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Characterization of creatinine error in ketotic patients. A prospective comparison of alkaline picrate methods with an enzymatic method.

Creatinine measurement by alkaline picrate reagents is subject to positive interference by acetoacetate. Enzymatic reagents avoid this interference and have been adapted to instruments such as the Ektachem-400 (Kodak). By documenting the discrepancy between alkaline picrate and Ektachem determinations for creatinine, the authors prospectively identified ketotic patients in whom the presence of ketones was responsible for a significant creatinine error. During their three-month survey, they identified 50 such ketotic inpatients. Those admitted to the medicine service represented almost 5% of all medicine admissions over this time. Of the total specimens, the mean discrepancy was 14 +/- 8 mg/L with a range of 4-44 mg/L. The greater the ketosis, the greater the discrepancy. Two-thirds of the samples were normal on the Ektachem but greater than normal by picrate methods. In addition to diabetes or ethanol abuse, 17% of the ketotic patients had severe or terminal illness that was generally associated with malnutrition.

Acetoacetates↗

[X-ray crystallographic analysis of picrates].

Picric acid forms stable picrates with various organic molecules through pi- bonding or ionic bonding, and such picrates have been very useful for identification and qualitative analysis. As it seemed desirable to determine the crystal structures and the bonding mode of picrates of basic organic compounds, we have investigated the crystal structures of aromatic hydrocarbons, aromatic amino compounds, heterocyclic compounds and so on. A series of our studies on the crystal structure of basic organic compounds have shown that the complexes of picric acid and aromatic hydrocarbons are formed through pi-bonding, and those of aromatic heterocyclic compounds are formed through ionic and hydrogen bonding; in addition, some of them also have pi-bonding.

Amines↗

The crystal structures of 3-TAPAP in complexes with the urokinase-type plasminogen activator and picrate.

The urokinase-type plasminogen activator (uPA) is a protein involved in tissue remodeling and other biological processes. The inhibitors of uPA have been shown to prevent the spread of metastasis and tumor growth, and accordingly this enzyme is widely accepted as a promising anticancer target. In this work, we have investigated the conformation of the uPA inhibitor 3-TAPAP in two different crystalline environments of a picrate and a uPA complex. These structures were compared to the known structure of the 3-TAPAP in the complex with trypsin. In the complexes with the proteins, trypsin, and uPA, the binding mode of 3-TAPAP is similar. A larger difference in the conformation, in the comparison to these structures, has been observed by us in the 3-TAPAP picrate crystal. This observation contradicts the hypothesis that 3-TAPAP derivatives inhibit serine proteinases in preformed stable conformations.

Amidines↗

Pyridoxinium picrate.

The title compound [systematic name: 3-hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridinium 2,4,6-trinitrophenolate], C(8)H(12)NO(3)(+)xC(6)H(2)N(3)O(7)(-), is a complex of picric acid with pyridoxine. The asymmetric part of the unit cell contains one pyridoxinium cation and one picrate anion. The aromatic rings of the picrate anion and the pyridoxinium cation are inclined with a dihedral angle of 83.19 (7) degrees . An intramolecular hydrogen bond between OH and a nearby CH(2)OH group is observed in the cation. The hydrophobic layers at y = {1/2} are packed between the hydrophilic layers at y = 0.

Anions↗

Dipotassium and sodium/potassium crystalline picrate complexes with the crown ether 6,7,9,10,12,13,20,21,23,24,26,27-dodecahydrodibenzo[b,n]-[1,4, 7,10,13,16,19,22]octaoxacyclotetracosin (dibenzo-24-crown-8).

The crystal structures of the dipotassium and the mixed sodium/potassium picrate complexes with the crown ether dibenzo-24-crown-8 (DB24C8) were solved and found to be nearly identical. (I): NaK-pic2(DB24C8), [NaK(C6H2N3O7)2(C24H32O8)]. Mr = 966.8, triclinic, P1, a = 8.164 (2), b = 9.960 (2), c = 13.368 (3) A, alpha = 103.92 (3), beta = 108.03 (2), gamma = 93.23 (2) degrees, V = 993.0 (7) A3, Z = 1, Dm = 1.54 (T = 298 K). Dx = 1.62 (1) g cm-3, lambda = (Mo K alpha) 0.71069 A, mu = 2.37 cm-1, F(000) = 500, T = 103 K, R = 0.086 for 2904 unique reflections. (II): K2pic2(DB24C8), [K2(C6H2N3O7)2(C24H32O8)]. Mr = 982.9, triclinic, P1, a = 8.231 (4), b = 9.850 (2), c = 13.346 (4) A, alpha = 103.91 (2), beta = 106.82 (3), gamma = 93.37 (2) degrees, V = 995.7 (9) A3, Z = 1, Dm = 1.59 (T = 298 K), Dx = 1.638 (8) g cm-3, lambda (Mo K alpha) = 0.71069 A, mu = 3.30 cm-1, F(000) = 508, T = 163 K, R = 0.042 for 4835 unique reflections. Both structures feature eight-coordinated cations between alternating layers of relatively flat crown ligands and paired picrates. In the mixed-metal system the two cations are disordered between two P1-related sites; these metal sites have a coordination environment only slightly different from that in the dipotassium structure. Na+ is able to occupy an environment similar to that of K+ under the conditions of these crystals, a situation not previously observed in the chemistry of crown ethers or macrocylic multidentates.

Chelating Agents↗

Crystal structure of serotonin picrate, a donor-acceptor complex.

The crystal structure of the red picric acid salt of serotonin was determined by x-ray diffraction methods. The structure consists of parallel hydroxyindole and picrate planes which are intimately stacked with an interplanar separation of 3.3 to 3.4 angstroms. The stacking interaction appears to be of the donor-acceptor (charge-transfer) type, involving specific contacts between picrate nitro groups and atoms of the hydroxyindole moieties. Similar interactions might mediate biological processes involving serotonin.

Electron Transport↗

Kinetic potentiometric determination of creatinine in serum with a picrate ion-selective membrane electrode.

We describe a new kinetic method for potentiometric determination of creatinine in serum, based on the creatinine--picrate reaction in alkaline medium (Jaffé reaction). The reaction is monitored with a picrate-selective electrode, and the increase in electrode potential during 270 s is measured and related directly to the creatinine concentration. Small cation-exchange columns are used to separate creatinine from interfering substances. Analytical recovery of creatinine added to serum was 100.7%. Results for a series of samples compared well with results obtained with a spectrophotometric method (r = 0.994).

Creatinine↗

[UV-spectroscopic study of complex formation between nonactin and picrates of monovalent cations].

A macrotetrolide preparation including nonactin (about 75 per cent), monactin (about 23 pr cent) and traces of dinactin and trinactin was analyzed with the method of UV spectroscopy. It was shown to form hydrophobic complexes in organic solvents with picrates of univalent cations of ammonium, potassium and sodium. The complex strength depended not only on the cation nature, but also on the solvent and pH of the picrate aqueous solutions. The comparison of methylene chloride used for tetrananactin with chloroform demonstrated that nonactin formed stable complexes in chloroform at neutral pH of the aqueous phase, a solution of picric acid and ammonium chloride.

Anti-Bacterial Agents↗

Vibrational spectroscopic studies of an organic non-linear optical crystal 8-hydroxyquinolinium picrate.

8-hydroxyquinolinium picrate (8-HQP) was synthesized by the addition of equimolar quantities of 8-hydroxyquinoline (8-HQ) and picric acid (PA). Single crystals were grown from N,N dimethyl formamide (DMF) by restricted evaporation method at room temperature. The solubility of 8-HQP was determined in different solvents at various temperatures. The structural characterization of the grown crystals was carried out by X-ray diffraction. Vibrational modes were classified on the basis of group theoretical analysis and the spectral bands were compared with those of parent compounds in order to propose a tentative assignment by recording FT-IR, FT-Raman and polarized Raman spectra in different crystal orientations. The crystal possess lower cut-off at 230 nm and good transparency as confirmed by optical transmittance studies.

Crystallography, X-Ray↗

Trichrome staining of Gyrodactylus sclerites and soft tissues following fixation in ammonium picrate-glycerin, including an improved rendition of the haptoral bars of G. turnbulli.

A simple technique using modified Mallory stain in the transferral of Gyrodactylus specimens from ammonium picrate-glycerin to a permanent mountant is described. Hamuli, their connecting bars and the penis sclerites are well defined by the technique as are muscles and tendons, cell nuclei, tegument and gland cells. As well as being useful in the study of general anatomy, the technique enhances the observation of the taxonomically important ventral and dorsal bars. In order to show this, improved illustrations of the dorsal and ventral bars of G. turnbulli are given along with explicit demonstrations of differences in morphology of the ventral bars of G. bullatarudis and G. rasini-two easily confused species.

Animals↗

[Effect of selective application of sodium picrate to the hypogastric ganglion in the hypogastric nerve-vas deferens preparation of the guinea pig (author's transl)].

Effect of sodium picrate (picric acid-Na; PA) on the hypogastric ganglion in the hypogastric nerve-vas deferens preparation of the guinea pig was studied and the results are as follows: PA or acetylcholine (ACh) at doses (g/ml) of 10(-5) approximately 10(-4) applied to the ganglion increased the height of the response (R-NS) of the vas deferens to the hypogastric nerve stimulation. Neither drug restored R-NS blocked by hexamethonium 3 X 10(-5). Effects of PA and ACh on R-NS were potentiated by neostigmine 10(-7) and the potentiation was considerably greater for ACh than for PA. Effects of PA on R-NS were not influenced by pretreatment with atropine. Both PA and ACh recovered R-NS which was partially reduced by hemicholinium-3 (HC-3), although the recovery of R-NS by PA was rapidly abolished more than that by ACh when these drugs were repeatedly applied in the presence of HC-3 3 X 10(-5). PA markedly recovered the R-NS reduced by morphine 10(-4) and ACh slightly restored that R-NS. These results suggest that the site of action of PA on the hypogastric ganglion of the guinea pig is different from that of ACh and the effect of PA on R-NS may be due to the acceleration of ACh-release from preganglionic nerve endings.

Acetylcholine↗

Reaction of alkaline sodium picrate with creatinine: I. Kinetics and mechanism of formation of the mono-creatinine picric acid complex.

Spectrophotometric, kinetic, and nuclear magnetic resonance studies indicate that alkaline sodium picrate and creatinine react to form a 1/1 aduct between picric and creatinine, with a stability constant of log K= 4.26. Kinetic studies indicate that the forward reaction is first order with respect to picric acid, hydroxide, and creatinine concentration. The reverse reaction, the dissociation of the 1/1 complex, shows a complex dependence on hydroxide concentration. The expression for the observed pseudo-first-order rate constant in the presence of excess picric acid is: Kobsd = K1K0[P][OH] +[K2[OH]x. A value of K1K0 = 5.0 (mol/liter)-2s-1 is obtained. For accurate analytical results with this reaction, hydroxide concentration must be maintained at a constant value for both samples and standards.

Chemical Phenomena↗

Lactulose interferes in the alkaline picrate assay for creatinine.

Errors of more than 10 mg/L in measured serum creatinine concentrations were encountered for an azotemic patient who was given lactulose orally. The magnitude of the apparent error fluctuated with the dose of lactulose. Additions of lactulose to serum produced a linear increase in the creatinine measured by each of two automated methods that involve use of the alkaline picrate (Jaffé) reaction. A lactulose concentration of 100 g/L produced positive interferences of 30 and 65 mg/L in kinetic (Beckman Astra) and continuous-flow (Technicon SMAC) assays, respectively, but caused no problem in an enzymatic assay for creatinine. The results of creatinine assays must be interpreted with caution in patients treated with lactulose.

Creatinine↗

Physicochemical Properties of Dodecylammonium Picrate.

A novel surfactant, dodecylammonium picrate (DDAP), was synthesized and its crystal structure was determined by X-ray diffraction analysis. DDAP's physicochemical properties were examined by spectral (infrared and nuclear magnetic resonance), thermal, microscopic, and conductometric studies. The results revealed the influence of counterion specificity on thermal solid-state transitions and solution properties: the Krafft point, the aqueous solubility, the critical micelle concentration, the degree of counterion binding, and thermodynamic parameters of micellization. Copyright 2000 Academic Press.

Journal Article↗

Synthesis and crystal structure of a unique linear homoditopic ligand bifacially complexed to lithium picrate

[structure: see text] Preparation of the first rigid homoditopic tris(tetrahydrofuranyl) ligand with a pair of exotopic binding sites specifically tailored for effective coordination to lithium ions is described. The crystallographically defined structural parameters of the monomeric building block and a 1:2 complex of the dimer with lithium picrate reveal the unique features of these materials.

Journal Article↗