[Poisoning caused by phthalic anhydride, maleic anhydride and phthalates].
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Benzoates↗
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Steroids. 3. Pyrolysis of maleic anhydride and maleic ester adducts of 9,11-epoxy-5,7-dienes.
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Alkenes↗
Biological activity of maleic anhydride copolymers. I. Biocompatibility and antitumoural effects of maleic anhydride-vinyl acetate, maleic anhydride-methyl methacrylate and maleic anhydride-styrene copolymers.
A series of maleic anhydride (MA)-vinyl acetate (VA), MA-methyl methacrylate (MM), and MA-styrene (S) copolymers were prepared and characterized. On employing various amounts of initiator, maleic anhydride-vinyl acetate, methyl methacrylate, and styrene copolymers with molecular weights ranging between 18,000 and 200,000 have been obtained. The in vivo and in vitro tests performed on K562 cellular cultures (human chronic myeloid leukemia) have shown that, as a function of the molecular weight, the synthesized copolymers demonstrate a 50% in vitro cytotoxicity and an average tumour regression of maximum 68%.
Animals↗
Determination of maleic anhydride in occupational atmospheres.
Maleic anhydride has many uses in industry, but workers' exposure to it is poorly known. Our new method allows airborne maleic anhydride to be determined with a limit of quantification of 1 microg/m3 per 12 1 of air, i.e., the concentration of about 0.01 times the occupational exposure standard (0.4 mg/m3). Air samples are collected in Tenax tubes containing sodium sulfate as a drying agent. Maleic anhydride is eluted with methyl tert.-butyl ether containing 5% acetonitrile and 0.1% acetic anhydride, and determined by capillary gas chromatography with electron-capture detection without interference from generic anhydrides. The tested method suits both long-term and short-term measurements.
Air Pollutants, Occupational↗
The role of maleic anhydride in adhesive resin cements.
The adherence of resin cements depends upon, among other factors, the polar interactions across the interface: resin cement/restorative material. The polar interactions may be augmented by inclusion of polar additives such as maleic anhydride to the cement monomer. However, maleic anhydride is slowly converted to maleic acid when exposed to an aqueous environment. This may affect mechanical properties of such a cement in a negative way. It was the aim of the present investigation to analyze the role of maleic anhydride dissolved in the monomer of resin cements. The resin cement monomers used were common methacrylates, to which maleic anhydride in amounts of up to 30 mol% was added. Polymerization initiators were included to make the materials dual curing. Finally, the preparations were mixed with silanated fillers. The adherence energy of the cements bonded to a chromium-cobalt alloy was assessed by means of the double cantilever beam test. The strength and stiffness of the resin cements were recorded at base line and after two months storage in water. The initial adherence energy increased by a factor of about two as a result of addition of maleic anhydride. However, resin cements containing maleic anhydride suffered significant reductions in long-term adherence, strength and stiffness. These reductions were particularly pronounced in non-irradiated specimens. The use of resin cements containing maleic anhydride is not a viable means of conveying adhesiveness to resin cements.
Adhesiveness↗
A 6-month multispecies inhalation study with maleic anhydride.
This study was initiated to assess the safety of atmospheres containing maleic anhydride. Accordingly, rats (15/sex/group), hamsters (15/sex/group), and monkeys (3/sex/group) were treated 6 hr a day 5 days a week for 6 months. Atmospheres were generated by subliming maleic anhydride and were monitored using Tenax collection columns and gas chromatography to detect total maleic; i.e., maleic anhydride plus maleic acid. The mean analytical concentrations were 0, 1.1, 3.3, and 9.8 mg/m3 of total maleic. Dose-related signs of nasal and ocular irritation were observed at each test level in all three species; signs included discharge, sneezing, gasping, and coughing. No significant treatment-related mortality was observed in any species. While reduced weight gains were observed only in mid- and high-dose rats, their terminal body weights were greater than 90% of control values. No treatment-related effects were observed in hematology, clinical chemistry, urinalysis, and pulmonary function tests. Although microscopic evaluation of tissue revealed evidence of nasal irritation in all species, there was no evidence of systemic toxicity which was directly attributed to maleic anhydride. While the results of this study support the current ACGIH TLV and OSHA PEL of 1 mg/m3 regarding systemic toxicity, continuous exposure at this level during the day may produce some signs of irritation.
Administration, Inhalation↗
Teratology and multigeneration reproduction studies with maleic anhydride in rats.
These studies were initiated to evaluate the effects of maleic anhydride on development and reproduction in CD rats. In the teratology study, pregnant rats (19-23/group) received 0, 30, 90, or 140 mg/kg/day maleic anhydride in corn oil orally from Days 6-15 of gestation and fetuses were examined for gross soft tissue and skeletal defects. A reduced weight gain or weight loss was observed in all maleic anhydride-treated groups between Days 6 and 9; however, mean weights of all groups were within 5% of control on Days 15 and 20. No treatment-related effects on fetal development were observed. In the multigeneration study, rats (10 males and 20 females/group) received 0, 20, 55, or 150 mg/kg/day maleic anhydride in corn oil orally and were mated to produce two generations, each with two litters. Groups of the same size from the second litter were used for subsequent generations and were given the same dose of maleic anhydride as were their parents. The high-dose group was terminated during the second generation due to treatment-related mortality in adults. Renal cortical necrosis occurred in high-dose Fo males and females. Increased kidney weights were observed in low- and mid-dose adult F1 females. No treatment-related effects on reproduction were observed with maleic anhydride at doses up to 55 mg/kg/day over two generations.
Animals↗
Laticyclic Conjugated Polyenes. Study on Diels-Alder Cycloadditions of a Facially Dissymmetric Maleic Anhydride.
The tetracyclic ring-fused, facially dissymmetric maleic anhydride 2 was synthesized from compound 9 obtained from the Diels-Alder cycloaddition of the bicyclic ring-fused cyclohexadiene 1 and acetylenedicarboxylate. Maleic anhydride 2 readily underwent the Diels-Alder cycloadditions with anthracene, 1,3-diphenylisobenzofuran, cyclopentadiene, 1,3-cyclohexadiene, 6,6-dimethylfulvene, and o-quinodimethane. All the cycloadditions occurred exclusively on the pi-face syn to the etheno bridge of 2, thereby in cases of the cycloadditions with anthracene, cyclopentadiene, 1,3-cyclohexadiene, and 6,6-dimethylfulvene producing the corresponding adducts 11a, 18b, 22b, and 23b that contain three double bonds aligned in parallel. The structures of 18b and 22b were unequivocally established by the X-ray structural determinations. The molecular structure of maleic anhydride 2 was analyzed by X-ray crystallography to have a pyramidalized dienophilic double bond, which appeared to correlate well with the observed pi-facial selectivity.
Journal Article↗
Teratological evaluation of an injectable male antifertility agent, styrene maleic anhydride, in rats.
Polymer styrene Maleic anhydride (SMA) dissolved in dimethylsulphoxide (DMSO) was injected into the lumen in each vas deferens of male rats at dose levels of 0.25 mg, 0.50 mg, 1.0 mg, 2.5 mg, and 5.0 mg, while control rats (groups 1) received 0.03 mL DMSO in each vas deferens. After 4 weeks, the lumen was flushed with 0.1 mL DMSO and the animals were left for another 6 weeks to regain fertility. These rats were mated with virgin and coeval females. No anomaly was observed which could be related to teratogenic action of the polymer in pregnant mothers or fetuses.
Abnormalities, Drug-Induced↗
Maleic anhydride adsorption on silicon (001).
The adsorption of maleic anhydride on the Si(001) surface has been investigated using the first-principles pseudopotential formalism. Our total-energy calculations suggest that maleic anhydride (C2H2-C2O3) adsorbs preferentially through a [2+2] cycloaddition of the C=C bond ([2+2]) with an adsorption energy of around 42 kcal/mol. Besides the [2+2] configuration we have also considered other possible coverages and adsorption models, including the adsorption on inter-row and intrarow dimer sites. Based on the analysis of the relative stability of different adsorption models, we propose the formation of mixed domains, containing the [2+2] unit and an interdimer unit. The comparison of our calculated electronic band structure, vibrational modes, and scanning tunneling microscopy images for the [2+2] and the favored interdimer adsorbed structures corroborate our proposed mixed domain model.
Adsorption↗
Status of spermatogenesis and sperm parameters in langur monkeys following long-term vas occlusion with styrene maleic anhydride.
Vas occlusion by styrene maleic anhydride (SMA), trade name RISUG (one of the promising male contraceptive procedures currently in phase III clinical trials), at 60 mg/vas deferens dissolved in 120 micro L dimethyl sulphoxide (DMSO) at up to a 540-day study period caused severe oligospermia in the first 2 to 3 ejaculations and uniform azoospermia in the subsequent ejaculations without toxicity in langur monkeys. The ejaculated spermatozoa were necroasthenoteratozoospermic, suggesting instant sterility. Routine hematology and clinical chemistry parameters and the serum testosterone and sperm antibody titers remained unchanged from their pretreatment values until 540 days vas occlusion. Histology of testes revealed continued spermatogenesis throughout the study period. The stages of spermatogenesis appeared normal until 300 days of vas occlusion. At 360 days of vas occlusion, germ cells appeared in the lumen. Degeneration of seminiferous epithelium was evident in some of the tubules. Following 420 days of vas occlusion, the central portion of the testis showed regressed seminiferous tubules depicting various shapes and devoid of germ cells, which continued until 540 days of vas occlusion. Ultrastructure of the testes after 540 days of vas occlusion revealed vacuolization in the cytoplasm of Sertoli cells and degenerative features in the membranes of the spermatocytes and spermatids in the affected seminiferous tubules. The sub-cellular features of the normal tubules were similar to those of controls. The results suggest focal degeneration of seminiferous epithelium in the central portion of the testis following long-term vas occlusion with SMA.
Animals↗
Crosslinked poly(methyl vinyl ether-co-maleic anhydride) as topical vehicles for hydrophilic and lipophilic drugs.
Poly(methyl vinyl ether-co-maleic anhydride) crosslinked with ethylene glycol (GZ-ET), 1,4-butanediol (GZ-BUT), 1,6-exandiol (GZ-EX), 1,8-octanediol (GZ-OCT), 1,10-decanediol (GZ-DEC) or 1,12-dodecanediol (GZ-DOD) was prepared and employed as a supporting material for aqueous topical gels containing pyridoxine hydrochloride (PYCL) chosen as a hydrophilic model molecule or for O/A emulsion containing beta-carotene chosen as a hydrophobic model molecule. We analyzed the effect of the nature of the crosslinker on the permeation of hydrophilic and lipophilic vitamins through porcine skin by in vitro permeation studies. The vehicles formed by crosslinked poly(methyl vinyl ether-co-maleic anhydride) showed enhanced vitamins permeation with respect to the same vehicles formed by noncrosslinked poly(methyl vinyl ether-co-maleic anhydride) (GZ). The decrease in the crosslinker acyl chain length provides vehicles accelerating the drug permeability through the skin.
Administration, Topical↗
[Coupling of enzymes to modified styrene-maleic anhydride copolymers].
A copolymer of styrene and maleic anhydride is modified with low molecular weight polyoles in a very convenient manner, so that it can be applied as a carried for the fixation of biologically active compounds without further pretreatment. The modified products show storage stability over a long time without loss of coupling capacity. Examples for the fixation of trypsin, alkaline phosphatase and a bacterial glutamate dehydrogenase are given, and some properties of the resulting enzyme products are described.
Alkaline Phosphatase↗
Synthesis and biological evaluation of dialkylsubstituted maleic anhydrides as novel inhibitors of Cdc25 dual specificity phosphatases.
An efficient synthesis of dialkylsubstituted maleic anhydrides 1a-j is described. The inhibitory potential of these original anhydride derivatives was tested toward the three human isoforms A, B and C of dual specific phosphatases Cdc25. A micromolar range inhibition of Cdc25s was observed with the maleic anhydrides bearing simple alkyl side chains longer than C(9), to reach the optimal activity with a C(17) chain length.
Alkaline Phosphatase↗
[Computational study on the electronic absorption transitions for 2,3-diaryl maleic anhydrides].
The electronic absorption transitions for 2, 3-bis (2, 4-dimethylthiophen-3-yl) maleic anhydride were calculated by time-dependent method with 6-31G(d) basis at structures optimized at B3LYP/6-31G(d) level. The S1, S2, and S3 transitions calculated for the open and the closed forms of the compound are 390, 360.5, 339.4; 584.6, 395.8, 370.2 nm, respectively. The results are comparable to the electronic absorption spectrum of 2,3-bis(2,4,5-trimethylthiophen-3-yl) maleic anhydride which bears extra methyl groups that should not have much effects on the spectrum. The oscillator strengths are well correlated to the spectrum peak heights.
Maleic Anhydrides↗
Functional films of maleic anhydride copolymers under physiological conditions.
Reactivity and swelling of nanometer films of alternating maleic anhydride copolymers were investigated in dependence on the kind of comonomer and molar mass of copolymer in aqueous solution at pH 7.4 and pH 3.0 in order to reveal their characteristics under physiological conditions. Fully hydrolyzed (maleic acid) chains of the copolymers with styrene, propene, and ethylene comonomers covalently bound to SiO2 substrates showed a "mushroom" swelling behavior at pH 7.4 with a layer thickness scaling of N3/5. Decreasing the environmental pH was found to induce a comonomer-dependent shrinking or collapse of the immobilized polymers due to the change in ionization. From the swelling kinetics of non-hydrolyzed chains, the time constants and characteristics of swelling and anhydride hydrolysis were determined and found to depend on the type of comonomer. The short- and long-term swelling kinetics [l approximately t and approximately ln(t)1/2] were found to be in agreement with theoretical models of polymer swelling, while at intermediate time scales enhanced swelling was observed due to hydrolysis reaction of maleic anhydride groups. The findings elucidate the variety of properties of maleic anhydride copolymer films under physiological conditions, which can advantageously be applied for biofunctionalization of different templates.
Alkenes↗
Immobilization of protein ligands with methyl vinyl ether-maleic anhydride copolymer.
Methyl vinyl ether-maleic anhydride copolymer (MMAC) is a water-insoluble polymer with an acid anhydride group which reacts with amino groups of ligands to form stable amide bonds. MMAC was used to immobilize protein ligands on two kinds of supports, the wells of plastic microtitre plates for enzyme-linked immunosorbent assay and related methods, and gels for affinity adsorbents. The wells were first coated with MMAC and then allowed to react with proteins. The immobilization of proteins by this method was efficient and occurred in a dose-dependent manner. Shodex Et123, a gel having amino groups, was incubated with MMAC, and then the activated Shodex was used to immobilize high concentrations of proteins. Concanavalin A-Shodex thus obtained had high affinities and was successfully used for the high-performance liquid affinity chromatography of sugar derivatives on a short column.
Chromatography, High Pressure Liquid↗
Enhanced macrophage and natural killer cell antitumor activity by various molecular weight maleic anhydride divinyl ethers.
A series of Maleic anhydride divinyl ether (MVE) polyanions, synthesized with molecular weight ranging from 12500 to 52600, were found capable of enhancing macrophage tumoricidal activity of MBL-2 leukemia cells. These agents also augmented Natural Killer cell activity against the YAC lymphoma and M109 adenocarcinoma cell lines.
Adenocarcinoma, Bronchiolo-Alveolar↗