Reaction of phosphofructokinase with maleic anhydride, succinic anhydride, and pyridoxal 5'-phosphate.
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Adenine Nucleotides↗
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Differential labeling of the subunits of respiratory complex III with [3H]succinic anhydride, [14C]succinic anhydride, and p-diazobenzene-[35S]sulfonate.
Exposure of antimycin-treated Complex III (ubiquinol-cytochrome c reductase) purified from bovine heart mitochondria to [3H]succinic anhydride plus [35S]p-diazobenzenesulfonate (DABS) resulted in somewhat uniform relative labeling of the eight measured subunits of the complex by [3H]succinic anhydride. In contrast, relative labeling by [35S]DABS was similar to [3H]succinic anhydride for the subunits of high molecular mass, i.e., core proteins, cytochromes, and the iron-sulfur protein, but greatly reduced for the polypeptides of molecular mass below 15 kDa. With Complex II depleted in the iron-sulfur protein the relative labeling of core protein I by exposure of the complex to [3H]succinic anhydride was significantly enhanced, whereas labeling of the polypeptides represented by SDS-PAGE bands 7 and 8 was significantly inhibited. Dual labeling of the subunits of Complex III by 14C- and 3H-labeled succinic anhydride before and after dissociation of the complex by sodium dodecyl sulfate, respectively, was measured with the complex in its oxidized, reduced, and antimycin-inhibited states. Subunits observed to be most accessible or reactive to succinic anhydride were core protein II, the iron-sulfur protein, and polypeptides of SDS-PAGE bands 7,8, and 9. Two additional polypeptides of molecular masses 23 and 12kDa, not normally resolved by gel-electrophoresis, were detected. Reduction of the complex resulted in a significant change of 14C/3H labeling ratio of core protein only, whereas treatment of the complex with antimycin resulted in decreases in 14C/3H labeling ratios of core proteins I and II, cytochrome c1, and a polypeptide of molecular mass 13kDa identified as an antimycin-binding protein.
Animals↗
Kinetics of synthesis of d 4 -succinic anhydride from succinic anhydride and d 1 -acetic acid.
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Acetates↗
GC-MS measurement of deuterium in succinic anhydride and TMS-succinate. An isotope memory effect with succinic anhydride.
Direct GC-MS of succinic and glutaric anhydrides has been investigated, and shown to be feasible. In the GC-MS determination of deuterium in succinic anhydride, an isotope memory effect was observed, shown to be due to strong adsorption of solute onto the column. This phenomenon was investigated, together with possible methods for its suppression. Succinate TMS ester also was found to be a suitable derivative for direct GC-MS of deutero-succinic acid.
Anhydrides↗
NTP Toxicology and Carcinogenesis Studies of Succinic Anhydride (CAS No. 108-30-5) in F344/N Rats and B6C3F1 Mice (Gavage Studies).
Succinic anhydride, a food additive, is also used in the manufacture of polymeric materials, pharmaceuticals, and agricultural and industrial chemicals. NTP Toxicology and Carcinogenesis studies were conducted by administering suspensions of succinic anhydride (97% pure) in corn oil by gavage to groups of F344/N rats and B6C3F1 mice of each sex for 16 or 20 days, 13 weeks, or 2 years. Genetic toxicology studies were conducted in Salmonella typhimurium and Chinese hamster ovary (CHO) cells. Twenty-Day or Sixteen-Day and Thirteen-Week Studies: In the 20-day studies in rats, doses of succinic anhydride given on 14 exposure days ranged from 47 to 750 mg/kg. Compound-related deaths occurred in the groups of males that received 375 mg/kg or higher doses and in females that received 187 mg/kg or higher doses. Necrosis and inflammation of the upper respiratory tract were seen in 3/10 male and 3/10 female rats given 750 mg/kg and 2/10 female rats given 375 mg/kg. In the 16-day studies in mice, doses of succinic anhydride given on 12 exposure days ranged from 219 to 3,500 mg/kg. All animals that received 875 mg/kg or higher doses of succinic anhydride died before the end of the studies. No compound-related lesions were seen in male or female mice examined from the 438 mg/kg dose group. In the 13-week studies in rats, doses of succinic anhydride ranged from 25 to 400 mg/kg for males and from 12.5 to 200 mg/kg for females. Deaths of 8/10 male rats that received 400 mg/kg and 4/10 males and 5/10 females that received 200 mg/kg were compound related. At necropsy, the mean body weights of male rats that received 200 or 400 mg/kg were 9% or 15% lower than that of vehicle controls, whereas the mean body weights of dosed and vehicle control female rats were similar. No compound-related gross or microscopic lesions were observed. In the 13-week studies in mice, doses of succinic anhydride ranged from 37 to 600 mg/kg. All 10 males and 8/10 females that received 600 mg/kg and 2/10 males and 2/10 females that received 300 mg/kg died before the end of the studies. The final mean body weights of mice that received 150 or 300 mg/kg were 13% or 9% lower than that of vehicle controls for males and 8% or 7% lower for females. Mild inflammation of the stomach was observed in 7/10 male mice that received 150 mg/kg and 5/10 males that received 300 mg/kg compared with 2/10 vehicle controls. Based primarily on the effects of administration of succinic anhydride on survival and mean body weights of rats and mice, doses for the 2-year studies were 0, 50, or 100 mg/kgto groups of 60 rats of each sex; 0, 38, or 75 mg/kg to groups of 50 male mice; and 0, 75, or 150 mg/kg to groups of 50 female mice. Succinic anhydride was administered as a suspension in corn oil by gavage, 5 days per week for 103 weeks. Body Weights and Survival in the Two-Year Studies: Mean body weights of high dose rats were 5%-11% lower than those of vehicle controls during the second year of the studies. No significant differences in survival after 2 years were observed between any groups of rats of either sex (male: vehicle control, 36/60; low dose, 33/60; high dose, 32/60; female: 31/60; 27/60; 27/60). For mice, mean body weights of high dose males were generally 5%-12% lower than those of vehicle controls throughout the study. Mean body weights of high dose female mice were 10%-32% lower than those of vehicle controls; mean body weights of low dose female mice were 10%-20% lower than those of vehicle controls. The survival of high dose male mice was significantly greater than that of vehicle controls after week 77 (survival after 2 years--male: 27/50; 30/50; 42/50; female: 37/50; 38/50; 41/50). No other differences in survival were observed between any groups of mice of either sex. Nonneoplastic and Neoplastic Effects in the Two-Year Studies: At no site in rats or mice was there a chemical-related increase in the incidence of nonneoplastic or neoplastic lesions. A sufficient number of animals in each dose group lived long enough to allow evaluation of the potential carcinogenicity ofr of animals in each dose group lived long enough to allow evaluation of the potential carcinogenicity of succinic anhydride. Genetic Toxicology: Succinic anhydride was not mutagenic in S. typhimurium with or without exogenous metabolic activation. The chemical did not induce sister chromatid exchanges or chromosomal aberrations in cultured CHO cells in the presence or absence of exogenous metabolic activation. Conclusions: Under the conditions of these 2-year studies, there was no evidence of carcinogenic activity of succinic anhydride for male or female F344/N rats given 50 or 100 mg/kg succinic anhydride. There was no evidence of carcinogenic activity for male B6C3F1 mice given 38 or 75 mg/kg succinic anhydride or for female B6C3F1 mice given 75 or 150 mg/kg. Synonyms: butanedioic anhydride; dihydro-2,5-furandione; 2,5-diketotetrahydrofuran; succinic acid anhydride; succinyl anhydride; succinyl oxide; tetrahydro-2,5-dioxofuran
Journal Article↗
X-ray diffraction and molecular simulation study of the crystalline and liquid states of succinic anhydride.
The crystal structure of succinic anhydride was studied at five temperatures between 100 K and the melting point by single-crystal X-ray diffraction. The temperature dependence of molecular libration tensors was determined. Intermolecular interactions, in particular through unusually close molecule-molecule contacts, are discussed, with a detailed calculation of electrostatic energies. A method for the adaptation of existing crystal force fields to molecular dynamics has been developed; the adapted force field was used to study molecular motion and rotational diffusion with increasing temperature. Equilibration of the crystalline system becomes impossible at a temperature very close to the experimental melting temperature, where a sudden transition to the liquid state occurs, and a partial kinetic picture of the melting process is obtained. After validation of the force field against experimental crystal data, the state equation of the liquid was predicted. Enthalpies of sublimation, melting, and vaporization were calculated. The dynamics of a solution of succinic anhydride in a nonpolar solvent was simulated, for a discussion of the aggregation process leading to demixing and to crystal nucleation.
Journal Article↗
The mitochondrial voltage-dependent channel, VDAC, is modified asymmetrically by succinic anhydride.
In the accompanying paper, succinic anhydride was shown to react with the outer mitochondrial membrane channel-forming protein, VDAC, resulting in the loss of its voltage dependence. In this paper, the anhydride was added to VDAC held in a particular conformational state by means of an applied electric field. VDAC was inserted into the membranes from the cis side and the anhydride was added either to the cis or trans side. Channels modified in the open state behaved similarly whether anhydride was added to the cis or trans side. Modifications of VDAC in either of the two closed states did not. Modifications resulting in the loss of voltage-dependence occurred primarily when anhydride was added to the negative side of the membrane irrespective of which closed state the VDAC was in indicating that the accessibility of the gating charges alternated between the cis and trans sides as the channel's conformation was changed from one closed state to the other. Despite the pronounced asymmetry, in general the resulting channels behaved in the same way in response to either positive or negative fields. A model consistent with the results is presented which proposes that the same gating charges are responsible for channel closure at both positive and negative fields.
Animals↗
Streptavidin in antibody pretargeting. 3. Comparison of biotin binding and tissue localization of 1,2-cyclohexanedione and succinic anhydride modified recombinant streptavidin.
Recombinant streptavidin (rSAv) is of interest as a carrier of alpha-emitting radionuclides in pretargeting protocols for cancer therapy. Due to the inherently high kidney localization of rSAv, modification of this protein is required before it can be useful in pretargeting. Previous studies (Wilbur, D. S., Hamlin, D. K. et al. (1998) Bioconjugate Chem. 9, 322-330) have shown that succinylation of rSAv using succinic anhydride decreases the kidney localization appreciably. In continuing studies, the biotin binding characteristics and biodistribution in mice of rSAv modified by reaction with succinic anhydride (amine modification) or 1,2-cyclohexanedione (arginine modification) have been compared. Modification of rSAv was conducted using 5-50 mol equiv of succinic anhydride and 60-200 mol equiv of 1,2-cyclohexanedione. Most studies were conducted using rSAv modified with the highest quantities of reagents. Succinylation of rSAv did not alter binding with biotin derivatives, but a small increase in the biotin derivative dissociation rate was noted for arginine-modified rSAv. Amino acid analysis of 1,2-cyclohexanedione-treated rSAv indicated about 40% of the arginine residues, or an average of 1.6 residues per subunit, were modified, whereas none of the lysine residues were modified. IEF analyses showed that the pI of the arginine-modified rSAv was 5.3-6, whereas the pI for the succinylated rSAv was approximately 4. Electrospray mass spectral analyses indicated that one to three conjugates of 1,2-cyclohexanedione, and two to three conjugates of succinic anhydride, were obtained per subunit. Both modification reactions resulted in greatly decreasing the kidney localization of rSAv (normally 20-25% ID/g at 4, 24, and 48 h pi). However, the kidney concentration for the succinylated rSAv continued to decrease (5% ID/g to 1.5% ID/g) from 4 to 48 h pi, whereas the concentration (5% ID/g) remained constant over that period of time for the arginine-modified rSAv. In contrast to this, the liver concentration appeared to be slightly higher (3% ID/g vs 2% ID/g) at the later time points for the succinylated rSAv. When less than 50 mol equiv of succinic anhydride were employed in the modification of rSAv, a correlation between increasing kidney localization with decreasing equivalents reacted was observed. Although the differences in the two modified rSAv are not substantial, succinylated rSAv appears to have more favorable properties for pretargeting studies.
Animals↗
Studies on the modification of Escherichia coli ribosomal protein L7/L12 by succinic anhydride.
Lysine modification by increasing quantities of succinic anhydride in the Escherichia coli ribosomal protein L7/L12 produces loss of its ability in reconstitution of elongation-factor-G-dependent GTP hydrolysis and polyphenylalanine synthesis activities, showing lower antigenicity and loss of antigenic determinants.
Epitopes↗
Synthesis and paste properties of octenyl succinic anhydride modified early Indica rice starch.
Octenyl succinic anhydride (OSA) modified early Indica rice starch was prepared in aqueous slurry systems using response surface methodology. The paste properties of the OSA starch were also investigated. Results indicated that the suitable parameters for the preparation of OSA starch from early Indica rice starch were as follows: reaction period 4 h, reaction temperature 33.4 degrees C, pH of reaction system 8.4, concentration of starch slurry 36.8% (in proportion to water, w/w), amount of OSA 3% (in proportion to starch, w/w). The degree of substitution was 0.0188 and the reaction efficiency was 81.0%. The results of paste properties showed that with increased OSA modification, the starch derivatives had higher paste clarity, decreased retrogradation and better freeze-thaw stability.
Biochemistry↗
Voltage dependence and ion selectivity of the mitochondrial channel, VDAC, are modified by succinic anhydride.
The mitochondrial protein VDAC forms voltage-dependent anion-selective channels in planar phospholipid membranes. When succinic anhydride was added to these membranes, it virtually eliminated VDAC's voltage-dependence and changed its selectivity from anion to cation. These results were obtained without large changes in open-channel conductance or in energy difference between the open and closed states in the absence of a field. Since succinic anhydride converts amino groups into carboxyl groups, we propose that amino groups are responsible for VDAC's voltage-dependence and anion selectivity. Perhaps the same charges are responsible for both functions.
Animals↗
Enhanced film-forming properties for ethyl cellulose and starch acetate using n-alkenyl succinic anhydrides as novel plasticizers.
PURPOSE: The aim of this study was to investigate the ability of n-alkenyl succinic anhydrides (n-ASAs) to improve the film-forming characteristics of a novel coating polymer, potato starch acetate degree of substitution 2.8 (SA). n-ASAs were also applied to improve the otherwise brittle properties of ethyl cellulose (EC) aqueous dispersion (Aquacoat) and EC solvent-based films. METHODS: The effectiveness of two n-ASAs, 2-octenyl succinic anhydride (OSA) and 2-dodecen-1-ylsuccinic anhydride were evaluated as plasticizers. Mechanical properties, both water vapor and drug permeabilities, and glass transition temperatures of the cast free films were measured. Triethyl citrate and dibutyl sebacate were used as reference plasticizers. RESULTS: The long hydrocarbon chain of n-ASA, with its accessible carbonyl groups, enabled a strong plasticization effect on the tested polymers. Due to the excellent mechanical properties (i.e., a tough film structure with considerable flexibility) and low permeability of the plasticized films, n-ASAs, and especially OSA proved to be an ideal plasticizer particularly for EC based coatings. Also, the EC aqueous dispersion plasticized with n-ASAs resulted in a markedly enhanced coalescence of the colloidal polymer particles, even at low drying temperatures. CONCLUSIONS: In applications where a coating with high flexibility is required, n-ASAs can be used as plasticizers at moderately high concentrations (up to 60-70%, w/w) without losing the high tensile strength, excellent toughness and low permeability of EC and SA films.
Algorithms↗
Catalytic carbonylation of beta-lactones to succinic anhydrides.
A well-defined, highly active and selective catalyst for the synthesis of succinic anhydrides from CO and beta-lactones is reported. At 200 psi of CO, the catalyst [(N,N'-bis(3,5-di-tert-butylsalicylidene)phenylenediamino)Al(THF)2][Co(CO)4] carbonylates beta-propiolactones to succinic anhydrides in high yield. (R)-beta-Butyrolactone is carbonylated to (S)-methylsuccinic anhydride with clean inversion of stereochemistry, while cis-2,3-dimethyl-beta-propiolactone yields exclusively trans-2,3-dimethylsuccinic anhydride. These data are consistent with a mechanism involving nucleophilic attack by [Co(CO)4]- on the beta carbon of the lactone, followed by CO insertion and anhydride formation.
Journal Article↗
Properties of human serum low density lipoproteins after modification by succinic anhydride.
Human serum low density lipoprotein of d 1.019-1.063 (LDL(2)) treated with succinic anhydride at pH 7.5-8.0 showed the same chemical composition, hydrodynamic properties (flotation and sedimentation coefficients, intrinsic viscosity) and optical properties (circular dichroism) as untreated LDL(2). However, in contrast to LDL(2), the succinylated product (s-LDL(2)) failed to react with rabbit anti-LDL(2) antisera. Extraction with ethanol-ether 3:1 yielded the succinylated apoprotein (s-apo-LDL(2)), which was, unlike untreated apoprotein, soluble in aqueous buffers. Succinylated apoprotein, which was also immunologically unreactive, appeared to differ in structure from s-LDL(2), as assessed by the parameters of intrinsic viscosity and circular dichroism. The molecular weights of both LDL(2) and s-LDL(2) obtained by the technique of sedimentation equilibrium were 2.1-2.3 x 10(6). By the same method, s-apo-LDL(2) gave an uncorrected figure of 3.95-4.15 x 10(4) and, after correction for succinyl functions, of 3.60-3.80 x 10(4). Because of the assumptions made in the computations, the latter figure was considered approximate. The marked differences in molecular weight between s-apo-LDL(2) and whole apo-LDL(2) ( approximately 5 x 10(5)) were taken to support the subunit structure of apo-LDL(2), which is envisaged as an aggregate of about 12 subunits which dissociate upon succinylation. Further, the large percentage (about 90%) of the free amino groups of LDL(2) found to react with succinic anhydride suggests that these groups are at the surface of the molecule.
Amino Acids↗
[Passive Ca2+ influx into vesicles of the sarcoplasmic reticulum, modified by succinic anhydride].
Treatment of the sarcoplasmic reticulum (SR) vesicles with succinic anhydride in concentration of 1-2 mM modifies about 20% of amino groups. It increases initial rate and changes the pH-dependence of the passive influx of Ca2+ into vesicles and does not affect either Ca(2+)-binding or maximal passive Ca(2+)-loading of the SR vesicles. It is supposed that this effect may be caused by modification of the Ca-channel gating behaviour as a result of replacement of positive surface amino groups by carboxyl groups.
Animals↗
(E)-2-(2-adamantylidene)-3-(1-ferrocenylethylidene)succinic anhydride.
The title compound, [Fe(C(5)H(5))(C(21)H(21)O(3))], was obtained from successive Stobbe condensations between ketones and dimethyl succinate. The succinic anhydride five-membered ring is distorted significantly from planarity, with the butadiene moiety being twisted by 49.3 (2) degrees from planarity and the C atoms at the succinic anhydride end of the alkene bonds showing significant pyramidalization. The cyclopentadiene rings of the ferrocenyl moiety adopt an almost eclipsed conformation.
Journal Article↗
Glycemic response to a food starch esterified by 1-octenyl succinic anhydride in humans.
To evaluate the glycemic response to a food starch esterified by 1-octenyl succinic anhydride (OSA), 30 healthy nondiabetic adult subjects were studied in a double-blind crossover design. After an overnight fast, subjects consumed a product containing either 25 g of glucose or 25 g of OSA-substituted starch. Finger-prick capillary blood was obtained at baseline and 15, 30, 45, 60, 90, and 120 min postprandial for glucose measurement. After OSA treatment, the rise in blood glucose was reduced (P < 0.05) at 15 and 30 min and tended (P < 0.08) to be lower at 45 min. Mean peak rise in glucose was reduced 19% (P < 0.01) by OSA (3.30 +/- 0.19 versus 2.66 +/- 0.16 mmol/L) compared to glucose, but time to peak did not differ between treatments. Net incremental area under the curve was also lower (P < 0.05) on OSA compared to glucose. Minimal effects on gastrointestinal symptoms (intensity and frequency of nausea, cramping, distention, and flatulence) were noted for both products, with no clinically significant difference between products. In conclusion, starch substitution with OSA attenuated the postprandial glycemic excursion compared to an equivalent glucose challenge and was well tolerated by fasting healthy adult subjects.
Adult↗
Physical properties of octenyl succinic anhydride modified rice, wheat, and potato starches.
The physical properties of octenyl succinic anhydride (OSA) starches prepared from rice, wheat, and potato starches were studied. Rice and wheat OSA starches had significantly higher peak viscosity (PV), hot paste viscosity (HPV), and cool paste viscosity (CPV), but potato OSA starch had only significantly higher CPV, relative to the native starch. The gel hardness was higher with lower degree of substitution (DS) but lower with higher DS OSA compared to native starch. The swelling volumes (SV) of rice and wheat OSA starches were significantly higher compared to native starch, but the SV of potato OSA starch was slightly lower at high DS. The gelatinization temperature (GT) of rice OSA starches was sharply lower at low DS; for wheat OSA starch it was slightly lower even at high DS, but potato OSA starches had higher GT than the native starch. The enthalpy of all the OSA starches decreased gradually with increased DS. This study showed that the magnitude of changes in physical properties of OSA-modified starches depends not only on their DS but also on the botanical origin of the native starches.
Chemical Phenomena↗