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Journal of Agricultural and Food... Feb 2023The use of skin repellents against hematophagous mosquitoes is an important personal protection practice wherever these insects are abundant and where they are vectors...
The use of skin repellents against hematophagous mosquitoes is an important personal protection practice wherever these insects are abundant and where they are vectors of diseases. DEET and Icaridin are the major synthetic insect repellents in commercial formulations and are considered the most effective. Here, we tested against the mosquito several cyclic hydroxyacetals synthesized by acetalization of commercially available aliphatic carbonyl compounds (ranging from C3 to C15) with either glycerol, 1,1,1-trismethyloletane, or 1,1,1-trismethylolpropane and compared their efficacy with commercial repellents. We found that several hydroxyacetals were comparable with DEET and Icaridin both in terms of the required dose and repellence duration, while a few performed better. For those most active, toxicity was investigated, finding that a few of them were less cytotoxic than DEET and less prone to permeate through cell layers. Therefore, such results indicate that novel safe mosquito repellents could be developed among cyclic hydroxyacetals.
Topics: Animals; Insect Repellents; DEET; Acetals; Mosquito Vectors; Aedes
PubMed: 36649540
DOI: 10.1021/acs.jafc.2c05537 -
Chemical & Pharmaceutical Bulletin 2020Oxygen atoms have a lone pair of electrons, so they have high chelation ability, high nucleophilic ability, stabilizing ability of adjacent cations, and take a chelate... (Review)
Review
Oxygen atoms have a lone pair of electrons, so they have high chelation ability, high nucleophilic ability, stabilizing ability of adjacent cations, and take a chelate or oxocarbenium ion structure with Lewis acids and metals. I took advantage of these properties to develop three new reactions, 1) asymmetric synthesis of chiral quaternary carbon centers, 2) asymmetric synthesis using acetal functions, and 3) organic chemistry using acetal-type reactive salt chemical species, and applied them to biologically active natural products synthesis. New reactions described here are all innovative and useful for natural products synthesis. In particular, the first asymmetric synthesis of fredericamycin A, and concise asymmetric synthesis of anthracycline antibiotics, scyphostatin, (+)-Sch 642305, (-)-stenine, clavolonine, (+)-rubrenolide, (+)-rubrynolide, (+)-centrolobine, and decytospolide A and B, etc., are noteworthy. Furthermore, since reactions using acetal-type reactive salt chemical species allow the coexistence of functional groups that normally cannot coexist, the reactions using reactive salts have potential to change the retrosynthesis planned based on conventional reactions.
Topics: Acetals; Alkaloids; Alkynes; Amides; Anthracyclines; Catalysis; Chemistry Techniques, Synthetic; Isoquinolines; Macrolides; Oxygen; Pyrans; Pyrones; Quinolizines; Spiro Compounds; Stereoisomerism
PubMed: 32999145
DOI: 10.1248/cpb.c20-00178 -
The Journal of Clinical Investigation Sep 1979Plasma acetate turnover and oxidation were determined in 11 healthy subjects by the constant infusion of a trace amount of [1-14C]acetate for 6 h. The subjects ages... (Comparative Study)
Comparative Study
Plasma acetate turnover and oxidation were determined in 11 healthy subjects by the constant infusion of a trace amount of [1-14C]acetate for 6 h. The subjects ages ranged from 22 to 57 yr. There was a positive correlation (P less than 0.001) between plasma acetate concentration and turnover rate, and a negative correlation (P less than 0.001) between turnover and age. The plasma acetate concentration in the subjects 22--28 yr old was 0.17 vs. 0.13 mM (P less than 0.02) in subjects 40--57 yr old. The plasma acetate turnover rate was also greater in the younger age group (8.23 +/- 0.66 vs. 4.98 +/- 0.64 mumol/min . kg, P less than 0.01). Approximately 90% of the plasma acetate turnover was immediately oxidized to CO2 in both age groups, however, 13.2 +/- 0.89% of the CO2 output in the younger group was derived from plasma acetate oxidation compared to 7.9 +/- 0.94% in the older group (P less than 0.01). The mean plasma acetate concentration, turnover, and oxidation in six cancer patients 47--63 yr old were similar to the values observed in the age-matched healthy subjects. Uptake or output of acetate by various tissues was measured by arterial-venous plasma acetate concentration differences. In seven of eight subjects undergoing elective surgery, the arterial-portal venous concentration difference was negative, which indicated that the gastrointestinal tract can contribute to plasma acetate production. Uptake of plasma acetate by both the leg and liver appeared to be dictated by the arterial acetate concentration. Net production of acetate by both the leg and liver was most often observed at arterial plasma acetate concentrations less than 0.08 mM.
Topics: Acetates; Adult; Age Factors; Arteries; Female; Humans; Kinetics; Male; Middle Aged; Neoplasms; Oxidation-Reduction; Tissue Distribution; Veins
PubMed: 468985
DOI: 10.1172/JCI109513 -
Current Opinion in Lipidology Dec 2016
Topics: Acetates; Cell Hypoxia; Gene Expression Regulation; Lipogenesis; Neoplasms
PubMed: 27805975
DOI: 10.1097/MOL.0000000000000360 -
The Biochemical Journal May 1953
Topics: Acetates; Acetic Acid; Acetylation; Collagen
PubMed: 13058855
DOI: 10.1042/bj0540181 -
Journal of Bacteriology Jan 1986Azotobacter vinelandii mutants defective for acetate utilization that were resistant to fluoroacetate (FA) were isolated. FA-resistant mutant AM6 failed to transport...
Azotobacter vinelandii mutants defective for acetate utilization that were resistant to fluoroacetate (FA) were isolated. FA-resistant mutant AM6 failed to transport [14C]acetate and lacked enzymatic activity for both acetate kinase and phosphotransacetylase. Growth of wild-type A. vinelandii was sensitive to 10 mM glycine; however, all FA-resistant strains were resistant to glycine toxicity. Isolated mutants that were spontaneously resistant to glycine were also resistant to FA and lacked both acetate kinase and phosphotransacetylase activity. The glycine-resistant mutant AM3, unlike mutant AM6, was capable of growth on acetate. The mutant strain AM6 was unable to growth under acetate-glucose diauxie conditions. Glucose utilization in this mutant, unlike that in wild-type A. vinelandii, was permanently arrested in the presence of acetate. Revertants of strain AM6 were selected on plates with acetate or acetate-glucose. Two classes of revertants were isolated. Class I revertant mutants AM31 and AM35 were positive for both acetate kinase and phosphotransacetylase activities. These revertants were also sensitive to both FA and glycine. Class II revertant strains AM32 and AM34 still lacked acetate kinase and phophotransacetylase activity. Both of these revertants remained resistant to FA and glycine.
Topics: Acetate Kinase; Acetates; Acetic Acid; Acetyltransferases; Azotobacter; Fluoroacetates; Glucose; Mutation; Oxygen Consumption; Phosphate Acetyltransferase; Phosphotransferases
PubMed: 3001033
DOI: 10.1128/jb.165.1.6-12.1986 -
Journal of Analytical Toxicology Oct 2022Presented is the analysis of four cannabinoid-based products. These products were part of a case involving visual and auditory hallucinations that precipitated the...
Presented is the analysis of four cannabinoid-based products. These products were part of a case involving visual and auditory hallucinations that precipitated the commission of a felony and subsequent arrest. The products were labeled to contain ∆8-tetrahydrocannabinol (∆8-THC) or THC acetate (THC-O-A). Primary reference materials were not available for ∆8-THC-O-A, ∆10-THC-O-A, cannabidiol di-acetate (CBD-di-O-A) or respective deuterated internal standards. THC-O-A and CBD-di-O-A standards were prepared by derivatizing ∆8-THC, ∆9-THC, ∆10-THC, CBD, ∆9-THC-d3 and CBD-d3 using acetic anhydride. The cannabinoid-based products were determined to contain ∆8-THC, ∆8-THC-O-A, ∆9-THC-O-A and CBD-di-O-A and/or other phytocannabinoids using three different analytical techniques. Direct analysis in real-time-time-of-flight mass spectrometry was used for identifying exact masses. A gas chromatograph-mass spectrometer was used for the identification of compounds and to quantitate THC-O-As in the products. A liquid chromatograph-tandem mass spectrometer was used to identify and quantitate phytocannabinoids and CBD-di-O-A in the products. To the authors' knowledge, this is the first case report involving the identification of THC-O-As and CBD-di-O-A in commercially available products. Minimal clinical/pharmacological data is available for these emerging synthetic cannabinoids/novel psychoactive substances.
Topics: Acetates; Acetic Anhydrides; Cannabidiol; Cannabinoids; Dronabinol; Humans
PubMed: 35674405
DOI: 10.1093/jat/bkac036 -
Journal of Magnetic Resonance (San... Jan 2012In vivo detection of carboxylic/amide carbons is a promising technique for studying cerebral metabolism and neurotransmission due to the very low RF power required for...
In vivo detection of carboxylic/amide carbons is a promising technique for studying cerebral metabolism and neurotransmission due to the very low RF power required for proton decoupling. In the carboxylic/amide region, however, there is severe spectral overlap between acetate C1 and glutamate C5, complicating studies that use acetate as an astroglia-specific substrate. There are no known in vivo MRS techniques that can spectrally resolve acetate C1 and glutamate C5 singlets. In this study, we propose to spectrally separate acetate C1 and glutamate C5 by a two-step J-editing technique after introducing homonuclear (13)C-(13)C scalar coupling between carboxylic/amide carbons and aliphatic carbons. By infusing [1,2-(13)C(2)]acetate instead of [1-(13)C]acetate the acetate doublet can be spectrally edited because of the large separation between acetate C2 and glutamate C4 in the aliphatic region. This technique can be applied to studying acetate transport and metabolism in brain in the carboxylic/amide region without spectral interference.
Topics: Acetates; Algorithms; Carbon Isotopes; Computer Simulation; Magnetic Resonance Spectroscopy; Models, Chemical; Models, Molecular
PubMed: 22172286
DOI: 10.1016/j.jmr.2011.11.012 -
The Journal of Biological Chemistry Oct 1988Acetate kinase was purified 102-fold to a specific activity of 656 mumol of ADP formed/min/mg of protein from acetate-grown Methanosarcina thermophila. The enzyme was...
Acetate kinase was purified 102-fold to a specific activity of 656 mumol of ADP formed/min/mg of protein from acetate-grown Methanosarcina thermophila. The enzyme was not intrinsically membrane bound. The native enzyme (Mr 94,000) was an alpha 2 homodimer with a subunit Mr of 53,000. The activity was optimum between pH 7.0 and 7.4. A pI of 4.7 was determined. The enzyme was stable to O2 and stable to heating at 70 degrees C for 15 min but was rapidly inactivated at higher temperatures. The apparent Km for acetate was 22 mM and for ATP was 2.8 mM. The enzyme phosphorylated propionate at 60% of the rate with acetate but was unable to use formate. TTP, ITP, UTP, GTP, and CTP replaced ATP as the phosphoryl donor to acetate. The enzyme required one of several divalent cations for activity; the maximum rate was obtained with Mn2+. Western blots of cell extract proteins showed that acetate grown cells synthesized higher quantities of the acetate kinase than did methanol grown cells.
Topics: Acetate Kinase; Acetates; Acetic Acid; Blotting, Western; Euryarchaeota; Hot Temperature; Hydrogen-Ion Concentration; Isoelectric Point; Magnesium; Molecular Weight; Phosphotransferases
PubMed: 2844814
DOI: No ID Found -
Transports of acetate and haloacetate in Burkholderia species MBA4 are operated by distinct systems.BMC Microbiology Nov 2012Acetate is a commonly used substrate for biosynthesis while monochloroacetate is a structurally similar compound but toxic and inhibits cell metabolism by blocking the...
BACKGROUND
Acetate is a commonly used substrate for biosynthesis while monochloroacetate is a structurally similar compound but toxic and inhibits cell metabolism by blocking the citric acid cycle. In Burkholderia species MBA4 haloacetate was utilized as a carbon and energy source for growth. The degradation of haloacid was mediated by the production of an inducible dehalogenase. Recent studies have identified the presence of a concomitantly induced haloacetate-uptake activity in MBA4. This uptake activity has also been found to transport acetate. Since acetate transporters are commonly found in bacteria it is likely that haloacetate was transported by such a system in MBA4.
RESULTS
The haloacetate-uptake activity of MBA4 was found to be induced by monochloroacetate (MCA) and monobromoacetate (MBA). While the acetate-uptake activity was also induced by MCA and MBA, other alkanoates: acetate, propionate and 2-monochloropropionate (2MCPA) were also inducers. Competing solute analysis showed that acetate and propionate interrupted the acetate- and MCA- induced acetate-uptake activities. While MCA, MBA, 2MCPA, and butyrate have no effect on acetate uptake they could significantly quenched the MCA-induced MCA-uptake activity. Transmembrane electrochemical potential was shown to be a driving force for both acetate- and MCA- transport systems.
CONCLUSIONS
Here we showed that acetate- and MCA- uptake in Burkholderia species MBA4 are two transport systems that have different induction patterns and substrate specificities. It is envisaged that the shapes and the three dimensional structures of the solutes determine their recognition or exclusion by the two transport systems.
Topics: Acetates; Acetic Acid; Biological Transport; Burkholderia; Cell Membrane; Metabolic Networks and Pathways; Transcriptional Activation
PubMed: 23167477
DOI: 10.1186/1471-2180-12-267