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  • 1
    Electronic Resource
    Electronic Resource
    Cyclic anhydrides. III. Equilibrium constants for the acid-anhydride equilibrium in aqueous solutions of certain vicinal diacids (1971)
    s.l. : American Chemical Society
    Journal of the American Chemical Society 93 (1971), S. 5821-5826 
    Details
    ISSN: 1520-5126
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1021/ja00751a040
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  • 2
    Electronic Resource
    Electronic Resource
    Immunologic tests of specific antibodies to organic acid anhydrides (1991)
    Oxford, UK : Blackwell Publishing Ltd
    Allergy 46 (1991), S. 0 
    Details
    ISSN: 1398-9995
    Source: Blackwell Publishing Journal Backfiles 1879-2005
    Topics: Medicine
    Notes: The outcome of immunologic tests of antibodies directed against hapten conjugates of organic acid anhydrides and human serum albumin (HSA) has been studied in workers exposed to phthalic anhydride (PA), methyltetrahydroplithalic anhydride (MTHPA), hexahydrophthalic anhydride (HHPA), and methylhexahydrophthalie anhydride (MHHPA). HSA conjugates of PA, MTHPA, HHPA, MHHPA, and nialeic anhydride (MA) have been prepared and used in the tests. The hapten densities (HD) of the conjugates were varied by different molar ratios of hapten and macromolecule in the preparative procedure. Skin prick reactions to MTHPA-HSA increased with rising HD over the range 6-13 mol/mol. The achieved HD was tested by spectrometric and gas chromatographic methods. In RAST of IgE antibodies MTHPA-HSA with HD six and 25 showed significantly lower bindings than conjugates with intermediate HD. There was a good correlation between skin prick tests and RAST. Of 234 workers tested [MTHPA (n= 145), and HHPA (n= 89)], 45 had a skin prick reaction 〉 50% of the histamine reaction (1 mg/ml). All but two of these were RAST positive (RAST value 〉 0.3%; 0.3% upper range in 147 controls; MTHPA, n= 63; HHPA, n= 84). Nine RAST positive workers had no obvious skin prick reaction. However, their RAST values were low (〈0.8%). In exposed workers, the ELISA value of specific IgG antibodies to MTHPA-HSA showed optimal values when tested with the HD 13 conjugate. The specific antibodies in workers exposed to either MTHPA or HHPA/MHHPA showed a marked cross-reactivity to MTHPA-HSA, HHPA-HSA, and MHHPA-HSA as proven by skin prick tests, RAST, and RAST inhibition. In workers exposed lo PA (here was less cross reactivity to the other anhydrides.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1111/j.1398-9995.1991.tb00630.x
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  • 3
    Electronic Resource
    Electronic Resource
    Relationship between IgG1 levels and airway responses in guinea pigs actively and passively sensitized to hexahydrophthalic anhydride (1998)
    Oxford, UK : Blackwell Publishing Ltd
    Allergy 53 (1998), S. 0 
    Details
    ISSN: 1398-9995
    Source: Blackwell Publishing Journal Backfiles 1879-2005
    Topics: Medicine
    Notes: Organic acid anhydrides (OAAs) are industrial chemicals that may cause induction of specific IgE and airway symptoms in exposed workers. They are a good model for studies of relationships between chemical structure and the sensitizing potential of reactive low-molecular-weight compounds. Hexahydrophthalic anhydride (HHPA) is such a compound. This study aimed to evaluate the relationship between specific IgG1 levels and airway responses in a model to predict the sensitizing potential of OAAs. Guinea pigs were either actively or passively sensitized to HHPA. For active sensitization, guinea pigs were injected i.d. with 0.1 ml of olive oil (vehicle) or 0.05, 0.5, or 5% HHPA in olive oil. Passive sensitization was performed by i.p. injection of different volumes of antisera (0.75–6 ml, either unheated to keep IgE or heated to destroy IgE) taken form HHPA-sensitized guinea pigs. Specific antibody levels were evaluated with ELISA and passive cutaneous anaphylaxis. Animals were challenged 16–18 days after active sensitization, or 2 days after passive sensitization, by interatracheal instillation with HHPA conjungated to guinea pig serum albumin (HHPA-GPSA; 0.05% in saline), and the immediate effects on lung resistance (R1), and plasma extravasation, measured as Evans blue dye extravasation, for up to 6 min were recorded. Active sensitization caused production of specific IgG1. Provocation with HHPA-GPSA caused an increase of both (R1), and Evans blue dye extravasation, which was dependent upon the active sensitization dose. Challenge with HHPA-GPSA in passively sensitized guinea pigs also produced an increase in both (R1), and Evans blue dy extravasation which was related to IgG1 level. In the guinea pig model of HHPA-induced airway allergy, the airway responses are closely related to the serum levels of specific IgG1. Thus, the IgG1 levels induced by the immunization may reflect the sensitizing potential of HHPA.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1111/j.1398-9995.1998.tb03769.x
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  • 4
    Electronic Resource
    Electronic Resource
    Specific antibodies to methyltetrahydrophthalic anhydride in exposed workers (1990)
    Oxford, UK : Blackwell Publishing Ltd
    Clinical & experimental allergy 20 (1990), S. 0 
    Details
    ISSN: 1365-2222
    Source: Blackwell Publishing Journal Backfiles 1879-2005
    Topics: Medicine
    Notes: A group of 145 workers exposed to methyltetrahydrophthalic anhydride (MTHPA) was investigated. They were working in a plant which, since 1983, handled an epoxy resin with MTHPA as a hardener. Specific IgE antibodies (RAST) to a conjugate between MTHPA and human serum albumin (HSA) were statistically significantly increased (P= 0·001; 26 subjects = 18% positive) in the exposed group, compared to a non-exposed control group (n= 33). One positive worker was only exposed for 2 months. Twenty-three exposed subjects were also skin-prick test positive to MTHPA-HSA. The exposed group was divided into three different exposure categories, according to their contact with the epoxy resin. The average exposure levels at the time of the investigation were, in zone 10·085 mg/m3, in zone II0·014 mg/m3, and in zone III 0·010 mg/m3, though the exposure probably had been higher earlier. There was an association between exposure intensity and RAST-positive persons (P= 0·0025, chi-square trend test). Forty-four persons (30%) were smokers, and 16(11%) atopics. No association between sensitization and either atopy or smoking was found. There was an association between exposure intensity and specific IgG antibodies (P= 0·0003, chi-square trend test). Specific IgG4 antibodies were closely related to specific total IgG antibodies (P= 0·0001). These findings demonstrate that MTHPA is a sensitizing agent at low levels of exposure.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1111/j.1365-2222.1990.tb02702.x
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  • 5
    Electronic Resource
    Electronic Resource
    Association of HLA-DQ5 and HLA-DR1 with sensitization to organic acidanhydrides (2004)
    Oxford, UK : Blackwell Science Ltd
    Clinical & experimental allergy 34 (2004), S. 0 
    Details
    ISSN: 1365-2222
    Source: Blackwell Publishing Journal Backfiles 1879-2005
    Topics: Medicine
    Notes: Background Organic acid anhydrides are low molecular weight industrial chemicals, able to cause rhinoconjunctivitis and asthma associated with specific IgE against hapten–carrier protein conjugate. Only a proportion of exposed workers develop IgE-associated allergy to acid anhydrides.Objective We determined whether genetic susceptibility, in particular, HLA Class II alleles may be a risk factor.Methods We undertook HLA typing in 52 cases who had confirmed specific IgE and in 73 referents matched on site, age and duration of acid anhydride exposure identified in cross-sectional studies of workers exposed to hexahydrophthalic (HHPA), methylhexahydrophthalic (MHHPA) and methyltetrahydrophthalic (MTHPA) anhydrides.Results The linked alleles DQ5 (odds ratio [OR]=4.3; 95% confidence interval [95% CI]=1.7, 11) and DR1 (OR 3.0; 95% CI 1.2, 11) were more prevalent in cases than in referents. Within DQ5, DQB1*0501 was particularly frequent (OR 3.0; 95% CI 1.2, 7.4).Conclusion DQB1*05 gene confers susceptibility to develop specific IgE antibodies against HHPA, MHHPA and a non-significant trend with MTHPA. DQB1*0501 is protective for other low molecular chemical sensitizers (isocyanates and plicatic acid) which may indicate varying affinities for the corresponding specific class II molecules.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1111/j.1365-2222.2004.1956.x
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  • 6
    Electronic Resource
    Electronic Resource
    IgG antibodies against polyisocyanates in car painters (1988)
    Oxford, UK : Blackwell Publishing Ltd
    Clinical & experimental allergy 18 (1988), S. 0 
    Details
    ISSN: 1365-2222
    Source: Blackwell Publishing Journal Backfiles 1879-2005
    Topics: Medicine
    Notes: A group of thirty car painters exposed to vapours and aerosols of paint containing prepolymer and monomer of hexametylene diisocyanate (HDI) was investigated. Specific antibodies against monomer HDI and prepolymerized HDI were analysed with RAST (IgE) and ELISA (IgG) assays after conjugation of the haptens with human serum albumin. There was no significant increase of serum IgG antibodies against HDI monomer, nor of specific IgE antibodies against HDI monomer or prepolymer. Specific IgG antibodies against prepolymerized HDI were significantly increased, as compared with non-exposed referents (medians 0.11 vs 0.03 absorbance (A)). Six car painters were found to have specific IgG antibodies of subclass 4 against HDI prepolymer, four also against HDI monomer. This shows an association between exposure and specific IgG antibodies. Thirteen subjects had suffered symptoms of rhinitis and/or conjunctivitis, and ten had symptoms from the bronchi (two asthma). There was no significant association between symptoms and levels of specific antibodies. Most of the symptoms were slight and unspecific, probably due to irritative effects of the exposure.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1111/j.1365-2222.1988.tb02847.x
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  • 7
    Electronic Resource
    Electronic Resource
    Serum albumins are the major site for in vivo formation of hapten-carrier protein adducts in plasma from humans and guinea-pigs exposed to type-1 allergy inducing hexahydrophthalic anhydride (2001)
    Oxford, UK : Blackwell Science, Ltd
    Clinical & experimental allergy 31 (2001), S. 0 
    Details
    ISSN: 1365-2222
    Source: Blackwell Publishing Journal Backfiles 1879-2005
    Topics: Medicine
    Notes: Background Organic acid anhydrides (OAAs) are highly allergenic compounds used in the chemical industry. The OAAs probably act as haptens but the proteins that form conjugates with OAAs in vivo are still unknown. Conjugates between the anhydrides and serum albumins (SAs) have routinely been used when testing for OAA-specific antibodies. However, the use of SA as the carrier-protein in these tests has never been evaluated.Objective The aim of this study was to identify major and also immunologically relevant protein conjugates of a particularly sensitizing OAA, hexahydrophthalic anhydride (HHPA), in plasma.Methods Plasma was obtained from a HHPA-exposed worker, from a guinea-pig (GP) exposed to HHPA in an exposure chamber for 2 weeks (8 h/day, 5 days/week) and from a GP exposed once, nose-only, to tritium-labelled HHPA for 8 h. The plasma was fractionated using ion exchange chromatography and gel filtration. These fractions and also aliquots of unfractioned plasma were hydrolysed, derivatized and analysed for anhydride adduct content using gas chromatography–mass spectrometry. Further, plasma from the tritium labelled HHPA-exposed GP was separated by SDS gel electrophoresis and analysed by autoradiography. In addition, immunologically relevant proteins were identified through specific IgE and IgG immunoblottings using sera from exposed workers.Results For humans 〉 85% and for GPs 〉 74% of the HHPA-adducts coeluted with SA in plasma. Autoradiography of GP-plasma shows a single 66 kDa protein that binds HHPA. IgE immunoblotting shows a major 66 kDa and a minor 28 kDa protein which could be inhibited by HHPA-SA conjugate. IgG immunoblotting showed a major 66 kDa protein and several minor protein bands.Conclusion This study shows SA to be the major protein in plasma that forms adducts in vivo with HHPA. The results also show that in an in vitro synthesized HHPA plasma protein conjugate, HHPA-specific IgE and IgG antibodies bind preferably to the SA.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1046/j.1365-2222.2001.01109.x
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  • 8
    Electronic Resource
    Electronic Resource
    Symptoms and immunologic markers induced by exposure to methyltetrahydrophthalic anhydride (1994)
    Oxford, UK : Blackwell Publishing Ltd
    Allergy 49 (1994), S. 0 
    Details
    ISSN: 1398-9995
    Source: Blackwell Publishing Journal Backfiles 1879-2005
    Topics: Medicine
    Notes: A study was performed in 43 workers exposed to methyltetrahydrophthalic anhydride (MTHPA) used as a hardener in an epoxy resin system. Ten workers sensitized to MTHPA (group SS; presence of serum IgE antibodies against a conjugate of MTHPA and human serum albumin (HSA) detected by RAST) had significantly higher levels of tryptase in nasal lavage fluid than 19 nonsensitized workers with work-related nasal symptoms (group NS) and 14 nonsensitized workers without nasal symptoms (group NN). This suggests an ongoing mast-cell-mediated reaction in the sensitized group. No statistically significant differences were found in the three groups concerning eosinophil cationic protein (ECP) and TAME-activity in lavage fluid. However, there was a significant increase in serum ECP in the SS group, as compared with a group of unexposed controls. Nasal challenge with MTHPA-HSA, performed in a subsequent study in seven workers from the SS group, six from the NS group, and seven from the NN, caused a larger increase of symptom score and a more pronounced decrease in nasal inspiratory peak flow in the SS group than in the other two groups. No significant rise was recorded for tryptase and ECP in lavage fluid in any of the three groups after challenge. The combined results of the two studies indicate that specific IgE antibodies play a pathogenetic role in at least some of the cases of work-related nasal symptoms associated with MTHPA exposure.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1111/j.1398-9995.1994.tb02661.x
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  • 9
    Electronic Resource
    Electronic Resource
    Anaphylactic bronchoconstriction in immunized guinea pigs provoked by inhalation and intravenous administration of hexahydrophthalic anhydride and methyltetrahydrophthalic anhydride (1997)
    Oxford, UK : Blackwell Publishing Ltd
    Allergy 52 (1997), S. 0 
    Details
    ISSN: 1398-9995
    Source: Blackwell Publishing Journal Backfiles 1879-2005
    Topics: Medicine
    Notes: We established a guinea-pig model of anaphylactic bronchoconstriction provoked in immunized animals by inhalation and intravenous administration of 4,4-methyltetrahydrophthalic anhydride (MTHPA) and hexahydrophthalic anhydride (HHPA). Guinea pigs were immunized intradermally with either MTHPA (n= 8) or HHPA (n= 8) suspended in olive oil. Control animals (n= 8) were injected with olive oil alone. After 4 weeks, the animals were challenged during mechanical ventilation by inhalation or intravenous administration of MTHPA or HHPA conjugated with guinea-pig serum albumin (GPSA). Airway flow, and airway and esophageal pressures were measured. Resistance (R) and static compliance (Cst) of the respiratory system (rs), lung (1), and chest wall were studied with the flow-interruption technique. After challenge with MTHPA-GPSA or HHPA-GPSA, R, rs and R, 1 increased dramatically while Cst, rs and Cst,1 decreased, and severe arterial hypoxia developed. The reaction occurred at a well-defined dose of anhydride and lasted about 30 min. When the same dose was repeated after 30 min, the response was much attenuated. MTHPA and HHPA can induce asthma in guinea pigs. The dose-response curve at antigen challenge is steep. Once a threshold dose is reached, a severe reaction occurs. The reactivity is then exhausted. This model may be suitable for assessing occupational asthma caused by acid anhydrides and possibly by other low-molecular-weight chemicals.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1111/j.1398-9995.1997.tb02541.x
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  • 10
    Electronic Resource
    Electronic Resource
    Determination of hexahydrophthalic anhydride in air using gas chromatography
    Amsterdam : Elsevier
    Journal of Chromatography A 558 (1991), S. 247-256 
    Details
    ISSN: 0021-9673
    Source: Elsevier Journal Backfiles on ScienceDirect 1907 - 2002
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://linkinghub.elsevier.com/retrieve/pii/0021-9673(91)80130-9
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