Effect of Alkyl Chain Length on Interfacial Performance of Alkyl Gallates in Supramolecular Oxidation of Soybean Bulk Phase Oil

From an interfacial phenomena standpoint, the effect of length of alkyl chain was evaluated on activities of gallic acid and its alkyl ester derivatives in supramolecular oxidation of stripped soybean oil. The gallic acid molecules (log P = -0.47) with an electron-donating carboxylate anion had a higher scavenging activity against DPPH• than alkyl gallates. Interfacial activities of gallates in emulsion and bulk oil improved as the lengths of the alkyl chain were reached until a critical chain length; after that, further chain length extension causes a decrease in potency. In β-carotene bleaching and Rancimat assays higher inhibitory effect was observed for dodecyl and propyl gallate, respectively. Evaluation of interfacial tension, water content, and droplet size of hydroperoxides reverse micelles in parallel with lipid peroxidation indicated that the inhibitory effect of the alkyl gallates, especially methyl gallate, was significantly better than the gallic acid in the bulk phase oil.

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Biodegradation of L-Valine Alkyl Ester Ibuprofenates by Bacterial Cultures

Materials ◽

10.3390/ma14123180 ◽

2021 ◽

Vol 14 (12) ◽

pp. 3180

Author(s):

Edyta Makuch ◽

Paula Ossowicz-Rupniewska ◽

Joanna Klebeko ◽

Ewa Janus

Keyword(s):

Activated Sludge ◽

Chain Length ◽

Alkyl Chain ◽

Water System ◽

Alkyl Chain Length ◽

Log P ◽

Alkyl Esters ◽

Bacterial Cultures ◽

The World ◽

Medicinal Substances

Nowadays, we consume very large amounts of medicinal substances. Medicines are used to cure, halt, or prevent disease, ease symptoms, or help in the diagnosis of illnesses. Some medications are used to treat pain. Ibuprofen is one of the most popular drugs in the world (it ranks third). This drug enters our water system through human pharmaceutical use. In this article, we describe and compare the biodegradation of ibuprofen and ibuprofen derivatives—salts of L-valine alkyl esters. Biodegradation studies of ibuprofen and its derivatives have been carried out with activated sludge. The structure modifications we received were aimed at increasing the biodegradation of the drug used. The influence of the alkyl chain length of the ester used in the biodegradation of the compound was also verified. The biodegradation results correlated with the lipophilic properties (log P).

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Characterization of in situ prepared nanocomposites of PS and TIO2nanoparticles surface modified with alkyl gallates: Effect of alkyl chain length

Polymer Composites ◽

10.1002/pc.22423 ◽

2013 ◽

Vol 34 (3) ◽

pp. 399-407 ◽

Cited By ~ 10

Author(s):

Enis S. Džunuzović ◽

Jasna V. Džunuzović ◽

Tijana S. Radoman ◽

Milena T. Marinović-Cincović ◽

Ljubiša B. Nikolić ◽

...

Keyword(s):

Chain Length ◽

Alkyl Chain ◽

Alkyl Chain Length ◽

Alkyl Gallates ◽

Surface Modified

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The Inhibition of Uric Acid Formation Catalyzed by Xanthine Oxidase Properties of the Alkyl Caffeates and Cardol

Journal of Food Research ◽

10.5539/jfr.v1n3p257 ◽

2012 ◽

Vol 1 (3) ◽

pp. 257 ◽

Cited By ~ 6

Author(s):

Noriyoshi Masuoka ◽

Ken-ichi Nihei ◽

Takayoshi Masuoka ◽

Kouhei Kuroda ◽

Kenji Sasaki ◽

...

Keyword(s):

Uric Acid ◽

Xanthine Oxidase ◽

Chain Length ◽

Inhibitory Activity ◽

Alkyl Chain ◽

Alkyl Chain Length ◽

Acid Formation ◽

Alkyl Gallates ◽

Xanthine Oxidase Inhibitors ◽

Specific Structural Feature

Xanthine oxidase inhibitors may serve as therapeutic agents for hyperuricaemia and/or oxidative stress. From our continuing investigation, we proposed that some inhibitors for reactions catalyzed by xanthine oxidase consisted of a head portion and a tail portion and that each portion had different functions for inhibition. In a previous study on the effect of alkyl gallates on the uric acid formation catalyzed by xanthine oxidase it was shown that the alkyl chain length needs to be longer than C6 to exert inhibitory activity. In the current study, compounds having different head portions, alkyl caffeates, alkyl protocatechuates, alkyl 3,5-dihydroxybenzoates, 3,4- dihydroxyphenylalkanoates and 3,5-dihydroxyphenylalkanoates were prepared, and their effects on the uric acid formation were examined. A series of alkyl caffeates (C1-C10) was demonstrated effective in inhibiting the uric acid formation, and the inhibitory activity increased by increasing the alkyl chain length. However, none of the other compounds was effective in inhibiting the uric acid formation. These results indicate that head portions in these compounds are important for the inhibition of uric acid formation and require further a specific structural feature to elicit the inhibitory activity.

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Synthesis and Assessment of Novel Anti-chlamydial Benzylidene Acylhydrazides Derivatives

Letters in Drug Design & Discovery ◽

10.2174/1570180814666170526170227 ◽

2018 ◽

Vol 15 (1) ◽

pp. 31-36 ◽

Cited By ~ 5

Author(s):

Xiaofeng Bao ◽

Ying Xue ◽

Chao Xia ◽

Yin Lu ◽

Ningjing Yang ◽

...

Keyword(s):

Inhibitory Effect ◽

Dependent Manner ◽

Iron Starvation ◽

Hydrochloride Salt ◽

Obligate Intracellular ◽

Biphasic Life Cycle ◽

Ic50 Value ◽

Ic50 Values ◽

Dose Dependent ◽

Better Than

Background: Chlamydiae, characterized by a unique biphasic life cycle, are a group of Gram-negative obligate intracellular bacterial pathogens responsible for diseases in a range of hosts including humans. Benzylidene acylhydrazide CF0001 could inhibit chlamydiae independent of iron starvation and T3SS inhibition. This finding promoted us to design and synthesize more benzylidene acylhydrazides to find novel anti-chlamydial agents. Methods: The carboxylic acids 1a-1d were coupled with Boc-hydrazide inpresence of EDCI and DMAP to obtain the intermediate 2a-2d in 60-62% yields. N-Boc deprotections were performed to obtain hydrazide hydrochloride salt 3a-3d. Nextly, the hydrazides were subjected to condensation with aldehydes to obtain benzylidene acylhydrazides 4a-4g in 30-52% yields in two steps. Results: Compound 4d exhibited best inhibitory effect on the formation and growth of chlamydial inclusions. The IC50 value of compound 4d for infectious progenies was 3.55 µM, better than 7.30 µM of CF0001. Conclusion: To find novel anti-chlamydial agents, we have designed and synthesized benzylidene acylhydrazides 4a-4g. Compounds 4a, 4d, 4g showed inhibitory activity on C. muridarum with the IC50 values from 3.55-12 µM. The 3,5-dibromo-4-hydroxyl substitutes on ring B are critical to keep their anti-chlamydial activity. Compound 4d inhibited C. muridarum in a dose-dependent manner without apparent cytotoxicity.

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Influence of alkyl chain length on the action of acetylated monoglycerides as plasticizers for poly (vinyl chloride) food packaging film

Food Packaging and Shelf Life ◽

10.1016/j.fpsl.2020.100619 ◽

2021 ◽

Vol 27 ◽

pp. 100619

Author(s):

Chang Woo Kwon ◽

Pahn-Shick Chang

Keyword(s):

Chain Length ◽

Vinyl Chloride ◽

Food Packaging ◽

Alkyl Chain ◽

Alkyl Chain Length ◽

Packaging Film ◽

Poly Vinyl Chloride

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Silver Nanoparticles Stabilized with Phosphorus-Containing Heterocyclic Surfactants: Synthesis, Physico-Chemical Properties, and Biological Activity Determination

Nanomaterials ◽

10.3390/nano11081883 ◽

2021 ◽

Vol 11 (8) ◽

pp. 1883

Author(s):

Martin Pisárčik ◽

Miloš Lukáč ◽

Josef Jampílek ◽

František Bilka ◽

Andrea Bilková ◽

...

Keyword(s):

Silver Nanoparticles ◽

Biological Activity ◽

Zeta Potential ◽

Chain Length ◽

Alkyl Chain ◽

Chemical Properties ◽

Alkyl Chain Length ◽

Microbial Pathogens ◽

Physico Chemical ◽

Phosphorus Containing

Phosphorus-containing heterocyclic cationic surfactants alkyldimethylphenylphospholium bromides with the alkyl chain length 14 to 18 carbon atoms were used for the stabilization of silver nanodispersions. Zeta potential of silver nanodispersions ranges from +35 to +70 mV, which indicates the formation of stable silver nanoparticles (AgNPs). Long-chain heptadecyl and octadecyl homologs of the surfactants series provided the most intensive stabilizing effect to AgNPs, resulting in high positive zeta potential values and smaller diameter of AgNPs in the range 50–60 nm. A comparison with non-heterocyclic alkyltrimethylphosphonium surfactants of the same alkyl chain length showed better stability and more positive zeta potential values for silver nanodispersions stabilized with heterocyclic phospholium surfactants. Investigations of biological activity of phospholium-capped AgNPs are represented by the studies of antimicrobial activity and cytotoxicity. While cytotoxicity results revealed an increased level of HepG2 cell growth inhibition as compared with the cytotoxicity level of silver-free surfactant solutions, no enhanced antimicrobial action of phospholium-capped AgNPs against microbial pathogens was observed. The comparison of cytotoxicity of AgNPs stabilized with various non-heterocyclic ammonium and phosphonium surfactants shows that AgNPs capped with heterocyclic alkyldimethylphenylphospholium and non-heterocyclic triphenyl-substituted phosphonium surfactants have the highest cytotoxicity among silver nanodispersions stabilized by the series of ammonium and phosphonium surfactants.

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