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1.
Identification of intermediates formed during the degradation of hexachlorocyclohexanes by Clostridium sphenoides. 总被引:5,自引:3,他引:2
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Washed cell suspensions of Clostridium sphenoides degraded the alpha-isomer of 1,2,3,4,5,6-hexachlorocyclohexane via delta-3,4,5,6-tetrachloro-1-cyclohexene and the gamma-isomer via gamma-3,4,5,6-tetrachloro-1-cyclohexene. Both intermediates were further metabolized to unknown substances. The tetrachlorocyclohexene intermediates were identified by gas chromatography and mass spectrometry. 相似文献
2.
C M Tu 《Archives of microbiology》1975,105(2):131-134
Three lindane (gamma-1,2,3,4,5,6-hexachlorocyclohexane) treated soils were studied under laboratory conditions to determine the interaction between lindane and the soil microorganisms. Microbial populations and respiration were monitored to study insecticide effects. Formation of lindane degradation products and chloride content were examined to determine effects of the microorganisms. Some populations in lindane treated soils showed temporary declines but all ultimately recovered to at least the level of the controls in 16 weeks. Respiration was stimulated over a 9-week period especially in the sandy and clay loams, suggesting the possibility of microbial degradation of the insecticide. Lindane degradation products separated and identified by TLC included gamma-2,3,4,5,6-pentachloro-1-cyclohexene (gamma-PCCH), gamma-3,4,5,6,-tetrachloro-1-cyclohexene (gamma-TCCH), gamma-3,4,5,6-tetrachloro-1-cyclohexene (gamma-TCCH), and pentachlorobenzene (PCB). Chloride production increased in soils treated with higher levels of lindane. 相似文献
3.
Cell-free preparation of Clostridium sphenoides degraded the insecticide lindane, the gamma-isomer of 1,2,3,4,5,6-hexachlorocyclohexane, to the gamma-isomer of 3,4,5,6-tetrachloro-1-cyclohexene. The activity appeared to be associated with the membrane fraction and required reduced glutathione. The tetrachlorocy-clohexene intermediate was further metabolized by the membrane fraction to unknown substances. 相似文献
4.
Degradation of lindane by cell-free preparations of Clostridium sphenoides. 总被引:6,自引:3,他引:3
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Cell-free preparation of Clostridium sphenoides degraded the insecticide lindane, the gamma-isomer of 1,2,3,4,5,6-hexachlorocyclohexane, to the gamma-isomer of 3,4,5,6-tetrachloro-1-cyclohexene. The activity appeared to be associated with the membrane fraction and required reduced glutathione. The tetrachlorocy-clohexene intermediate was further metabolized by the membrane fraction to unknown substances. 相似文献
5.
C. M. Tu 《Archives of microbiology》1976,108(3):259-263
Of 147 microorganisms isolated from a loamy sand, 71 showed good growth with lindane (-1,2,3,4,5,6-hexachlorocyclohexane) and produced chloride in an aqueous medium. Thirteen soil microorganisms were selected to study the utilization of lindane. Lindane was metabolized by the microbes to -2,3,4,5,6-pentachloro-1-cyclohexene (-PCCH), -3,4,5,6-tetrachloro-1-cyclohexene (-TCCH), -3,4,5,6-tetrachloro-1-cyclohexene (-TCCH), -3,4,5,6-tetrachloro-1-cyclohexene (-TCCH), and pentachlorobenzene (PCB). Cells of Pseudomonas sp. No. 62 grown on lindane simultaneously adapted to -PCCH, -TCCH, -TCCH, -TCCH, PCB, 1,2,3,4-tetrachlorobenzene (1,2,3,4-TCB) and 1,2,4,5-tetrachlorobenzene (1,2,4,5-TCB). The bacteria degraded each of these chemicals at least partially as indicated by an increased rate of oxygen consumption.Abbreviations Lindane
-1,2,3,4,5,6-hexachlorocyclohexane
- -PCCH
-2,3,4,5,6-pentachloro-1-cyclohexene
- -TCCH
-3,4,5,6-tetrachloro-1-cyclohexene
- -TCCH
-3,4,5,6-tetrachloro-1-cyclohexene
- -TCCH
-3,4,5,6-tetrachloro-1-cyclohexene
- PCB
pentachlorobenzene
- 1,2,3,4-TCB
1,2,3,4-tetrachlorobenzene
- 1,2,3,5-TCB
1,2,3,5-tetrachlorobenzene
- 1,2,4,5-TCB
1,2,4,5-tetrachlorobenzene
- 1,2,3-tCB
1,2,3-trichlorobenzene
- 1,2,4-tCB
1,2,4-trichlorobenzene
- 1,3,5-tCB
1,3,5-trichlorobenzene
- 1,2-DCB
1,2-dichlorobenzene
- 1,3-DCB
1,3-dichlorobenzene
- 1,4-DCB
1,4-dichlorobenzene
- MCB
monochlorobenzene
Contribution No. 631, Research Institute, Agriculture Canada, University Sub Post Office, London, Ontario N6A 5B7 相似文献
6.
C. M. Tu 《Archives of microbiology》1975,105(1):131-134
Three lindane (-1,2,3,4,5,6-hexachlorocyclohexane) treated soils were studied under laboratory conditions to determine the interaction between lindane and the soil microorganisms. Microbial populations and respiration were monitored to study insecticide effects. Formation of lindane degradation products and chloride content were examined to determine effects of the microorganisms. Some populations in lindane treated soils showed temporary declines but all ultimately recovered to at least the level of the controls in 16 weeks. Respiration was stimulated over a 9-week period especially in the sandy and clay loams, suggesting the possibility of microbial degradation of the insecticide. Lindane degradation products separated and identified by TLC included -2,3,4,5,6-pentachloro-1-cyclohexene (-PCCH), -3,4,5,6-tetrachloro-1-cyclohexene (-TCCH), -3,4,5,6-tetrachloro-1-cyclohexene (-TCCH), and pentachlorobenzene (PCB). Chloride production increased in soils treated with higher levels of lindane.Contribution No. 609, Research Institute, Agriculture Canada, University Sub Post Office, London, Ontario N6A 5B7. 相似文献
7.
Xiang-long Wu Min Tian Huai-zhen He Wei Sun Jian-li Li Zhen Shi 《Bioorganic & medicinal chemistry letters》2009,19(11):2957-2959
Two novel chlorinated fluoresceins 2′,4′,5′,7′-tetrachloro-6-(5-carboxypentyl)-4,7-dichloro fluorescein succinimidyl ester (1G) and 2′,4′,5′,7′-tetrachloro-6-(3-carboxypropyl)-4,7-dichlorofluorescein succinimidyl ester (2G) were synthesized as fluorescent probes for labeling proteins. Structures of target compounds and intermediates were determined via IR, MS, 1H NMR and element analysis. The investigation in immunofluorescence histochemistry showed them had strong fluorescence, high photostability and good biocompatibility. 相似文献
8.
Makoto Kiso Masahide Nohta Hiroyuki Ohashi Norio Kurihara Minoru Nakajima 《Bioscience, biotechnology, and biochemistry》2013,77(2):405-410
dl-(1245/36)-4,5,6-Trichloro-l,2,3-trimethoxycyclohexane and dl-(1245/36)-2,3,4,5,6-penta-chloro-1-methylthiocyclohexane were synthesized from (1245/36)-3,4,5,6-tetrachlorocyclo-hexane-1, 2-diol. dl- (1245/36) -1, 4, 5, 6-Tetrachloro-2-methoxy-3-methylthiocyclohexane and dl-(1245/36)-l,4,5,6-tetrachloro-2,3-dimethoxycyclohexane were synthesized from (12345/6)-1, 4, 5, 6-tetrachloro-2, 3-epoxycyclohexane. meso- (1245) -1,2,4,5-Tetrachlorocyclohexane was synthesized from benzene via cyclohexadiene-1,4. 相似文献
9.
In the rat, cyclohexanecarboxylate was metabolized and excreted (mostly in the urine) as hippurate, hexahydrohippurate, 3,4,5,6-tetrahydrohippurate and benzoyl and cyclohexylcarbonyl beta-glucuronides. The pattern of metabolism is dose-dependent. With decreasing dose a progressive increase in the conversion into hippurate occurred. This was largely at the expense of glucuronide formation, although the proportions of hexahydro- and tetrahydro-hippurate were also decreased. The observed formation of hexahydrohippurate and 3,4,5,5-tetrahydrohippurate substantiates the proposed mechanism of aromatization of cyclohexanecarboxylate. It appears that these compounds arise via glycine conjugation of active intermediates in the aromatization process. Hexahydrohippurate and 3,4,5,6-tetrahydrohippurate may occur in the urine of rats as new mitabolities of shikimate, dependent for their formation on microbial metabolism. 相似文献
10.
The hydrogen-abstracting quinone derivative 3,4,5,6-tetrachloro-1,2-benzoquinone (o-chloranil) caused a strong, near stoichiometric, irreversible inactivation of the collagenases from Bacillus cereus, Clostridium histolyticum and Achromobacter iophagus. p-Chloranil was a weaker inactivator. o-Chloranil reacted rapidly with a site that affected substrate binding. Amino acid analyses of native and totally inactivated enzymes, and the pH-profile of inactivation suggest that the dissociated form of a tyrosine residue was modified. 相似文献
11.
Clifford C. Leznoff 《Inorganica chimica acta》2006,359(9):2690-2699
Highly hindered magnesium and metal-free green 1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-hexadecaneopentoxyphthalocyanine and 1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-hexadeca(cyclohexylmethyloxy)phthalocyanine were prepared via magnesium 1-octanolate and 3,4,5,6-tetraneopentoxyphthalonitrile or 3,4,5,6-tetra(cyclohexylmethyloxy)phthalonitrile. Treatment of the metal-free phthalocyanine with Mn(OAc)2 yielded deep red manganese(III) hexadecaalkoxy phthalocyanines. Electrochemical and spectroelectrochemical studies led to the characterization, in solution, of a series of species in a range of different manganese and phthalocyanine oxidation states. 相似文献
12.
Yu. A. Sayapin E. A. Gusakov I. V. Dorogan I. O. Tupaeva M. G. Teimurazov N. K. Fursova K. V. Ovchinnikov V. I. Minkin 《Russian Journal of Bioorganic Chemistry》2016,42(2):224-228
2-(4H-1,3-Benzoxazin-4-on-2-yl)-4,5,6-trichloro-1,3-tropolone, structural properties of which were studied using 1H NMR, IR-spectroscopy, mass spectrometry, and quantum chemistry has been obtained for the first time using an acid-catalyzed condensation reaction of 3,4,5,6-tetrachloro-1,2-benzoquinone with 2-methyl-4H-3,1-benzoxazin-4-one. It has been shown that the new tropolone possesses antibacterial activity against hospital-acquired strains of gram-negative (Escherichia coli, Salmonella enterica sv. Enteritidis, Acinetobacter baumannii, and Pseudomonas aeruginosa) and Gram-positive (Staphylococcus aureus) bacteria. The obtained substance is suggested for development of a new antibacterial drug. 相似文献
13.
Commercial formulations of hexachlorocyclohexane (HCH) consist of a mixture of four isomers, alpha, beta, gamma and delta. All these four isomers are toxic and recalcitrant pollutants. Sphingobium (formerly Sphingomonas) sp. strain BHC-A is able to degrade all four HCH isomers. Eight lin genes responsible for the degradation of gamma-HCH in BHC-A were cloned and analysed for their role in the degradation of delta-HCH, and the initial conversion steps in delta-HCH catabolism by LinA and LinB in BHC-A were found. LinA dehydrochlorinated delta-HCH to produce 1,3,4,6-tetrachloro-1,4-cyclohexadiene (1,4-TCDN) via delta-pentachlorocyclohexene (delta-PCCH). Subsequently, both 1,4-TCDN and delta-PCCH are catalysed by LinB via two successive rounds of hydrolytic dechlorinations to form 2,5-dichloro-2,5-cyclohexadiene-1,4-diol (2,5-DDOL) and 2,3,5-trichloro-5-cyclohexene-1,4-diol (2,3,5-TCDL) respectively. LinB could also catalyse the hydrolytic dechlorination of delta-HCH to 2,3,5,6-tetrachloro-1,4-cyclohexanediol (TDOL) via 2,3,4,5,6-pentachlorocyclohexanol (PCHL). 相似文献
14.
Five anhydronium bases were isolated by preparative HPLC from a methanolic extract of Rauvolfia serpentina roots. For the first time 3,4,5,6-tetradehydroyohimbine, 3,4,5,6-tetradehydro-(Z)-geissoschizol, 3,4,5,6-tetradehydrogeissoschizol and 3,4,5,6-tetradehydrogeissoschizine-17-O-beta-D-glucopyranoside were isolated from a natural source. In addition, the well-known anhydronium base serpentine was isolated. The structures of the compounds were determined by 1H and 13C NMR, MS and UV. 相似文献
15.
Hong HB Chang YS Nam IH Fortnagel P Schmidt S 《Applied and environmental microbiology》2002,68(5):2584-2588
Aerobic biotransformation of the diaryl ethers 2,7-dichlorodibenzo-p-dioxin and 1,2,3,4-tetrachlorodibenzo-p-dioxin by the dibenzo-p-dioxin-utilizing strain Sphingomonas wittichii RW1, producing corresponding metabolites, was demonstrated for the first time. Our strain transformed 2,7-dichlorodibenzo-p-dioxin, yielding 4-chlorocatechol, and 1,2,3,4-tetrachlorodibenzo-p-dioxin, producing 3,4,5,6-tetrachlorocatechol and 2-methoxy-3,4,5,6-tetrachlorophenol; all of these compounds were unequivocally identified by mass spectrometry both before and after N,O-bis(trimethylsilyl)-trifluoroacetamide derivatization by comparison with authentic standards. Additional experiments showed that strain RW1 formed a second metabolite, 2-methoxy-3,4,5,6-tetrachlorophenol, from the original degradation product, 3,4,5,6-tetrachlorocatechol, by methylation of one of the two hydroxy substituents. 相似文献
16.
Synthesis of myo-inositol 1,3,4,5,6-pentakisphosphate from inositol phosphates generated by receptor activation. 总被引:10,自引:6,他引:4
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myo-[3H]Inositol 1,3,4,5,6-pentakisphosphate can be made from myo-[3H]inositol 1,4,5-trisphosphate in a rat brain homogenate or soluble fraction. Although D-myo-inositol 3,4,5,6-tetrakisphosphate can be phosphorylated by a soluble rat brain enzyme to give myo-inositol 1,3,4,5,6-pentakisphosphate, it is not an intermediate in the pathway from myo-inositol 1,4,5-trisphosphate. The intermediates in the above pathway are myo-inositol 1,3,4,5-tetrakisphosphate, myo-inositol 1,3,4-trisphosphate and myo-inositol 1,3,4,6-tetrakisphosphate [Shears, Parry, Tang, Irvine, Michell & Kirk (1987) Biochem. J. 246, 139-147; Balla, Guillemette, Baukal & Catt (1987) J. Biol. Chem. 262, 9952-9955], and it is catalysed by soluble kinase activities of similar anion-exchange mobility and Mr value. Compounds with chromatographic and chemical properties consistent with the structures myo-inositol 1,3,4,5-tetrakisphosphate, myo-inositol 1,3,4,6-tetrakisphosphate and myo-inositol 3,4,5,6-tetrakisphosphate are present in avian erythrocytes, human 1321 N1 astrocytoma cells and primary-cultured murine bone-marrow-derived macrophages. The amounts of these inositol tetrakisphosphates rise upon muscarinic cholinergic stimulation of the astrocytoma cells or stimulation of macrophages with platelet-activating factor. 相似文献
17.
云南蒜油化学成分的研究 总被引:3,自引:0,他引:3
本文对云南曲靖产大蒜(Allium sativum L.)蒜油用气相色谱和色谱-质谱法进行了分析,鉴定了20个化合物。其中:6-甲基-1-硫杂-2,4-环己二烯(6-methyl-1-thi-2,4-cyclohexadiene),5-甲基-1,2-二硫杂-3-环戊烯(5-methyl-1,2-dithi-3-cyclopentene),4-甲基-1,2-二硫杂-3-环戊烯(4-methyl-1,2-dithi-3-cyclopentene),4-乙烯基-1,2,3-三硫杂-5-环己烯(4-vinyl-1,2,3-trithi-5-cyclohexene)及甲基烯丙基五硫醚(allyl methyl pentasulfide)等为蒜油中首次报道的化合物。 相似文献
18.
Does inositol 3,4,5,6-tetrakisphosphate (Ins(3,4,5,6)P(4)) inhibit apical Ca(2+)-activated Cl(-) conductance (CaCC)? We studied this question using human CFPAC-1 pancreatoma cells grown in polarized monolayers. Cellular Ins(3,4,5,6)P(4) levels were acutely sensitive to purinergic receptor activation, rising 3-fold within 1 min of agonist addition. Intracellular Ins(3,4,5,6)P(4) levels were therefore specifically elevated, independently of receptor activation, by incubating cells with a cell-permeant bioactivable analogue, 1,2-di-O-butyl-myo-inositol 3,4,5,6-tetrakisphosphate octakis(acetoxymethyl)ester (Bt(2)Ins (3,4,5,6)P(4)/AM). The latter inhibited Ca(2+)-activated Cl(-) secretion by 60%. We next used nystatin to selectively permeabilize the basolateral membrane to monovalent anions and cations, thereby preventing this membrane from electrochemically dominating ion movements through the apical membrane. Thus, we studied autonomous regulation of apical Cl(-) channels in situ. The properties of Cl(-) flux across the apical membrane were those expected of CaCC: niflumic acid sensitivity, outward rectification, and 2-fold greater permeability of I(-) over Cl(-). Following nystatin-treatment, we elevated intracellular levels of Ins(3,4,5,6)P(4) with either purinergic agonists or with Bt(2)Ins(3,4,5,6)P(4)/AM. Both protocols inhibited Ca(2+)-activated Cl(-) secretion (up to 70%). These studies provide the first demonstration that, in a physiologically relevant context of a polarized monolayer, there is an apical, Ins(3,4,5,6)P(4)-inhibited CaCC. 相似文献
19.
Rudolf MT Dinkel C Traynor-Kaplan AE Schultz C 《Bioorganic & medicinal chemistry》2003,11(15):3315-3329
Cystic fibrosis (CF) patients suffer from a defect in hydration of mucosal membranes due to mutations in the cystic fibrosis transmembrane regulator (CFTR), an apical chloride channel in mucosal epithelia. Disease expression in CF knockout mice is organ specific, varying with the level of expression of calcium activated Cl(-) channels (CLCA). Therefore, restoring transepithelial Cl(-) secretion by augmenting alternate Cl(-) channels, such as CLCA, could be beneficial. However, CLCA-mediated Cl(-) secretion is transient, due in part to the inhibitory effects of myo-inositol 3,4,5,6-tetrakisphosphate [Ins(3,4,5,6)P(4)]. This suggests that antagonists of Ins(3,4,5,6)P(4) could be useful in treatment of CF. We have, therefore, synthesized a series of membrane-permeant Ins(3,4,5,6)P(4) derivatives, carrying alkyl substituents on the hydroxyl groups and screened them for effects on Cl(-) secretion in a human colonic epithelial cell line, T(84). While membrane-permeant Ins(3,4,5,6)P(4) derivatives had no direct effects on carbachol-stimulated Cl(-) secretion, Ins(3,4,5,6)P(4) derivatives, but not enantiomeric Ins(1,4,5,6)P(4) derivatives, reversed the inhibitory effect of Ins(3,4,5,6)P(4) on subsequent thapsigargin activation of Cl(-) secretion. The extent of the antagonistic effect of the Ins(3,4,5,6)P(4) derivatives varied with the position of the alkyl substituents. Derivatives with a cyclohexylidene ketal or a butyl-chain at the 1-position reversed the Ins(3,4,5,6)P(4)-mediated inhibition of Cl(-) secretion by up to 96 and 85%, respectively, whereas butylation of the 1- and 2-position generated a reversal effect of only 65%. Derivatives carrying the butyl chain only at the 2-position showed no antagonistic effect. These data: (1) Support the hypothesis that Ins(3,4,5,6)P(4) stereospecifically inhibits Ca(2+) activated Cl(-) secretion and that Ins(3,4,5,6)P(4) mediates most, if not all of the cholinergic-mediated inhibition of chloride secretion in T(84) cells; (2) Demonstrate Ins(3,4,5,6)P(4)-mediated inhibition can be completely reversed with rationally designed membrane-permeant Ins(3,4,5,6)P(4) antagonists; (3) Demonstrate that a SAR for membrane-permeant Ins(3,4,5,6) P(4) antagonists can be generated and screened in a physiologically relevant cell-based assay; (4) Indicate that Ins(3,4,5,6)P(4) derivatives could serve as a starting point for the development of therapeutics to treat cystic fibrosis. 相似文献
20.
4-Vinyl-1-cyclohexene (VCH), is converted by multiple forms of cytochrome P450 (CYP) to two monoepoxides (4-vinyl-1-cyclohexene 1,2-epoxide [VCH-1,2-epoxide], 4-vinyl-1-cyclohexene 7,8-epoxide [VCH-7,8-epoxide]), and 4-vinyl-1-cyclohexene diepoxide (VCD). A greater degree of formation of these epoxides by female B6C3F1 mice as compared to Fischer 344 rats correlates with the ovarian toxicity observed only in the mice. Understanding which isoforms of CYP are involved in VCH bioactivation will better explain the species-dependent ovotoxicity of VCH. Present studies focus on the role of CYP2E1, as this isoform is responsible for the bioactivation of several structurally related small molecular weight compounds, including 1,3-butadiene. Hepatic microsomes prepared from either mice or rats pretreated with the CYP inducer acetone demonstrated 2-fold increases in the formation of VCH-1,2-epoxide. However, incubations with microsomes from cyp2e1-deficient mice compared to those from wild type mice revealed no differences in the rates of bioactivation of VCH to the monoepoxides. Since repeated exposure to VCH is required for VCH-induced ovotoxicity, rodents were dosed with VCH for 5 or 10 d to observe effects on the hepatic concentration of CYP2E1 and/or associated activities. VCH pretreatment failed to increase the concentration of CYP2E1 or CYP2E1 activity in either species, as measured by immunoblotting analysis and p-nitrophenol hydroxylation. Based on these data, it is concluded that CYP2E1 does not play a role in the species differences between mice and rats in the bioactivation of VCH following repeated exposure to VCH. Other isoforms, such as those in CYP2A and CYP2B subfamilies, are likely involved in VCH bioactivation. 相似文献