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PubMed1991

Conditioning the elevation of body temperature, a host defensive reflex response.

We hypothesize that a number of host defense responses such as natural killer (NK) cell activity, cytotoxic lymphocyte (CTL) activity, antibody production, and elevated body temperature (TR) might be conditionable. We have designated such specifically learned response to be a defensive reflex response. Here we describe a simple single trial association paradigm for conditioning the TR response in BALB/c mice. Animals are conditioned on day 0 by exposing them to the odor of camphor for 1 hr, followed by injection of the pyrogen poly I:C 20 microgram ip. Control groups are injected with either poly I:C or saline and not exposed to the camphor odor. Reexposure of all groups to the conditioned stimulus (CS) on day 2 or 3 cause elevation of body temperature in the conditioned group mice but not in the nonconditioned or saline control groups. Since we have conditioned the natural killer cell response with the same paradigm, these results suggest that multiple defensive responses might be conditionable simultaneously and they might have important survival value for the species.

Animals↗
PubMed1991

The comparative antimicrobial effect of calcium hydroxide.

The antimicrobial effectiveness of calcium hydroxide, camphorated paramonochlorophenol, and formocresol in root canals of extracted human teeth was compared. Canals in single-rooted teeth were enlarged and inoculated with Streptococcus mutans, Actinomyces viscosus, and Bacteroides gingivalis or Bacteroides fragilis. After treatment with a test agent and sealing and incubation for 1 hour, the canal contents were analyzed for the number of viable test bacteria and compared with that of inoculated teeth not treated with test agents. All test agents exhibited antimicrobial activity against all bacteria, with percent reductions in viable bacteria ranging from 64.3% to 100%. The combined data for Pulpdent paste and calcium hydroxide showed significantly higher antimicrobial activity than the combined data for camphorated paramonochlorophenol and formocresol for S. mutans and B. gingivalis or B. fragilis but showed no difference for A. viscosus.

Actinomyces↗
PubMed1995

Thermodynamic aspects of the CO-binding reaction to cytochrome P-450cam. Relevance with their biological significance and structure.

The CO-binding kinetics of cytochrome P-450cam(+) and P-450cam(-) have been measured in the millisecond time domain using a flash photolysis method. We have determined the reaction coordinates for free energy, enthalpy and entropy from the temperature dependence of the overall rate constants of the bimolecular forward (on) and backward (off) reactions. Comparing the thermodynamic profiles of P-450cam with that of myoglobin (Mb) reported so far, the enthalpy and the entropy coordinates exhibit the following remarkable characteristics. The CO-binding equilibrium: The stability of the CO-complex is perfectly entropy-driven for P-450cam, while enthalpy-driven for Mb. This entropy-driven feature for P-450cam is enhanced by the dissociating d-camphor. The on and off activation processes: The on and off reactions for P-450cam are dominantly controlled by the enthalpy and entropy terms, respectively, while those for Mb are rather the reverse of the case of P-450cam. The dissociation of d-camphor has a significant effect on the on reaction but no effect on the off reaction. Analyzing these thermodynamic features on the basis of the physical chemistry in the solution reaction, it was found that these characteristic profiles arise from the difference in the global structural change between the proteins. Namely, during the equilibrium process of the CO binding, this structural change is accompanied by a larger increase in the degree of freedom in P-450cam than in Mb. We discussed the correlations between the structural changes and their biological significance.

Camphor↗
PubMed2004

Conformational states of cytochrome P450cam revealed by trapping of synthetic molecular wires.

Members of the ubiquitous cytochrome P450 family catalyze a vast range of biologically significant reactions in mammals, plants, fungi, and bacteria. Some P450s display a remarkable promiscuity in substrate recognition, while others are very specific with respect to substrate binding or regio and stereo-selective catalysis. Recent results have suggested that conformational flexibility in the substrate access channel of many P450s may play an important role in controlling these effects. Here, we report the X-ray crystal structures at 1.8A and 1.5A of cytochrome P450cam complexed with two synthetic molecular wires, D-4-Ad and D-8-Ad, consisting of a dansyl fluorophore linked to an adamantyl substrate analog via an alpha,omega-diaminoalkane chain of varying length. Both wires bind with the adamantyl moiety in similar positions at the camphor-binding site. However, each wire induces a distinct conformational response in the protein that differs from the camphor-bound structure. The changes involve significant movements of the F, G, and I helices, allowing the substrate access channel to adapt to the variable length of the probe. Wire-induced opening of the substrate channel also alters the I helix bulge and Thr252 at the active site with binding of water that has been proposed to assist in peroxy bond cleavage. The structures suggest that the coupling of substrate-induced conformational changes to active-site residues may be different in P450cam and recently described mammalian P450 structures. The wire-induced changes may be representative of the conformational intermediates that must exist transiently during substrate entry and product egress, providing a view of how substrates enter the deeply buried active site. They also support observed examples of conformational plasticity that are believed be responsible for the promiscuity of drug metabolizing P450s. Observation of such large changes in P450cam suggests that substrate channel plasticity is a general property inherent to all P450 structures.

Adamantane↗
PubMedDate not supplied

Assessment of hormonal activity of UV filters in tadpoles of frog Xenopus laevis at environmental concentrations.

Residues of UV filters used as ultraviolet absorbers in sunscreens, cosmetics and in light protection have been found in surface water and fish. Recently some of them were shown bearing estrogenic activity, however, very little is known about possible adverse effects to aquatic life. Here we investigate whether two UV filters, 4-methylbenzylidene camphor (4-MBC) and 3-benzylidene camphor (3-BC), interfere with the thyroid and sex hormone system during frog metamorphosis. Xenopus laevis tadpoles were exposed to 1, 5 and 50 microg/L of 4-MBC and 3-BC, respectively, for 35 days (NF stage 52-66). The rate of metamorphosis was not affected, and no obvious differences in body and tail length compared to controls were observed. Neither 4-MBC, nor 3-BC led to effects on the sex ratio or gross gonad morphology of X. laevis at stage 66. Our results indicate that these UV filters do not negatively affect the thyroid system and sex ratio of frogs at environmental concentrations.

Animals↗
PubMed2004

Evaluation of pH levels and calcium ion release in various calcium hydroxide endodontic dressings.

OBJECTIVE: The purpose of this study was to evaluate Ca(2+) release and pH of 3 calcium hydroxide-based products used routinely as intracanal dressings, as well as the new gutta-percha points with calcium hydroxide. STUDY DESIGN: The pH and Ca(2+) release were assessed using Calen with camphorated paramonochlorophenol, saline calcium hydroxide paste, LC paste (Lopes and Costa paste-calcium hydroxide with olive oil), and calcium hydroxide containing gutta-percha points. The materials were inserted in polyethylene tubes and immersed in deionized water. The pH variation and Ca(2+) release were monitored periodically for 4 weeks. RESULTS: After 72 hours, materials 1 and 2 raise the pH from 9.6 and 8.2 to 11.4 and 11.3, respectively, while a small change was observed for materials 3 and 4. The calcium concentration released from materials 1, 2, 3, and 4 after 72 hours was 6.54, 4.98, 1.31, and 1.74 mg/dL, respectively. CONCLUSION: Calen plus camphorated paramonochlorophenol and saline calcium hydroxide paste exhibited the highest calcium release and pH levels.

Analysis of Variance↗
PubMed2002

Transglucosidation of methyl and ethyl D-glucopyranosides by alcoholysis.

The transglucosidations of methyl 4-O-methyl-alpha- and -beta-D-glucopyranoside in ethanolic camphor-10-sulfonic acid, and of ethyl 4-O-methyl-alpha- and -beta-D-glucopyranoside in methanolic camphor-10-sulfonic acid, have been studied. Samples were removed at intervals and the proportions of the glucosides determined by GC of their acetates. The results show that the anomer with the inverted configuration predominates in the initially formed product (approximately 59-70%). This indicates that all the studied reactions proceed via the same mechanism, involving exocyclic C-O cleavage and formation of a glucopyranosylium ion, but that the eliminated alcohol exerts some steric hindrance, which favors the approach of the other alcohol from the opposite side.

Camphor↗
PubMed1996

Disinfection by calcium hydroxide pastes of dentinal tubules infected with two obligate and one facultative anaerobic bacteria.

Bovine dentine cylinders were experimentally infected with Actinomyces israelii, Fusobacterium nucleatum, or Enterococcus faecalis. The latter is a facultative anaerobic bacteria and the others are obligate anaerobes commonly found in endodontic infections. The infected specimens were exposed to pastes of calcium hydroxide mixed with saline solution or camphorated paramonochlorophenol for periods of 1 h, 1 day, and 1 week. The viability of bacteria after these exposure times was evaluated by specimen incubation in culture medium to compare the effectiveness of the pastes in disinfecting dentinal tubules. The calcium hydroxide/camphorated paramonochlorophenol paste effectively killed bacteria in the tubules after a 1-h period of exposure, except for E. faecalis that required one day of exposure. In contrast, the calcium hydroxide/saline paste was ineffective against E. faecalis and F. nucleatum even after 1 week of exposure. The results showed that camphorated paramonochlorophenol increased the antibacterial effects of calcium hydroxide.

Actinomyces↗
PubMed1998

Vapor emissions resulting from Nd:YAG laser interaction with tooth structure.

UNLABELLED: The Neodymium:yttrium aluminum garnet (Nd:YAG) dental laser has been cleared by the United States Food and Drug Administration (FDA) for marketing in intraoral soft tissue treatment. The efficacy and safety of the Nd:YAG laser in the treatment of hard dental tissue as well as the effects of dental irradiation on the pulp and periodontium have been investigated. Odors resulting from laser irradiation have been reported, but the nature and toxicity of associated decomposition vapors is unknown and the health consequences of their inhalation have not yet been studied. OBJECTIVES: The purpose of this in vitro study was to identify vapors emitted during interaction of the Nd:YAG laser with carious human enamel and dentin and sound enamel and dentin coated with organic ink. METHODS: Vapor emissions were collected from prepared sections of extracted human teeth receiving laser irradiation of 100 mJ and 10 Hz for a duration of 1, 10, or 60 s. Emissions were collected by means of charcoal absorption tubes, and subsequently analyzed using a Gas Chromatograph equipped with Mass Selective (GC/MS) and Flame Ionization Detectors to identify the chemical constituents of the vapors. RESULTS: No compounds were identified in Nd:YAG laser-treated caries, enamel and dentin. No volatile vapors were identified from samples of tooth materials exposed to the laser for 1 or 10 s. Camphor was positively identified in the test sample which consisted of India ink-coated dentin and the reference sample of India ink-coated glass beads, both exposed to the laser for 60 s. 2,5-norbornadiene was tentatively identified in these samples. The Threshold Limit Value (TLV) of camphor is 2 ppm with a Lethal Dose Level (LDLo) of 50 mg/kg (human oral), while the TLV and LDLo of 2,5-norbornadiene is unknown. SIGNIFICANCE: Occupational and public health safety measures are discussed in this article. Further research is needed to quantify the compounds produced and to determine their toxicity to patients and to dental care providers.

Air Pollution, Indoor↗
PubMed1993

Conformational dynamics of cytochrome P-450cam as monitored by photoacoustic calorimetry.

Conformational transitions of cytochrome P-450cam following the dissociation of CO from the ferrous heme were investigated by using photoacoustic calorimetry. The effect of substrate association on the acoustic signal was also examined. Results show that the conformational dynamics of cytochrome P-450cam substrate-free protein occur faster than 10 ns, which is the time scale of the instrument response. The enthalpy and volume change for the dissociation reaction are 2.2 kcal mol-1 and 1.8 mL mol-1, respectively. Upon addition of camphor, the reaction is markedly slowed. An intermediate is formed whose lifetime is 130 ns at 17 degrees C. The overall enthalpy and volume changes are -15.9 kcal mol-1 and 10.3 mL mol-1, respectively. These results, together with published transient Raman spectra [Wells, A. V., Pusheng, L., Champion, P. M., Martinis, S. A., & Sligar, S. G. (1992) Biochemistry 31, 4384-4393] suggest that camphor leaves the heme pocket concomitant with the photoinduced expulsion of CO into the solvent and induces a considerable conformational change in the protein.

Calorimetry↗
PubMed1990

Formation, crystal structure, and rearrangement of a cytochrome P-450cam iron-phenyl complex.

Cytochrome P-450cam reacts with phenyldiazene (PhN = NH), or less efficiently with phenylhydrazine, to give a catalytically inactive complex with an absorption maximum at 474 nm. The prosthetic group extracted anaerobically from the inactivated protein has the spectroscopic properties of a sigma phenyl-iron complex and rearranges, on exposure to air and acid, to an approximately equal mixture of the four N-phenylprotoporphyrin IX regioisomers. The crystal structure of the intact protein complex, refined at 1.9-A resolution to an R factor of 20%, confirms that the phenyl group is directly bonded through one of its carbons to the iron atom. The phenyl ring is tilted from the heme normal by about 10 degrees in the opposite direction from that in which carbon monoxide tilts when bound to P-450cam. Camphor, the natural substrate for P-450cam, is larger than a phenyl group and hydrogen bonds to Tyr 96, the only hydrophilic residue near the active site. Electron density in the active site in addition to that contributed by the phenyl group suggests that two water molecules occupy part of the camphor binding site but are not within hydrogen-bonding distance of Tyr 96. As observed in a previous crystallographic study of inhibitor-P-450cam complexes [Poulos, T.L., & Howard, A.J. (1987) Biochemistry 26, 8165-8174], there are large changes in both the atomic positions and mobilities of the residues in the proposed substrate access channel region of the protein.(ABSTRACT TRUNCATED AT 250 WORDS)

Bacterial Proteins↗
PubMed1997

Origin of the photoacoustic signal in cytochrome P-450cam: role of the Arg186-Asp251-Lys178 bifurcated salt bridge.

The origin of the photoacoustic signal in ferrous CO-camphor-cytochrome P-450cam was investigated. Recently, the Arg186-Asp251-Lys178 bifurcated salt bridge, located above the heme pocket, has been shown to play a key role in the control of the diffusion step of camphor binding [Deprez, E., Gerber, N. C., Di Primo, C., Douzou, P., Sligar, S. G., & Hui Bon Hoa, G. (1994) Biochemistry 33, 14464-14468]. We considered the hypothesis that electrostriction resulting from the transient exposure of these charged residues to the solvent could be responsible for part of the photoacoustic signal. We thus examined the effects of a site-directed mutation of these linkages and ionic strength increases. Upon replacement of the Asp251 residue by an asparagine residue, the overall enthalpy and volume change of the CO dissociation reaction decrease from -5 to -24 kcal/mol and from 11 to 5.4 mL/mol, respectively. The mutation has the same effect on the thermodynamic parameters as increasing the ionic strength of the medium over a range of potassium or sodium concentrations from 0 to 500 mM. For the D251N mutant, the overall enthalpy of the reaction does not change with the ionic strength whereas a small effect is observed on the volume change. The results indicate that electrostriction around the bifurcated salt bridge contributes to the photoacoustic signal and suggest a scheme in which, following photodissociation of CO and diffusion of the molecule through the protein matrix, the structure relaxes and the bifurcated salt bridge desolvates.

Camphor↗
PubMed1996

Probing the heme iron coordination structure of pressure-induced cytochrome P420cam.

Cytochrome P450cam was subjected to high pressures of 2.2 kbar, converting the enzyme to its inactive form P420cam. The resultant protein was characterized by electron paramagnetic resonance, magnetic circular dichroism, circular dichroism, and electronic absorption spectroscopy. A range of exogenous ligands has been employed to probe the coordination structure of P420cam. The results suggest that conversion to P420cam involves a conformational change which restricts the substrate binding site and/or alters the ligand access channel. The reduction potential of P420cam is essentially the same in the presence or absence of camphor (-211 +/- 10 and -210 +/- 15 mV, respectively). Thus, the well-documented thermodynamic regulation of enzymatic activity for P450cam in which the reduction potential is coupled to camphor binding is not found with P420cam. Further, cyanide binds more tightly to P420cam (Kd = 1.1 +/- 0.1 mM) than to P450cam (Kd = 4.6 +/- 0.2 mM), reflecting a weakened iron-sulfur ligation. Spectral evidence reported herein for P420cam as well as results from a parallel investigation of the spectroscopically related inactive form of chloroperoxidase lead to the conclusion that a sulfur-derived proximal ligand is coordinated to the heme of ferric cytochrome P420cam.

Camphor 5-Monooxygenase↗
PubMed1999

Dynamics of protein-bound water in the heme domain of P450BM3 studied by high-pressure spectroscopy: comparison with P450cam and P450 2B4.

Pressure-induced transitions in the heme domain of cytochrome P450BM3 (P450BMP) were studied versus the concentration of palmitic acid. An increase in hydrostatic pressure causes a high- to low-spin shift and subsequent P450 to P420 transition. Conversion of P450BMP to P420 is associated with important conformational and hydration changes of the protein. Treating the pressure-induced changes in the high-spin content in P450 in terms of the four-state model of spin transitions and substrate binding, we evaluated and compared the barotropic parameters of these transitions for P450MBP, P450cam, and P450 2B4 (2B4). In the current study, the pressure-induced transitions in P450cam were reinvestigated versus the concentration of camphor. The interactions of 2B4 and P450BMP with their substrates (benzphetamine and palmitic acid) were accompanied by larger changes in the partial volume of the proteins (+267 and +248 mL/mol, respectively) than the interactions of P450cam with camphor (+106 mL/mol). For 2B4 and P450BMP, substrate binding apparently requires hydration of regions outside the active site. The reaction volumes of the low- to high-spin transitions of the substrate-free cytochromes (20-23 mL/mol) are consistent with the displacement of one water molecule. The volume changes in the high- to low-spin transition of the substrate-bound P450cam, 2B4, and P450BMP (-90, -49, and -16 mL/mol correspondingly) reveal a linear relationship with DeltaG degrees of the spin transition, suggesting that modulation of the spin state by substrate binding is driven by a common mechanism in all three heme proteins.

Animals↗
PubMed1999

Changes in secondary structure and salt links of cytochrome P-450cam induced by photoreduction: a Fourier transform infrared spectroscopic study.

Tris(2,2'-bipyridyl)ruthenium(II) was used as a light-induced artificial electron donor for the transfer of the first electron to cytochrome P-450(cam) bound with (1R)-camphor and camphane substrates, and in the substrate-free form. Fourier transform infrared spectroscopy was used to detect changes of the amide I' band and the CO ligand stretch vibration of heme-bound carbon monoxide associated with the heme redox transition. The reduced-minus-oxidized difference spectra show that not only the heme group but also the protein backbone and individual amino acid side chains were affected by the redox transition. Observed secondary structure changes were almost identical for (1R)-camphor-bound and camphane-bound cytochrome P-450(cam), with a remarkable negative signal at 1724.3 cm(-)(1) and a positive signal at 1716.0 cm(-)(1). These signals were not observed in substrate-free P-450(cam). On the basis of known crystallographic data, we assign these signals to a change of hydrogen bonds of a salt link between Arg112, His355, and the heme 6-propionic group.

2,2'-Dipyridyl↗
PubMed2003

Volatile metabolites from Salvia fruticosa as antifungal agents in soilborne pathogens.

The volatile metabolites of Salvia fruticosa plants, growing wild in 15 localities scattered across Greece, were analyzed by means of GC and GC-MS. The essential oil content ranged from 0.69 to 4.68%, and the results of the analyses showed a noticeable variation in the amounts of the five main components [1,8-cineole, alpha-thujone, beta-thujone, camphor, and (E)-caryophyllene]. The antifungal activities of the essential oils from two localities, belonging in two different groups of cluster and principal component analysis, and their main components (1,8-cineole and camphor) were evaluated in vitro against five phytopathogenic fungi. Both oils were slightly effective against Fusarium oxysporum f. sp. dianthi and Fusarium proliferatum, whereas against Rhizoctonia solani, Sclerotinia sclerotiorum, and Fusarium solani f. sp. cucurbitae the oils exhibited high antifungal activities.

Bicyclic Monoterpenes↗
PubMed2003

Supercritical carbon dioxide extraction of essential oils from Perovskia atriplicifolia Benth.

The supercritical fluid extraction (SFE) of the aerial parts of Perovskia atriplicifolia Benth. was studied. The effect of different parameters such as pressure, temperature, modifier identity, and modifier volume on the SFE of the plant was investigated. The extracts were analyzed by GC and GC-MS and compared with the essential oil obtained from P. atriplicifolia Benth by steam distillation. The supercritical extracts and the steam-distilled products had very different compositions. The main constituents of the oil obtained by steam distillation were 1,8-cineole, limonene, camphor, beta-caryophyllene, alpha-pinene, camphene, and alpha-humulene. On the other hand, the major components of SFE extracts were 1,8-cineole, limonene, camphor, beta-caryophyllene, gamma-cadinene, alpha-pinene, and alpha-terpinyl acetate. The results showed that increasing the temperature from 35 to 65 degrees C (at a constant pressure of 100 atm) drastically reduced the number of extracted components. Also, the number of extracted constituents and the percent of main analytes increased when lower pressures were used. Using different modifiers (e.g., methanol, ethanol, dichloromethane, and hexane) for the extraction of the plant at low pressure (100 atm) and temperature (35 degrees C) showed that hexane was more selective than the other modifiers.

Bicyclic Monoterpenes↗
PubMed1973

Genetic fusion of incompatible plasmids in Pseudomonas.

The genes specifying enzymes responsible for the degradation of camphor and octane occur on transmissible plasmids in Pseudomonas putida strain PpG1 and P. oleovorans. Since the presence of the plasmids is vital for the oxidative metabolism of camphor or octane (by the cells) in the absence of other carbon sources, such naturally occurring, energy-generating plasmids have been designated as degradative plasmids. The two degradative plasmids, CAM and OCT, are incompatible with each other and cannot coexist in the same cell. By the use of UV irradiation and suitable selection techniques, it has been possible to fuse these two plasmids so they become part of the same replicon and coexist. Such a technique might be useful in introducing several degradative pathways in the same cell.

Alkanes↗