Rapid hydrolysis of amides under physiological conditions: Influence of the microenvironment on the stability of the amide bond

1998 ◽  
Vol 8 (3) ◽  
pp. 285-288 ◽  
Author(s):  
K.-H. Glüsenkamp ◽  
C. Mengede ◽  
W. Drosdziok ◽  
E. Jähde ◽  
M.F. Rajewsky
1998 ◽  
Vol 5 (4) ◽  
pp. 207-215 ◽  
Author(s):  
George Mokdsi ◽  
Margaret M. Harding

The rate of hydrolysis of the aromatic rings of Cp2TiX2 [X = CI 1, O2CCCl3  8 and O2CCH2NH3Cl  13], in aqueous solutions, 10%DMSO and 100% DMSO have been studied by H1NMR spectroscopy. Rapid hydrolysis of both the carboxylate and cyclopentadienyl ligands in Cp2TiX2[X = O2CCCl3,O2CCH2NH3Cl] occurs in DMSO to give biologically inactive species. The rate of these reactions are concentration dependent as dilution of these samples with saline or water to give the therapeutic conditions of 10%DMSO/90%H2O slows the hydrolysis chemistry. In contrast, samples of Cp2TiX2 [X = CI 1, O2CCH2NH3Cl  13], dissolved in water give solutions containing the presumed antitumour active species in which the halide or glycine ligands have been hydrolysed but the Cp rings remain metal bound.


2010 ◽  
Vol 93 (2) ◽  
pp. 380-388 ◽  
Author(s):  
Carmen Ferrer ◽  
Ana Agüera ◽  
Milagros Mezcua ◽  
Amadeo R Fernández-Alba ◽  
Dorothea Mack ◽  
...  

Abstract This paper compares the performance of the three most widely employed multiresidue methods [quick, easy, cheap, effective, rugged, and safe (QuEChERS), mini-Luke, and ethyl acetate] currently used for the determination of amitraz residues in fruits. A fast and differentiated analysis of amitraz and its two main metabolites, N-2,4-dimethylphenyl-N-methylformamidine and 2,4-dimethylformanilide, was performed by HPLC-electrospray ionization-MS/MS using a triple quadrupole mass spectrometer in the positive mode. A test of the stability of the standard solutions showed a rapid hydrolysis of amitraz to the amide and amidine derivatives in solutions containing water, including QuEChERS extracts of crops that were previously acidified. Two useful mass transitions were used to confirm the presence of each analyte in the sample extracts. LOD values ranging from 0.4 to 2.0 g/kg were obtained. Linearity of response over 2 orders of magnitude was demonstrated (r2 > 0.999) in solvent and pear extract. The recovery studies were performed on pear blanks spiked at two concentration levels, 50 and 500 g/kg (N 5). Best recoveries, ranging from 75 to 103, were obtained by the application of the QuEChERS method with CV <8 in all cases. The QuEChERS method was applied to a monitoring study carried out by the Chemical and Veterinary Investigation Office Stuttgart laboratory. From the 63 pear samples analyzed, 21 contained amitraz residues (expressed as sum) ranging from 0.02 to 2.9 mg/kg. Amitraz parent was detected only in a few cases at very low concentration levels, with N-2,4-dimethylphenyl-N-methylformamidine being the metabolite almost entirely representing the total residue. These results emphasize that the residue situation is clearly underestimated if only the parent compound is targeted, and they reinforce how important it is to include amitraz in the target scope of pesticide residue laboratories, especially since the concentrations detected exceeded the Acute Reference Dose in the majority of cases and pose a health risk to the consumer.


1965 ◽  
Vol 18 (5) ◽  
pp. 651 ◽  
Author(s):  
RW Green ◽  
PW Alexander

The Schiff base, N-n-butylsalicylideneimine, extracts more than 99.8% beryllium into toluene from dilute aqueous solution. The distribution of beryllium has been studied in the pH range 5-13 and is discussed in terms of the several complex equilibria in aqueous solution. The stability constants of the complexes formed between beryllium and the Schiff base are log β1 11.1 and log β2 20.4, and the distribution coefficient of the bis complex is 550. Over most of the pH range, hydrolysis of the Be2+ ion competes with complex formation and provides a means of measuring the hydrolysis constants. They are for the reactions: Be(H2O)42+ ↔ 2H+ + Be(H2O)2(OH)2, log*β2 - 13.65; Be(H2O)42+ ↔ 3H+ + Be(H2O)(OH)3-, log*β3 -24.11.


2021 ◽  
Vol 14 (8) ◽  
pp. 733
Author(s):  
Julia Aresti-Sanz ◽  
Markus Schwalbe ◽  
Rob Rodrigues Pereira ◽  
Hjalmar Permentier ◽  
Sahar El Aidy

Methylphenidate is one of the most widely used oral treatments for attention-deficit/hyperactivity disorder (ADHD). The drug is mainly absorbed in the small intestine and has low bioavailability. Accordingly, a high interindividual variability in terms of response to the treatment is known among ADHD patients treated with methylphenidate. Nonetheless, very little is known about the factors that influence the drug’s absorption and bioavailability. Gut microbiota has been shown to reduce the bioavailability of a wide variety of orally administered drugs. Here, we tested the ability of small intestinal bacteria to metabolize methylphenidate. In silico analysis identified several small intestinal bacteria to harbor homologues of the human carboxylesterase 1 enzyme responsible for the hydrolysis of methylphenidate in the liver into the inactive form, ritalinic acid. Despite our initial results hinting towards possible bacterial hydrolysis of the drug, up to 60% of methylphenidate is spontaneously hydrolyzed in the absence of bacteria and this hydrolysis is pH-dependent. Overall, our results indicate that the stability of methylphenidate is compromised under certain pH conditions in the presence or absence of gut microbiota.


2019 ◽  
Vol 118 ◽  
pp. 03048
Author(s):  
Changchun Li ◽  
Yuxin Wu

Hydrogen generation from rapid hydrolysis of aluminum in sodium fluoride solution was investigated through a hydrolysis experiment. Rapid and instant hydrogen yield were observed using sodium fluoride as additive. The experimental results demonstrate that the increase of temperature and the amount of additives in a certain range will boost the hydrogen production. The amount of additives outside the range only has an effect on the rapid hydrolysis of the aluminum during the initial stage, but the total amount of hydrogen produced doesn’t increased significantly. Theoretical analysis of the effects of the mixing ratio and the temperature on the hydrogen production rates were performed using the shrinking core model and the kinetic model. The shrinking core model parameter a and k indicate the film change degree of porosity and thickness and the effect of time on the diffusion coefficient. the kinetic model is verified and the activation energy confirming hydrogen yield control by a molecular diffusion process. Correspondingly, mechanisms of Al corrosion in NaF solutions under low and high alkalinity were proposed, respectively.


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