids, in which the acyl group has from 2 to 20 carbon atoms, together with a cosmetically acceptable vehicle for the hair growth promoter.
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- Melting Behaviour of Some Pure N-Acyl Amino Acids and Peptides
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Fifty three tlc pure N-acyl amino acids were synthesized by Schotten-Baumann reaction from glc pure odd and even chain fatty acids and chromatographycally homogeneous amino acids and a few N-acyl peptides were prepared through the carboxylic carbonic anhydride intermediates.The melting points are reported and discussed.
- Iyer, Venkataraman N.,Sheth, Geeta N.,Subrahmanyam, V. V. R.
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p. 856 - 859
(2007/10/02)
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- Dermatological compositions containing an acylamino-carboxylic acid or an alkyl ester thereof
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Topical dermatological compositions containing an acylamino-carboxylic acid compound of the formula STR1 wherein R1 is hydrogen, alkyl of 1 to 3 carbon atoms, trifluoromethyl, phenyl, halo-phenyl, nitro-phenyl or biphenylyl, R2 is hydrogen or alkyl of 1 to 3 carbon atoms, R3 is hydrogen, alkyl of 1 to 6 carbon atoms, methylthio-(alkyl of 1 to 6 carbon atoms) or benzyl, R4 is alkyl of 10 to 22 carbon atoms, n is 0, 1 or 2, R5 is alkyl of 8 to 22 carbon atoms, phenyl or biphenylyl, and R6 is hydrogen or alkyl of 1 to 3 carbon atoms; the compositions are useful for the care of the skin.
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