Disease relevance of MOLI001243

• A strain of Klebsiella pneumoniae that used aliphatic nitriles as the sole source of nitrogen was adapted to benzonitrile as the sole source of carbon and nitrogen [1].
• Mycolic acid-containing actinomycetes capable of metabolizing nitriles were recovered from deep-sea sediments and terrestrial soils by enrichment culture on acetonitrile, benzonitrile, succinonitrile or bromoxynil [2].
• The growth inhibitory effect of a new non-steroidal aromatase inhibitor, CGS16949A (Fadrozole hydrochloride: [4-(5,6,7,8-tetrahydro-imidazo-[1,5a]-pyridin-5-yl) benzonitrile monohydro chloride]) was studied in human breast cancer cells MCF-7 and T47D [3].
• In group 1 (13 compounds), acute toxicity was greatly reduced by CCl4 pretreatment, in group 2 (seven compounds), toxicity was not significantly changed or was somewhat enhanced, and in group 3, benzonitrile only, toxicity was clearly enhanced [4].
• Contact urticaria syndrome from occupational benzonitrile exposure [5].

High impact information on MOLI001243

• Compared to the Co complexes 9, Co4, and Co1, the first oxidation of Co3 is considerably shifted to more positive potentials, if benzonitrile instead of dichloromethane is used as solvent [6].
• The final CS state decays obeying first-order kinetics with a lifetime of 19 micros in benzonitrile at 295 K [7].
• In benzonitrile, on the other hand, the photoexcitation of the triad results in the fast electron transfer (< 1 ps) from photoexcited Zn(II)chlorin to fullerene [8].
• These compounds have been synthesized by the reductive amination of 2-(3-bromophenyl)propionaldehyde with the respective amine followed by lithiation of this product and condensation with the appropriate benzonitrile [9].
• One-electron oxidation of triarylphosphines (Ar(3)P, Ar = phenyl and substituted phenyl) in benzonitrile (PhCN) has been studied using pulse radiolysis technique [10].

Chemical compound and disease context of MOLI001243

• Therefore the toxicity of DFBN, DFBA and of some structurally related compounds including benzonitrile (BN) and the herbicides bromoxynil (3,5-dibromo-4-hydroxybenzonitrile) and ioxynil (3,5-diiodo-4-hydroxybenzonitrile) in the mouse olfactory mucosa was examined [11].

Biological context of MOLI001243

• The effect of whole cell immobilisation on the biotransformation of benzonitrile and the use of direct electric current for enhanced product removal [12].
• Analysis of nutrient elements in extracts, along with measuring degradation in soil extract with nutrient supplements and subsequent stepwise multiple-regression, suggested that the char nutrients stimulated cell growth and degradation of benzonitrile, for which P was primarily responsible [13].
• Acetonitrile and benzonitrile, when used as growth substrates for enzyme induction experiments, had a significant influence on the biotransformation activities towards various nitriles and amides [14].
• The solvents benzonitrile and methyl ethyl ketone induced significantly elevated chromosome loss levels [15].
• Substantial reduction in the biodegradation of benzonitrile in the presence of wheat ash was apparently due to sorption of benzonitrile by the ash, slow desorption from the ash, and the increased acclimation period [16].

Anatomical context of MOLI001243

• To study mechanisms of aromatase inhibition in brain cells, a highly effective non-steroidal aromatase inhibitor (Fadrozole; 4-[5,6,7,8-tetra-hydroimidazo- (1,5-a)-pyridin-5-yl] benzonitrile HCl; CGS 16949A) was compared with endogenous C-19 steroids, known to be formed in the preoptic area, which inhibit oestrogen formation [17].
• In order to investigate the chromosomal genotoxicity of nitrobenzene and benzonitrile, we studied the induction of micronuclei (MN) by these test compounds in V79 cells, as well as effects on the formation and stability of microtubules and on motor protein functions [18].
• The experiments demonstrate that both nitrobenzene and benzonitrile, in millimolar concentration ranges, may lead to interference with tubulin assembly in a cell-free system [18].

Associations of MOLI001243 with other chemical compounds

• Cells encapsulated within alginate beads (2.9 mm diameter) for protection against the current biotransformed benzonitrile to benzoic acid with a 26% reduction in the biotransformation rate, from 0.054 mmol/min/g dcw with free cells to 0.040 mmol/min/g dcw with immobilised cells [12].
• Gas-phase complex ions containing the vanadyl (VO(2+)), vanadyl hydroxide (VOOH(+)), or vanadium(V) dioxo (VO(2)(+)) cation and nitrile (acetonitrile, propionitrile, butyronitrile, or benzonitrile) ligands were generated by electrospray ionization (ESI) for study by multiple-stage tandem mass spectrometry [19].
• Eleven free-base corroles with different electron-donating or electron-withdrawing meso substituents were characterized as to their electrochemistry and UV-visible spectroscopy in benzonitrile (PhCN) or pyridine containing tetra-n-butylammonium perchlorate (0.1 M) [20].
• Both, nitrobenzene and benzonitrile, induced mostly kinetochor (CREST)-positive micronuclei, thus characterising the chromosomal effects as aneugenic [18].
• To investigate the effect of ash on the biodegradation of pesticides in soils, we measured the sorption, desorption, and biodegradation of benzonitrile in a silt loam in the presence and absence of an ash resulting from burning of wheat (Triticum aestivum L.) residue [16].

Gene context of MOLI001243

• BACKGROUND: A phase II study of a non-steroidal selective aromatase inhibitor, YM511, 4-[N-bromobenzyl]-N-(4H-1,2,4-triazol-4-yl)amino) benzonitrile, was conducted to evaluate the anti-tumor response, dose-dependence of response rate and tolerability in postmenopausal patients with advanced breast cancer [21].
• No histopathological changes in the olfactory mucosa or in the liver were observed following a single ip dose of any of these compounds [0.145 mmol/kg (all compounds); 0.58 mmol/kg (DFBN, DFBA and BN)] [11].
• The nature of the effects of nitrobenzene and benzonitrile on the association of tubulin to form microtubules was confirmed by electron microscopy [18].
• 3D-QSAR analysis has been performed on a series of previously synthesized benzonitrile derivatives, which were screened as farnesyltransferase inhibitors, using comparative molecular field analysis (CoMFA) with partial least-square fit to predict the steric and electrostatic molecular field interactions for the activity [22].
• Resting cells cultivated on YCB-propionitrile medium showed nitrilase activity against benzonitrile [23].

Analytical, diagnostic and therapeutic context of MOLI001243

• Periodic trends in electrode-chemisorbate bonding: benzonitrile on platinum-group and other noble metals as probed by surface-enhanced Raman spectroscopy combined with density functional theory [24].
• Over the course of a 24-hour biotransformation, benzonitrile was converted to benzoic acid which was completely removed from the bioreactor chamber and concentrated 3-fold in a separate chamber [25].
• Liquid chromatography analysis indicated that Cryptococcus sp. UFMG-Y28 metabolized 12 mM benzonitrile to 10 mM benzoic acid [23].

References