Gene/Protein Disease Symptom Drug Enzyme Compound
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Query: CAS:5292-21-7 (cyclohexylacetic acid)
 16 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

The lipids of the gram-negative bacterium Marinobacter hydrocarbonoclasticus grown in a synthetic seawater medium supplemented with various hydrocarbons as the sole carbon source were isolated, purified, and their structures determined. The hydrocarbons were normal, iso, anteiso, and mid-chain branched alkanes, phenylalkanes, cyclohexylalkanes, and a terminal olefin. According to the sequential procedure used for lipid extraction, three pools were isolated: unbound lipids extracted with organic solvents (corresponding to metabolic lipids and to the main part of membrane lipids), OH- labile lipids [mainly ester-bound in the lipopolysaccharides (LPS)], and H+ labile lipids (mainly amide-bound in the LPS). Each pool contained FA, fatty alcohols, and beta-hydroxy acids. The proportions of these lipids in the unbound lipid pools were 84-98%, 1.1-11.6%, and 0.1-3.6% (w/w), respectively. The chemical structures of the lipids were strongly correlated with those of the hydrocarbons fed; analytical data suggested a metabolism essentially through oxidation into primary alcohol, then into FA and degradation via the beta-oxidation pathway. Sub-terminal oxidation of the hydrocarbon chains, alpha-oxidation of FA or double-bond oxidation in the case of the terminal olefin, were minor, although sometimes substantial, routes of hydrocarbon degradation. Cyclohexyldodecane did not support growth, likely because of the toxicity of cyclohexylacetic acid formed in the oxidation of the alkyl side chain. In the OH- and H+ labile lipid pools, beta-hydroxy acids, the lipophilic moiety of LPS, generally dominated (28-72% and 64-98%, w/w, respectively). The most remarkable feature of these cultures on hydrocarbons was the incorporation in LPS of beta-hydroxy acids with Codd, omega-unsaturated, iso, or anteiso alkyl chains in addition to the specific beta-hydroxy acid of M. hydrocarbonoclasticus, 3-OH-n-12:0. These beta-hydroxy acids were tolerated insofar as their geometry and steric hindrance were close to those of the 3-OH-n-12:0 acid.
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PMID:Effects of hydrocarbon structure on fatty acid, fatty alcohol, and beta-hydroxy acid composition in the hydrocarbon-degrading bacterium Marinobacter hydrocarbonoclasticus. 1550 46

Aqueous solution, 10 mm, of cyclohexanecarboxylic, cyclohexylacetic, cyclohexylpropionic, cyclohexylbutyric acids (all components of naphthenic acid); cis-1,2-, and trans-1, 4-cyclohexyldicarboxylic acids; 3-cyclohexene-1-carboxylic and cyclohexylsulfamic acids; and cyclohexyl mercaptan were applied to 14-day-old bush bean plants, Phaseolus vulgaris L. cv. Top Crop. Only cyclohexanecarboxylic and cyclohexylacetic acid resulted in a statistically significant (P = 0.05) increase in pod production per plant in all experiments. The stimulation by the first four monocarboxylic acids decreased as the number of methylene groups in the side chain increased from 0 to 3. The effective compounds possessed an H-saturated 6-carbon ring with a single carboxyl group attached directly to the ring or separated from it by no more than one methylene group.
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PMID:Structure of some cyclohexyl compounds as related to their ability to stimulate plant growth. 1665 47

Six cyclohexylacetic acid-degrading strains were isolated from soil samples in Japan and identified as members of the genera Cupriavidus (strain KUA-1), Rhodococcus, and Dietzia by 16S rRNA gene sequence analysis. For the first time members of these genera were shown to be capable of degrading cyclohexylacetic acid. A selected strain, KUA-1, which is the first reported Gram-negative organism capable of growth on cyclohexylacetic acid, was identified as a Cupriavidus metallidurans, based on morphologic and physiologic characteristics and its 16S rRNA gene sequence. Metabolite analysis by HPLC-MS indicated that 1-cyclohexenylacetic acid is an intermediate of cyclohexaneacetic acid metabolism in strain KUA-1.
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PMID:Isolation and characterization of new cyclohexylacetic acid-degrading bacteria. 1839 90

A new cyclohexylacetic acid derivative, named 2-{4-hydroxy-7-oxabicyclo [2.2.1] heptanyl}-acetic acid (1), was isolated from Emilia sonchifolia, together with a known analogue, 2-(1,4-dihydroxy cyclohexanyl)-acetic acid (2). Their structures were determined on the basis of spectroscopic techniques including IR, NMR, HR-ESI-MS and X-ray diffraction.
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PMID:A new cyclohexylacetic acid derivative from the aerial parts of Emilia sonchifolia. 2316 44

Through synthetic lethality screening of isogenic cell lines with and without the oncogenic KRAS gene and through lead compound optimization, we recently developed a novel anticancer agent designated NSC-743380 (oncrasin-72) that has promising in vitro and in vivo anticancer activity in a subset of cancer cell lines, including KRAS-mutant cancer cells. However, NSC-743380 tends to form dimers, which dramatically reduces its anticancer activity. To improve the physicochemical properties of NSC-743380, we synthesized a prodrug of NSC-743380, designated oncrasin-266, by modifying NSC-743380 with cyclohexylacetic acid and evaluated its in vitro and in vivo properties. Oncrasin-266 spontaneously hydrolyzed in phosphate-buffered saline in a time-dependent manner and was more stable than NSC-743380 in powder or stock solutions. In vivo administration of oncrasin-266 in mice led to the release of NSC-743380 which improved the pharmacokinetics of NSC-743380. Tissue distribution analysis revealed that oncrasin-266 was deposited in liver, whereas released NSC-743380 was detected in liver, lung, kidney, and subcutaneous tumor. Oncrasin-266 was better tolerated in mice at a higher dose level treatment (150-300 mg/kg, ip) than the parent agent was, suggesting that the prodrug reduced the acute toxicity of the parent agent. Our results demonstrated that the prodrug strategy could improve the stability, pharmacokinetic properties, and safety of NSC-743380.
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PMID:Prodrug oncrasin-266 improves the stability, pharmacokinetics, and safety of NSC-743380. 2518 64

The cycloalkanes, comprising up to 45% of the hydrocarbon fraction, occur in crude oil or refined oil products (e.g., gasoline) mainly as alkylated cyclohexane derivatives and have been increasingly found in environmental samples of soil and water. Furthermore, short-chain alkylated cycloalkanes are components of the so-called volatile organic compounds (VOCs). This study highlights the biotransformation of methyl- and ethylcyclohexane by the alkane-assimilating yeast Candida maltosa and the phenol- and benzoate-utilizing yeast Trichosporon mucoides under laboratory conditions. In the course of this biotransformation, we detected 25 different metabolites, which were analyzed by HPLC and GC-MS. The biotransformation process of methylcyclohexane in both yeasts involve (A) ring hydroxylation at different positions (C2, C3, and C4) and subsequent oxidation to ketones as well as (B) oxidation of the alkyl side chain to hydroxylated and acid products. The yeast T. mucoides additionally performs ring hydroxylation at the C1-position and (C) oxidative decarboxylation and (D) aromatization of cyclohexanecarboxylic acid. Both yeasts also oxidized the saturated ring system and the side chain of ethylcyclohexane. However, the cyclohexylacetic acid, which was formed, seemed not to be substrate for aromatization. This is the first report of several new transformation reactions of alkylated cycloalkanes for eukaryotic microorganisms.
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PMID:Fungal biotransformation of short-chain n-alkylcycloalkanes. 3094 61


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