Disease relevance of cyclohexanone

• Chronic toxicity study of cyclohexanone in rats and mice [1].
• The incidence of lymphomas in male mice and of hepatocellular neoplasms in female mice given cyclohexanone did not differ from that in the controls [1].
• Male rats receiving 3,300 ppm cyclohexanone had a 13% incidence of adrenal cortex adenomas (7 animals) compared with an incidence of 2% in controls; the incidence of this neoplasm did not increase in the male rats receiving 6,500 ppm or in the female rats given either dose [1].
• Survival and weight gain were similar to those of controls at the lowest cyclohexanone dose in both sexes of both species, but weight gain was depressed at all of the higher doses [1].
• Male mice given 6,500 ppm cyclohexanone showed an increased incidence of hepatocellular adenomas and carcinomas, 50% versus 32.5% in controls, but the incidence of these neoplasms was only 37% in the male mice given 13,000 ppm cyclohexanone [1].

Psychiatry related information on cyclohexanone

• In this work, complementary experimental and theoretical techniques are employed to address the radical-chain initiation in the autoxidation of cyclohexane with a particular focus on the "lighting-off" of the oxidation by (added) cyclohexanone [2].
• Influence of cyclohexanone carboxymethoxime on behaviour and electroshock susceptibility of young chicks [proceedings] [3].

High impact information on cyclohexanone

• A 2-year chronic toxicity assay of cyclohexanone (CAS: 108-94-1) was conducted in F344 rats and (C57BL/6 X C3H)F1 mice by administering a solution of cyclohexanone in drinking water [1].
• We have demonstrated that the cyclohexanone method for the extraction of hematin can be used to measure hemoglobin synthesis induced by erythropoietin (epo) in mouse bone marrow cells cultured in medium containing methyl cellulose [4].
• These two esterase stable cyclohexanone derivatives, which bind to nuclear type II sites with high affinity (Kd 1-7 nM), mimic MeHPLA as cell growth-regulating agents [5].
• NH2OH, the first intermediate in the oxidation of NH4+ to nitrite by the nitrifying bacterium, Nitrosomonas europaea, was recovered as the oxime of cyclohexanone [6].
• Cyclization reactions of group 6 Fischer carbene complexes with cyclopentanone and cyclohexanone enamines are described [7].

Chemical compound and disease context of cyclohexanone

• With 4-tolyl ethyl sulfide as substrate, cyclohexanone monooxygenase from Acinetobacter produces predominantly the (S)-(-)-sulfoxide (82% S, 18% R), a modest enantioselectivity [8].
• The N-terminal sequence did not show any similarity to other proteins, but an internal sequence was very similar to part of the proposed NADPH binding site in the Baeyer-Villiger monooxygenase cyclohexanone monooxygenase from an Acinetobacter sp [9].
• Several ORFs in each gene cluster encoded proteins homologous to cyclohexanol and cyclohexanone oxidation enzymes from Acinetobacter [10].
• Occupational contact dermatitis from cyclohexanone as a PVC adhesive [11].
• We have shown that whole Escherichia coli cells overexpressing NADPH-dependent cyclohexanone monooxygenase carry out a model Baeyer-Villiger oxidation with high volumetric productivity (0.79 g epsilon-caprolactone/L.h ) under nongrowing conditions (Walton, A. Z.; Stewart, J. D. Biotechnol. Prog. 2002, 18, 262-268) [12].

Biological context of cyclohexanone

• The inhibitors are based upon a cyclohexanone nucleus and are designed to probe binding interactions in the S2 and S2' binding sites [13].
• Whereas one ORF showed high homology to cyclohexanone monooxygenase from Acinetobacter sp. strain NCIB 9871, most of the ORFs showed only moderate homology to proteins in GenBank [14].
• These unusual kinetics are followed by 2,2'-methylene-bis(4-methyl-6-tert-butylphenol), BIS, in five solvents (acetonitrile, benzonitrile, acetone, cyclohexanone, and DMSO) [15].
• The diastereoselective Michael alkylation of alpha-substituted and alpha,alpha'-disubstituted cyclohexanone benzylimines with ethylidenemalonate diesters was carried out for mechanistic and synthetic purposes [16].
• The catalytic activity of 2-8a,b in transfer hydrogenation of cyclohexanone, as well as theoretical calculations on the models [Ru(eta(6)-C(6)H(6))Cl(kappa(2)-P,N-H(2)PCH(2)P[=NP(=O)(OH)(2)]H(2))]+ and [Ru(eta(6)-C(6)H(6))Cl(kappa(2)-P,O-H(2)PCH(2)P[=NP(=O)(OH)(2)]H(2))]+, has been also studied [17].

Anatomical context of cyclohexanone

• Hepatocytes were isolated from fed female rats and incubated with a redox indicator system consisting of cyclohexanone and unlabelled or perdeuterated cyclohexanol [18].
• The flowmeter probe was placed over the left frontal cortex while propionic acid, cyclohexanone, amyl acetate or butanol was delivered to the nasal cavity via an olfactometer [19].
• The Golgi technique was used to study the development of spines on the external dendrites of granule cells in the olfactory bulbs of young rats that had been continuously exposed to cyclohexanone vapor, deodorized air, or rat odors [20].
• These results suggest that TRPV1 serves as a receptor for both cyclohexanone and capsaicin in trigeminal nerve endings [21].
• Here, we show that the intracellular stability of cyclohexanone monooxygenase and the rate of substrate transport across the cell membrane were the key limitations on the overall reaction duration and rate, respectively [12].

Associations of cyclohexanone with other chemical compounds

• The kinetic 15N isotope effect for LADH catalysis was 0.9989 +/- 0.0006 for cyclohexanol oxidation and 0.997 +/- 0.002 for cyclohexanone reduction [22].
• Both the quantum-chemical results and the kinetic study indicate that the reaction follows mechanism 1, and that the catalyst active site consists of two centers: the Lewis acid Sn atom to which cyclohexanone has to coordinate, and the oxygen atom of the Sn-OH group that interacts with H(2)O(2) forming a hydrogen bond [23].
• The requirement in catalysis of the deprotonated flavin C4a-peroxide, a nucleophile, is consistent with a Baeyer-Villiger rearrangement mechanism for the enzymatic oxygenation of cyclohexanone [24].
• The reaction catalyzed involves the four-electron reduction of O2 at the expense of a two-electron oxidation of NADPH and a two-electron oxidation of cyclohexanone to form epsilon-caprolactone [24].
• Conformational analysis of the Diels-Alder adducts based on both (1)H NMR spectrometry and X-ray diffraction data indicates that the newly created cyclohexene and cyclohexanone rings adopt a pseudoboat conformation [25].

Gene context of cyclohexanone

• Multiple forms of cyclohexanone oxygenase from Nocardia globerula CL1 [26].
• Furthermore, the high stability of the "derivatizing" reagent, cyclohexanone, compared with acyl and TMS derivatizing reagents, is a useful property in method development [27].
• Enantioselective synthesis of tert-butyl tert-butanethiosulfinate catalyzed by cyclohexanone monooxygenase [28].
• This highly specific reaction of carcinogen with alcohol dehydrogenase lowers its Vmax and increases its Km with cyclohexanone thereby reducing its catalytic efficiency for this substrate [29].
• The crystal structure of cyclohexanone oxime, C(6)H(11)NO, was reported as severely disordered in the trigonal non-centrosymmetric space group P3 [Olivato, Ribeiro, Zukerman-Schpector & Bombieri (2001). Acta Cryst. B57, 705-713] [30].

Analytical, diagnostic and therapeutic context of cyclohexanone

• mRNA differential display in a microbial enrichment culture: simultaneous identification of three cyclohexanone monooxygenases from three species [31].
• Acinetobacter cyclohexanone monooxygenase: gene cloning and sequence determination [32].
• mRNA differential display has been used to identify cyclohexanone oxidation genes in a mixed microbial community derived from a wastewater bioreactor [31].
• High-performance liquid chromatography of cyclohexanone oxime in urine and plasma [33].
• Determination of cyclohexanone in intravenous solutions stored in PVC bags by gas chromatography [34].

References