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PubMed2004

Relationship between fluorine in drinking water and dental health of residents in some large cities in China.

In this project, the relationship between fluorine content in drinking water and dental health of residents in some large cities in China was evaluated. The concentration of fluorine in tap water and in urine of local subjects of 28 cities and 4 high fluorine villages in China shows a strong positive correlation (r(2)=0.96, S.E.=0.9881). Our studies indicate that drinking water is the most important source of fluorine intake for Chinese people, and in more than 90% of urban cities, fluorine concentrations in drinking water are below levels recommended by the WHO (approximately 0.5-1.0 mg/l). A 1995 investigation by The National Committee on Oral Health of China (NCOH) shows the relationship between average number of decayed, missing and filled teeth (DMFT) of urban residents and fluorine concentration in drinking water to be negatively correlated but not forming a good linear relationship. Our results, together with the previous study, suggest that: (1) dental caries of the study population can be reduced by drinking water fluoridation and that (2) other factors such as economic level, weather, lifestyle, food habits, living condition, etc., of a city can also affect the incidence of dental caries that cannot be predicted by fluoridation alone. Research on the relation between index of fluorosis (IF) and the fluorine concentration in drinking water for the four high fluorine villages showed that the recommended concentration of fluorine in drinking water can protect from dental fluorosis.

Adolescent↗

PubMed1999

Substituent effect of a fluorine atom on the mutagenicity of nitroquinolines.

Some 16 nitroquinolines (NQs) and their fluorinated derivatives were tested for mutagenicity in Salmonella typhimurium TA100 without S9 mix to investigate the effect of fluorine-substitution on the mutagenicity. These NQs consist of 5-NQs, 5-nitroquinoline N-oxides (5-NQOs), N-methyl-5-nitroquinolinium methanesulfonates (N-Me-5-NQs) and 8-NQs, including three ortho-F-NQs, one meta-F-NQ, four para-F-NQs and four 3-F-NQs. For this purpose, eight F-NQs were newly synthesized. The data indicated that the ratio of the mutagenic activities (revertants/plate/nmol) of fluorinated NQs to those of the corresponding parent non-fluorinated compounds ranged from 0.6- to 119-fold. The fluorine atom located para to the nitro group markedly enhanced the mutagenicity (24-fold and more), while three ortho-fluorinated derivatives showed no significant increase in mutagenicity (enhancement ratio were 0.6, 0.8 and 1.7). With respect to 8-NQs, its meta-fluorinated derivative also had an enhanced mutagenicity over the parent compound (53-fold). In addition, although N-Me-5-NQ was less mutagenic than 5-NQ and 5-NQO, the mutagenicity of N-Me-5-NQ was most significantly enhanced by fluorine-substitution. These results suggest that introduction of a fluorine atom to the molecule in question may be a useful tool to modify their mutagenic potency and to better understand the mechanism of mutation.

Chromatography, Gel↗

PubMed2004

Crystal structure and mechanism of a bacterial fluorinating enzyme.

Fluorine is the thirteenth most abundant element in the earth's crust, but fluoride concentrations in surface water are low and fluorinated metabolites are extremely rare. The fluoride ion is a potent nucleophile in its desolvated state, but is tightly hydrated in water and effectively inert. Low availability and a lack of chemical reactivity have largely excluded fluoride from biochemistry: in particular, fluorine's high redox potential precludes the haloperoxidase-type mechanism used in the metabolic incorporation of chloride and bromide ions. But fluorinated chemicals are growing in industrial importance, with applications in pharmaceuticals, agrochemicals and materials products. Reactive fluorination reagents requiring specialist process technologies are needed in industry and, although biological catalysts for these processes are highly sought after, only one enzyme that can convert fluoride to organic fluorine has been described. Streptomyces cattleya can form carbon-fluorine bonds and must therefore have evolved an enzyme able to overcome the chemical challenges of using aqueous fluoride. Here we report the sequence and three-dimensional structure of the first native fluorination enzyme, 5'-fluoro-5'-deoxyadenosine synthase, from this organism. Both substrate and products have been observed bound to the enzyme, enabling us to propose a nucleophilic substitution mechanism for this biological fluorination reaction.

Catalysis↗

PubMed2004

[Effect of fluorine, selenium and cadmium on anti-oxidase and microelements in rat's body].

OBJECTIVE: To study the effect of fluorine, selenium and cadmium on lipid peroxide(LPO), the activity of glutathione peroxidase (GSH-Px) and microelements such as cadmium, selenium and zinc in rats. METHODS: Measurement of the contents of LPO, GSH-Px and microelements such as cadmium, selenium and zinc in SD rats after killing that have drunk water containing fluorine, selenium and cadmium eight-week ago. RESULTS: The contents of GSH-Px in the serum, liver and kidney of rats that were contaminated with fluorine, selenium and cadmium respectively remarkably reduced and the content of LPO noticeably increased in comparison with those of rats without being contaminated. The contents of GSH-Px noticeably increased and LPO remarkably reduced in those contaminated with the combination of any two of the three elements when compared with those in the rats contaminated with any one element of them, while the contents of GSH-Px in those contaminated with the combination of the three elements increased even more. Excessive selenium or cadmium led to the increase of selenium content in kidney and cadmium content in liver by several times. Excessive fluorine or cadmium gave rise to the lack of selenium and zinc. Selenium brought out universal increase of zinc in liver and kidney. The combination of fluorine and selenium or the combination of cadmium and selenium or that of fluorine, selenium and cadmium produced remarkable decrease of the accumulation of selenium in kidney and cadmium in liver. They also lowed the loss of zinc caused by fluorine or cadmium. CONCLUSION: Excessive fluorine, selenium or cadmium could inhabit the activity of GSH-Px in rats, which could diminish the antioxidation ability of the body. But when two or three of the chemical elements coexisted, they reduced the inhabitation of each of them on the activity of GSH-Px and in the meantime decreased the accumulation of cadmium and selenium and diminished the loss of zinc caused by fluorine and cadmium.

Animals↗

PubMed2004

[Insight into surface structure and hemocompatibility of fluorinated poly(ether urethane)s and poly(ether urethane)s blends].

It has been well known that fluorinated polyurethanes exhibit unique low surface energy, biocompatibility, biostability and nonsticking behavior. Consequently, these polymers have attracted considerable interest. In this study, the effect of various concentrations of fluorinated polyurethanes in the polyurethanes on the surface structures of the blends and their hemocompatibility were investigated by XPS, AFM, contact angle and platelet adhesion. It was found that the high concentration fluorine on the outer surfaces of the blends obtained with the low concentration of fluorinated polyurethanes (F: 0.342 wt%) in the blends was the same as that of the fluorinated poly(ether urethane)s, and all of the blends and the fluorinated poly(ether urethane)s had good hemocompatibility, compared with poly(ether urethane)s. The polymer blends and fluorinated poly(ether urethane)s suppressed platelet adhesion due to their high hydrophobicity and low surface tension. The XPS, AMF and contact angle results indicated that the high hydrophobicity of outer surface of the polyurethane blends is independent of the fluorinated polyurethanes content in the polymer blends but related to the concentration of the CF3 groups because the lower critical surface tensions and higher contact angle of many fluorinated surfaces reflect the concentration of CF3 groups.

Coated Materials, Biocompatible↗

PubMed2005

[Content and distribution of fluorine in Chinese coals].

Nationwide sampling program is designed according to the resources distribution and coal-forming periods as well as coal rank and yield of coal in China, and 305 coal samples were collected from 26 provinces, municipalities and autonomous regions. Fluorine in coal is determined by pyrohydrolysis / fluoride-ion selective electrode method. Fluorine in coals is mainly of an inorganic nature. Coal rank has no effect on fluorine content. The influence of a factor, such as geological age, on fluorine contents might be concealed by other factors, more research should be done to discern it. The distribution of fluorine in each province, municipality and autonomous region's coals is studied, and the fluorine source in coal-burning endemic fluorosis areas should be estimated over again. The contents of fluorine in Chinese coals show logarithm normal distribution, and 90% of values ranged from 47mg/kg to 347mg/kg, the average fluorine content in Chinese coals was designated as the geometric mean, 136mg/kg. Fluorine in Chinese coals is within the world coal's range.

Air Pollutants↗

PubMed2004

[Fluorine and calcium in bones of the woodpigeon (Columba palumbus)].

A total of 90 woodpigeons shot in August and September 2002 in an area west of Szczecin were obtained from hunters. Based on their age and sex, the birds were divided into the following 4 groups: young males, young females, adult males, and adult females. Content of dry matter, ash, calcium, and fluorine were determined in the tarsometatarsus of each bird. No inter-group differences in per cent dry weight and ash contents were found. There was no correlation between fluorine and calcium contents with either dry weight or ash of the bones. However, significant differences in fluorine and calcium contents of bone ash were revealed between young and adult birds, regardless of sex, the two elements being more abundant in adult birds. Moreover, adult females differed from adult males, demonstrating higher fluorine content per bone dry weight. Adult birds regardless of sex showed higher fluorine content than young birds. A significant fluorine vs. calcium correlation was found in adult birds only. Correlation between per cent calcium and ash contents in bone dry weight was highly significant (r = 0.95; p < 0.0001). The present study corroborates observations of other authors regarding age-related increase in the fluorine content in birds and a general lack of a clearcut relationship between the bone fluorine content and sex outside of breeding season. As shown by this study and the available literature, bones of herbivorous birds, including pigeons and geese are more representative for assessment of environmental fluorine pollution than bones of birds feeding on a mixed diet, carnivores, and scavengers. In view of the large variability in birds, comparisons should be made by studying analogous bones.

Age Factors↗

PubMed1994

Fluorinated vesicles.

Stable fluorinated vesicles--i.e. vesicles with a hydrophobic and lipophobic fluorinated film within their bilayer membranes--have been obtained from a variety of neutral, zwitterionic or anionic fluorinated amphiphiles, including single chain phosphocholine derivatives, double-chain phospholipids, glycolipids and glycophospholipids, as well as from combinations of standard phospholipids with amphiphilic mixed fluorocarbon/hydrocarbon compounds. The strong hydrophobic interactions developed by perfluoroalkyl chains result in increased membrane stability, as strikingly illustrated by the fact that even short single-chain fluorinated amphiphiles can form stable, heat-sterilizable vesicles without the need for any additive. They also result in increased versatility in the aggregation behavior of fluorinated surfactants, as shown by the formation, depending on molecular structure and experimental conditions, of a range of supramolecular assemblies other than vesicles, including disks, helical tubules and fibers, for example from fluorinated glycolipids. The more impermeable, adjustable fluorinated core within the liposomal membrane confers to liposomes added drug and probe encapsulation stability as compared to their hydrogenated analogs, whether in buffer or in serum. Fluorinated vesicles made from perfluoroalkylated phospholipids were also found to have 3 to 6 times longer circulation half-lives in mice than similarly sized conventional DSPC/cholesterol liposomes. Finally, the incorporation of mixed fluorocarbon/hydrocarbon alkanes or alkenes into standard liposomes may provide an alternative, straightforward and cost efficient approach to fluorinated vesicles.

Animals↗

PubMed1998

Long-term Effects of Various Iodine and Fluorine Doses on the Thyroid and Fluorosis in Mice.

OBJECTIVE: To elucidate the participation of the independent and combined long term effect of various concentrations of iodine and fluorine on the pathogenesis of goiter and fluorosis in mice. METHODS: Nine drinking water supplies with different iodine and fluorine content were prepared by combination of potassium iodate and sodium fluoride solutions in bidistilled water. The concentrations of iodide were: 1. iodine deficiency (ID): 0.0; 2. iodine normal (IN): 20.0; 3. iodine excess (IE) 2500.0 ug/l; and these of fluoride were: 1. fluoride deficiency (FD) 0.0; 2. fluoride normal 0.6; 3. fluoride excess (FE), 30.0 mg/l. A total of 288 Kunmim mice was divided into 9 groups consisting of 32 animals each and each group, in addition to basal diet, received one of following iodide/fluoride mixtures: ID+FD, ID+FN, ID+FE, IN+FD, IN+FN, IN+FE, IE+FD, IE+FN, IE+FE. By such manner, one half of the animals of each group was treated for 100 days and the other half for 150 days. RESULTS: It was found that ID only and IE only could both induce the goiter. FE induced dental fluorosis and increased fluorine content in the bone. In addition, fluorine also affected the thyroid changes induced by ID or IE. After 100 days of treatment, fluorine showed some stimulatory effect on the thyroid in ID conditions and inhibitory effect in IE conditions. After 150 days, however, the effects of fluorine on the thyroid reversed as compared with that of 100 days. On the other hand, difference of iodide intake could also increase the toxic effects of FE on the incisors and bones. The rate and degree of the incisor fluorosis, the fluorine contents in the bone were significantly higher in the ID+FE group than those in the IN+FE and IE+FE groups. CONCLUSIONS: Both iodine deficiency and excess induced goiter as well as other functional and histopathological changes in the mouse thyroid. Excessive fluorine caused fluorosis of incisors and limb bones. In addition, iodine and fluorine do have mutually interacting effects on both goiter and fluorosis in the experimental mice.

Journal Article↗

PubMed2002

[Monitoring of fluoride levels in children receiving fluorinated milk for a long time and time course of their permanent teeth].

Measurements of fluorine concentrations in 1320 urine samples collected from 440 children in the city of Maikop showed low levels of fluorine (0.43-0.72 mg) in this group in comparison with the groups receiving prophylactic treatment with optimal safe doses of fluorine with milk (0.88-1.19 mg). Consumption of physiological amounts of fluorine does not lead to its accumulation in the body even after long (up to 5 years) consumption of fluorinated milk. Permanent ratio between the values in the control and prophylactic groups allows less frequent monitoring of fluorine levels: during the first month of prevention and then after 2 and 4 years of prophylaxis with fluorinated milk. Clinical evaluation of anticaries efficiency of fluorinated milk in 920 children aged 6-8 years (309 in the control and 611 in prophylactic groups) showed a significant decrease of caries prevalence (by 12.5-24.5%) and intensity in permanent teeth (by 50.6-56.7% by the CDL index and by 47.6-52.9% by the CDLp index) after 3-5 years of regular consumption of fluorinated milk.

Animals↗

PubMed2004

Fluorine in medicinal chemistry.

Fluorinated compounds are synthesized in pharmaceutical research on a routine basis and many marketed compounds contain fluorine. The present review summarizes some of the most frequently employed strategies for using fluorine substituents in medicinal chemistry. Quite often, fluorine is introduced to improve the metabolic stability by blocking metabolically labile sites. However, fluorine can also be used to modulate the physicochemical properties, such as lipophilicity or basicity. It may exert a substantial effect on the conformation of a molecule. Increasingly, fluorine is used to enhance the binding affinity to the target protein. Recent 3D-structure determinations of protein complexes with bound fluorinated ligands have led to an improved understanding of the nonbonding protein-ligand interactions that involve fluorine.

Fluorine↗

PubMed1990

The significance of detecting serum fluorine level in the diagnosis of drowning.

In view of the high content of fluorine in the water of a vast area of Guangdong Province, we detected the serum fluorine level in rabbits that died of drowning and compared them with those obtained from rabbits immersed in water after death from hanging. The fluorine content in water is about 15-fold higher than in the normal serum content. In drowned rabbits, the serum fluorine values are significantly higher than normal while in control cases the serum fluorine values are slightly lower than normal. The fluorine content in human serum is similar with that of rabbits. It suggests that detection of serum fluorine content might be a valuable method for the diagnosis of drowning in those areas where there are high water fluorine content.

Animals↗

PubMed2004

Development of fluorinated low temperature glassy carbon films for solid-phase microextraction.

Solid-phase microextraction (SPME) fibers with supported fluorinated glassy carbon are demonstrated for the first time. Oligo[1,3-dibutadiynylene-1,3-(tetrafluoro)phenylene] was synthesized and heated to temperatures that varied from 200 to 1000 degrees C to produce the fluorinated glassy carbon. The extent of graphitization of the glassy carbon increased as the processing temperature increased. The fluorinated glassy carbon selectively extracted monohalogenated benzenes from an aqueous solution when compared to the extraction of toluene. The selectivity increased in the order of phi-F < phi-Cl < phi-Br < phi-I. The selectivity for the halogenated compounds was greatest for the fluorinated glassy carbon phase processed at temperature below approximately 400 degrees C. Preliminary studies on the retention mechanism of the LTGC phase show that dispersive interactions are very important to the retention of halocarbons on the fluorinated LTGC. Finally, the selectivity of the fluorinated LTGC for halogenated compounds was compared to that of commercially available SPME fibers, such as poly(dimethylsiloxane), poly(dimethylsiloxane)/divinylbenzene (PDMS/DVB), and poly(dimethylsiloxane)/Carboxen (PDMS/Carboxen) fibers. As expected the fluorinated LTGC was more selectivity for the halogenated compounds. Interestingly the order of the increase in selectivity is opposite when comparing the fluorinated-LTGC and the three commercial fibers. A decrease in selectivity was observed going from fluorobenzene to iodobenzene using PDMS/DVB and PDMS/Carboxen fibers. While for the pure PDMS phase, there is a slight increase in selectivity from fluorobenzene to chlorobenzene but the remaining trend shows little change for bromobenzene and iodobenzene.

Carbon↗

PubMed2000

Influence of glass composition on the properties of glass polyalkenoate cements. Part IV: influence of fluorine content.

The influence of fluorine content of the glass in a series of glasses based on: 4.5SiO2-3.0Al2O3-1.5P2O5-(5.0-X)CaO-XCaF2 was investigated on their cement formation with poly(acrylic acid). Increasing the fluorine content of the glass was found to reduce the glass transition temperature, as a result of fluorine replacing bridging oxygens by non-bridging fluorines. Working and setting times of the cement pastes reduced with increasing fluorine content of the glass. Compressive strength and Young's moduli increased with fluorine content initially and then remained approximately constant. Fracture toughness, toughness and un-notched fracture strength were not significantly influenced by fluorine content. The results are consistent with fluorine simultaneously disrupting the glass network and reducing the basicity of the glass.

Fluorine↗

PubMedDate not supplied

In vitro cationic lipid-mediated gene delivery with fluorinated glycerophosphoethanolamine helper lipids.

There is a need for the development of nonviral gene transfer systems with improved and original properties. "Fluorinated" lipoplexes are such candidates, as supported by the remarkably higher in vitro and in vivo transfection potency found for such fluorinated lipoplexes as compared with conventional ones or even with PEI-based polyplexes (Boussif, O., Gaucheron, J., Boulanger, C., Santaella, C., Kolbe, H. V. J., Vierling, P. (2001) Enhanced in vitro and in vivo cationic lipid-mediated gene delivery with a fluorinated glycerophosphoethanolamine helper lipid. J. Gene Med. 3, 109-114). Here, we describe the synthesis of fluorinated glycerophosphoethanolamines (F-PEs), close analogues of dioleoylphosphatidylethanolamine (DOPE), and report on their lipid helper properties vs that of DOPE, as in vitro gene transfer components of fluorinated lipoplexes based on pcTG90, DOGS (Transfectam), or DOTAP. To evaluate the contribution of the F-PEs to in vitro lipoplex-mediated gene transfer, we examined the effect of including the F-PEs in lipoplexes formulated with these cationic lipids (CL) for various CL:DOPE:F-PE molar ratios [1:(1 - x):x with x = 0, 0.5 and 1; 1:(2 - y):y with y = 0, 1, 1.5, and 2], and various N/P ratios (from 10 to 0.8, N = number of CL amines, P = number of DNA phosphates). Irrespective of the F-PE chemical structure, of the colipid F-PE:DOPE composition, and of the N/P ratio, comparable transfection levels to those of their respective control DOPE lipoplexes were most frequently obtained when using one of the F-PEs as colipid of DOGS, pcTG90, or DOTAP in place of part of or of all DOPE. However, a large proportion of DOGS-based lipoplexes were found to display a higher transfection efficiency when formulated with the F-PEs rather than with DOPE alone while the opposite tendency was evidenced for the DOTAP-based lipoplexes. The present work indicates that "fluorinated" lipoplexes formulated with fluorinated helper lipids and conventional cationic lipids are very attractive candidates for gene delivery. It confirms further that lipophobicity and restricted miscibility of the lipoplex lipids with the endogenous lipids does not preclude efficient gene transfer and expression. Their transfection potency is rather attributable to their unique lipophobic and hydrophobic character (resulting from the formulation of DNA with fluorinated lipids), thus preventing to some extent DNA from interactions with lipophilic and hydrophilic biocompounds, and from degradation.

Calorimetry, Differential Scanning↗

PubMed2005

Effects of fluorine substitution on the edge-to-face interaction of the benzene dimer.

To gain some insight into the effects of fluorination on the aromatic-aromatic interactions found in protein-ligand complexes, like those observed in the set of N-(4-sulfamylbenzoyl)benzylamine (SBB) inhibitors bound to Human Carbonic Anhydrase II (HCAII), we have produced potential energy curves for the edge-to-face interactions of a set of fluorinated benzene dimer compounds. All calculations were carried out at the MP2/aug-cc-pVDZ level of theory using the counterpoise method of Boys and Bernardi (Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553) to account for the basis set superposition error. Fluorine substitutions are made onto the face molecule of the edge-to-face benzene dimer. As one might expect, the substitution of additional fluorines into this system generally resulted in a decrease of the binding energy. It was also found that the positioning of the fluorine substituents on isosubstituted compounds has a large effect on the total binding energy of these types of systems. More specifically, complexes with fluorines that are substituted closer to the hydrogen atoms of the edge benzene will tend to be stabilized by an electrostatic interaction between the partially negative fluorine atoms and the partially positive hydrogen atoms. However, our findings do not explain the recent crystallographic findings for the SBB-HCAII protein-ligand complex, where increased fluorination resulted in closer edge-to-face contacts, which suggests that there are factors, other than edge-to-face aromatic interactions, influencing this system's behavior.

Benzene Derivatives↗

PubMed2006

Health effects of occupational exposure to fluorine and its compounds in a small-scale enterprise.

A 7-yr study was conducted to evaluate the respiratory effects of fluorine compounds on exposed workers in a small-scale enamel enterprise. Air monitoring was done and 75 pairs, exposed and non-exposed workers were examined. The applied tests were: an epidemiological questionnaire, the bronchitis record, clinical examinations and urinary fluorine. Linear regression analysis was done. The values of fluorine in the air of workplaces ranged from 0.1 to 3.7 mg/m3 air during the study. Twenty five point and seven percent of exposed workers presented chronic rhinitis, laryngotracheitis and bronchitis. The smoking habit was similar in both groups. The incidence of chronic bronchitis was significantly higher in exposed workers compared to the non-exposed ones. The values of urinary fluorine were higher in the exposed versus the control group. Linear regression analysis has shown positive correlations between the fluorine exposure and incidence of chronic bronchitis (r=0.75), as well as the incidence of chronic respiratory diseases (r=0.71). Fluorine exposure may be responsible for the high incidence of chronic irritative respiratory diseases, especially for chronic bronchitis in exposed workers. For diseases prevention it is advisable to reduce the levels of fluorine in the air of workplaces and to decrease the concentration of fluorine compounds in the composition of enamel.

Adult↗

PubMed1990

Bioavailability of fluorine in sepiolite for laying hens.

The purpose of the present work was to compare the bioavailability of structural fluorine contained in sepiolite and in sodium fluoride for laying hens. Three hundred 27-wk-old laying hens were fed one of three diets: 1) a control based on corn, barley, and soybean meal containing 21 mg/kg of fluorine; 2) a sepiolite diet in which 2% sepiolite replaced 2% barley in the control diet and which contained 217 mg/kg of fluorine; and 3) a NaF diet, consisting of the same control diet to which NaF was added to contain 217 mg/kg of fluorine (the same level of F- as the sepiolite diet). The experiment ended when hens were 64 wk old. Fluorine concentration in the tibial bone of hens fed the NaF diet was four times higher than in the control, and twice as high in eggshell. In contrast, hens fed sepiolite had fluorine concentrations in tibial bone and eggshell not significantly higher than fluorine concentrations in the controls. These results indicate that fluorine from sepiolite was not available. The effects of the different diets on egg production, feed intake, feed conversion, egg weight, shell and interior egg quality, dry matter of feces, and body weight gain were also determined but no significant differences due to the dietary treatment were observed.

Animals↗