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At least 19 recordsLinked to original sources
PubMed2003

Antioxidant action of a lipophilic nitroxyl radical, cyclohexane-1-spiro-2'-(4'-oxyimidazolidine-1'-oxyl) -5'-spiro-1"-cyclohexane, against lipid peroxidation under hypoxic conditions.

Nitroxyl radicals are known to act as radical scavenging antioxidants. In the present study, a lipophilic nitroxyl radical, cyclohexane-1-spiro-2'-(4'-oxyimidazolidine-1'-oxyl)-5'-spiro-1"-cyclohexane (nitroxyl radical I) was synthesized and its antioxidant capacity was assessed in comparison with a hydrophilic nitroxyl radical, 4-hydroxy-2,2,6,6-tetra-methylpiperidine-N-oxyl (Tempol). Both nitroxyl radical I and Tempol inhibited methyl linoleate oxidation induced by free radicals, and the efficacy increased with decreasing partial pressure of oxygen, the effect being more pronounced for nitroxyl radical I than Tempol. Their hydroxylamines inhibited lipid peroxidation more effectively than their corresponding parent nitroxyl radicals. In liposomal membranes, a synergistic effect was observed in the combination of nitroxyl radical I with ascorbic acid, whereas only an additive effect was observed between Tempol and ascorbic acid. The present study suggests that nitroxyl radical I and its hydroxylamine may act as potent antioxidants, especially in combination with ascorbic acid under hypoxic conditions.

Air↗
PubMed1995

Inhibition of 4-hydroxyphenylpyruvate dioxygenase by 2-(2-nitro-4-trifluoromethylbenzoyl)-cyclohexane-1,3-dione and 2-(2-chloro-4-methanesulfonylbenzoyl)-cyclohexane-1,3-dione.

The administration of the compound 2-(2-nitro-4-trifluoromethylbenzoyl)-cyclohexane-1,3-dione (NTBC) to rats (10 mg/kg body wt) caused an elevation in the concentration of plasma tyrosine and gave products in urine that were identified as 4-hydroxyphenylpyruvate (HPPA) and 4-hydroxyphenyllactate (HPLA). This observed chemically induced tyrosinemia established that this compound perturbs tyrosine catabolism and suggested that the causal effect is the inhibition of 4-hydroxyphenylpyruvate dioxygenase (HPPD). This was confirmed when rat liver HPPD was found to be markedly inhibited by NTBC when the enzyme and chemical were incubated, in vitro, for 3 min at 37 degrees C prior to the initiation of the enzyme reaction by the addition of substrate. At 100 nM NTBC, approximately 90% of the enzyme activity was lost and an IC50 was calculated at approximately 40 nM. The inhibition of HPPD by NTBC (50 nM) is time-dependent; the enzyme activity was reduced by > 50% within 30 sec. Progress curve data of loss of enzyme activity with time gave a rate constant for the inactivation of rat liver HPPD [k*, formation of an HPPD-inhibitor (EI) complex] by NTBC of 9.9 +/- 2.5 x 10(-5) sec-1 nM-1. It was established that NTBC is not irreversibly bound in the EI complex but slowly dissociates with a recovery of enzyme activity of 13.7 +/- 1.0% over a 7-hr period (t1/2, 25 degrees C estimated at 63 hours). In comparison, the compound 2-(2-chloro-4-methanesulfonylbenzoyl)-cyclohexane-1,3-dione (CMBC), an analog of NTBC, gave a similar rate for the inactivation of HPPD (k*, 3.3 +/- 0.8 x 10(-5) sec-1 nM-1), whereas 45 +/- 8% of the enzyme activity was recovered over a 7-hr period (t1/2, 25 degrees C approximately 10 hr). These studies establish that NTBC and CMBC are potent, time-dependent (tight-binding) reversible inhibitors of HPPD. The inhibition is characterized by a rapid inactivation of the enzyme by the formation of an HPPD-inhibitor complex that dissociates with recovery of enzyme activity. In vivo, the inhibition of HPPD causes a tyrosinemia that abates with the recovery of enzyme activity. The understanding of the mechanism by which NTBC perturbs tyrosine catabolism has led to the clinical use of this chemical as the first effective pharmacological therapy for the hereditary disorder tyrosinemia I.

4-Hydroxyphenylpyruvate Dioxygenase↗
PubMed2005

Universal isotope effect in thermal diffusion of mixtures containing cyclohexane and cyclohexane-d12.

The Soret coefficients S(T) of the liquids acetone, benzene, benzene-d1, 1,3,5-benzene-d3, benzene-d5, benzene-13C6, benzene-d6, n-hexane, toluene, 1,2,3,4-tetrahydronaphthalene, isobutylbenzene, and 1,6-dibromohexane have been measured in protonated and perdeuterated cyclohexane by a transient holographic grating technique. It has been found that S(T) can be either positive or negative and even change its sign as a function of concentration. The isotope effect DeltaS(T)=-0.99 x 10(-3) K(-1), which is the change of S(T) after isotopic substitution of cyclohexane, neither depends on concentration nor on the nature of the mixing partner. Only in the case of the polar acetone is DeltaS(T) approximately 30% larger but still concentration independent. Based on the experimental findings, some general conclusions about the dependence of the Soret coefficient on molecular properties are drawn.

Journal Article↗
PubMed2002

Dispiro[2H-benzimidazole-2,1'-cyclohexane-4',2''-[2H]benzimidazole] 1-oxide and dispiro[2H-benzimidazole-2,1'-cyclohexane-4',2''-[2H]benzimidazole] 1,1''-dioxide.

Oxidation of tetrahydrodispirobenzimidazole by m-chloroperbenzoic acid did not produce dispiro-2H-benzimidazole, which is the product obtained by oxidation with MnO(2). Instead, a mixture of two compounds was identified, namely dispiro[2H-benzimidazole-2,1'-cyclohexane-4',2''-[2H]benzimidazole] 1-oxide, C(18)H(16)N(4)O, (III), and dispiro[2H-benzimidazole-2,1'-cyclohexane-4',2''-[2H]benzimidazole] 1,1''-dioxide, C(18)H(16)N(4)O(2), (IV). In (III), the molecules are disordered about a twofold rotation axis and have 2/m site symmetry. In (IV), the crystals are triclinic and the molecules occupy crystallographic inversion centers. Although the two compounds are very similar and are arranged in layers, they adopt completely different packing modes within the layers, viz. herring-bone in (III) and parallel molecules in (IV). The molecules within the layers are held together by C-H...O and C-H...N hydrogen bonds.

Journal Article↗
PubMed1977

The metabolism of trans-cyclohexan-1,2-diol by an Acinetobacter species.

1. Acinetobacter TD63 was one of some thirty organisms isolated by elective culture with trans-cyclohexan-1,2-diol as sole source of carbon. The great majority of these isolates displayed the same growth spectrum as Nocardia globerula CL1 and Acinetobacter NCIB 9871 being capable of utilizing trans-cyclohexan-1,2-diol, 2-hydroxycyclohexan-1-one, cyclohexanol, cyclohexanone,1-oxa-2oxocycloheptane and adipate and were assumed to use well described metabolic pathways. 2. Acinetobacter TD63 was distinctive in being incapable of growth with cyclohexanol, cyclohexanone or 1-oxa-2-oxocycloheptane and because of this it was hoped that it would display an alternative pathway for the oxidation of trans-cyclohexan-1,2-diol. 3. Studies with cell extracts have shown the presence of inducible dehydrogenase for the conversion of trans-cyclohexan-1,2-diol to 2-hydroxycyclohexan-1-one and cyclohexan-1,2-dione and of 6-oxohexanoate to adipate. These enzymes are linked into a metabolic sequence by the action of a monooxygenase of broad specificity but efficiently capable of converting 2-hydroxy-cyclohexan-1-one into the lactone 1-oxa-2-oxo-7-hydroxycycloheptane that spontaneously rearranges to yield 6-oxohexanoate. 4. An enzyme capable of attacking cyclohexan-1,2-dione (mono-enol) in the absence of an electron donor or oxygen has also been detected. Evidence has been presented indicating that this enzyme catalyses a keto-enol tautomerization between cyclohexan-1,2-dione (mono-enol) and cyclohexan-1,2-dione (mono-hydrate) and is not involved in the pathway of ring cleavage. 5. The failure of Acinetobacter TD63 to grow with cyclohexanol, cyclohexanone or 1-oxa-2-oxocycloheptane is due not to this organism possessing a distinctive metabolic sequence but to a narrow inducer specificity coupled with an inability to form a lactone hydrolase enabling it to cleave the stable 1-oxa-2-oxocycloheptane which is an intermediate in the established pathway of cyclohexanol and cyclohexanone oxidation.

Acinetobacter↗
PubMed1985

Isolation and Characterization of a Cyclohexane-Metabolizing Xanthobacter sp.

An unusual Xanthobacter sp., capable of independent growth on cyclohexane as the sole source of carbon and energy, has been isolated from soil by using classical enrichment techniques. The mean generation time for growth on cyclohexane was 6 h. The microorganism showed a limited ability to utilize hydrocarbons, with only alicyclic hydrocarbons closely related to cyclohexane supporting growth. Ultrastructural studies indicated the presence of electron-transparent vesicles in the cyclohexane-grown Xanthobacter sp., but the presence of complex intracytoplasmic membranes could not be identified. A soluble inducible enzyme capable of oxidizing cyclohexane was identified in cell extracts. This enzyme had a pH optimum of 6.5, an absolute specificity for NADPH, and a stoichiometric requirement for molecular O(2) which was consistent with the formation of cyclohexanol. The enzyme showed no activity towards straight chain alkanes and only a limited activity towards unsaturated ring compounds. Enzymatic studies with cell extracts have indicated the main route of metabolism of cyclohexane by this Xanthobacter sp. to proceed via cyclohexane --> cyclohexanol --> cyclohexanone --> 1-oxa-2-oxocycloheptane (epsilon-caprolactone) --> 6-hydroxyhexanoate (6-hydroxycaproate) --> --> adipic acid. Alternative routes involving initial double hydroxylation of the cyclohexane ring may operate fortuituously but are unlikely to represent major pathways for the dissimilation of cyclohexane by this microorganism.

Journal Article↗
PubMed1996

Investigation on neurotoxicity of occupational exposure to cyclohexane: a neurophysiological study.

OBJECTIVES: To examine the effect of occupational exposure to cyclohexane on the peripheral nervous system. METHODS: A nerve conduction study was performed on 18 workers exposed to cyclohexane in a luggage factory and on age and sex matched occupationally unexposed controls. 12 workers had been exposed to n-hexane (median 2.8 years) before the start of exposure to cyclohexane. To confirm the effect of exposure, a follow up study was performed on nine workers one year after the first study. The mean exposure to cyclohexane was 1.2 years in the first study. A symptom survey was performed. The exposure was measured by air sampling of the breathing zone of each worker. The urinary metabolite cyclohexanol was also monitored. RESULTS: The concentration of airborne cyclohexane ranged from 5 to 211 ppm. The urinary concentration of cyclohexanol ranged from 0.12 to 1.51 mg/l. There was a strong correlation between the cyclohexane exposure in personal air and urinary cyclohexanol. No differences were found in nerve conduction velocities (NCV) between workers exposed to cyclohexane and age and sex matched controls. The results of the follow up study showed significant improvements in peroneal motor NCV (P < 0.01) and sural sensory NCV (P < 0.05) and in ulnar motor distal latency (MDL, P < 0.05) and peroneal MDL (P < 0.05) compared with the first study. Although the past n-hexane exposure affected the first neurophysiological study, the effect had disappeared in the second study, one year later. CONCLUSION: Occupational exposure to the concentrations of cyclohexane experienced in this study had no adverse effects on the peripheral nervous system.

Adult↗
PubMed2006

Cyclohexane carboxylate and benzoate formation from crotonate in Syntrophus aciditrophicus.

The anaerobic, syntrophic bacterium Syntrophus aciditrophicus grown in pure culture produced 1.4 +/- 0.24 mol of acetate and 0.16 +/- 0.02 mol of cyclohexane carboxylate per mole of crotonate metabolized. [U-13C]crotonate was metabolized to [1,2-(13)C]acetate and [1,2,3,4,5,7-(13)C]cyclohexane carboxylate. Cultures grown with unlabeled crotonate and [13C]sodium bicarbonate formed [6-(13)C]cyclohexane carboxylate. Trimethylsilyl (TMS) derivatives of cyclohexane carboxylate, cyclohex-1-ene carboxylate, benzoate, pimelate, glutarate, 3-hydroxybutyrate, and acetoacetate were detected as intermediates by comparison of retention times and mass spectral profiles to authentic standards. With [U-(13)C]crotonate, the m/z-15 ion of TMS-derivatized glutarate, 3-hydroxybutyrate, and acetoacetate each increased by +4 mass units, and the m/z-15 ion of TMS-derivatized pimelate, cyclohex-1-ene carboxylate, benzoate, and cyclohexane carboxylate each increased by +6 mass units. With [13C]sodium bicarbonate and unlabeled crotonate, the m/z-15 ion of TMS derivatives of glutarate, pimelate, cyclohex-1-ene carboxylate, benzoate, and cyclohexane carboxylate each increased by +1 mass unit, suggesting that carboxylation occurred after the synthesis of a four-carbon intermediate. With [1,2-(13)C]acetate and unlabeled crotonate, the m/z-15 ion of TMS-derivatized 3-hydroxybutyrate, acetoacetate, and glutarate each increased by +0, +2, and +4 mass units, respectively, and the m/z-15 ion of TMS-derivatized pimelate, cyclohex-1-ene carboxylate, benzoate, cyclohexane carboxylate, and 2-hydroxycyclohexane carboxylate each increased by +0, +2, +4, and +6 mass units. The data are consistent with a pathway for cyclohexane carboxylate formation involving the condensation of two-carbon units derived from crotonate degradation with CO2 addition, rather than the use of the intact four-carbon skeleton of crotonate.

Benzoates↗
PubMed1990

Mouse skin ornithine decarboxylase induction and tumor promotion by cyclohexane.

Cyclohexane, a frequently used solvent in industry, was assessed for its tumorigenic potential on mouse skin following multistage initiation-promotion protocols. The activity of ornithine decarboxylase (ODC), a marker of tumor promotion was found to be induced by the topical application of cyclohexane. This ODC induction was dependent on the dose of cyclohexane used and the duration of application. Effect of protein synthesis inhibitors and the modifiers of tumor promotion on the cyclohexane induced ODC activity was also studied. ODC induction was inhibited by cycloheximide and also, up to some extent, by actinomycin D. Inhibitors of stage II tumor promotion showed more effect on the ODC induction by cyclohexane as compared to the inhibitors of stage I tumor promotion. In chronic animal bioassay experiments topical application of cyclohexane to DMBA initiated mouse skin resulted in just 10% of tumor bearing animals while prior application of TPA for two weeks resulted in 45% of tumor bearing animals. Collectively, the present study demonstrates that cyclohexane is more effective as a stage II tumor promoter over mouse skin and possibly affects the biochemical events at the molecular level.

9,10-Dimethyl-1,2-benzanthracene↗
PubMed1999

Cytochrome P450 isoforms responsible for the N-deethylation and cyclohexane-hydroxylation of NS-21.

1. Cytochrome P450 (P450) isoforms responsible for the N-deethylation and cyclohexane-hydroxylation of (+/-)-4-diethylamino-1,1-dimethylbut-2-yn-1-yl 2-cyclohexyl-2-hydroxy-2-phenylacetate monohydrochloride monohydrate (NS-21) have been identified in rat and man. 2. Anti-CYP2C11 antibody inhibited the N-deethylation of S- and R-NS-21 in rat hepatic microsomes by 84 and 66% respectively, indicating that CYP2C11 is mainly responsible for these activities in male rats. 3. Of several human recombinant P450 isoforms, CYP3A4 had the activities for the N-deethylation of S- and R-NS-21. In addition, triacetyloleandomycin (TAO), an inhibitor of the CYP3A subfamily, significantly inhibited the N-deethylation of S- and R-NS-21 in human hepatic microsomes by 67 and 69%, respectively. CYP3A4 therefore contributes to it in man. 4. Quinine, an inhibitor of the rat CYP2D subfamily, significantly inhibited the cyclohexane-4-cis-hydroxylation of S-NS-21 by 48% in rat hepatic microsomes. In contrast, this inhibitor had little effect on the cyclohexane-4-trans-hydroxylation of S-NS-21, and the cyclohexane-4-cis- and trans-hydroxylation of R-NS-21. 5. Human recombinant CYP3A4 catalysed the cyclohexane-4-trans-hydroxylation of S-NS-21, and CYP2D6 supported the cyclohexane-4-cis- and trans-hydroxylation of S-NS-21. Quinidine, an inhibitor of human CYP2D6, had little effect on these latter activities in human hepatic microsomes. TAO significantly inhibited the cyclohexane-4-trans-hydroxylation of S-NS-21 by 75%, indicating that CYP3A4 catalyses this reaction.

Animals↗
PubMed2006

Overexpression of marA, soxS and acrB in veterinary isolates of Salmonella enterica rarely correlates with cyclohexane tolerance.

OBJECTIVES: To determine the contribution of the AcrAB efflux system to cyclohexane tolerance in Salmonella enterica. METHODS: The expression of the efflux pump gene, acrB, and regulators marA and soxS from 46 isolates of S. enterica of 14 different serovars was determined by comparative RT-PCR and denaturing HPLC analysis. RESULTS: Twenty-one of the 46 isolates were cyclohexane tolerant, a phenotype associated with multiple antibiotic resistance (MAR) and overexpression of efflux pumps. Of the cyclohexane-tolerant isolates 81% were MAR, whereas only 44% of the cyclohexane-susceptible isolates were MAR, confirming the association between cyclohexane tolerance and MAR. However, there was no correlation between cyclohexane tolerance or MAR and overexpression of acrB, soxS or marA. CONCLUSIONS: These data suggest that cyclohexane tolerance in S. enterica can be mediated by an acrB-independent mechanism.

Animals↗
PubMed2005

Farm disinfectants select for cyclohexane resistance, a marker of multiple antibiotic resistance, in Escherichia coli.

AIMS: The aim of this study was to determine if three classes of farm disinfectants were able to select for ciprofloxacin or cyclohexane tolerant [indicative of a multiple antibiotic resistance (MAR) phenotype] Escherichia coli and if cyclohexane-tolerant E. coli could be isolated from farms. METHODS AND RESULTS: Chicken slurry containing ca 1 : 99 ratio ciprofloxacin resistant : susceptible E. coli (10 different resistant strains examined) was treated for 24 h with each of the disinfectants and examined for survival of resistant : susceptible strains. Ciprofloxacin-sensitive (n=5) and -resistant (n=5) E. coli were grown with sublethal concentrations of the disinfectants and then plated to agar containing ciprofloxacin or overlaid with cyclohexane. Escherichia coli (n=389) isolated from farms were tested for cyclohexane tolerance. Minimum inhibitory concentrations (MIC) were determined against representative isolates and mutants. The disinfectants did not select for the ciprofloxacin-resistant E. coli in poultry slurry but following growth with each of the three disinfectants, higher numbers (P < or = 0.023) of cyclohexane-tolerant E. coli were isolated and these had a MAR phenotype. Of the 389 farm E. coli tested, only one was cyclohexane tolerant. CONCLUSIONS: It is possible that in a farm environment, E. coli could be exposed to similar concentrations of the disinfectants that are selected for MAR type organisms under these laboratory conditions. SIGNIFICANCE AND IMPACT OF THE STUDY: Data from this study suggest that cyclohexane-resistant E. coli are not common on farms, but in view of the ease of isolating them in the laboratory with farm disinfectants, further investigations on farms are warranted.

Agrochemicals↗
PubMed2001

Cyclohexane as an alternative vapor of carbon tetrachloride for the assessment of gas removing capacities of gas masks.

An alternative vapor was explored to replace carbon tetrachloride (CCl4) for testing breakthrough times of cartridges and canisters of gas masks in the National Approval Test of Respirators. Cyclohexane was single out as a candidate for the alternative vapor out of six vapors: trichloroethylene, n-pentane, n-hexane, n-heptane, toluene and cyclohexane from the viewpoints of similarity of vapor pressure and water-solubility to CCl4, lower toxicity than CCl4, and technical feasibility in generating an airflow of 30 L/min containing the vapor ranging from 300 to 5000 ppm. Breakthrough times of cartridges and canisters were examined by generating cyclohexane vapor in a test airflow of 30 L/min in comparison with CCl4 vapor under various test conditions with different vapor concentrations and relative humidities (RH). As the results, the breakthrough times of the cartridges and canisters for cyclohexane were found to almost coincide with those for CCl4 under all examined range of concentrations and RH. By an increase of humidity from 50% RH to 80% RH, the cartridges showed significant shortening of breakthrough times for both of CCl4 and cyclohexane, but the susceptibility of the breakthrough time of cyclohexane to humidity was also similar to that of CCl4. It was, therefore, concluded that cyclohexane can be recommended as the alternative vapor of CCl4 for testing the breakthrough times of gas mask cartridges and canisters in the National Approval Test.

Air Pollutants, Occupational↗