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At least 145 records · Page 8Linked to original sources
PubMed1986

Effects of phthalic acid esters on the liver and thyroid.

The effects, over periods from 3 days to 9 months of administration, of diets containing di-2-ethylhexyl phthalate are very similar to those observed in rats administered diets containing hypolipidemic drugs such as clofibrate. Changes occur in a characteristic order commencing with alterations in the distribution of lipid within the liver, quickly followed by proliferation of hepatic peroxisomes and induction of the specialized P-450 isoenzyme(s) catalyzing omega oxidation of fatty acids. There follows a phase of mild liver damage indicated by induction of glucose-6-phosphatase activity and a loss of glycogen, eventually leading to the formation of enlarged lysosomes through autophagy and the accumulation of lipofuscin. Associated changes are found in the kidney and thyroid. The renal changes are limited to the proximal convoluted tubules and are generally similar to changes found in the liver. The effects on the thyroid are more marked. Although the levels of thyroxine in plasma fail to about half normal values, serum triiodothyronine remains close to normal values while the appearance of the thyroid varies, very marked hyperactivity being noted 7 days after commencement of treatment, this is less marked at 14 days, but even after 9 months treatment there is clear cut evidence for hyperactivity with colloid changes which indicate this has persisted for some time. Straight chain analogs of di-2-ethylhexyl phthalate, di-n-hexyl phthalate and di-n-oxtyl phthalate differ entirely in their short-term effects on the liver and kidney but have similar effects on the thyroid. The short-term in vivo hepatic effects of the three phthalate esters can be reproduced in hepatocytes in tissue culture. All three phthalate esters, as well as clofibrate, have early marked effects on the metabolism of fatty acids in isolated hepatocytes. The nature of these changes is such as to increase storage of lipid in the liver. A hypothesis is presented to explain the progress from these initial metabolic effects to the final formation of liver tumors.

Animals↗
PubMed1983

[Antihistaminic effect of a hydrogel with the components diphenhydramine, N,N-diethyl-m-toluamide and phthalic acid dimethyl ester].

The combination of the antihistamine diphenhydramine as well as the repellents N,N-diethyl-m-toluamide and dimethylphthalate as the active constituents of an insect repellent (Pellit) guarantees a remarkable antihistaminic effect. Surprisingly the repellent N,N-diethyl-m-toluamide proved itself to be an antihistamine. The UV-erythema model was used on the dorsal skin of male volunteers.

Adult↗
PubMed1985

Effects of phthalic acid esters on drug metabolizing enzymes of rat liver.

Di(2-ethylhexyl)phthalate (DEHP) inhibited UDP-glucuronyltransferase activity of rat liver in vitro and in vivo. Diethyl phthalate and dimethoxyethyl phthalate also inhibited this enzyme in vitro. On the other hand, DEHP did not inhibit the activity of the cytosolic enzyme N-acetyltransferase; it also did not alter the levels of rat liver microsomal cytochrome P-450 in vitro. It is suggested that DEHP may alter the composition of microsomal phospholipids.

Acetyltransferases↗
PubMed1983

The occurrence of phthalic acid esters in various samples of commercially available sodium chloride injections (Indian Pharmacopoeia).

Conclusive evidence for the presence of di(2-ethylhexyl) phthalate (DEHP) in 15 out of 17 commercially available sodium chloride injection (Indian Pharmacopoeia) samples was obtained and concentration levels as high as 11.0 mg/500 ml of saline were detected. The presence of such contaminants in i.v. fluids, avoidable by the institution of appropriate quality control measures before manufacturing and marketing, is a matter of serious concern. Stipulated specifications in different pharmacopoeias are meant only to ensure sterility and pyrogenicity, and it is advisable that cognisance be taken of the presence of toxic contaminants e.g. di(2-ethylhexyl) phthalate.

Diethylhexyl Phthalate↗
PubMed2000

Microbial degradation of phthalic acid esters under anaerobic digestion of sludge.

The microbial degradation by anaerobic sludge of three phthalates, priority pollutants, listed by both China National Environmental Monitoring Center and the U.S.EPA, namely, dimethyl (DMP), di-n-butyl (DBP) and di-n-octyl (DOP) phthalates was investigated. The experimental results indicated that the biodegradation rate and the biodegradability of three phthalates under anaerobic conditions appeared to be related to the length of the alkyl-side chains. More than 90% of DMP and DBP with the short alkyl-side chain phthalates can be degraded, whereas the DOP degradation appeared to be relatively slow under the same experimental conditions. The quantity of methane produced was measured and the results showed that both the ester groups and the phthalate ring were mineralized at a significant rate. The kinetics study demonstrated that the biodegradation of three phthalates conformed to the first-order model with respect to their concentrations.

Bacteria, Anaerobic↗
PubMed1990

Effects of phthalic acid esters on testicular mitochondrial functions in the rat.

Although it is well established that high dose administration of di(2-ethylhexyl) phthalate (DEHP) and its monoester metabolite (MEHP) induces severe testicular atrophy in rats, the mechanisms of this testicular injury is not clear. The present experiment was undertaken to examine the effects of DEHP and MEHP on mitochondrial functions of rat testis. DEHP and di-n-octyl phthalate (DOP), a DEHP isomer which causes less severe testicular injury, did not inhibit the state 3 oxygen consumption up to 0.65 mumole/ml in vitro. On the other hand, MEHP and mono-n-octyl phthalate (MOP), a metabolite of DOP, inhibited the state 3 oxygen consumption down to a concentration of 0.065 mumole/ml. Testicular mitochondrial respiratory functions of rats administered 2 g/kg DEHP were lower than those of control or DOP-treated rats. These differences were verified by characteristics of pharmacokinetic parameters and testicular concentrations of MEHP and MOP. It may be suggested that a possible mechanism of testicular atrophy induced by DEHP may be due to direct inhibition by MEHP (and partially DEHP) of the respiratory functions of Sertoli cell mitochondria in rat testis.

Animals↗
PubMed1996

[Phthalic acid esters in the peritoneal cavity of patients treated with continuous ambulatory peritoneal dialysis].

A solution for peritoneal dialysis stored in bags made from material which does not contain diethylhexyl phthalate is significantly less contaminated with this plasticizer, as compared with a solution stored in bags made from PVC with diethylhexyl phthalate. The afferent tube which contains diethylhexyl phthalate in all sets investigated by the authors is not an important source of this plasticizer for the peritoneal solution. Contamination of the peritoneal solution with dibutyl phthalate added to colours used for print on the bags (inscription on the outside of the bag) was found in both types of bags (no significant differences were found). It may be thus assumed that dibutyl phthalate penetrates through the wall of both types of bags with the same intensity. This applies only, provided that the peritoneal solution is not contaminated with dibutyl phthatate during preparation, before it is filled into bags. After six hours instillation in the peritoneal cavity diethylhexyl phthalate and dibutyl phthalate was not detectable in the peritoneal solution (detection limit 0.5 microgram/l). They are completely retained and metabolized resp. in the patient's peritoneal cavity.

Ascitic Fluid↗
PubMed2005

Sorption and biodegradation of phthalic acid esters in freshwater sediments.

Pathalic acid esters (PAEs) have been used as plasticizers in many products so that they could enter the aquatic environment. Three freshwater sediments in Taiwan were selected to explore the sorption and biodegradation processes of PAEs. Results indicated that di-n-butyl phthalate (DBP) and di-2-ethylhexyl phthalate (DEHP) are the only detectable PAEs which ranged in 24.9-68.3 mg/kg and 39.1-71.9 mg/kg in this study. The adsorption capacities of DBP and DEHP were identified by Kf values of the nonlinear Freundlich model associated with R2 values more than 0.90. This is expected that partition is the main mechanism controlling the transfer of PAEs between water and sediment phases. After 30 days contact, much of DBP and DEHP were removed immediately within 1 day in the desorption process. Because microorganism is as the major routes of breakdown of PAEs in the environment, much lower degraded amounts of DBP and DEHP occurred in the sterilized sediment than those in the unsterilized sediments.

Adsorption↗
PubMed1989

Reproductive toxicity of three phthalic acid esters in a continuous breeding protocol.

A continuous breeding protocol was utilized to examine the reproductive toxicity of three phthalate esters. CD-1 mice were given diets with either di-n-propyl phthalate (DPrP: 0.0, 1.25, 2.5, or 5.0%), di-n-pentyl phthalate (DPP: 0.0, 0.5, 1.25, or 2.5%), or di-n-octyl phthalate (DOP: 0.0, 1.25, 2.5, or 5.0%). Both male and female mice (20 pairs per treatment group, 40 pairs of control animals) were dosed for 7 days prior to and during a 98-day cohabitation period. Reproductive function was evaluated during the cohabitation period by measuring number of litters per pair, live pups per litter, and pup weight. There was no apparent effect on reproductive function in the animals exposed to DOP at dose levels sufficient to cause a significant increase in liver weight. Both DPP and DPrP were toxic to the reproductive system as evidenced by a complete inhibition of fertility at 1.25 and 2.5% DPP or 5.0% DPrP, and reduced fertility (litters/pair and live pups/litter, 0.5% DPP; live pups/litter, 2.5% DPrP). Toxicity of DPP had a strong male component and female component, whereas DPrP was more toxic to the female than the male reproductive system. DPP and DPrP treatment was associated with decreased body weight, increased liver weight, decreased testis and epididymis weights, decreased epididymal sperm concentration, and elevated seminiferous tubule atrophy. A comparison of seven phthalate esters tested using this continuous breeding protocol indicates the relative order of reproductive toxicity as diethylhexyl, dihexyl, dipentyl, dibutyl, dipropyl; diethyl and dioctyl are nontoxic.

Animals↗
PubMed1972

Action of some bisquaternary derivatives of phthalic acids and related substances on neuromuscular transmission.

1. All the bisquaternary derivatives of terephthalic acid with three methyl groups on each nitrogen atom (PK-107, PK-95, PK-97 and PK-126) were depolarizing neuromuscular blocking agents. The most active was the compound PK-97, in which the two quaternary groups are separated by sixteen atoms and are about 20 A (2 nm) apart. Activity was reduced many fold either by decreasing the separation to twelve atoms or by increasing it to eighteen atoms. It was also reduced several hundred fold when one trimethylammonium group in PK-97 was replaced by a hydrogen atom (as in PK-119).2. The presence and position of the ester groups in these compounds is important; depolarizing activity is in most cases greatest when the ester groups are the same distance from the quaternary nitrogen atoms as in acetylcholine, that is, in carbolonium, sebacoyldicholine and PK-154. The monoquaternary analogues of carbolonium and sebacoyldicholine are appreciably active, having between about one-tenth to one-fifth of the activity of their bisquaternary analogues.3. The relationships between the structure and activity of these compounds are discussed, particular consideration being given to the structure of the chain separating the quaternary groups and the arrangement of acetylcholine receptors on cells and of esterbinding groups within these receptors.

Acetylcholine↗
PubMed1987

Reproductive effects of four phthalic acid esters in the mouse.

These studies compared the reproductive toxicity of four phthalates by a continuous breeding protocol. Mice were given diets with diethyl phthalate (DEP) (0.0, 0.25, 1.25, or 2.5%), di-n-butyl phthalate (DBP) (0.0, 0.03, 0.3, or 1.0%), di-n-hexyl phthalate (DHP) (0.0, 0.3, 0.6, or 1.2%), or di(2-ethylhexyl) phthalate (DEHP) (0.0, 0.01, 0.1, or 0.3%). Both male and female CD-1 mice were dosed for 7 days prior to and during a 98-day cohabitation period. Reproductive function was evaluated during the cohabitation period by measuring the numbers of litters per pair and of live pups per litter, pup weight, and offspring survival. There was no apparent effect on reproductive function in the animals exposed to DEP, despite significant effects on body weight gain and liver weight. DBP exposure resulted in a reduction in the numbers of litters per pair and of live pups per litter and in the proportion of pups born alive at the 1.0% amount, but not at lower dose levels. A crossover mating trial demonstrated that female mice, but not males, were affected by DBP, as shown by significant decreases in the percentage of fertile pairs, the number of live pups per litter, the proportion of pups born alive, and live pup weight. DHP in the diet resulted in dose-related adverse effects on the numbers of litters per pair and of live pups per litter and proportion of pups born alive at 0.3, 0.6, and 1.2% DHP in the diet. A crossover mating study demonstrated that both sexes were affected. DEHP (at 0.1 and 0.3%) caused dose-dependent decreases in fertility and in the number and the proportion of pups born alive. A crossover mating trial showed that both sexes were affected by exposure to DEHP. These data demonstrate the ability of the continuous breeding protocol to discriminate the qualitative and quantitative reproductive effects of the more and less active congeners as well as the large differences in reproductive toxicity attributable to subtle changes in the alkyl substitution of phthalate esters.

Animals↗
PubMed2000

Hydrogen bonding and C-H.O interactions in 3-(3-aminophthalimido)phthalic acid dihydrate

The title compound, C(16)H(10)N(2)O(6).2H(2)O, crystallized in the centrosymmetric triclinic space group P-1 with one organic molecule and two water molecules as the asymmetric unit. Eight intermolecular hydrogen bonds have donor.acceptor distances in the range 2.602 (2)-3.289 (2) A, with angles in the range 137 (2)-177 (2) degrees. These generate a three-dimensional hydrogen-bond network. There is a single intramolecular hydrogen bond. There are six significant intermolecular C-H.O interactions with H.O distances in the range 2. 39-2.74 A, and C-H.O angles in the range 131-157 degrees.

Journal Article↗
PubMed2004

Thermodynamics of complexation of dimethyl esters of tere-, iso-, and phthalic acids with alpha- and beta-cyclodextrins.

Thermodynamics of inclusion of alpha- and beta-cyclodextrins (CDs) with three diester precursors of polyesters, dimethyl terephthalate (DMT), dimethyl isophthalate (DMI), and dimethyl phthalate (DMP) were studied with different fluorescence spectroscopy techniques. The stoichiometry, association constants, and other thermodynamics parameters were investigated from the fluorescence intensity decrease that takes place upon CD addition and temperature changes. Apart from DMP, which did not form a complex with alphaCD, all other systems showed 1:1 stoichiometry complexes with different stabilities. The complexes formed with the DMT guest are the most stable, whereas the stability constant for DMP:betaCD is the lowest. Binding constants are also larger for complexes formed with betaCD than for those formed with alphaCD. Fluorescence polarization, quenching, and lifetime measurements provide information about the structure of the complexes formed. This geometry explains the values of enthalpy and entropy changes during complexation. Van der Waals interactions seem to be involved in the formation of these complexes.

Journal Article↗