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PubMed2002

Quantitative analysis of a model opioid peptide and its cyclic prodrugs in rat plasma using high-performance liquid chromatography with fluorescence and tandem mass spectrometric detection.

Two analytical methods were developed for quantitative determination of DADLE (H(2)N-Tyr-D-Ala-Gly-Phe-D-Leu-COOH) and its two cyclic prodrugs in rat plasma. For high-performance liquid chromatography with fluorescence detection (LC-FLU), precolumn derivatization of DADLE was accomplished by labeling the N-terminal amino group with the reagent naphthalene-2,3-dicarboxaldehyde in the presence of cyanide (NDA/CN) to form a highly fluorescent 1-cyanobenz[f]isoindole (CBI) derivative. A multi-dimensional LC system was employed to improve selectivity, and solid-phase extraction (SPE) was used for plasma sample preparation. The cyclic prodrugs were converted to DADLE prior to their derivatization. With fluorescence detection after derivatization, the limit of quantitation (LOQ) was 6 ng ml(-1) for the analysis of DADLE, and good linearity was observed up to 6000 ng ml(-1) in rat plasma. Quantitative analysis of DADLE and its cyclic prodrugs was also performed using liquid chromatography interfaced to electrospray ionization tandem mass spectrometry (LC-ESI-MS-MS). Chromatographic separation was achieved on a C(18) column using gradient elution in a water-acetonitrile system containing 0.1% (v/v) formic acid. The tandem mass spectrometric analysis was performed in the multiple reaction monitoring mode using internal standardization to improve assay precision and accuracy. For plasma sample pretreatment, acetonitrile was added first to precipitate proteins and SPE was used to minimize matrix effects. Using LC-ESI-MS-MS, the LOQ was 0.5 ng ml(-1) for DADLE and 2 to 5 ng ml(-1) for its prodrugs. Good linearity was observed from the LOQ up to 1000 ng ml(-1) for all compounds. For the analysis of DADLE, both analytical methods showed good precision, accuracy and stability. However, for prodrug analysis, LC-FLU showed some sensitivity and accuracy problems, while the LC-ESI-MS-MS method provided consistent and satisfactory results. In conclusion, LC-ESI-MS-MS is the method of choice for the analysis of DADLE and its cyclic prodrugs in rat plasma samples due to its good selectivity, high sensitivity, and fast analysis. Its application was demonstrated through biodisposition and bioconversion studies of the coumarinic acid-based prodrug after intravenous administration in rats.

Animals↗
PubMed1999

Poroelastic finite element analysis of a bone specimen under cyclic loading.

It had been suggested that the fluid embodied in bone lacunar-canalicular porosity may play an important role in bone remodelling [Weinbaum et al., 1994. Journal of Biomechanics 27, 339-360]. In this paper a finite element model of a poroelastic prismatic solid of rectangular cross-section is considered to simulate bone behaviour, precisely as in the previous work by Zhang and Cowin [Zhang and Cowin, 1994. Journal of Mechanical Physics of Solids 42, 1575-1599]. This solid is subject to combined cyclic axial and bending loads at its end. The objectives of the study are: (1) to verify the accuracy of the simplifying hypotheses underlying the analytical solutions established by the above authors; (2) to provide further insight into the behaviour of that solid; (3) to test the advantages in generality and versatility and the computing costs of general-purpose finite element codes in poroelastic analysis. The study is parametric with respect to the fluid leakage coefficient, to the ratio of the bending moment and axial load, and to the ratio of the characteristic relaxation time of the pore pressure over the excitation period. Results show that, for all the cases considered, the pore pressure distribution along the section height of the poroelastic beam exhibits a very good matching with previous analytical results. Stresses transversal with respect to the beam axis (assumed as constant or zero in previous analytical solutions) are evaluated. The analysis pointed out that: (1) the effects due to end-loads with zero resultants practically extinguish within a distance from the beam end almost equal to a typical length of the cross-section; (2) cross-sections remain plane above that distance; (3) the transversal total stresses are three orders of magnitude lower than axial stress.

Adaptation, Physiological↗
PubMed2005

cDNA microarray analysis of endothelial cells subjected to cyclic mechanical strain: importance of motion control.

Microarrays were utilized to determine gene expression of vascular endothelial cells (ECs) subjected to mechanical stretch for insight into the role of strain in vascular pathophysiology. Over 4,000 genes were screened for expression changes resulting from cyclic strain (10%, 1 Hz) of human umbilical vein ECs for 6 and 24 h. Comparison of t-statistics and adjusted P values identified genes having significantly different expression between strained and static cells but not between strained and motion control. Relative to static, 6 h of cyclic stretch upregulated two genes and downregulated two genes, whereas 24 h of cyclic stretch upregulated eight genes but downregulated no genes. However, incorporating the motion control revealed that fluid agitation over the cells, rather than strain, is the primary regulator of differential expression. Furthermore, no gene exceeded a threefold change when comparing cyclic strain to either static or motion control. Quantitative real-time polymerase chain reaction confirmed the dominance of fluid agitation in gene regulation with the exception of heat shock protein 10 at 24 h and plasminogen activator inhibitor 1 at 6 h. Taken together, the small number of differentially expressed genes and their low fold expression levels indicate that cyclic strain is a weak inducer of gene regulation in ECs. However, many of the differentially expressed genes possess antioxidant properties, suggesting that oxidative mechanisms direct EC adaptation to cyclic stretch.

Antioxidants↗
PubMed1977

[Periodic variations in motor endplate potentials].

The amplitudes of motor end-plate potentials in the Frog have been measured during repetitive stimulations of the motor nerve at frequencies between 0,5 and 30 Hz. A serial analysis showed that cyclic variations of these amplitudes were superimposed on the random fluctuation of epp due to the quantal nature of transmitter release. The period of these cyclic variations varied between 3 and 10 stimulations. This period was not significantly related to the frequency of the stimulation. The frequency spectrum analysis of the epp amplitudes showed similar values for the period of the cyclic variation of epp. The same kind of analysis applied to a binomial series of random numbers did not significantly present periodic fluctuations. The same analysis was applied to mean amplitudes of groups of 5 to 120 successive epps at the same end-plate. Periodic fluctuations were identified with periods of about 10 to 180 sec. It is suggested that periodic failures of nerve spike propagation in nerve terminals at sites of low safety factor, as at branchings, are responsible for the observed cyclic variation of epp.

Animals↗
PubMed1981

Characterization of 2':3'-cyclic nucleotide 3'-phosphodiesterase: rapid isolation, native enzyme analysis, identification of a serum-soluble activity, and kinetics.

The enzyme 2':3'-cyclic nucleotide 3'-phosphodiesterase (CNPase) was isolated from bovine brain white matter by a rapid (72 h) procedure. The minimum molecular weight (MW) of the enzyme was approximately 52,500 as estimated by sucrose density gradient analysis. When this isolated enzyme was stimulated with bovine serum albumin (BSA), the peak of activity was shifted to approximately 90,000 MW. Prior treatment by trypsin blocked the expression of the higher MW form of CNPase, but not the BSA activation of the enzyme. If the trypsin digestion was allowed to progress, the MW was gradually lowered to a broad peak sedimenting between 20,000 and 50,000 MW. An apparently soluble form of CNPase found in serum is described. Kinetic and MW comparisons between the serum soluble enzyme and CNPase isolated from bovine brain, as well as an analysis of substrate specificity, were made and it was concluded that the two enzymes were identical.

2',3'-Cyclic-Nucleotide Phosphodiesterases↗
PubMed1989

Cyclic AMP-dependent protein phosphorylation in isolated neuronal growth cones from developing rat forebrain.

We have shown recently that neuronal growth cones isolated from developing rat forebrain possess an appreciable activity of adenylate cyclase, which produces cyclic AMP and can be stimulated by various neurotransmitter receptor agonists and by forskolin. To investigate cyclic AMP-mediated biochemical mechanisms in isolated growth cones, we have centered the present study on cyclic AMP-dependent protein phosphorylation. One-dimensional gel electrophoretic analysis showed that cyclic AMP analogs increased incorporation of 32P into several phosphoproteins in molecular mass ranges of 50-58 and 76-82 kilodaltons, including those of 82, 76, and 51 kilodaltons. Two-dimensional electrophoresis, using isoelectric focusing in the first dimension, resolved phosphorylated alpha- and beta-tubulin species, actin, a very acidic protein (isoelectric point 4.0) with a molecular mass of 93 kilodaltons, and two proteins (x and x') closely neighboring beta-tubulin. Two other phosphoproteins seen in the gels had molecular masses of 56 and 51 kilodaltons (respective isoelectric points, 4.5 and 4.4) and, along with the 93-kilodalton phosphoprotein, were highly enriched in the isolated growth cones. Only the tubulin and actin species were major proteins in the isolated growth cones. Cyclic AMP analogs enhanced incorporation of 32P into phosphoproteins x and x', and, as assessed by immunoprecipitation, into beta-tubulin. Peptide digest experiments suggested that phosphoproteins x and x' are unrelated to beta-tubulin. Nonequilibrium two-dimensional electrophoresis resolved many phosphoproteins, of which a 79- and 75-kilodalton doublet, a 74-kilodalton species, and a 58-kilodalton doublet showed enhanced incorporation of 32P in the presence of cyclic AMP.

Actins↗
PubMed1995

Solution forms of antitumor cyclic pentapeptides with 3,4-dichlorinated proline residues, astins A and C, from Aster tataricus.

Conformational analysis of antitumor cyclic pentapeptides, astins A (1) and C (3), was made by a combination of NMR and computational techniques. These results indicated that the backbone conformations of 1 and 3, with lower activity than astin B (2), were different from that of 2. The backbone conformation together with a cis 3,4-dichlorinated proline residue was considered to play an important role in the antitumor activities of astins.

Antineoplastic Agents, Phytogenic↗
PubMedDate not supplied

[Usefulness of anti-cyclic citrullinate peptide antibody determination in synovial fluid analysis of patients with rheumatoid arthritis].

OBJECTIVE: To assess the role of anti-cyclic citrullinated peptide (CCP) antibody detection in synovial fluid (SF) of RA patients compared to OA patients. METHODS: We evaluated in 25 RA subjects and 14 OA patients, presenting a knee-joint effusion, the main clinical and laboratory parameters including the number of painful and/or swollen joints, Ritchie index, morning stiffness, ESR, CRP and analysis of SF obtained by therapeutic arthrocentesis. IgG anti-CCP (ELISA), rheumatoid factor (RF) and total IgG (nephelometry method) were measured in SF and paired serum samples. RESULTS: We found anti-CCP antibodies and RF in 64% (16/25) and 60% (15/25) of RA sera, respectively; 72% (18/25) of RA patients were positive for anti-CCP antibodies or RF. We found a higher SF/serum ratio for anti-CCP (p<0.004) compared to that for total IgG. The calculation of anti-CCP concentration as IgG anti-CCP (units)/total IgG (g L-1) revealed higher values in SF than in serum (p<0.046) in RA patients. Among these, correlation analysis showed that anti-CCP/total IgG values in SF correlated with the relative concentration of serum anti-CCP/total IgG (rs=0.842; p<0.00001) and serum anti-CCP antibody levels (rs=0.799; p<0.0001). We did not find any correlation between SF anti-CCP levels and the main characteristics of SF as well as the clinical or laboratory parameters. CONCLUSION: Our study give evidence for a preferential production of anti-CCP antibodies at RA joint level, confirming the pathogenetic role of these autoantibodies. Moreover, SF determination of anti-CCP, corrected for the total amount of the corresponding immunoglobulin, may be helpful as diagnostic tool in selected cases.

Adult↗
PubMed1996

Low level cyclic adenosine 3',5'-monophosphate accumulation analysis of [des-His1, des- Phe6, Glu9] glucagon-NH2 identifies glucagon antagonists from weak partial agonists/antagonists.

[des-His1, des-Phe6,Glu9]Glucagon-NH2 is a newly designed glucagon antagonist. This analog has a binding IC50 of 48 nM (compared to glucagon IC50 of 1.5 nM) and demonstrates pure antagonism in an adenylate cyclase assay. Although the number of glucagon antagonists has grown rapidly recently, closer examination suggested that many of these antagonists retained very low, almost imperceptible levels of cAMP accumulation that were sufficient to elicit an in vivo biological response. To investigate more carefully this secondary biological signal, we measured cAMP accumulation in a revised assay using isolated hepatocytes in the presence of the phosphodiesterase (PDE) inhibitor Rolipram. The PDE inhibitors Rolipram and isobutyl-1-methylxanthine (IBMX) increased the sensitivity of the cAMP accumulation assay from approximately 10-fold for the native hormone to 35-fold above basal levels. On the other hand, amrinone, another PDE inhibitor, did not affect the cAMP accumulation caused by glucagon. The use of PDE inhibitors indicated that three glucagon analogs that had previously been reported to have strong antagonist properties in classical adenylate cyclase assays were actually weak partial agonists in this new assay system. [N alpha-Trinitrophenyl-His1, homo-Arg12]glucagon, [des-amino-His1,D-Phe4,Tyr5, Arg12, Lys17,18,Glu21]glucagon, and [des-His1,Glu9]glucagon-NH2 demonstrated 233%, 21%, and 5.5% cAMP accumulation relative to the native hormone in the presence of 25 microM Rolipram. On the other hand, [des-His1,des-Phe6,Glu9]glucagon-NH2, a newly designed glucagon antagonist, did not activate adenylate cyclase in the presence of Rolipram up to a maximal physiological concentration of 1 microM, indicating that it was a pure antagonist of glucagon-induced adenylate cyclase activity and also the first one in this class. This compound and others were tested in a glycogen phosphorylase assay. As [des-His1,des- Phe6,Glu9]glucagon-NH2 did not activate phosphorylase activity, it was chosen as our candidate for in vivo testing in streptozotocin-induced diabetic rats. An initial dose of 0.75 mg/kg was found to cause the greatest lowering of blood glucose levels (to 63% of the initial levels in 15 min) when the bolus was followed by continuous infusion of 25 micrograms/kgxmin for 1 h.

1-Methyl-3-isobutylxanthine↗
PubMed1975

2-substituted derivatives of adenosine and inosine cyclic 3',5'-phosphate. Synthesis, enzymic activity, and analysis of the structural requirements of the binding locale of the 2-substituent on bovine brain protein kinase.

A number of 2-substituted cyclic nucleotide derivatives were synthesized and investigated as activators of cAMP-dependent protein kinase and as substrates for and inhibitors of cAMP phosphodiesterase. Ring closure of 5-amino-1-beta-D-ribofuranosylimidazol-4-carboxamide cyclic 3',5'-phosphate (1) with various aldehydes according to a new procedure (Meyer, R. B., Jr., Shuman, D.A., and Robins, R. K. (1974), J. Am. Chem. Soc. 96, 4962) gave new derivatives of adenosine cyclic 3',5'-phosphate with the following 2-substituents: n-propyl, n-hexl, n-octyl, n-decyl, styryl, o-methoxyphenyl, and 2-thienyl. Alkylation of 2-mercaptoadenosine cyclic 3',5'-phosphate (20, Meyer et al., 1974) gave new cAMP derivatives with the following 2-substituent: ethylthio, n-propylthio, isopropylthio, allylthio, n-decylthio, and benzylthio. Deamination of 2-methyl-,2-n-butyl-, and 2-ethylthioadenosine cyclic 3',5'-phosphate. Using multiple regression analysis, a striking relationship was found between the relative potency of the compounds as activators of bovine brain cAMP-dependent protein kinase and parameters describing the hydrophobic, steric, and electronic character of the substituents on these compounds. All compounds were substrates for a cyclic nucleotide phosphodiesterase preparation from rabbit kidney. Additionally, the compounds were as a group, good inhibitors of the hydrolysis of cAMP by phosphodiesterase preparations from rabbit lung, beef heart, and dog heart.

Animals↗
PubMed2006

Lengthening of a single-loop tibialis tendon graft construct after cyclic loading: a study using Roentgen stereophotogrammetric analysis.

Although single-loop tibialis tendon allografts have increased in popularity owing to their many advantages over patellar tendon and double-loop hamstring tendon autografts, some percentage of the patient population do not have clinically stable knees following anterior cruciate ligament reconstruction with single-loop tibialis tendon allografts. Therefore, it would be advantageous to determine the causes of increased anterior laxity which ultimately must be traced to lengthening of the graft construct. One objective of this study was to demonstrate the feasibility of using Roentgen stereophotogrammetric analysis (RSA) to determine the causes of lengthening of a single-loop graft construct subjected to cyclic loading. A second objective was to determine which cause(s) contributes most to an increase in length of this graft construct. Radio-opaque markers were inserted into ten grafts to measure the lengthening at the sites of the tibial and femoral fixations and between the sites of fixation. Each graft was passed through a tibial tunnel in a calf tibia, looped around a rigid cross-pin, and fixed to the tibia with a Washerloc fixation device. The grafts were cyclically loaded for 225,000 cycles from 20 to 170 N. Prior to and at intervals during the cyclic loading, simultaneous radiographs were taken. RSA was used to determine the three-dimensional coordinates of the markers from which the lengthening at the sites of fixation and between the sites of fixation was computed at each interval. The sites of the femoral and tibial fixations were the largest contributors to the increase in length of the graft construct, with maximum average values of 0.68 and 0.55 mm, respectively, after 225,000 cycles. The graft substance between the sites of fixation contributed least to lengthening of the graft, with a maximum average value of 0.31 mm. Ninety percent of the maximum average values occurred before 100,000 cycles of loading for the largest contributors. RSA proved to be a useful method for measuring lengthening due to all three causes. Lengthening of the graft construct at the sites of both fixations is sufficiently large that the combined contributions may manifest as a clinically important increase in anterior laxity.

Animals↗
PubMed2005

GC-MS analysis of penta- and tetra-cyclic triterpenes from resins of Pistacia species. Part I. Pistacia lentiscus var. Chia.

Pistacia species contain oleoresins with bioactive triterpenes. In this study triterpenes, including minor components, were identified and quantified in both neutral and acidic fraction of Pistacia lentiscus var. Chia resin, grown exclusively in Chios island (Greece), collected traditionally, as well as by the use of stimulating agents (liquid collection). It was proved that these two resin samples were composed of several different minor triterpenes. In the traditional collection of the resin, 36 triterpenes were identified, 23 of which are new minor compounds (five in the acidic and eighteen in the neutral fraction). In the liquid collection resin eight compounds were identified in the acidic and 11 in the neutral fraction, while seven compounds were not contained in resin traditionally collected. The main triterpenes in both resin samples collected traditionally and by use of stimulating agents were in the following order: isomasticadienonic acid (24 and 22.5% w/w of triterpenic fraction respectively), masticadienonic acid (9.3 and 14.7% w/w of triterpenic fraction) and 28-norolean-17-en-3-one (19 and 36% w/w of triterpenic fraction respectively). The aim of this study was to compare the qualitative and quantitative composition of triterpenes in the resin samples collected using the traditional and new liquid techniques, and examine whether the collection technique influences the contained triterpenes in P. lentiscus var. Chia resin samples. Finally, since there is confusion on interpreting mass spectra of triterpenes we present an analytical review on the base peaks, main fragments and fragmentation mechanism/pattern of several skeleton penta- and tetra- cyclic triterpenes reported in P. lentiscus resin. Also, a biosynthetic route for triterpene skeletons contained in P. lentiscus resin was approached.

Gas Chromatography-Mass Spectrometry↗
PubMed2005

GC-MS analysis of penta- and tetra-cyclic triterpenes from resins of Pistacia species. Part II. Pistacia terebinthus var. Chia.

Pistacia species contain oleoresins with bioactive triterpenes. In this study triterpenes, including minor components, were identified and quantified in both neutral and acidic fractions of Pistacia terebinthus var. Chia resin, grown exclusively in Chios island (Greece), collected traditionally, as well as using stimulating agents (liquid collection). It was proved that these two resin samples were composed of several different minor triterpenes, while major constituents were similar but in different proportions. Compounds that differentiated two resin samples of P. lentiscus and P. terebinthus var. Chia, both traditionally collected, were detected, in order to identify the nature of resins present in archaeological materials. In the traditionally collected resin, 37 triterpenes were identified, 12 in the acidic and 25 in the neutral fraction. In the liquid collection resin 10 compounds were identified in the acidic and 23 in the neutral fraction, while 16 compounds were not contained in the traditionally collected resin. The main triterpenes in both resin samples collected traditionally and using stimulating agents were: isomasticadienonic acid (23.6 and 26.3% w[sol ]w of the triterpenic fraction, respectively), 28-norolean-17-en-3-one (16.3 and 17.5% w[sol ]w of the triterpenic fraction, respectively) and masticadienonic acid (5.8 and 6.0% w[sol ]w of the triterpenic fraction). In this study the qualitative and quantitative composition of triterpenes was compared in the Pistacia lentiscus and P. terebinthus var. Chia resin samples collected with the traditional and new liquid techniques, and also triterpenes in resins of P. terebinthus obtained by the traditional technique and using stimulating agents. The aim of the study was also to examine whether the collection technique influenced the triterpenes contained in P. terebinthus var. Chia resin samples.

Gas Chromatography-Mass Spectrometry↗
PubMed1994

Analysis of transcriptional activation of a cyclic AMP response element by 2,6,10,14-tetramethylpentadecane (pristane) in JB6 mouse epidermal cells.

Pristane is a naturally occurring isoprenoid that is believed to be derived from the phytyl moiety of chlorophyll. Thus, it is not surprising that pristane is present in many common fruits and vegetables. Furthermore, pristane can be detected in the tissues of fish and mammals. In animal models using rodents, pristane can function as a potent tumor promoter. At the molecular level, pristane can induce changes in the plasma membrane, alter the conformation of chromatin, and selectively activate gene expression. Addition of pristane to a mouse epidermal cell line (JB6 P+) allows these cells to grow in an anchorage-independent manner. In contrast, JB6 P-cells are not transformed by pristane. Our study was undertaken to correlate transformation of P+ cells with changes induced by pristane. Transcriptional activation of a cyclic AMP response element (CRE) was induced by pristane in P+ and P-cells. Point mutations in the CRE abolished activation by pristane, thus indicating that an intact CRE was necessary for pristane activation. In P+ cells, pristane repressed phosphodiesterase activity. However, protein kinase A was activated by pristane in P+ and P-cells. Taken together, these results indicated pristane induced novel changes in P+ cells that in turn may facilitate neoplastic transformation.

Activating Transcription Factor 2↗
PubMed1987

Nuclear magnetic resonance analysis and conformational characterization of a cyclic decapeptide antagonist of gonadotropin-releasing hormone.

Two-dimensional proton nuclear magnetic resonance spectroscopy at 500 MHz has been carried out on the cyclic decapeptide antagonist of gonadotropin-releasing hormone: cyclo-(delta 3-Pro1-D-pClPhe2-D-Trp3-Ser4-Tyr5-D-Trp6-NMeLeu7-Arg8- Pro9-beta-Ala 10). The antagonist exists in two slowly interconverting conformations. All data are consistent with the conclusion that one form has all-trans peptide bonds and the other has a cis beta-Ala10-delta3-Pro1 bond. With the use of sequential assignment methods, chemical shift assignments were obtained for all backbone and side-chain protons of both conformational isomers except for the serine and tyrosine hydroxyl groups and the C gamma, C delta, and guanidinium group protons of the arginine. Temperature dependence of spectral parameters and magnitudes of observed nuclear Overhauser effects support the interpretation that both conformers of the antagonist consist of two beta-turns (type II', D-Trp6-NMeLeu7; type II, delta 3-Pro1-D-pClPhe2) connected by extended antiparallel beta-like strands.

Gonadotropin-Releasing Hormone↗