Disease relevance of cyclohexanol

• Identification of a transcriptional activator (ChnR) and a 6-oxohexanoate dehydrogenase (ChnE) in the cyclohexanol catabolic pathway in Acinetobacter sp. Strain NCIMB 9871 and localization of the genes that encode them [1].
• A set of transposon mutants with a single insertion in each of the ORFs was screened for cyclohexanol oxidation in E. coli [2].
• An esterase homologue located directly upstream of the Xanthobacter BVMO gene and a dehydrogenase homologue encoded directly downstream of the Comamonas sp. NCIMB 9872 BVMO gene were also expressed in E. coli and shown to specify lactone hydrolase and cyclohexanol dehydrogenase activity respectively [3].
• Enzyme reactions involved in anaerobic cyclohexanol metabolism by a denitrifying Pseudomonas species [4].
• The ability of cyclohexanol to inhibit the mutagenicity of tobacco-specific nitrosamine 4-(N-nitrosomethylamino)-1-(3-pyridyl)-1-butanone (NNK) and of N-nitrosodiethylamine (NDEA) was tested on Salmonella typhimurium strain TA100 [5].

High impact information on cyclohexanol

• Transient kinetics experiments show that cyclohexanol inhibition is due to a slower rate of dissociation of NADH from the abortive enzyme-NADH-cyclohexanol complex than from the enzyme-NADH complex [6].
• MmADH alpha reacts 130-fold slower (V/K) with ethanol and 3-25-fold slower with 2-methyl alcohols but 20-fold faster with cyclohexanol, as compared with horse (Equus caballus) liver EE isoenzyme (EqADH) [7].
• Docking of cyclohexanol-derivatives into the active site of liver alcohol dehydrogenase. Using computer graphics and energy minimization [8].
• A highly efficient MEEKC separation method was achieved within 14 min by using a microemulsion solution of pH 2.0 containing 2.89% w/v SDS, 1.36% w/v heptane, 7.66% w/v cyclohexanol, and 2% w/v ACN [9].
• The reaction is found to be first-order with respect to acetic anhydride, cyclohexanol, and DMAP, and zero-order with respect to triethyl amine [10].

Chemical compound and disease context of cyclohexanol

• The enzymes involved in the anaerobic degradation of cyclohexanol were searched for in a denitrifying Pseudomonas species which metabolizes this alicyclic compound to CO2 anaerobically [4].
• 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 [11].
• Nicomol (2,2,6,6,-tetrakis (nicotinoyloxymethyl) cyclohexanol), an inhibitor for the rapid rise of plasma FFA, was effective in the treatment and prevention of arrhythmia in ischemic heart disease and diabetes mellitus [12].

Biological context of cyclohexanol

• This lattice was oriented and positioned into the active site using the productive binding mode of cyclohexanol derivatives obtained from model building [8].
• Addition of alcohol does not affect the selectivity, but allows displacement of the optimum separation conditions to higher cyclodextrin concentration through either competitive binding (with cyclohexanol) or preferential solvation of reactants (with methanol) [13].
• A second gene cluster (11 kb) contains almost all the genes required for the oxidation of cyclohexanol to adipic acid [14].
• A region that was essential for cyclohexanol oxidation was localized to a 14-kb fragment on the cosmid DNA [2].
• The acylation of cyclic and aromatic alcohols, such as cyclohexanol or phenylethanol, further underlines the unspecific character of this enzyme [15].

Anatomical context of cyclohexanol

• Acetylcholine synthesis and release by a sympathetic ganglion in the presence of 2-(4-phenylpiperidino) cyclohexanol (AH5183) [16].
• Isolated hepatocytes from fed rats were incubated with cyclohexanone and cyclohexanol or with [1,1-2H2]-and [2,2,2-2H3]ethanol, followed by gas chromatographic determination of the redox state and isotope analysis of the ethanol by gas chromatography-mass spectrometry, respectively [17].
• Acetylcholine efflux at the rat neuromuscular junction was assayed following blockage of ACh transport into synaptic vesicles by 2-(4-phenylpiperidino) cyclohexanol (AH5183) [18].
• Only the small intestine showed (-)-3-[2-hydroxyl-4-(1,1-dimethylheptyl)-phenyl]-4-(3-hydroxylpropyl) cyclohexan-1-ol) ([3H]CP 55,940) specific binding (27%) [19].
• In the guinea-pig myenteric plexus preparation, it antagonized WIN 55.212-2 [(R)-(+)-[2,3-dihydro-5-methyl-3-[(4-morpholino)methyl]pyrrolo-[1,2,3-de ]-1, 4-benzoxazin-6-yl](1-naphthyl)methanone] and CP 55.940 [(-)-3-[2-hydroxy-4-(1,1-dimethylheptyl)phenyl]-4-(3-hydroxypropyl ) cyclohexan-1-ol] with Kd values of 0.65 and 0.27 nM, respectively [20].

Associations of cyclohexanol with other chemical compounds

• The nonhyperbolic saturation kinetics for oxidation of ethanol, cyclohexanol, and 1-butanol are quantitatively explained with the abortive complex mechanism [6].
• A conformational change, termed the T --> R transition, which can be detected by visible, circular dichoric, and fluorescence spectroscopy, occurs in native insulin and tryptophan substituted insulin analogs ([TrpB25]-, [TrpB26]-, [GlyB24,TrpB25]-, and [GlyB24,TrpB26]insulin) upon binding specific alcohol ligands, including phenol and cyclohexanol [21].
• To impart porosity to the product, cyclohexanol and 1-dodecanol were added as inert diluents to the polymerization mixture [22].
• The kinetics and interactions of cyclohexanol and benzyl alcohol with the isozymes were judged by docking experiments using an interactive fitting program.(ABSTRACT TRUNCATED AT 400 WORDS)[23]
• An autoradiographic analysis of high-affinity binding sites for the vesicular acetylcholine transport blocker [3H]vesamicol (2-(4-phenylpiperidino) cyclohexanol; AH 5183) was conducted in rat brain [24].

Gene context of cyclohexanol

• Here, we tested the effect upon Arc expression of a novel antidepressant and selective 5-hydroxytryptamine/noradrenaline reuptake inhibitor (SNRI), (-)1-(1-dimethylaminomethyl) 5-methoxybenzocyclobutan-1-yl) cyclohexanol (S33005) [25].
• Oxidation of cyclohexanol by the homodimers beta 2 beta 2 and gamma 1 gamma 1 follows conventional Michaelis-Menten kinetics [26].
• Cyclohexanol and methylcyclohexanols. A family of inhibitors of hepatic HMGCoA reductase in vivo [27].
• In addition, the 7' (a = 15.9712(18) angstroms, b = 15.9253(19) angstroms, c = 18.475(2) angstroms, Pbca), a compound isostructural with 7, is synthesized by using cyclohexanol as a template [28].
• Immunoglobulin G, which recognizes each stereoisomeric cyclohexanol moiety, was coupled to cyanogen bromide-activated Sepharose 4B to prepare re-usable immobilized antibody, and its specificity was improved by examination of a washing process after charging of samples [29].

Analytical, diagnostic and therapeutic context of cyclohexanol

• We isolated an Acinetobacter sp. from an industrial wastewater bioreactor that utilized cyclohexanol as a sole carbon source [2].
• In order to confirm the results of the spectrophotometric assay, a direct method utilizing isotope dilution gas chromatography/mass spectrometry (GC/MS) has been developed for detecting low levels of the hydroxylated product, cyclohexanol [30].
• Bacterial mutagenicity tests with specific pro-mutagens were good predictors of the P450 induction properties of cyclohexanol [31].
• Western blot analysis confirmed the results of the mutagenicity assay, showing an increase in the intensity of CYP2E1 and CYP2B1/B2 protein bands in hepatic microsomes from cyclohexanol treated rats in comparison with non-treated controls [31].
• Cyclohexanone in alveolar air and cyclohexanol in urine were determined with gas chromatography with a flame ionization detector [32].

References